USRE36856E - Catalysts for production of phenol and its derivatives - Google Patents
Catalysts for production of phenol and its derivatives Download PDFInfo
- Publication number
- USRE36856E USRE36856E US09/073,730 US7373098A USRE36856E US RE36856 E USRE36856 E US RE36856E US 7373098 A US7373098 A US 7373098A US RE36856 E USRE36856 E US RE36856E
- Authority
- US
- United States
- Prior art keywords
- catalyst
- phenol
- benzene
- catalysts
- zeolite
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 92
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000010457 zeolite Substances 0.000 claims abstract description 33
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 27
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000001272 nitrous oxide Substances 0.000 claims abstract description 19
- 238000010335 hydrothermal treatment Methods 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 230000003197 catalytic effect Effects 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 20
- 230000008569 process Effects 0.000 abstract description 11
- 230000033444 hydroxylation Effects 0.000 abstract description 9
- 238000005805 hydroxylation reaction Methods 0.000 abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 150000001491 aromatic compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- -1 10 mol % or more Chemical compound 0.000 description 1
- 229910018404 Al2 O3 Inorganic materials 0.000 description 1
- 229910017344 Fe2 O3 Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/10—Heat treatment in the presence of water, e.g. steam
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/36—Steaming
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/40—Special temperature treatment, i.e. other than just for template removal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/064—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing iron group metals, noble metals or copper
- B01J29/072—Iron group metals or copper
-
- 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
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/10—Capture or disposal of greenhouse gases of nitrous oxide (N2O)
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Definitions
- phenol by partial oxidation of benzene using nitrous oxide over a variety of catalysts ranging from vanadium pentoxide on silica to zeolites, e.g. ZSM-5 and ZSM-11 zeolite catalysts, at elevated temperatures, e.g. 300° to 450° C., has been disclosed.
- a benzene derivative such as chlorobenzene, fluorobenzene, toluene or ethylbenzene
- the corresponding substituted phenol can be produced.
- the reaction products include dihydroxybenzenes such as hydroquinone, resorcinol and catechol.
- Phenol and its derivatives for example, dihydric phenols, chlorophenols, nitrophenols, cresols and other hydroxyl-containing aromatic compounds are valuable products that find wide applications in industry.
- the most common commodity chemical of this class is phenol, which is used mainly in production of phenolic resins, caprolactam, nitrophenols and chlorophenols, etc.
- the researchers have searched for simple and efficient methods of syntheses of phenol and its derivatives. Iwamoto et al. in J. Physical Chemistry (ACS), Vol. 87, No. 6, (1983) p.
- Zholobenko reported in Mendeleev Commun., (1993) No. 1, p. 28-29, a method for phenol production using zeolite catalyst that had been activated by high-temperature calcination in air.
- a drawback of this Zholobenko's method is that it does not provide any increase in catalyst activity at calcination temperatures below 700° C. More particularly, because the activation effect is significant at higher temperatures (750° C. and higher), Zholobenko's method is difficult to practically implement.
- This invention solves several problems associated with insufficient performance and efficiency of zeolite catalysts in the nitrous oxide hydroxylation of benzene and its derivatives in the production of phenol and its derivatives. These problems are surprisingly solved by the use of a zeolite catalyst that is activated by simple and efficient method, e.g. exposure to water vapor at elevated temperature.
- This invention provides an improved zeolite catalyst for the production of phenol and its derivatives by oxidative hydroxylation of the corresponding aromatic compounds using nitrous oxide.
- the catalytic performance properties of such zeolite catalysts are enhanced using methods of this invention by treated the zeolite catalyst with a vapor-containing gas phase at a temperature in the range of 350° to 950° C.
- the amount of water vapor in the gas phase is not critical and can range from a low level of water vapor in a diluent gas to essentially pure water vapor.
- the gas phase can range comprise as low as 3 mole percent (mol %) water vapor in air or preferably in a substantially inert diluent gas phase comprising nitrogen, argon, helium, carbon dioxide and the like or mixtures thereof.
- the gas phase should, of course be essentially devoid of components that tend to poison catalysts.
- the gas phase can preferably comprise higher amounts of water vapor, e.g. 10 mol % or more, up to 100 mol %.
- the duration of the high temperature exposure of the catalyst to water vapor can vary depending on the desired enhancement and can readily be determined by routine experimentation.
- Zeolites amenable to enhancement by the method of this invention include ZSM-5 and ZSM-11 zeolites which preferably are in the acid form and contain iron. Such zeolites are well-known in the art, are used for a variety of commercial processes and can be readily obtained from catalyst vendors, such as UOP, Mobil and others. Commercial zeolite catalysts are typically provided in a porous matrix of alumina or silica to provide in a durable pellet form that resists attrition in packed or fluid bed reactors. It has been discovered that the method of this invention can be advantageously applied to powdered or pelletized zeolite.
- the enhanced performance zeolite catalysts prepared by the method of this invention are especially useful in the oxidation of aromatic compounds like benzene and benzene derivatives, e.g. chlorobenzene, fluorobenzene, toluene, ethylbenzene and the like including phenol.
- oxidation is effected by passing a feed gas mixture of the phenol, nitrous oxide and, optionally, diluent gas such as nitrogen, argon, carbon dioxide and the like, to a zeolite catalyst bed at a temperature in the range of 225° C. to 450° C. or higher, e.g. above 500° C.
- Process conditions including feed composition, reaction temperature, flow rates and the like can be varied by those skilled in the art depending on the desired process parameters, e.g. selectivity of phenol production, conversion of nitrous oxide, phenol concentration in the product gas, catalyst productivity and the like.
- the molar ratio of nitrous oxide to benzene in the feed gas mixture can range from 100:1 to 1:100.
- the zeolite catalysts that have been hydrothermally treated are characterized by stable performance in a desired catalytic conversion, i.e. low reduction of benzene conversion in the production of phenol by oxidation of benzene with nitrous oxide at 350° C.
- Preferred catalysts of this invention e.g. ZSM-5 or ZSM-11 zeolite catalysts, will exhibit a ratio of benzene conversion after 3 hours of continuous operation to initial benzene conversion is at least 40%. In more preferred catalysts the ratio will be at least 50%. The following examples illustrate catalysts where such ratio is about 70%.
- the catalysts of this invention having been hydrothermally treated can be identified by a resistance to hydrothermal treatment.
- an iron-containing, acidified, zeolite catalyst of this invention can be characterized in that hydrothermal treatment of such a catalyst for two hours with a gas consisting of 50 mole percent air and 50 mole percent water and at a temperature of 600° C. does not increase by more than 10% the benzene conversion performance of the catalyst when used in the catalytic hydroxylation of benzene to phenol in a gas stream consisting of 75 mole percent helium, 5 mole percent benzene and 20 mole percent nitrous oxide at 350° C.
- An SiO 2 -based zeolite catalyst containing 4.3 ⁇ 10 -4 moles of Fe 2 O 3 and 2.3 ⁇ 10 -2 moles of Al 2 O 3 per mole SiO 2 was prepared according to the methods disclosed by Kharitonov in U.S. Pat. No. 5,110,995. After the organic template material was burned off, the zeolite was treated with acid to transform it into the H-form and calcined in a flow of dry air at 550° C. for two hours.
- a tubular reactor was prepared by loading about 2 cc of a 0.5-1.0 mm fraction of the zeolite into a quartz tube having a 0.7 cm internal diameter. The zeolite-filled tubular reactor was heated to 350° C.
- Catalyst prepared substantially in the manner of Example 1 was additionally subjected to hydrothermal treatment for two hours by exposure to air containing 50 mol % water at 500° C. for two hours in the presence of air containing 50 mol % water.
- Catalytic properties of the hydrothermally treated catalyst reported in Table 1 shows a substantial increase in initial benzene conversion to 18.5%.
- This example illustrates aspects of this invention where the water content of the hydrothermal treatment gas varied.
- catalyst samples were prepared essentially in the manner of Example 2 except that hydrothermal treatment was carried out with a treatment gas at 600° C. and containing from 2.5 to 100 mol % water vapor.
- the catalytic data reported in Table 2 shows that increasing the concentration of water vapor in the hydrothermal treatment gas can provide a catalyst with substantially increased process efficiency. For instance, benzene conversion increased from 8.6% to 38.5% with simultaneous increase in stability and some increase in selectivity.
- Example 9 hydrothermal treatment was carried out under conditions potentially similar to calcination of the catalyst in air, e.g. at 2.5 mol % water vapor. Comparison of Examples 9 and 1 shows that such concentration of water is not sufficient for noticeable activation of the catalyst.
Abstract
Description
TABLE 1 ______________________________________ Initial Activity after Catalytic 3 hours Treatment Properties on-stream Example temp. ° C. X.sub.o (%) S.sub.o (%) X (%) X/X.sub.o (%) ______________________________________ 1 no treatment 8.5 92.5 3.0 35 2 500 18.5 93.5 4.5 24 3 550 33.5 93.0 12.0 34 4 600 37.0 95.0 15.5 42 5 650 36.5 93.5 18.0 49 6 700 31.5 95.5 22.0 70 7 750 27.5 96.0 18.5 67 8 1000 5.5 95.0 2.7 49 ______________________________________
TABLE 2 ______________________________________ Initial Activity after Catalytic 3 hours C.sub.H2O Properties on-stream Example (mol. %) X.sub.o (%) S.sub.o (%) X (%) X/X.sub.o (%) ______________________________________ 9 2.5 8.6 92.5 3.0 35 10 10 15.5 93.0 5.0 33 11 50 35.0 94.0 15.5 45 12 100 38.5 95.0 19.0 50 ______________________________________
TABLE 3 ______________________________________ Catalytic Properties Chemical Before treatment After treatment Example Composition X.sub.o (%) S.sub.o (%) X.sub.o (%) S.sub.o (%) ______________________________________ 14 1.1 × 10.sup.-2 8.0 97.0 30.0 98.0 of Al.sub.2 O.sub.3 SiO.sub.2 15 3.4 × 10.sup.-3 21.5 83.5 46.5 87.5 of Fe.sub.2 O.sub.3 8.6 × 10.sup.-3 Al.sub.2 O.sub.3 SiO.sub.2 5.7 × 10.sup.-3 of Fe.sub.2 O.sub.3 SiO.sub.2 16 15.0 91.0 31.5 90.0 ______________________________________
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/073,730 USRE36856E (en) | 1994-04-12 | 1998-05-06 | Catalysts for production of phenol and its derivatives |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU9494013071A RU2074164C1 (en) | 1994-04-12 | 1994-04-12 | Method of producing phenol and derivatives thereof |
RU94/013071 | 1994-04-12 | ||
US41936195A | 1995-04-10 | 1995-04-10 | |
US08/608,541 US5672777A (en) | 1994-04-12 | 1996-02-28 | Catalysts for production of phenol and its derivatives |
US09/073,730 USRE36856E (en) | 1994-04-12 | 1998-05-06 | Catalysts for production of phenol and its derivatives |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US41936195A Division | 1994-04-12 | 1995-04-10 | |
US08/608,541 Reissue US5672777A (en) | 1994-04-12 | 1996-02-28 | Catalysts for production of phenol and its derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE36856E true USRE36856E (en) | 2000-09-05 |
Family
ID=26653783
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/608,541 Ceased US5672777A (en) | 1994-04-12 | 1996-02-28 | Catalysts for production of phenol and its derivatives |
US09/073,730 Expired - Lifetime USRE36856E (en) | 1994-04-12 | 1998-05-06 | Catalysts for production of phenol and its derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/608,541 Ceased US5672777A (en) | 1994-04-12 | 1996-02-28 | Catalysts for production of phenol and its derivatives |
Country Status (5)
Country | Link |
---|---|
US (2) | US5672777A (en) |
EP (1) | EP0755301A1 (en) |
CA (1) | CA2187649C (en) |
RU (1) | RU2074164C1 (en) |
WO (1) | WO1995027560A1 (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2058286C1 (en) * | 1994-04-12 | 1996-04-20 | Институт катализа им.Г.К.Борескова СО РАН | Method for production of phenol or its derivatives |
US5874646A (en) * | 1996-08-07 | 1999-02-23 | Solutia Inc. | Preparation of phenol or phenol derivatives |
US5892132A (en) * | 1996-08-08 | 1999-04-06 | Solutia Inc. | Transport hydroxylation reactor |
US5808167A (en) * | 1996-08-20 | 1998-09-15 | Solutia Inc. | Selective introduction of active sites for hydroxylation of benzene |
US5874647A (en) * | 1996-08-20 | 1999-02-23 | Solutia Inc. | Benzene hydroxylation catalyst stability by acid treatment |
KR100544044B1 (en) | 1996-10-07 | 2006-01-23 | 솔루티아인코포레이티드 | Process for the hydroxylation of aromatic compounds and benzenes and reaction mixtures therefor |
US6156938A (en) * | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
RU2127721C1 (en) | 1997-07-29 | 1999-03-20 | Институт органической химии им.Зелинского РАН | Process for preparing phenol and derivatives thereof |
CA2240612A1 (en) * | 1997-07-29 | 1999-01-29 | Vladimir Borisovich Kazansky | Preparation of phenol and its derivatives |
EP0953558B1 (en) * | 1998-04-30 | 2001-11-21 | CREAVIS Gesellschaft für Technologie und Innovation mbH | Process for the preparation of aromatic compounds containing hydroxyl groups |
RU2155181C1 (en) | 1999-04-05 | 2000-08-27 | Кустов Леонид Модестович | Method of oxidation of toluene into phenol, and/or cresols |
US6573413B2 (en) * | 2000-04-19 | 2003-06-03 | Solutia Inc. | Process for activating catalyst for the hydroxylation of aromatics |
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Also Published As
Publication number | Publication date |
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EP0755301A1 (en) | 1997-01-29 |
CA2187649A1 (en) | 1995-10-19 |
RU2074164C1 (en) | 1997-02-27 |
CA2187649C (en) | 2001-06-19 |
WO1995027560A1 (en) | 1995-10-19 |
US5672777A (en) | 1997-09-30 |
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