GB980272A - Production of carbinols - Google Patents
Production of carbinolsInfo
- Publication number
- GB980272A GB980272A GB309/63A GB30963A GB980272A GB 980272 A GB980272 A GB 980272A GB 309/63 A GB309/63 A GB 309/63A GB 30963 A GB30963 A GB 30963A GB 980272 A GB980272 A GB 980272A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxide
- r1r2r3
- hydroxyisopropyl
- diisopropylbenzene
- cumene
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 5
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000012074 organic phase Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 abstract 1
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 abstract 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 abstract 1
- XZISOEPNTDOUEA-UHFFFAOYSA-N 1-fluoro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(F)C=C1 XZISOEPNTDOUEA-UHFFFAOYSA-N 0.000 abstract 1
- JWCFSPUNILJEOV-UHFFFAOYSA-N 2,4-ditert-butyl-6-methylbenzene-1,3,5-triol Chemical compound CC(C=1C(=C(C(=C(C1O)C)O)C(C)(C)C)O)(C)C JWCFSPUNILJEOV-UHFFFAOYSA-N 0.000 abstract 1
- PSYUWKPFWPMEAY-UHFFFAOYSA-N 2-[3,5-di(propan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)(C)O)=C1 PSYUWKPFWPMEAY-UHFFFAOYSA-N 0.000 abstract 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 abstract 1
- -1 Aralkyl tertiary alcohols Chemical class 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001717 carbocyclic compounds Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 abstract 1
- 229930007927 cymene Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229940083608 sodium hydroxide Drugs 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aralkyl tertiary alcohols are made by the action of elementary oxygen, under the conditions set out below, on carbocyclic compounds substituted in the nucleus with a group -CHC(R1R2R3)C(R1R2R3), in which R1, R2 and R3 are hydrogen atoms or hydrocarbon groups, or all three carbon atoms form part of a carbocyclic ring. The reaction is effected in the liquid phase at a temperature of at least 80 DEG C. in the presence of aqueous sodium or potassium hydroxide of a concentration of 40-90% by weight in a proportion of 20-400 g. of aqueous hydroxide per 100 ml. of the organic phase. Atmospheric or higher pressure may be used. In a typical series of examples, cumene yields dimethylphenyl carbinol when treated with air at 100 DEG C. in the presence of sodium-hydroxide of 40-60% concentration in a proportion of 25-400 g. per 100 ml. of organic phase. Other examples describe the preparation of p-isopropyl-a ,a -dimethylbenzyl alcohol and 1,4-bis-(a -hydroxyisopropyl)benzene from p-diisopropylbenzene, and of 3,5-diisopropylphenyl dimethyl carbinol, 3,5 - bis - (a - hydroxyisopropyl)cumene and of hexamethylmesitylenetriol of the formula <FORM:0980272/C2/1> from 1,3,5 - triisopropylbenzene. Other examples describe the oxidation of b -isopropylnaphthalene, m - diisopropylbenzene, phenylcyclohexane and cymene. Reference is made also to the oxidation of p-fluorocumene, sec.-butylbenzene and polystyrene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16596062A | 1962-01-12 | 1962-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB980272A true GB980272A (en) | 1965-01-13 |
Family
ID=22601205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB309/63A Expired GB980272A (en) | 1962-01-12 | 1963-01-29 | Production of carbinols |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB980272A (en) |
| LU (1) | LU42994A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382286A (en) * | 1965-01-21 | 1968-05-07 | Allied Chem | Preparation of aromatic tertiary alcohols by oxidation |
| EP0267759A2 (en) * | 1986-11-07 | 1988-05-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Oxidation process of aromatic compounds |
| US4746757A (en) * | 1985-07-19 | 1988-05-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing (2-hydroxy-2-propyl)-naphthalene compounds |
-
1963
- 1963-01-10 LU LU42994D patent/LU42994A1/xx unknown
- 1963-01-29 GB GB309/63A patent/GB980272A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382286A (en) * | 1965-01-21 | 1968-05-07 | Allied Chem | Preparation of aromatic tertiary alcohols by oxidation |
| US4746757A (en) * | 1985-07-19 | 1988-05-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing (2-hydroxy-2-propyl)-naphthalene compounds |
| EP0267759A2 (en) * | 1986-11-07 | 1988-05-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Oxidation process of aromatic compounds |
| EP0267759A3 (en) * | 1986-11-07 | 1989-06-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | Oxidation process of aromatic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| LU42994A1 (en) | 1963-03-11 |
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