GB2017098A - Preparation of phenol and formaldehyde - Google Patents
Preparation of phenol and formaldehydeInfo
- Publication number
- GB2017098A GB2017098A GB7909740A GB7909740A GB2017098A GB 2017098 A GB2017098 A GB 2017098A GB 7909740 A GB7909740 A GB 7909740A GB 7909740 A GB7909740 A GB 7909740A GB 2017098 A GB2017098 A GB 2017098A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formaldehyde
- phenol
- toluene
- oxygen
- acetic anhydride
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title abstract 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-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 2
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- -1 cresyl acetates Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229940049953 phenylacetate Drugs 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000000197 pyrolysis Methods 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
Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde. In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates. It has also been found that benzylidene acetate may be converted to phenyl acetate and methylene diacetate by acid-catalyzed reaction in the presence of oxygen and acetic anhydride.
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 |
|---|---|
| GB2017098A true GB2017098A (en) | 1979-10-03 |
| GB2017098B GB2017098B (en) | 1983-02-16 |
Family
ID=27420538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7909740A Expired GB2017098B (en) | 1978-03-27 | 1979-03-20 | Preparation of phenol and fomaldehyde |
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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| NL151976B (en) * | 1969-12-02 | 1977-01-17 | Inst Neftechimicheskogo Sintez | PROCESS FOR PREPARING PHENOLS. |
| DE1960520C3 (en) * | 1969-12-02 | 1974-04-25 | Institut Neftechimitscheskowo Sintesa Imeni A.W. Toptschijewa Akademii Nauk, Moskau | Process for the production of phenols |
| JPS5343941B2 (en) * | 1975-01-31 | 1978-11-24 | ||
| CA1146585A (en) * | 1978-11-03 | 1983-05-17 | Sun Tech, Inc. | Co-oxidation of methyl benzenes and benzaldehyde |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6445339A (en) | 1989-02-17 |
| JPS6445323A (en) | 1989-02-17 |
| NL7902258A (en) | 1979-10-01 |
| DE2912098A1 (en) | 1979-10-18 |
| JPS54130510A (en) | 1979-10-09 |
| FR2421162A1 (en) | 1979-10-26 |
| 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 |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |