FR2421162A1 - CATALYTIC CONVERSION OF TOLUENE TO PHENOL AND FORMALDEHYDE - Google Patents
CATALYTIC CONVERSION OF TOLUENE TO PHENOL AND FORMALDEHYDEInfo
- Publication number
- FR2421162A1 FR2421162A1 FR7907648A FR7907648A FR2421162A1 FR 2421162 A1 FR2421162 A1 FR 2421162A1 FR 7907648 A FR7907648 A FR 7907648A FR 7907648 A FR7907648 A FR 7907648A FR 2421162 A1 FR2421162 A1 FR 2421162A1
- Authority
- FR
- France
- Prior art keywords
- formaldehyde
- toluene
- phenol
- catalytic conversion
- dithiosemibenzil
- 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.)
- Granted
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title abstract 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 3
- 230000003197 catalytic effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/035—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Procédé d'obtention de quantités équimolaires de phénol et de formaldéhyde à partir du toluène. Il consiste à oxyder le toluène avec de l'oxygène ou de l'air, à température et pression élevées, en phase liquide, en présence d'anhydride acétique et d'un catalyseur fortement acide, de MoO 3 et/ou d'un initiateur tel qu'un composé persulfurique ou complexe de dithiosemibenzile avec un métal du groupe VIII, ce qui donne de l'acétate de phényle et du diacétate de méthylène, que l'on pyrolyse séparément pour obtenir respectivement du phénol et du formaldéhyde. Ce procédé permet de récupérer le groupe méthyle du toluène sous forme de produit intéressant, le formaldéhyde, au lieu qu'il se transforme en CO2 .Process for obtaining equimolar quantities of phenol and formaldehyde from toluene. It consists in oxidizing toluene with oxygen or air, at high temperature and pressure, in the liquid phase, in the presence of acetic anhydride and a strongly acidic catalyst, MoO 3 and / or a initiator such as a persulfuric compound or complex of dithiosemibenzil with a metal of group VIII, which gives phenyl acetate and methylene diacetate, which are pyrolyzed separately to obtain phenol and formaldehyde, respectively. This process makes it possible to recover the methyl group of toluene in the form of an interesting product, formaldehyde, instead of transforming it into CO2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/890,180 US4156783A (en) | 1978-03-27 | 1978-03-27 | Conversion of benzylidene diacetate to phenyl acetate and methylene diacetate |
| US94574778A | 1978-09-25 | 1978-09-25 | |
| US05/957,273 US4260808A (en) | 1978-11-03 | 1978-11-03 | Catalytic process for the conversion of toluene to equimolar amounts of phenol acetate and methylene diacetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2421162A1 true FR2421162A1 (en) | 1979-10-26 |
| FR2421162B1 FR2421162B1 (en) | 1983-01-28 |
Family
ID=27420538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7907648A Granted FR2421162A1 (en) | 1978-03-27 | 1979-03-27 | CATALYTIC CONVERSION OF TOLUENE TO PHENOL AND FORMALDEHYDE |
Country Status (7)
| Country | Link |
|---|---|
| JP (3) | JPS54130510A (en) |
| CA (1) | CA1146966A (en) |
| DE (1) | DE2912098A1 (en) |
| FR (1) | FR2421162A1 (en) |
| GB (1) | GB2017098B (en) |
| IT (1) | IT1113044B (en) |
| NL (1) | NL7902258A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3103551A4 (en) * | 2014-02-07 | 2018-05-23 | Sumitomo Chemical Company Limited | Catalyst, and method for manufacturing oxidation product |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU321518A1 (en) * | V. V. Kamzolkini Yu. A. Lapitsky Institute of Petrochemical Synthesis of the Academy of Sciences of the USSR | |||
| US1595299A (en) * | 1924-01-07 | 1926-08-10 | Dow Chemical Co | Manufacture of phenols |
| US2799698A (en) * | 1954-12-30 | 1957-07-16 | Hercules Powder Co Ltd | Oxidation of alkyl-substituted aromatic compounds to phenolic compounds |
| FR1489679A (en) * | 1965-08-18 | 1967-07-21 | Ici Ltd | Process for the production of organic compounds containing oxygen |
| US3590081A (en) * | 1966-07-21 | 1971-06-29 | Asahi Chemical Ind | Process for the preparation and recovery of acetic anhydride |
| FR2068133A5 (en) * | 1969-11-28 | 1971-08-20 | Inst Neftechimichesk | Preparation of phenyl esters and phenols |
| GB1244080A (en) * | 1969-12-02 | 1971-08-25 | Inst Neftechimicheskogo Sintez | Preparation of phenyl esters and phenols |
| FR2299303A1 (en) * | 1975-01-31 | 1976-08-27 | Ube Industries | PROCESS FOR THE PREPARATION OF CYCLOHEXANONE AND SUBSTITUTED OR NON-SUBSTITUTED PHENOL-ALKYL |
| FR2440930A1 (en) * | 1978-11-03 | 1980-06-06 | Suntech | CO-OXIDATION OF METHYLBENZENES AND BENZALDEHYDE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1960520C3 (en) * | 1969-12-02 | 1974-04-25 | Institut Neftechimitscheskowo Sintesa Imeni A.W. Toptschijewa Akademii Nauk, Moskau | Process for the production of phenols |
-
1979
- 1979-03-15 CA CA000323630A patent/CA1146966A/en not_active Expired
- 1979-03-20 GB GB7909740A patent/GB2017098B/en not_active Expired
- 1979-03-22 NL NL7902258A patent/NL7902258A/en not_active Application Discontinuation
- 1979-03-24 JP JP3384579A patent/JPS54130510A/en active Pending
- 1979-03-26 IT IT21301/79A patent/IT1113044B/en active
- 1979-03-27 DE DE2912098A patent/DE2912098A1/en active Granted
- 1979-03-27 FR FR7907648A patent/FR2421162A1/en active Granted
-
1988
- 1988-02-25 JP JP63040905A patent/JPS6445323A/en active Granted
- 1988-02-25 JP JP63040906A patent/JPS6445339A/en active Granted
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU321518A1 (en) * | V. V. Kamzolkini Yu. A. Lapitsky Institute of Petrochemical Synthesis of the Academy of Sciences of the USSR | |||
| US1595299A (en) * | 1924-01-07 | 1926-08-10 | Dow Chemical Co | Manufacture of phenols |
| US2799698A (en) * | 1954-12-30 | 1957-07-16 | Hercules Powder Co Ltd | Oxidation of alkyl-substituted aromatic compounds to phenolic compounds |
| FR1489679A (en) * | 1965-08-18 | 1967-07-21 | Ici Ltd | Process for the production of organic compounds containing oxygen |
| US3590081A (en) * | 1966-07-21 | 1971-06-29 | Asahi Chemical Ind | Process for the preparation and recovery of acetic anhydride |
| FR2068133A5 (en) * | 1969-11-28 | 1971-08-20 | Inst Neftechimichesk | Preparation of phenyl esters and phenols |
| GB1244080A (en) * | 1969-12-02 | 1971-08-25 | Inst Neftechimicheskogo Sintez | Preparation of phenyl esters and phenols |
| FR2299303A1 (en) * | 1975-01-31 | 1976-08-27 | Ube Industries | PROCESS FOR THE PREPARATION OF CYCLOHEXANONE AND SUBSTITUTED OR NON-SUBSTITUTED PHENOL-ALKYL |
| FR2440930A1 (en) * | 1978-11-03 | 1980-06-06 | Suntech | CO-OXIDATION OF METHYLBENZENES AND BENZALDEHYDE |
Non-Patent Citations (1)
| Title |
|---|
| CA1972 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6445339A (en) | 1989-02-17 |
| JPS6445323A (en) | 1989-02-17 |
| GB2017098A (en) | 1979-10-03 |
| NL7902258A (en) | 1979-10-01 |
| DE2912098A1 (en) | 1979-10-18 |
| JPS54130510A (en) | 1979-10-09 |
| GB2017098B (en) | 1983-02-16 |
| FR2421162B1 (en) | 1983-01-28 |
| CA1146966A (en) | 1983-05-24 |
| JPH036128B2 (en) | 1991-01-29 |
| JPH0260655B2 (en) | 1990-12-17 |
| IT7921301A0 (en) | 1979-03-26 |
| DE2912098C2 (en) | 1989-03-23 |
| IT1113044B (en) | 1986-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |