US20060042158A1 - Fuel products from plant or animal lipids - Google Patents
Fuel products from plant or animal lipids Download PDFInfo
- Publication number
- US20060042158A1 US20060042158A1 US10/926,459 US92645904A US2006042158A1 US 20060042158 A1 US20060042158 A1 US 20060042158A1 US 92645904 A US92645904 A US 92645904A US 2006042158 A1 US2006042158 A1 US 2006042158A1
- Authority
- US
- United States
- Prior art keywords
- products
- carbon
- fuel
- plant
- fatty acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000446 fuel Substances 0.000 title claims abstract description 36
- 150000002632 lipids Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 45
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052799 carbon Chemical group 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- 238000005809 transesterification reaction Methods 0.000 claims description 12
- 238000005336 cracking Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000009835 boiling Methods 0.000 abstract description 24
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 14
- 238000004821 distillation Methods 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 30
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 11
- 239000003925 fat Substances 0.000 description 10
- 235000019197 fats Nutrition 0.000 description 10
- 239000008158 vegetable oil Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000003225 biodiesel Substances 0.000 description 7
- -1 fatty acid triglycerides Chemical class 0.000 description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 description 6
- 235000021588 free fatty acids Nutrition 0.000 description 5
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 5
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- 239000010775 animal oil Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002551 biofuel Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 238000007248 oxidative elimination reaction Methods 0.000 description 2
- 238000006385 ozonation reaction Methods 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KSIKGJKZYDOVFA-UHFFFAOYSA-N (E)-15-Octadecenoic acid Natural products CCC=CCCCCCCCCCCCCCC(O)=O KSIKGJKZYDOVFA-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OXEDXHIBHVMDST-VOTSOKGWSA-N (e)-octadec-12-enoic acid Chemical compound CCCCC\C=C\CCCCCCCCCCC(O)=O OXEDXHIBHVMDST-VOTSOKGWSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OXEDXHIBHVMDST-UHFFFAOYSA-N 12Z-octadecenoic acid Natural products CCCCCC=CCCCCCCCCCCC(O)=O OXEDXHIBHVMDST-UHFFFAOYSA-N 0.000 description 1
- KSIKGJKZYDOVFA-ONEGZZNKSA-N 15E-octadecenoic acid Chemical compound CC\C=C\CCCCCCCCCCCCCC(O)=O KSIKGJKZYDOVFA-ONEGZZNKSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
Definitions
- This present invention relates to a novel processing method for producing fuels from plant or animal lipids by cracking carbon and carbon bonds in plant or animal lipids and distillating the mixing fuels after chemical treatments.
- Petroleum is a complex mixture of organic compounds, most of which are alkanes and aromatic hydrocarbons. Petroleum also contains small amounts of oxygen, nitrogen, and sulfur-containing compounds. The primary use of alkanes is as an energy source. Different fraction products are obtained after a distillation process. Most fuels that we use are natural gas, petroleum ester, ligroin, gasoline, kerosene/jet fuel, fuel oil/diesel oil, and lubrication oil. Natural gas fraction contains 1-4 carbons in the molecular formula with the boiling point below 20 degree C. Petroleum ester fraction contains 5-6 carbons in the molecular formula with the boiling point range at 20-60 degree C.
- Ligroin fraction contains 6-7 carbons in the molecular formula with the boiling point range at 60-100 degree C.
- Gasoline fraction contains 5-10 carbons in the molecular formula with the boiling point range at 40-200 degree C.
- Kerosene and jet fuel fraction contains 12-18 carbons in the molecular formula with the boiling point range at 175-325 degree C.
- Fuel oil and diesel oil fraction contains 12 and more carbons in the molecular formula with the boiling point range at 250-400 degree C.
- Lubrication oil fraction contains 20 and more carbons in the molecular formula with a much high boiling point. Fuels with lower molecular weights usually have lower boiling points. As we all know that the world's supply of petroleum will run out sometime in the future. It is a hard fact that our societies are so largely organized around machines depending on petroleum-based fuels, which continues the energy challenge. The solution to the energy crisis is to develop alternate sources of energy.
- 6,712,867 (2004) discloses a process for production of fatty acid methyl esters as biodiesel from fatty acid triglycerides with the ratio of alcohol to triglycerides at 15:1 to 35:1. Very high level alcohol is needed in the process.
- U.S. Pat. No. 6,532,918 (2003) discloses a method and device for lubricating and simultaneously supplying fuel in a vegetable oil-operated combustion engine. Fresh vegetable oil and additive-treated vegetable oil are used.
- U.S. Pat. No. 6,399,800 (2002) discloses a process for producing fatty acid alkyl esters by esterifying the dried saponified feedstock with an alcohol and an inorganic acid catalyst.
- U.S. Pat. No. 6,015,440 (2000) discloses a process for producing biodiesel fuel from triglycerides with methanol and a homogeneous basic catalyst.
- U.S. Pat. No. 5,885,946 (1999) discloses a process for preparing a synthetic ester from a vegetable oil by a two-stage transesterification process.
- U.S. Pat. No. 5,713,965 discloses a method to produce biofuels by utilizing lipases to transesterify triglyceride-containing substances and to esterify free fatty acids to alkyl esters using short chain alcohols.
- U.S. Pat. No. 5,525,126 discloses a process for producing esters from a fat or an oil with an alcohol and non-alkaline catalyst.
- the catalyst includes a mixture of calcium acetate and barium acetate.
- the reaction mixture is heated at a temperature effective to make esters.
- U.S. Pat. No. 5,116,546 (1992) discloses a process for producing fatty acid esters by transesterification, esterification, and recovery steps.
- 4,698,186 (1987) discloses a process for reducing the free fatty acid content of fats and oils by esterifying the free fatty acids with a lower monoalcohol in the presence of an acidic cation exchange resin as a solid esterification catalyst.
- U.S. Pat. No. 4,695,411 (1987) discloses a process for manufacturing fatty acid esters useful for combustion in diesel engines. There are three processing steps are involved in the esterification process.
- U.S. Pat. No. 4,557,734 (1985) discloses a process for producing microemulsions from vegetable oil, methanol or ethanol, a straight-chain isomer of octanol, and optionally water.
- the fuels are characterized by a relatively high water tolerance, acceptable viscosity, and performance properties comparable to No. 2 diesel fuel.
- U.S. Pat. No. 4,371,470 (1983) discloses a method for manufacturing fatty acid esters by a two-step transesterification from a natural oil or fat with methyl alcohol. The trace amounts of the colored or chromogenic impurities are removed by admixing an absorbent.
- U.S. Pat. No. 4,164,506 (1979) discloses a process for producing lower alcohol esters of fatty acids by esterifying free fatty acids of unrefined fats with a lower alcohol.
- This present invention provides a novel processing method for producing mixing fuels from plant or animal lipids by cracking carbon and carbon bonds in plant or animal lipids, chemical treatments, and distillating the mixing fuels. Then the issues such as viscosity, molecular weight, boiling point, pollution, and burning performance with biodiesel can be resolved.
- Plant or animal lipids are such as glyceryl trialkanoates (is also called triglycerides), carboxylic acids (free fatty acids), phospholipids, glycolipids, and terpenes.
- a glyceryl trialkanoate is made by three fatty acids and one glycerol in the molecular formula. There are saturated and unsaturated fatty acids. For unsaturated fatty acids, there are unsaturated (double) carbon-carbon bonds.
- a phospholipid is made by two fatty acids, one phosphoric acid, and one glycerol in the molecular formula.
- Terpenes such as essential oil and natural rubber have unsaturated carbon-carbon bonds and branched methyl groups in the molecular formula.
- the lipids which include such as raw materials, products, intermediate products, byproducts, and waste products from plant or animal lipid sources, are used in this process.
- Most common lipids such as oils and fats from plant or animal origin are glyceryl trialkanoates, which are usually have long-chain alkyl groups for fatty acids.
- Those glyceryl trialkanoates that are liquids at room temperature are generally as oils; those that are solids are usually called fats. The fats become oils after heat.
- Table 1 shows major fatty acid composition obtained by hydrolysis of common fats and oils TABLE 1 Major fatty acid composition of common fats and oils (mole, %) Unsaturated Saturated C18/ C18/ C18/ Vegetable Oils C16 C18 C16 oleic linoleic linolenic Soybean 6-10 2-4 20-30 50-58 5-10 Corn 7-11 3-4 1-2 25-35 50-60 Linseed 4-7 2-4 14-30 14-25 45-60 Olive 5-15 1-4 67-84 8-12 Animal Fats Lard 25-30 12-18 4-6 48-60 6-12 Beef tallow 24-34 15-30 35-45 1-3
- C16 is palmitic acid and C18 is stearic acid.
- C16 is palmitoleic acid and C18 is oleic acid (cis-9-octadecenoic acid with one double carbon-carbon bond —HC ⁇ CH—), linoleic acid (cis, cis-9,12-octadecenoic acid with two double carbon-carbon bonds —HC ⁇ CH—CH2-HC ⁇ CH—) or linolenic acid (cis, cis, cis-9, 12, 15-octadecenoic acid with three double carbon-carbon bonds bonds —HC ⁇ CH—CH2-HC ⁇ CH—CH2-HC ⁇ CH—).
- the products After cracking the double carbon-carbon bonds of the unsaturated fatty acids in plant or animal lipids, the products are the mixtures. The carbon numbers in the molecular formulas and molecular weights in the mixtures are reduced significantly, which changes the viscosity, boiling points, and burning performance for the fuels. Cracking the double carbon-carbon bonds of the unsaturated fatty acids can be done before or after the glycerol in the lipids is dissociated from the lipid molecules. Glycerol is water soluble and has a boiling point 290° C. and a density 1.26, which can also be separated by centrifugation process.
- the carbon number range for fuel products in the mixed products is usually from C3 to C18 such as C3 C6, C7, C8, C9, C12, and C18, which likes petroleum with wide carbon number range. There are also some compounds with carbon number more than 18 from the raw materials or intermediate products.
- aldehyde products such as hexanal are formed.
- Aldehyde products can be used directly.
- Aldehyde products can also be converted into alkane products (with —CH3 group) by such as hydrazones, which is called the Wolff-Kishner reduction.
- the boiling point is reduced from 128° C. (for hexanal CH3(CH2)4CHO) to 69° C. (for hexane CH3(CH2)4CH2).
- carboxylic acids fatty acids
- phospholipids phospholipids
- glycolipids glycolipids
- terpenes terpenes
- carboxylic acids fatty acids
- phospholipids phospholipids
- glycolipids glycolipids
- terpenes terpenes
- the most valuable products as fuels are the organic or carbohydrate products with smaller carbon numbers such as less than 15 in the molecular formula and lower boiling points such as lower than 300° C.
- the mixed products with carbon numbers from C3 to C18 and higher in the molecular formulas processed from plant or animal lipids with carbon numbers about C45 to C57 in the molecular formula may considered as biopetroleum.
- a distillation process is applied to produce the fraction products according to their boiling points, which is similar to the distillation process of normal petroleum.
- the products with low boiling points are used as better fuels.
- the products with high boiling points are used as oils.
- the nonvolatile products are used for other applications.
- the products as fuels are obtained from distillation process, which are totally different from current processes for biodiesel products.
- the products from distillation process have low molecular weight, low boiling points, and low viscosity. The method in this invention produces better products after distillation process.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A novel method for producing fuel products from plant or animal lipids is provided. The carbon-carbon bonds in the molecules of plant or animal lipids are cracked into the molecules with smaller molecular weights. The mixed fuel is formed after chemical treatments. Then the mixed fuel (biopetroleum) is processed by a distillation process to produce fuel products according to their boiling points. The method is particularly advantageous to produce the energy source from agricultural products, which provides a solution for energy crisis with a significant potential.
Description
- This present invention relates to a novel processing method for producing fuels from plant or animal lipids by cracking carbon and carbon bonds in plant or animal lipids and distillating the mixing fuels after chemical treatments.
- The energy crisis of recent years has been a significant challenge. Petroleum is a complex mixture of organic compounds, most of which are alkanes and aromatic hydrocarbons. Petroleum also contains small amounts of oxygen, nitrogen, and sulfur-containing compounds. The primary use of alkanes is as an energy source. Different fraction products are obtained after a distillation process. Most fuels that we use are natural gas, petroleum ester, ligroin, gasoline, kerosene/jet fuel, fuel oil/diesel oil, and lubrication oil. Natural gas fraction contains 1-4 carbons in the molecular formula with the boiling point below 20 degree C. Petroleum ester fraction contains 5-6 carbons in the molecular formula with the boiling point range at 20-60 degree C. Ligroin fraction contains 6-7 carbons in the molecular formula with the boiling point range at 60-100 degree C. Gasoline fraction contains 5-10 carbons in the molecular formula with the boiling point range at 40-200 degree C. Kerosene and jet fuel fraction contains 12-18 carbons in the molecular formula with the boiling point range at 175-325 degree C. Fuel oil and diesel oil fraction contains 12 and more carbons in the molecular formula with the boiling point range at 250-400 degree C. Lubrication oil fraction contains 20 and more carbons in the molecular formula with a much high boiling point. Fuels with lower molecular weights usually have lower boiling points. As we all know that the world's supply of petroleum will run out sometime in the future. It is a hard fact that our societies are so largely organized around machines depending on petroleum-based fuels, which continues the energy challenge. The solution to the energy crisis is to develop alternate sources of energy.
- One area of particular interest relates to fuels for commercial and agricultural vehicles is biodiesel after converting vegetable or animal oils into ester products. Another area is to use vegetable or animal oils and their blended oils with other fuel products for partial replacement for diesel and burning oils. But there are some important issues such as viscosity, boiling point, pollution, and burning performance because there are still mixed compounds in the fuels with high boiling points, sulfur-containing compounds, and nonvolatile compounds. Over the years, various attempts have been made to make biodiesel and lubricant oils. A number of patents have been issued for the processes. U.S. Pat. No. 6,712,867 (2004) discloses a process for production of fatty acid methyl esters as biodiesel from fatty acid triglycerides with the ratio of alcohol to triglycerides at 15:1 to 35:1. Very high level alcohol is needed in the process. U.S. Pat. No. 6,532,918 (2003) discloses a method and device for lubricating and simultaneously supplying fuel in a vegetable oil-operated combustion engine. Fresh vegetable oil and additive-treated vegetable oil are used. U.S. Pat. No. 6,399,800 (2002) discloses a process for producing fatty acid alkyl esters by esterifying the dried saponified feedstock with an alcohol and an inorganic acid catalyst. U.S. Pat. No. 6,015,440 (2000) discloses a process for producing biodiesel fuel from triglycerides with methanol and a homogeneous basic catalyst. U.S. Pat. No. 5,885,946 (1999) discloses a process for preparing a synthetic ester from a vegetable oil by a two-stage transesterification process. U.S. Pat. No. 5,713,965 (1998) discloses a method to produce biofuels by utilizing lipases to transesterify triglyceride-containing substances and to esterify free fatty acids to alkyl esters using short chain alcohols. U.S. Pat. No. 5,697,986 (1997) discloses a process to produce biofuels by carrying out the enzymatic transesterification of fatty acid-containing materials directly in automative fuels. U.S. Pat. No. 5,525,126 (1996) discloses a process for producing esters from a fat or an oil with an alcohol and non-alkaline catalyst. The catalyst includes a mixture of calcium acetate and barium acetate. The reaction mixture is heated at a temperature effective to make esters. U.S. Pat. No. 5,116,546 (1992) discloses a process for producing fatty acid esters by transesterification, esterification, and recovery steps. U.S. Pat. No. 4,698,186 (1987) discloses a process for reducing the free fatty acid content of fats and oils by esterifying the free fatty acids with a lower monoalcohol in the presence of an acidic cation exchange resin as a solid esterification catalyst. U.S. Pat. No. 4,695,411 (1987) discloses a process for manufacturing fatty acid esters useful for combustion in diesel engines. There are three processing steps are involved in the esterification process. U.S. Pat. No. 4,557,734 (1985) discloses a process for producing microemulsions from vegetable oil, methanol or ethanol, a straight-chain isomer of octanol, and optionally water. The fuels are characterized by a relatively high water tolerance, acceptable viscosity, and performance properties comparable to No. 2 diesel fuel. U.S. Pat. No. 4,371,470 (1983) discloses a method for manufacturing fatty acid esters by a two-step transesterification from a natural oil or fat with methyl alcohol. The trace amounts of the colored or chromogenic impurities are removed by admixing an absorbent. U.S. Pat. No. 4,164,506 (1979) discloses a process for producing lower alcohol esters of fatty acids by esterifying free fatty acids of unrefined fats with a lower alcohol.
- The principle of preparing biodiesel is transesterification or esterification, which is described in Organic Chemistry (Solomons, 1984). Transesterification or alcoholysis of triglycerides of vegetable oils and animal fats in the presence of an alcohol leads to the formation of fatty acid esters, which is also described in European Pat. No. 127,104 and U.S. Pat. No. 4,164,506. After the transesterification or esterification reactions, the viscosity and boiling points for the esters from vegetable or animal oils are reduced compared with vegetable or animal oils. But ester products still have 17-19 carbons in the molecular formula. Also the final fuel products still contains other compounds such as sulfur-containing compounds, nonvolatile compounds, and non-reacted triglycerides and fatty acids, which affects the burning performance and causes pollution.
- This present invention provides a novel processing method for producing mixing fuels from plant or animal lipids by cracking carbon and carbon bonds in plant or animal lipids, chemical treatments, and distillating the mixing fuels. Then the issues such as viscosity, molecular weight, boiling point, pollution, and burning performance with biodiesel can be resolved.
- Plant or animal lipids are such as glyceryl trialkanoates (is also called triglycerides), carboxylic acids (free fatty acids), phospholipids, glycolipids, and terpenes. A glyceryl trialkanoate is made by three fatty acids and one glycerol in the molecular formula. There are saturated and unsaturated fatty acids. For unsaturated fatty acids, there are unsaturated (double) carbon-carbon bonds. A phospholipid is made by two fatty acids, one phosphoric acid, and one glycerol in the molecular formula. Terpenes such as essential oil and natural rubber have unsaturated carbon-carbon bonds and branched methyl groups in the molecular formula. The lipids, which include such as raw materials, products, intermediate products, byproducts, and waste products from plant or animal lipid sources, are used in this process. Most common lipids such as oils and fats from plant or animal origin are glyceryl trialkanoates, which are usually have long-chain alkyl groups for fatty acids. Those glyceryl trialkanoates that are liquids at room temperature are generally as oils; those that are solids are usually called fats. The fats become oils after heat. Table 1 shows major fatty acid composition obtained by hydrolysis of common fats and oils
TABLE 1 Major fatty acid composition of common fats and oils (mole, %) Unsaturated Saturated C18/ C18/ C18/ Vegetable Oils C16 C18 C16 oleic linoleic linolenic Soybean 6-10 2-4 20-30 50-58 5-10 Corn 7-11 3-4 1-2 25-35 50-60 Linseed 4-7 2-4 14-30 14-25 45-60 Olive 5-15 1-4 67-84 8-12 Animal Fats Lard 25-30 12-18 4-6 48-60 6-12 Beef tallow 24-34 15-30 35-45 1-3 - (Solomons, 1984). For saturated fatty acids, C16 is palmitic acid and C18 is stearic acid. For unsaturated fatty acids, C16 is palmitoleic acid and C18 is oleic acid (cis-9-octadecenoic acid with one double carbon-carbon bond —HC═CH—), linoleic acid (cis, cis-9,12-octadecenoic acid with two double carbon-carbon bonds —HC═CH—CH2-HC═CH—) or linolenic acid (cis, cis, cis-9, 12, 15-octadecenoic acid with three double carbon-carbon bonds bonds —HC═CH—CH2-HC═CH—CH2-HC═CH—). To crack double carbon-carbon bonds of the unsaturated fatty acids in plant or animal lipids is technically feasible and practical with several chemical reactions and processes such as (1) oxidative cleavage of alkenes with an oxidant under base/acid and heat, (2) ozonization of alkenes with ozone, zinc, and water or (3) hydroxylation of the double bond using osmium tetroxide, dilute aqueous potassium permanganate, or a peroxy acid and subsequent cleavage of the glycol using periodic acid. The chemical reactions are as follows:
- (1) Oxidative cleavage: —HC═CH—→—COOH (under base and acid conditions)
- (2) Ozonization: RHC═CHR′→RHCO+R′HCO
- (R and R′ are long-chain alkyl groups with or without glycerol)
- (3) Hydroxylation: RHC═CHR′→RHCOH—COHHR′
- RHCOH—COHHR′→RHC═O+O═CHR′ (with HIO4)
- After cracking the double carbon-carbon bonds of the unsaturated fatty acids in plant or animal lipids, the products are the mixtures. The carbon numbers in the molecular formulas and molecular weights in the mixtures are reduced significantly, which changes the viscosity, boiling points, and burning performance for the fuels. Cracking the double carbon-carbon bonds of the unsaturated fatty acids can be done before or after the glycerol in the lipids is dissociated from the lipid molecules. Glycerol is water soluble and has a boiling point 290° C. and a density 1.26, which can also be separated by centrifugation process. The carbon number range for fuel products in the mixed products is usually from C3 to C18 such as C3 C6, C7, C8, C9, C12, and C18, which likes petroleum with wide carbon number range. There are also some compounds with carbon number more than 18 from the raw materials or intermediate products.
- When cracking the double carbon-carbon bonds of the unsaturated fatty acids is done before the glycerol in the lipids is dissociated from the lipid molecules, a transesterification is further processed to form ester products. When cracking the double carbon-carbon bonds of the unsaturated fatty acids is done after the glycerol in the lipids is dissociated and removed from the lipid molecules, an esterification is further processed to form ester products. The boiling points of ester products are much lower than fatty acids such as ethyl methyl ester (C2H5OCH3) has the boiling point at 8° C. and propanoic acid (C2H5COOH) has the boiling point at 141° C. even both products have the same carbon numbers (3). After the cracking the double carbon-carbon bonds of the unsaturated fatty acids, aldehyde products (with —CHO groups) such as hexanal are formed. Aldehyde products can be used directly. Aldehyde products can also be converted into alkane products (with —CH3 group) by such as hydrazones, which is called the Wolff-Kishner reduction. After hexanal is converted into hexane, the boiling point is reduced from 128° C. (for hexanal CH3(CH2)4CHO) to 69° C. (for hexane CH3(CH2)4CH2). Besides glyceryl trialkanoates, carboxylic acids (fatty acids), phospholipids, glycolipids, and terpenes can be similarly treated as above. The most valuable products as fuels are the organic or carbohydrate products with smaller carbon numbers such as less than 15 in the molecular formula and lower boiling points such as lower than 300° C.
- To crack saturated (single) carbon-carbon bonds of the saturated acids in plant or animal lipids is difficult. When a mixture of alkanes from the gas oil materials (C12 and higher) are heated to very high temperature in the presence of a variety of catalysts, then the molecular break apart and rearrange to smaller, more highly branched alkanes containing 5 to 10 carbons. The cracking can also be done at very high temperature without a catalyst. But this process to crack saturated single carbon-carbon bonds tends to have alkanes with unbranched chains (Solomons, 1984).
- After the cracking carbon-carbon bonds and the chemical reactions to convert such as from the fatty acids into their ester products with chemicals and catalysts, the mixed products with carbon numbers from C3 to C18 and higher in the molecular formulas processed from plant or animal lipids with carbon numbers about C45 to C57 in the molecular formula may considered as biopetroleum. Then a distillation process is applied to produce the fraction products according to their boiling points, which is similar to the distillation process of normal petroleum. The products with low boiling points are used as better fuels. The products with high boiling points are used as oils. The nonvolatile products are used for other applications. The products as fuels are obtained from distillation process, which are totally different from current processes for biodiesel products. The products from distillation process have low molecular weight, low boiling points, and low viscosity. The method in this invention produces better products after distillation process.
Claims (20)
1. A method of producing a fuel composition comprising cracking unsaturated carbon and carbon bonds in plant or animal lipids, converting into a mixed fuel, and distillating the mixing fuel to form the fuel products.
2. The method of claim 1 wherein the unsaturated carbon and carbon bonds are cracked chemically.
3. The method of claim 1 wherein the unsaturated carbon and carbon bonds are cracked before or after dissociating glycerol from plant or animal lipids.
4. The method of claim 1 wherein esterification or transesterification with the alcohol consisting carbon 1 to 4 is used to convert fatty acids into esters.
5. The method of claim 4 wherein an enzyme is used for the transesterification.
6. The method of claim 1 wherein the aldehydes are converted into alkanes.
7. The method of claim 1 wherein a catalyst is used.
8. The method of claim 1 wherein heat or cooling process is used.
9. The method of claim 1 wherein the products are used as fuel products.
10. The method of claim 1 wherein the products are used as organic products.
11. A method of producing a fuel composition comprising cracking carbon and carbon bonds in plant or animal lipids, converting into a mixed fuel, and distillating the mixing fuel to form the fuel products.
12. The method of claim 11 wherein the carbon and carbon bonds are cracked by catalyst and pressure cooker.
13. The method of claim 11 wherein the method the carbon and carbon bonds are cracked before or after dissociating glycerol from the plant or animal lipids.
14. The method of claim 11 wherein esterification or transesterification with the alcohol consisting carbon 1 to 4 is used to convert fatty acids into esters.
15. The method of claim 14 wherein an enzyme is used for the transesterification.
16. The method of claim 11 wherein the aldehydes are converted into alkanes.
17. The method of claim 11 wherein a catalyst is used.
18. The method of claim 11 wherein heat or cooling process is used.
19. The method of claim 11 wherein the products are used as fuel products.
20. The method of claim 11 wherein the products are used as organic products.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/926,459 US20060042158A1 (en) | 2004-08-26 | 2004-08-26 | Fuel products from plant or animal lipids |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/926,459 US20060042158A1 (en) | 2004-08-26 | 2004-08-26 | Fuel products from plant or animal lipids |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060042158A1 true US20060042158A1 (en) | 2006-03-02 |
Family
ID=35941012
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/926,459 Abandoned US20060042158A1 (en) | 2004-08-26 | 2004-08-26 | Fuel products from plant or animal lipids |
Country Status (1)
Country | Link |
---|---|
US (1) | US20060042158A1 (en) |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060270866A1 (en) * | 2005-05-25 | 2006-11-30 | Richard Sapienza | Processes for production of esters from olefin-containing hydrocarbon streams and vegetable or animal oils |
US7244771B1 (en) | 2006-08-11 | 2007-07-17 | Seymour Gary F | Commercial production of synthetic fuel from fermentation by-products system |
US20070299272A1 (en) * | 2006-06-27 | 2007-12-27 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
US20070299271A1 (en) * | 2006-06-27 | 2007-12-27 | Udaya Nayanskantha Wanasundara | Process for separating saturated and unsaturated fatty acids for producing cold-tolorant biodiesel fuel from soy oil |
US20080092436A1 (en) * | 2006-06-30 | 2008-04-24 | University Of North Dakota | Method for cold stable biojet fuel |
US20080171889A1 (en) * | 2007-01-16 | 2008-07-17 | National Kaohsiunh University Of Applied Sciences | Method of increasing transesterification of oils |
US20080171680A1 (en) * | 2007-01-12 | 2008-07-17 | Kwang Soon Kim | Composition of water-soluble metalworking fluid using distillation residue generated in production of biodiesel |
US20100071260A1 (en) * | 2004-12-22 | 2010-03-25 | John Lee Massingill | Method and System for Production of Biofuels Using a Fiber Conduit Reactor |
WO2010062932A1 (en) * | 2008-11-26 | 2010-06-03 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
US20100242348A1 (en) * | 2007-01-16 | 2010-09-30 | National Kaohsiung University Of Applied Sciences | Method of increasing transesterification conversion of oils |
US20110237850A1 (en) * | 2008-11-26 | 2011-09-29 | Elevance Renewable Sciences, Inc | Methods of producing jet fuel from natural oil feedstocks through metathesis reactions |
US8735640B2 (en) | 2009-10-12 | 2014-05-27 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
US8882861B2 (en) * | 2010-07-26 | 2014-11-11 | Sapphire Energy, Inc. | Oleaginous compounds from biomass |
US8906236B2 (en) | 2010-07-26 | 2014-12-09 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds and nutrients from biomass |
US8957268B2 (en) | 2009-10-12 | 2015-02-17 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
US9000246B2 (en) | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9028696B2 (en) | 2010-07-26 | 2015-05-12 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds from biomass |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US9133416B2 (en) | 2011-12-22 | 2015-09-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9139493B2 (en) | 2011-12-22 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9169447B2 (en) | 2009-10-12 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9168469B2 (en) | 2004-12-22 | 2015-10-27 | Chemtor, Lp | Method and system for production of a chemical commodity using a fiber conduit reactor |
US9169174B2 (en) | 2011-12-22 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9175231B2 (en) | 2009-10-12 | 2015-11-03 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils and methods of producing fuel compositions |
US9222056B2 (en) | 2009-10-12 | 2015-12-29 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9353331B2 (en) | 2012-11-13 | 2016-05-31 | Rrip, Llc | Method to recover free fatty acids from fats and oils |
US9365487B2 (en) | 2009-10-12 | 2016-06-14 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9382502B2 (en) | 2009-10-12 | 2016-07-05 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
US9388098B2 (en) | 2012-10-09 | 2016-07-12 | Elevance Renewable Sciences, Inc. | Methods of making high-weight esters, acids, and derivatives thereof |
US9468866B2 (en) | 2012-09-18 | 2016-10-18 | Chemtor, Lp | Use of a fiber conduit contactor for metal and/or metalloid extraction |
CN108676599A (en) * | 2018-05-14 | 2018-10-19 | 和县伊迈炭业有限责任公司 | A method of preparing charcoal using needle mushroom dreg |
US10526299B2 (en) | 2004-12-22 | 2020-01-07 | Chemtor, Lp | Fiber conduit reactor with a heat exchange medium inlet and a heat exchange medium outlet |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4164506A (en) * | 1977-03-17 | 1979-08-14 | Kao Soap Co., Ltd. | Process for producing lower alcohol esters of fatty acids |
US4371470A (en) * | 1980-02-28 | 1983-02-01 | Lion Corporation | Method for manufacturing high quality fatty acid esters |
US4557734A (en) * | 1984-08-08 | 1985-12-10 | The United States Of America As Represented By The Secretary Of Agriculture | Microemulsions from vegetable oil and lower alcohol with octanol surfactant as alternative fuel for diesel engines |
US4652406A (en) * | 1984-12-08 | 1987-03-24 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of fatty acid alkyl esters |
US4695411A (en) * | 1985-02-15 | 1987-09-22 | Institut Francais Du Petrol | Process for manufacturing a composition of fatty acid esters useful as gas oil substitute motor fuel with hydrated ethyl alcohol and the resultant esters composition |
US4698186A (en) * | 1985-01-21 | 1987-10-06 | Henkel Kommanditgesellschaft Auf Aktien | Process for the pre-esterification of free fatty acids in fats and oils |
US4992605A (en) * | 1988-02-16 | 1991-02-12 | Craig Wayne K | Production of hydrocarbons with a relatively high cetane rating |
US5114541A (en) * | 1980-11-14 | 1992-05-19 | Ernst Bayer | Process for producing solid, liquid and gaseous fuels from organic starting material |
US5116546A (en) * | 1989-04-05 | 1992-05-26 | Van Den Bergh Foods Co., Division Of Conopco, Inc. | Process for producing fatty-acid lower-alkyl mono-esters |
US5186722A (en) * | 1991-06-25 | 1993-02-16 | Cantrell Research, Incorporated | Hydrocarbon-based fuels from biomass |
US5524126A (en) * | 1994-11-15 | 1996-06-04 | Hughes Electronics | Symbol timing recovery using fir data interpolators |
US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
US5697986A (en) * | 1996-04-12 | 1997-12-16 | The United States Of America, As Represented By The Secretary Of Agriculture | Fuels as solvents for the conduct of enzymatic reactions |
US5713965A (en) * | 1996-04-12 | 1998-02-03 | The United States Of America As Represented By The Secretary Of Agriculture | Production of biodiesel, lubricants and fuel and lubricant additives |
US5885946A (en) * | 1994-09-07 | 1999-03-23 | Raision Tehtaat Oy Ab | Process for preparing a synthetic ester from a vegetable oil |
US5972057A (en) * | 1997-11-11 | 1999-10-26 | Lonford Development Limited | Method and apparatus for producing diesel fuel oil from waste edible oil |
US6015440A (en) * | 1997-10-31 | 2000-01-18 | Board Of Regents Of The University Of Nebraska | Process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit |
US6399800B1 (en) * | 1999-09-22 | 2002-06-04 | The United States Of America As Represented By The Secretary Of Agriculture | Process for the production of fatty acid alkyl esters |
US6532918B1 (en) * | 1997-10-30 | 2003-03-18 | Fuchs Petrolub Ag | Method and device for lubricating and simultaneously supplying fuel in a vegetable oil-operated combustion engine |
US6712867B1 (en) * | 1999-08-18 | 2004-03-30 | Biox Corporation | Process for production of fatty acid methyl esters from fatty acid triglycerides |
-
2004
- 2004-08-26 US US10/926,459 patent/US20060042158A1/en not_active Abandoned
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4164506A (en) * | 1977-03-17 | 1979-08-14 | Kao Soap Co., Ltd. | Process for producing lower alcohol esters of fatty acids |
US4371470A (en) * | 1980-02-28 | 1983-02-01 | Lion Corporation | Method for manufacturing high quality fatty acid esters |
US5114541A (en) * | 1980-11-14 | 1992-05-19 | Ernst Bayer | Process for producing solid, liquid and gaseous fuels from organic starting material |
US4557734A (en) * | 1984-08-08 | 1985-12-10 | The United States Of America As Represented By The Secretary Of Agriculture | Microemulsions from vegetable oil and lower alcohol with octanol surfactant as alternative fuel for diesel engines |
US4652406A (en) * | 1984-12-08 | 1987-03-24 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of fatty acid alkyl esters |
US4698186A (en) * | 1985-01-21 | 1987-10-06 | Henkel Kommanditgesellschaft Auf Aktien | Process for the pre-esterification of free fatty acids in fats and oils |
US4695411A (en) * | 1985-02-15 | 1987-09-22 | Institut Francais Du Petrol | Process for manufacturing a composition of fatty acid esters useful as gas oil substitute motor fuel with hydrated ethyl alcohol and the resultant esters composition |
US4992605A (en) * | 1988-02-16 | 1991-02-12 | Craig Wayne K | Production of hydrocarbons with a relatively high cetane rating |
US5116546A (en) * | 1989-04-05 | 1992-05-26 | Van Den Bergh Foods Co., Division Of Conopco, Inc. | Process for producing fatty-acid lower-alkyl mono-esters |
US5186722A (en) * | 1991-06-25 | 1993-02-16 | Cantrell Research, Incorporated | Hydrocarbon-based fuels from biomass |
US5885946A (en) * | 1994-09-07 | 1999-03-23 | Raision Tehtaat Oy Ab | Process for preparing a synthetic ester from a vegetable oil |
US5524126A (en) * | 1994-11-15 | 1996-06-04 | Hughes Electronics | Symbol timing recovery using fir data interpolators |
US5578090A (en) * | 1995-06-07 | 1996-11-26 | Bri | Biodiesel fuel |
US5697986A (en) * | 1996-04-12 | 1997-12-16 | The United States Of America, As Represented By The Secretary Of Agriculture | Fuels as solvents for the conduct of enzymatic reactions |
US5713965A (en) * | 1996-04-12 | 1998-02-03 | The United States Of America As Represented By The Secretary Of Agriculture | Production of biodiesel, lubricants and fuel and lubricant additives |
US6532918B1 (en) * | 1997-10-30 | 2003-03-18 | Fuchs Petrolub Ag | Method and device for lubricating and simultaneously supplying fuel in a vegetable oil-operated combustion engine |
US6015440A (en) * | 1997-10-31 | 2000-01-18 | Board Of Regents Of The University Of Nebraska | Process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit |
US5972057A (en) * | 1997-11-11 | 1999-10-26 | Lonford Development Limited | Method and apparatus for producing diesel fuel oil from waste edible oil |
US6712867B1 (en) * | 1999-08-18 | 2004-03-30 | Biox Corporation | Process for production of fatty acid methyl esters from fatty acid triglycerides |
US6399800B1 (en) * | 1999-09-22 | 2002-06-04 | The United States Of America As Represented By The Secretary Of Agriculture | Process for the production of fatty acid alkyl esters |
Cited By (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100071260A1 (en) * | 2004-12-22 | 2010-03-25 | John Lee Massingill | Method and System for Production of Biofuels Using a Fiber Conduit Reactor |
US9168469B2 (en) | 2004-12-22 | 2015-10-27 | Chemtor, Lp | Method and system for production of a chemical commodity using a fiber conduit reactor |
US10189806B2 (en) | 2004-12-22 | 2019-01-29 | Chemtor, LP. | Fiber conduit apparatus for conducting chemical reactions and chemical extractions |
US10526299B2 (en) | 2004-12-22 | 2020-01-07 | Chemtor, Lp | Fiber conduit reactor with a heat exchange medium inlet and a heat exchange medium outlet |
US8128825B2 (en) * | 2004-12-22 | 2012-03-06 | Chemtor, Lp | Method and system for production of biofuels using a fiber conduit reactor |
US20060270866A1 (en) * | 2005-05-25 | 2006-11-30 | Richard Sapienza | Processes for production of esters from olefin-containing hydrocarbon streams and vegetable or animal oils |
US8003813B2 (en) * | 2006-06-27 | 2011-08-23 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
US20100305347A1 (en) * | 2006-06-27 | 2010-12-02 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
US20070299272A1 (en) * | 2006-06-27 | 2007-12-27 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
US20070299271A1 (en) * | 2006-06-27 | 2007-12-27 | Udaya Nayanskantha Wanasundara | Process for separating saturated and unsaturated fatty acids for producing cold-tolorant biodiesel fuel from soy oil |
WO2008002776A1 (en) * | 2006-06-27 | 2008-01-03 | Soymor | Separating saturated and unsaturated fatty acids for producing cold-tolorant biodiesel fuel |
US20080092436A1 (en) * | 2006-06-30 | 2008-04-24 | University Of North Dakota | Method for cold stable biojet fuel |
US9206367B2 (en) * | 2006-06-30 | 2015-12-08 | University Of North Dakota | Method for cold stable biojet fuel |
US7244771B1 (en) | 2006-08-11 | 2007-07-17 | Seymour Gary F | Commercial production of synthetic fuel from fermentation by-products system |
US20080171680A1 (en) * | 2007-01-12 | 2008-07-17 | Kwang Soon Kim | Composition of water-soluble metalworking fluid using distillation residue generated in production of biodiesel |
US20100242348A1 (en) * | 2007-01-16 | 2010-09-30 | National Kaohsiung University Of Applied Sciences | Method of increasing transesterification conversion of oils |
US20080171889A1 (en) * | 2007-01-16 | 2008-07-17 | National Kaohsiunh University Of Applied Sciences | Method of increasing transesterification of oils |
US20150133706A1 (en) * | 2008-11-26 | 2015-05-14 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
US20110237850A1 (en) * | 2008-11-26 | 2011-09-29 | Elevance Renewable Sciences, Inc | Methods of producing jet fuel from natural oil feedstocks through metathesis reactions |
CN102227489A (en) * | 2008-11-26 | 2011-10-26 | 埃莱文斯可更新科学公司 | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
WO2010062932A1 (en) * | 2008-11-26 | 2010-06-03 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
US8889932B2 (en) | 2008-11-26 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
US8933285B2 (en) | 2008-11-26 | 2015-01-13 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through metathesis reactions |
CN102597185A (en) * | 2009-10-09 | 2012-07-18 | 约翰·李·马辛吉尔 | Method and system for production of biofuels using a fiber conduit reactor |
US9000246B2 (en) | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9365487B2 (en) | 2009-10-12 | 2016-06-14 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US10689582B2 (en) | 2009-10-12 | 2020-06-23 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
US8735640B2 (en) | 2009-10-12 | 2014-05-27 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
US9169447B2 (en) | 2009-10-12 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US8957268B2 (en) | 2009-10-12 | 2015-02-17 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
US9464258B2 (en) | 2009-10-12 | 2016-10-11 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US9175231B2 (en) | 2009-10-12 | 2015-11-03 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils and methods of producing fuel compositions |
US9732282B2 (en) | 2009-10-12 | 2017-08-15 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
US9222056B2 (en) | 2009-10-12 | 2015-12-29 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9284512B2 (en) | 2009-10-12 | 2016-03-15 | Elevance Renewable Sicences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9382502B2 (en) | 2009-10-12 | 2016-07-05 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
US9469827B2 (en) | 2009-10-12 | 2016-10-18 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
US8882861B2 (en) * | 2010-07-26 | 2014-11-11 | Sapphire Energy, Inc. | Oleaginous compounds from biomass |
US8906236B2 (en) | 2010-07-26 | 2014-12-09 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds and nutrients from biomass |
US9028696B2 (en) | 2010-07-26 | 2015-05-12 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds from biomass |
US9169174B2 (en) | 2011-12-22 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9481627B2 (en) | 2011-12-22 | 2016-11-01 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9139493B2 (en) | 2011-12-22 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9133416B2 (en) | 2011-12-22 | 2015-09-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9468866B2 (en) | 2012-09-18 | 2016-10-18 | Chemtor, Lp | Use of a fiber conduit contactor for metal and/or metalloid extraction |
US9815001B2 (en) | 2012-09-18 | 2017-11-14 | Chemtor, LP. | Use of a fiber conduit contactor for extraction |
US9388098B2 (en) | 2012-10-09 | 2016-07-12 | Elevance Renewable Sciences, Inc. | Methods of making high-weight esters, acids, and derivatives thereof |
US9353331B2 (en) | 2012-11-13 | 2016-05-31 | Rrip, Llc | Method to recover free fatty acids from fats and oils |
CN108676599A (en) * | 2018-05-14 | 2018-10-19 | 和县伊迈炭业有限责任公司 | A method of preparing charcoal using needle mushroom dreg |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20060042158A1 (en) | Fuel products from plant or animal lipids | |
Ma et al. | Biodiesel production: a review | |
Muniyappa et al. | Improved conversion of plant oils and animal fats into biodiesel and co-product | |
Dixit et al. | Linseed oil as a potential resource for bio-diesel: A review | |
Demirbas | Biodiesel from sunflower oil in supercritical methanol with calcium oxide | |
AU2003290414B2 (en) | Improved process for preparing fatty acid alkylesters using as biodiesel | |
Jagadale et al. | Review of various reaction parameters and other factors affecting on production of chicken fat based biodiesel | |
Cerveró et al. | Production of biodiesel from vegetable oils | |
Baldev et al. | Unveiling algal cultivation using raceway ponds for biodiesel production and its quality assessment | |
Wadumesthrige et al. | Effects of partial hydrogenation, epoxidation, and hydroxylation on the fuel properties of fatty acid methyl esters | |
US20100223842A1 (en) | Use of fuels or fuel additives based on triglycerides of modified structure and process for their preparation | |
JP2008527154A5 (en) | ||
WO2006081644A2 (en) | Catalytic process for the esterification of fatty acids | |
US20050108927A1 (en) | Process for the preparation of bio-diesel | |
Saifuddin et al. | Biodiesel production from waste cooking sunflower oil and environmental impact analysis | |
Lee et al. | A kinetic study on the transesterification of glyceryl monooleate and soybean used frying oil to biodiesel | |
Allawzi et al. | Parametric study of biodiesel production from used soybean oil | |
El Diwani et al. | Modification of thermal and oxidative properties of biodiesel produced from vegetable oils | |
Krishnakumar et al. | Physico-chemical properties of the biodiesel extracted from rubber seed oil using solid metal oxide catalysts | |
Bello et al. | Fatty acid compositions of six Nigeria's vegetable oils and their methyl esters | |
Ma | Biodiesel fuel: The transesterification of beef tallow | |
JP2005220227A (en) | Biodiesel fuel and method for producing the same | |
Hajinezhad et al. | Ultrasound assisted biodiesel production from Eruca Sativa as an indigenous species in Iran | |
Osawa | Two-stage chemical and enzymatic strategies for the preparation of biodiesel from croton megalocarpus oil and evaluation of its engine performance and oxidation stability | |
Omotoso et al. | Comparative Study of the properties of biodiesel prepared from Jatropha curcas oil and palm oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |