US1995615A - Motor fuel - Google Patents

Motor fuel Download PDF

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Publication number
US1995615A
US1995615A US560665A US56066531A US1995615A US 1995615 A US1995615 A US 1995615A US 560665 A US560665 A US 560665A US 56066531 A US56066531 A US 56066531A US 1995615 A US1995615 A US 1995615A
Authority
US
United States
Prior art keywords
esters
acids
barrels
pounds
gasoline
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.)
Expired - Lifetime
Application number
US560665A
Inventor
Alphons O Jaeger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US560665A priority Critical patent/US1995615A/en
Application granted granted Critical
Publication of US1995615A publication Critical patent/US1995615A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/19Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/223Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/232Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring

Definitions

  • unsaturated compounds such as, for ex- Exam le 1 ample, cracked gasoline.
  • These fuels are highly p desirable because of their excellent anti-knock 2-6 pounds of Pentasol acetate are mixed 5 properties, but the tendency to form a colored with 100 barrels of cracked gasoline, producing gum, especially under the influence of sunlight, a-well stabilized product.
  • Example 2 they are sold in the so-called visible dispensing pumps and are subject to the action of sunlight.
  • /zpounds 1 m hyl nthrflnllate are added 10 It has been proposed to stabilize the fuel by to 100 barrels of cracked gasoline, producing a the-addition of components which tend to pre m I fu of 11 ili yvent the formation of the colored gums.
  • two such stabilizers have been described,
  • esters of aliphatic acids are the Example 5 alwl esters of formic, acetic, propionic, butyric,
  • esters of the higher alcohols M r n f dlmethyl maleate are added as such as t butyl and mi t including the to 100 barrels of gasoline.
  • a well stabilized gasoesters from the mixed amyl alcohols obtained by line is 013158111941- the hydrolysis of chlorinated pentanes from nat- 7 Example 6 v ural gas and sold on the market under the name 24 pounds of methyl pymmucate are mixed w of Pentasol.
  • Glycerin esters are less eflective t 10 barrels of 395011116, thorgughly m... than the esters of mono and dihydric alcohols but bilized product being obtained.
  • Example 7 A very efiective class of aliphatic esters are 3-5 pounds of benzylbenzoate are added to loll 35 those 0! the dibaa 1 11 1 8 x lfi. m l i barrels of gasoline. A product of satisfactory fumaric, succinic, tartaric, citric, adipic, stability is obtained.
  • esters of aromatic acids are very desirable, Example 8 40 particularly the phthalates, benzoates and esters A ixture of 2 to 6 pounds of diethyl of the ketc aromatic acids such as benz yl phthalate and urea are added to 100 barrels oi zoate, naphthoylbenzoate, and their substitution oline, producing a well stabilized product. products; Esters of amino substituted aromatic acidsare particularly eflective, for example esters Example 9 of aminophthalic, anthranilic, para-aminoben A mixture of 3-5V pounds of butyl naphthoyl- 45 zoic, aminonaphthoic, etc. benzoate and acetanilide are mixed with 100 bar- Esters of hydroxy acids are also useful, such rels of gasoline, resulting in a well stabilized as lactates, salicylates, and the like and the dimotor fuel.
  • Example 10 Another group of esters are those of the hetero- 2-5 pounds of a mixture of ethyl ester of 2- cyclic acids such as pyromucic, various pyridine phenyl quinolin d-carboxylic acid and anthraand quinolin carboxylic acids, and the like. I cene are added to 100 barrels of gasoline. A The invention will be described in greater deproduct of satisfactory stability is obtained. as
  • esters of carboxylic acids can be used alone, but they may be used in conjunction with other stabilizers of difierent types. Naturally, of course, a plurality of esters of carboxylic acids may be used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Description

' basic hydroxy acids such as malic and tartaric Wuteuled or. 2, 1935 1,995,615 Moron FUEL No Drawing. Application September 1, 1931,
Serial No. 560,665
3 Claims. (Cl. 44-9) This invention relates to motor fuels and more tail in connection with the following specific particularly to motor fuels containing gumexamples:
forming unsaturated compounds such as, for ex- Exam le 1 ample, cracked gasoline. These fuels are highly p desirable because of their excellent anti-knock 2-6 pounds of Pentasol acetate are mixed 5 properties, but the tendency to form a colored with 100 barrels of cracked gasoline, producing gum, especially under the influence of sunlight, a-well stabilized product.
renders them objectionable particularly where Example 2 they are sold in the so-called visible dispensing pumps and are subject to the action of sunlight. /zpounds 1 m hyl nthrflnllate are added 10 It has been proposed to stabilize the fuel by to 100 barrels of cracked gasoline, producing a the-addition of components which tend to pre m I fu of 11 ili yvent the formation of the colored gums. In the Example 3 past, two such stabilizers have been described,
1!; namely, anthracene, phenanthrene and phenols /2 pounds of yl phthalate are mixed 15 and acid amines of aromatic amines such as with 100 barrels of cked gasoline, resulting in acctanilide. I have found that esters of cara Well stabilized motor fuel. boxylic acids are good stabilizers. While the Example 4 lower molecular esters such as esters of fatty acids may be used with effect, the esters oi higher Pounds of ethyl bemoylbenzoate are added as molecular acidsand particularly polybaslc acids to 100 barrels of asoline, esultin in a product and keto aromatic acids are preferable. of satisfactory stability.
Among the esters of aliphatic acids are the Example 5 alwl esters of formic, acetic, propionic, butyric,
26 etc., particularly esters of the higher alcohols M r n f dlmethyl maleate are added as such as t butyl and mi t including the to 100 barrels of gasoline. A well stabilized gasoesters from the mixed amyl alcohols obtained by line is 013158111941- the hydrolysis of chlorinated pentanes from nat- 7 Example 6 v ural gas and sold on the market under the name 24 pounds of methyl pymmucate are mixed w of Pentasol. Glycerin esters are less eflective t 10 barrels of 395011116, thorgughly m... than the esters of mono and dihydric alcohols but bilized product being obtained.
are included in the invention in its broader aspects. Example 7 A very efiective class of aliphatic esters are 3-5 pounds of benzylbenzoate are added to loll 35 those 0! the dibaa 1 11 1 8 x lfi. m l i barrels of gasoline. A product of satisfactory fumaric, succinic, tartaric, citric, adipic, stability is obtained.
etc.
The esters of aromatic acids are very desirable, Example 8 40 particularly the phthalates, benzoates and esters A ixture of 2 to 6 pounds of diethyl of the ketc aromatic acids such as benz yl phthalate and urea are added to 100 barrels oi zoate, naphthoylbenzoate, and their substitution oline, producing a well stabilized product. products; Esters of amino substituted aromatic acidsare particularly eflective, for example esters Example 9 of aminophthalic, anthranilic, para-aminoben A mixture of 3-5V pounds of butyl naphthoyl- 45 zoic, aminonaphthoic, etc. benzoate and acetanilide are mixed with 100 bar- Esters of hydroxy acids are also useful, such rels of gasoline, resulting in a well stabilized as lactates, salicylates, and the like and the dimotor fuel.
referred to above. Example 10 Another group of esters are those of the hetero- 2-5 pounds of a mixture of ethyl ester of 2- cyclic acids such as pyromucic, various pyridine phenyl quinolin d-carboxylic acid and anthraand quinolin carboxylic acids, and the like. I cene are added to 100 barrels of gasoline. A The invention will be described in greater deproduct of satisfactory stability is obtained. as
it will be apparent from the examples that not only can the esters of carboxylic acids be used alone, but they may be used in conjunction with other stabilizers of difierent types. Naturally, of course, a plurality of esters of carboxylic acids may be used.
While it is normally desirable to use as little stabilizer as possible and the examples show amounts of stabilizer on the order of a few hundredths of a percent, larger amounts of stabilizer may, of course, be used, without any harm, but practically the amount of stabilizer never need exceed 1% and preferably the amount used is from .01% to 1%.
US560665A 1931-09-01 1931-09-01 Motor fuel Expired - Lifetime US1995615A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429133A (en) * 1944-04-01 1947-10-14 Standard Oil Dev Co Aviation motor fuel
US2465209A (en) * 1946-08-05 1949-03-22 Standard Oil Dev Co Motor fuels
US2478045A (en) * 1946-12-02 1949-08-02 Shell Dev Stabilization of butadiene with salicylates
US2479326A (en) * 1946-08-05 1949-08-16 Standard Oil Dev Co Antiknock motor fuel
US2493713A (en) * 1946-05-21 1950-01-03 Gen Aniline & Film Corp Stabilized iron pentacarbonyl and motor fuel containing the same
US2600113A (en) * 1950-06-01 1952-06-10 Standard Oil Dev Co Motor fuel
US2843466A (en) * 1957-04-19 1958-07-15 Cities Service Res & Dev Co Fuel composition
US2922706A (en) * 1957-05-31 1960-01-26 Continental Oil Co Gasoline compositions
US3179506A (en) * 1962-05-02 1965-04-20 Shell Oil Co Gasoline composition
US3222146A (en) * 1961-01-09 1965-12-07 Sinclair Research Inc Glycerol esters in leaded gasoline
US3948618A (en) * 1975-06-05 1976-04-06 Ethyl Corporation Fuel compositions containing glycerides for reducing the plugging of exhaust gas catalysts
US3966429A (en) * 1974-05-16 1976-06-29 Standard Oil Company Manganese containing fuels
US4004894A (en) * 1972-11-18 1977-01-25 Basf Aktiengesellschaft Otto cycle engine fuels containing derivatives of cyclic polycarboxylic acids
US4005992A (en) * 1976-03-08 1977-02-01 Ethyl Corporation Novel gasoline compositions and additives therefor
US4028065A (en) * 1974-05-16 1977-06-07 Standard Oil Company Manganese containing fuels
US4052171A (en) * 1975-06-05 1977-10-04 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
US4141693A (en) * 1974-12-18 1979-02-27 Standard Oil Company (Ohio) Manganese containing fuels
US4444565A (en) * 1982-12-20 1984-04-24 Union Oil Company Of California Method and fuel composition for control of octane requirement increase
US5139700A (en) * 1988-08-23 1992-08-18 Cortec Corporation Vapor phase corrosion inhibitor material
US5178640A (en) * 1983-11-10 1993-01-12 Eni-Ente Nazionale Idrocarburi Method for preparing a synthetic fuel and/or synthetic components for fuels, and the product obtained thereby
US5209869A (en) * 1988-08-23 1993-05-11 Cortec Corporation Vapor phase corrosion inhibitor-dessiccant material
US5320778A (en) * 1988-08-23 1994-06-14 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5332525A (en) * 1988-08-23 1994-07-26 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5344589A (en) * 1988-08-23 1994-09-06 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
DE4344222A1 (en) * 1993-12-23 1995-06-29 Veba Oel Ag Otto fuels
US6039772A (en) * 1984-10-09 2000-03-21 Orr; William C. Non leaded fuel composition

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429133A (en) * 1944-04-01 1947-10-14 Standard Oil Dev Co Aviation motor fuel
US2493713A (en) * 1946-05-21 1950-01-03 Gen Aniline & Film Corp Stabilized iron pentacarbonyl and motor fuel containing the same
US2465209A (en) * 1946-08-05 1949-03-22 Standard Oil Dev Co Motor fuels
US2479326A (en) * 1946-08-05 1949-08-16 Standard Oil Dev Co Antiknock motor fuel
US2478045A (en) * 1946-12-02 1949-08-02 Shell Dev Stabilization of butadiene with salicylates
US2600113A (en) * 1950-06-01 1952-06-10 Standard Oil Dev Co Motor fuel
US2843466A (en) * 1957-04-19 1958-07-15 Cities Service Res & Dev Co Fuel composition
US2922706A (en) * 1957-05-31 1960-01-26 Continental Oil Co Gasoline compositions
US3222146A (en) * 1961-01-09 1965-12-07 Sinclair Research Inc Glycerol esters in leaded gasoline
US3179506A (en) * 1962-05-02 1965-04-20 Shell Oil Co Gasoline composition
US4004894A (en) * 1972-11-18 1977-01-25 Basf Aktiengesellschaft Otto cycle engine fuels containing derivatives of cyclic polycarboxylic acids
US4028065A (en) * 1974-05-16 1977-06-07 Standard Oil Company Manganese containing fuels
US3966429A (en) * 1974-05-16 1976-06-29 Standard Oil Company Manganese containing fuels
US4141693A (en) * 1974-12-18 1979-02-27 Standard Oil Company (Ohio) Manganese containing fuels
US3948618A (en) * 1975-06-05 1976-04-06 Ethyl Corporation Fuel compositions containing glycerides for reducing the plugging of exhaust gas catalysts
US4052171A (en) * 1975-06-05 1977-10-04 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
US4005992A (en) * 1976-03-08 1977-02-01 Ethyl Corporation Novel gasoline compositions and additives therefor
US4444565A (en) * 1982-12-20 1984-04-24 Union Oil Company Of California Method and fuel composition for control of octane requirement increase
US5178640A (en) * 1983-11-10 1993-01-12 Eni-Ente Nazionale Idrocarburi Method for preparing a synthetic fuel and/or synthetic components for fuels, and the product obtained thereby
US6039772A (en) * 1984-10-09 2000-03-21 Orr; William C. Non leaded fuel composition
US5209869A (en) * 1988-08-23 1993-05-11 Cortec Corporation Vapor phase corrosion inhibitor-dessiccant material
US5320778A (en) * 1988-08-23 1994-06-14 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5332525A (en) * 1988-08-23 1994-07-26 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5344589A (en) * 1988-08-23 1994-09-06 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5393457A (en) * 1988-08-23 1995-02-28 Miksic; Boris A. Vapor phase corrosion inhibitor-desiccant material
US5422187A (en) * 1988-08-23 1995-06-06 Cortec Corporation Vapor phase corrosion inhibitor-desiccant material
US5139700A (en) * 1988-08-23 1992-08-18 Cortec Corporation Vapor phase corrosion inhibitor material
DE4344222A1 (en) * 1993-12-23 1995-06-29 Veba Oel Ag Otto fuels

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