GB684039A - Phenol production - Google Patents
Phenol productionInfo
- Publication number
- GB684039A GB684039A GB10052/50A GB1005250A GB684039A GB 684039 A GB684039 A GB 684039A GB 10052/50 A GB10052/50 A GB 10052/50A GB 1005250 A GB1005250 A GB 1005250A GB 684039 A GB684039 A GB 684039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroperoxide
- decomposition
- reaction medium
- peroxide
- oxidation
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 238000000354 decomposition reaction Methods 0.000 abstract 4
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- 239000012429 reaction media Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- -1 aliphatic ketones Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 abstract 1
- GUUDUUDWUWUTPD-UHFFFAOYSA-N 1-ethyl-4-propan-2-ylbenzene Chemical compound CCC1=CC=C(C(C)C)C=C1 GUUDUUDWUWUTPD-UHFFFAOYSA-N 0.000 abstract 1
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002432 hydroperoxides Chemical class 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 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
- C07C45/53—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 hydroperoxides
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phenols and aliphatic ketones are produced by the decomposition of a hydroperoxide or a dihydroperoxide by adding such a peroxide to a homogeneous reaction medium of acetone and concentrated sulphuric acid under substantially anhydrous conditions, the concentration of the sulphuric acid being between 0.05 and 10 per cent by weight. The hydroperoxides for use according to the invention are prepared by the oxidation of alkyl substituted aromatic organic compounds of the general formula <FORM:0684039/IV (b)/1> where R1 and R2 are alkyl groups and Ar is aryl or alkaryl. The oxidation is carried out in the liquid phase using air or molecular oxygen as the oxidizing agent either in the presence of aqueous alkali or preferably in the absence of an aqueous phase, but in presence of an organic peroxide or hydroperoxide. Compounds mentioned which may be oxidized include p-cymene, cumene, di-isopropylbenzene, sec-butylbenzene, p-ethyl-isopropylbenzene and isopropylnaphthalene. The decomposition of the peroxide may be undertaken either on the pure product or on the crude oxidation mixture. It is preferred to purify the hydroperoxide by distillation under very low pressure. The reaction medium may include a proportion of the mixture of reaction products from a previous decomposition, or an amount of phenol may be added to serve as solvent. It is essential to add the hydroperoxide slowly to the reaction medium to avoid a build-up and subsequent uncontrollable decomposition. Examples of the process are given. Specification 629,429 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US684039XA | 1949-12-30 | 1949-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB684039A true GB684039A (en) | 1952-12-10 |
Family
ID=22082355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10052/50A Expired GB684039A (en) | 1949-12-30 | 1950-04-24 | Phenol production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB684039A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210878B (en) * | 1961-04-22 | 1966-02-17 | Distillers Co Yeast Ltd | Process for the production of phenols and ketones |
| JPS4945854B1 (en) * | 1969-06-18 | 1974-12-06 |
-
1950
- 1950-04-24 GB GB10052/50A patent/GB684039A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210878B (en) * | 1961-04-22 | 1966-02-17 | Distillers Co Yeast Ltd | Process for the production of phenols and ketones |
| JPS4945854B1 (en) * | 1969-06-18 | 1974-12-06 |
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