GB824631A - Production of phenols from aromatic carboxylic acids - Google Patents
Production of phenols from aromatic carboxylic acidsInfo
- Publication number
- GB824631A GB824631A GB1924258A GB1924258A GB824631A GB 824631 A GB824631 A GB 824631A GB 1924258 A GB1924258 A GB 1924258A GB 1924258 A GB1924258 A GB 1924258A GB 824631 A GB824631 A GB 824631A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cupric oxide
- phenol
- mass
- carboxyl group
- contact
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000002989 phenols Chemical class 0.000 title abstract 2
- -1 aromatic carboxylic acids Chemical class 0.000 title 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 14
- 229960004643 cupric oxide Drugs 0.000 abstract 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 230000001590 oxidative effect Effects 0.000 abstract 3
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- UPWOEMHINGJHOB-UHFFFAOYSA-N oxo(oxocobaltiooxy)cobalt Chemical compound O=[Co]O[Co]=O UPWOEMHINGJHOB-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 238000003763 carbonization Methods 0.000 abstract 1
- 230000001066 destructive effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
- C07C37/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by replacing a carboxyl or aldehyde group by a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing phenolic compounds comprises bringing a monocarboxylic acid of the benzene series in which the carboxyl group is attached to the ring and where there is at least one unsubstituted position ortho to the carboxyl group on the ring and where any other substituents are substantially inert to the oxidizing action of cupric oxide and are selected from phenyl, alkyl, alkoxy, nitro and halogen, into contact with an oxidizing agent consisting essentially of cupric oxide under atmospheric or superatmospheric pressure at a temperature of at least 200 DEG C. but below a temperature at which destructive carbonization takes place and in the absence of elemental oxygen, until oxidation and decarboxylation of the acid has occurred, if necessary releasing the pressure and finally recovering the so-produced free phenol from the reaction medium. An oxidation and decarboxylation reaction is considered to take place so that the product contains the hydroxy group ortho to the original carboxyl group. A preferred embodiment consists of heating benzoic acid with at least an equivalent amount of cupric oxide at 250-280 DEG C. and displacing the phenol from the reduced copper body by passing a stream of inert gas, e.g. steam, through it at 275-500 DEG C. A further embodiment comprises bringing in sequence a solid mass comprising cupric oxide, preferably in a multiple zone moving bed reactor system, into contact with benzoic acid at 200-400 DEG C. until substantial reduction of the cupric oxide has occurred, then into contact with an aqueous medium preferably liquid water, to strip phenol from the reduced mass, then into an oxidizing zone to convert the reduced mass to cupric oxide and finally repeating the cycle and recovering the phenol from the aqueous medium. The phenol may also be recovered from the reduced copper mass by steam stripping. The cupric oxide oxidant may be promoted with cobaltic oxide if desired. The phenolic products obtained from various acids are specified.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1924258A GB824631A (en) | 1958-06-16 | 1958-06-16 | Production of phenols from aromatic carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1924258A GB824631A (en) | 1958-06-16 | 1958-06-16 | Production of phenols from aromatic carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB824631A true GB824631A (en) | 1959-12-02 |
Family
ID=10126089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1924258A Expired GB824631A (en) | 1958-06-16 | 1958-06-16 | Production of phenols from aromatic carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB824631A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434140A1 (en) * | 1989-12-19 | 1991-06-26 | Dsm N.V. | Method for the preparation of a phenol |
| CN115636913A (en) * | 2022-09-27 | 2023-01-24 | 山东阳谷华泰化工股份有限公司 | Preparation method of low-free-phenol phenolic resin |
-
1958
- 1958-06-16 GB GB1924258A patent/GB824631A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0434140A1 (en) * | 1989-12-19 | 1991-06-26 | Dsm N.V. | Method for the preparation of a phenol |
| AU635592B2 (en) * | 1989-12-19 | 1993-03-25 | Stamicarbon B.V. | Method for the preparation of a phenol |
| CN115636913A (en) * | 2022-09-27 | 2023-01-24 | 山东阳谷华泰化工股份有限公司 | Preparation method of low-free-phenol phenolic resin |
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