CA1095076A - Process for the catalytic gas phase oxidation of toluene with a gas containing molecular oxygen - Google Patents
Process for the catalytic gas phase oxidation of toluene with a gas containing molecular oxygenInfo
- Publication number
- CA1095076A CA1095076A CA281,880A CA281880A CA1095076A CA 1095076 A CA1095076 A CA 1095076A CA 281880 A CA281880 A CA 281880A CA 1095076 A CA1095076 A CA 1095076A
- Authority
- CA
- Canada
- Prior art keywords
- vanadate
- toluene
- silver
- iron
- catalyst composition
- 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
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 13
- 230000003647 oxidation Effects 0.000 title claims description 13
- 238000007254 oxidation reaction Methods 0.000 title claims description 13
- 239000007789 gas Substances 0.000 title claims description 9
- 230000003197 catalytic effect Effects 0.000 title claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 title 1
- 229910001882 dioxygen Inorganic materials 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 45
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 31
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052742 iron Inorganic materials 0.000 claims abstract description 21
- RAVDHKVWJUPFPT-UHFFFAOYSA-N silver;oxido(dioxo)vanadium Chemical compound [Ag+].[O-][V](=O)=O RAVDHKVWJUPFPT-UHFFFAOYSA-N 0.000 claims abstract description 20
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 12
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 11
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000377 silicon dioxide Substances 0.000 claims description 16
- 150000002910 rare earth metals Chemical class 0.000 claims description 9
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000000975 co-precipitation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- -1 rare earth metal vanadate Chemical class 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000012808 vapor phase Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
- 229940095076 benzaldehyde Drugs 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 229910052684 Cerium Inorganic materials 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 4
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 241001281643 Solus Species 0.000 description 1
- QHZNZCGQESUVNU-UHFFFAOYSA-N [Fe].[Ce].[Ag] Chemical compound [Fe].[Ce].[Ag] QHZNZCGQESUVNU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- OVMJVEMNBCGDGM-UHFFFAOYSA-N iron silver Chemical compound [Fe].[Ag] OVMJVEMNBCGDGM-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/898—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with vanadium, tantalum, niobium or polonium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7607598 | 1976-07-09 | ||
| NL7607598A NL7607598A (nl) | 1976-07-09 | 1976-07-09 | Werkwijze voor de katalytische gasfaseoxidatie van tolueen met een molekulaire zuurstof bevat- tend gas. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095076A true CA1095076A (en) | 1981-02-03 |
Family
ID=19826566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,880A Expired CA1095076A (en) | 1976-07-09 | 1977-06-30 | Process for the catalytic gas phase oxidation of toluene with a gas containing molecular oxygen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4137259A (enExample) |
| JP (1) | JPS539732A (enExample) |
| BE (1) | BE856297A (enExample) |
| CA (1) | CA1095076A (enExample) |
| DE (1) | DE2730761A1 (enExample) |
| FR (1) | FR2357522A1 (enExample) |
| GB (1) | GB1522588A (enExample) |
| IT (1) | IT1079757B (enExample) |
| NL (1) | NL7607598A (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51933A (ja) * | 1974-06-21 | 1976-01-07 | Hitachi Metals Ltd | Jikihetsudo |
| JPS61260037A (ja) * | 1985-05-14 | 1986-11-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | タ−シヤリ−ブチルまたはフエノキシ置換ベンズアルデヒドの製造方法 |
| DE19502805C2 (de) * | 1995-01-30 | 2000-05-11 | Hoechst Ag | Verfahren zur Herstellung von Halogenbenzaldehyden |
| US6281378B1 (en) | 1995-06-08 | 2001-08-28 | Nippon Shokubai Co., Ltd. | Vanadium-containing catalysts, process for manufacturing and use of the same |
| US5877330A (en) * | 1995-06-08 | 1999-03-02 | Nippon Shokubai Co., Ltd. | Vanadium-containing catalysts, process for manufacturing and use of the same |
| DE19851786A1 (de) * | 1998-11-10 | 2000-05-11 | Basf Ag | Silber- und Vanadiumoxid enthaltendes Multimetalloxid und dessen Verwendung |
| DE10334132A1 (de) * | 2003-07-25 | 2005-04-07 | Basf Ag | Silber, Vanadium und ein Promotormetall enthaltendes Multimetalloxid und dessen Verwendung |
| JP2007205142A (ja) * | 2006-02-06 | 2007-08-16 | Shunsuke Irie | １枚板側壁パネルを備える組立柵渠 |
| CN103130639B (zh) * | 2011-11-23 | 2014-12-10 | 中国石油化工股份有限公司 | 单塔侧线精馏分离苯甲酸、苯甲醛、甲苯的方法 |
| FR2992872B1 (fr) * | 2012-07-04 | 2016-07-29 | Commissariat Energie Atomique | Catalyseur pour la production de monoxyde de carbone et son procede de fabrication. |
| CN103990457B (zh) * | 2014-06-11 | 2015-12-09 | 常州大学 | 一种银/钒酸银复合光催化剂的制备方法 |
| CN103990456B (zh) * | 2014-06-11 | 2015-09-09 | 常州大学 | 一种氧化银/钒酸银复合光催化剂的制备方法 |
| CN103990477B (zh) * | 2014-06-11 | 2015-12-30 | 常州大学 | 一种磷酸银/钒酸银复合光催化剂的制备方法 |
| CN104028287B (zh) * | 2014-06-26 | 2015-09-09 | 常州大学 | 一种铁酸镁/磷酸银复合光催化剂的制备方法 |
| CN104028282B (zh) * | 2014-06-26 | 2015-09-09 | 常州大学 | 一种铁酸镁/钒酸银复合光催化剂的制备方法 |
| EP3296015A1 (en) | 2016-09-15 | 2018-03-21 | Treibacher Industrie AG | Use of vanadates in oxidation catalysts |
| US10454114B2 (en) | 2016-12-22 | 2019-10-22 | The Research Foundation For The State University Of New York | Method of producing stable, active and mass-producible Pt3Ni catalysts through preferential co etching |
| CN115945193A (zh) * | 2021-10-08 | 2023-04-11 | 北京理工大学 | 一种复合银纳米光催化剂、制备方法和应用 |
| CN114700076A (zh) * | 2022-04-14 | 2022-07-05 | 大连理工大学 | 一种用于甲苯气相氧化制备苯甲醛的钒银铈催化剂、制备方法及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2749363A (en) * | 1951-11-23 | 1956-06-05 | Shell Dev | Purification of aromatic acids |
| US3170768A (en) * | 1959-04-22 | 1965-02-23 | Standard Oil Co | System for continuous preparation of terephthalic acid |
| NL142937B (nl) * | 1965-11-12 | 1974-08-15 | Stamicarbon | Werkwijze voor de katalytische gasfase-oxydatie van tolueen met zuurstof tot benzaldehyde. |
-
1976
- 1976-07-09 NL NL7607598A patent/NL7607598A/xx not_active Application Discontinuation
-
1977
- 1977-06-28 GB GB27027/77A patent/GB1522588A/en not_active Expired
- 1977-06-29 US US05/811,321 patent/US4137259A/en not_active Expired - Lifetime
- 1977-06-30 CA CA281,880A patent/CA1095076A/en not_active Expired
- 1977-06-30 BE BE178934A patent/BE856297A/xx not_active IP Right Cessation
- 1977-07-06 FR FR7720821A patent/FR2357522A1/fr active Granted
- 1977-07-06 IT IT50166/77A patent/IT1079757B/it active
- 1977-07-07 DE DE19772730761 patent/DE2730761A1/de not_active Withdrawn
- 1977-07-08 JP JP8188377A patent/JPS539732A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1079757B (it) | 1985-05-13 |
| FR2357522A1 (fr) | 1978-02-03 |
| BE856297A (nl) | 1977-12-30 |
| FR2357522B1 (enExample) | 1983-08-12 |
| GB1522588A (en) | 1978-08-23 |
| US4137259A (en) | 1979-01-30 |
| DE2730761A1 (de) | 1978-01-12 |
| NL7607598A (nl) | 1978-01-11 |
| JPS539732A (en) | 1978-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |