GB1128089A - Process for the oxidation of cycloalkanes - Google Patents
Process for the oxidation of cycloalkanesInfo
- Publication number
- GB1128089A GB1128089A GB54739/66A GB5473966A GB1128089A GB 1128089 A GB1128089 A GB 1128089A GB 54739/66 A GB54739/66 A GB 54739/66A GB 5473966 A GB5473966 A GB 5473966A GB 1128089 A GB1128089 A GB 1128089A
- Authority
- GB
- United Kingdom
- Prior art keywords
- organoperoxy
- tri
- oxidation
- carbon atoms
- alkyl
- 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
- 150000001924 cycloalkanes Chemical class 0.000 title abstract 4
- 230000003647 oxidation Effects 0.000 title abstract 3
- 238000007254 oxidation reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910000085 borane Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- -1 hydrocarbon radical Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002432 hydroperoxides Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000006413 ring segment Chemical group 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- 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
-
- 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
- C07C29/52—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 in the presence of mineral boron compounds with, when necessary, hydrolysis of the intermediate formed
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,128,089. Oxidation of cycloalkanes; tri- (organoperoxy) boranes. RHONE-POULENC S.A. 7 Dec., 1966 [10 Dec., 1965], No. 54739/66. Heading C2C. A cycloalkanol and a cycloalkane are obtained by heating a cycloalkane having 6-12 ring atoms with a tri-(organoperoxy) borane of formula B(OOR<SP>1</SP>) 3 , in which R<SP>1</SP> is a monovalent hydrocarbon radical containing at least 4 carbon atoms. The reaction is preferably carried out at 120-180‹ C. in the presence of an alkyl orthoborate in which the alkyl group has 1-4 carbon atoms. The tri-(organoperoxy) boranes may be obtained by reacting the corresponding organic hydroperoxide with a lower alkyl orthoborate as follows: 3R<SP>1</SP>OOH + B(OR<SP>11</SP>) 3 -# B(OOR<SP>1</SP>) 3 +3R<SP>11</SP>OH in which R<SP>1</SP> is as defined above and R<SP>11</SP> is an aliphatic radical having 1-4 carbon atoms. The reaction may be carried out in an excess of the alkyl borate or an inert solvent. Examples are given of the oxidation of cyclohexane to cyclohexanol and cyclohexanone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR41807A FR1466528A (en) | 1965-12-10 | 1965-12-10 | Cycloalkane oxidation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1128089A true GB1128089A (en) | 1968-09-25 |
Family
ID=8595136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54739/66A Expired GB1128089A (en) | 1965-12-10 | 1966-12-07 | Process for the oxidation of cycloalkanes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3479394A (en) |
| AT (1) | AT266072B (en) |
| BE (1) | BE690989A (en) |
| DE (1) | DE1593343B1 (en) |
| FR (1) | FR1466528A (en) |
| GB (1) | GB1128089A (en) |
| LU (1) | LU52547A1 (en) |
| NL (1) | NL6617026A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2953154B1 (en) | 2009-11-30 | 2013-07-12 | Rhodia Operations | PROCESS FOR PREPARING A DEPEROXIDATION CATALYST |
| FR2954314B1 (en) | 2009-12-17 | 2012-01-27 | Rhodia Operations | PROCESS FOR HYDROCARBON OXIDATION BY OXYGEN |
| FR2955321B1 (en) | 2010-01-21 | 2012-02-10 | Rhodia Operations | PROCESS FOR HYDROCARBON OXIDATION |
| FR2955322B1 (en) * | 2010-01-21 | 2013-09-06 | Rhodia Operations | PROCESS FOR PRODUCING ALKYL HYDROPEROXIDE |
| WO2021122955A1 (en) | 2019-12-18 | 2021-06-24 | Performance Polyamides, Sas | Process for producing cyclohexanol and cyclohexanone |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB892723A (en) * | 1959-11-04 | 1962-03-28 | Distillers Co Yeast Ltd | Production of alkanols |
| LU41564A1 (en) * | 1961-04-27 | 1963-10-17 | ||
| FR1346607A (en) * | 1963-01-15 | 1963-12-20 | Stamicarbon | Manufacture of cyclic alcohols |
| FR1361232A (en) * | 1963-06-28 | 1964-05-15 | Ici Ltd | Process for the catalytic oxidation of hydrocarbons |
-
1965
- 1965-12-10 FR FR41807A patent/FR1466528A/en not_active Expired
-
1966
- 1966-12-02 US US598635A patent/US3479394A/en not_active Expired - Lifetime
- 1966-12-02 NL NL6617026A patent/NL6617026A/xx unknown
- 1966-12-07 GB GB54739/66A patent/GB1128089A/en not_active Expired
- 1966-12-09 DE DE19661593343 patent/DE1593343B1/en not_active Withdrawn
- 1966-12-09 LU LU52547D patent/LU52547A1/xx unknown
- 1966-12-09 AT AT1138666A patent/AT266072B/en active
- 1966-12-09 BE BE690989D patent/BE690989A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE690989A (en) | 1967-06-09 |
| FR1466528A (en) | 1967-01-20 |
| NL6617026A (en) | 1967-06-12 |
| AT266072B (en) | 1968-11-11 |
| DE1593343B1 (en) | 1971-09-16 |
| LU52547A1 (en) | 1967-02-09 |
| US3479394A (en) | 1969-11-18 |
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