GB1122090A - Oxidation of paraffins to secondary aliphatic alcohols - Google Patents
Oxidation of paraffins to secondary aliphatic alcoholsInfo
- Publication number
- GB1122090A GB1122090A GB39530/66A GB3953066A GB1122090A GB 1122090 A GB1122090 A GB 1122090A GB 39530/66 A GB39530/66 A GB 39530/66A GB 3953066 A GB3953066 A GB 3953066A GB 1122090 A GB1122090 A GB 1122090A
- Authority
- GB
- United Kingdom
- Prior art keywords
- paraffin
- carbon atoms
- boric acid
- secondary alcohol
- aqueous boric
- 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
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An aliphatic secondary alcohol containing 6 to 40 carbon atoms is prepared by reacting the corresponding paraffin with molecular oxygen in the presence of a trialkoxyboroxine, hydrolysing the resulting boron containing ester to form aqueous boric acid and a secondary alcohol. Suitable trialkoxyboroxines include those wherein the alkoxy substituent contains 4 or more carbon atoms and has either at least two carbon atoms less than the paraffin, when the paraffin has less than 10 carbon atoms, or at least 4 carbon atoms less than the paraffin, when the paraffin has at least 10 carbon atoms. The oxidation step may be carried out at elevated temperature and under pressures greater than or equal to atmospheric optionally in the presence of a catalytic amount of a heavy metal compound such as an organic salt of cobalt, manganese, lead or iron which is soluble in the reaction mixture. Preferably at least part of the trialkoxyboroxine is obtained by partially hydrolysing a trialkyl borate ester (formed from aqueous boric acid and an alkanol of at least 4 carbon atoms), optionally in a solution of the paraffin to be oxidized, at a temperature from 130 DEG to 225 DEG C. in the presence of water vapour at a partial pressure of at most 250 mm. of Hg. The entire process may be carried out batchwise or continuously, the ketone by-product and unoxidized paraffin being removed from the intermediate boron containing ester prior to hydrolysis with water to give the desired secondary alcohol mixed with aqueous boric acid which may be re-converted to a trialkyl ester for re-use particularly in the specified continuous mode of operation. The oxidation of dodecane to a secondary alcohol together with the corresponding ketone and diol by-products is described. Tri-(n-butoxy) boroxine is prepared by controlled partial hydrolysis at elevated temperature of tri-(n-butyl) orthoborate in an atmosphere of nitrogen and water vapour. Tri-(n-butyl) orthoborate is prepared by esterification of aqueous boric acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US485564A US3375265A (en) | 1965-09-07 | 1965-09-07 | Production of trialkoxyboroxine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1122090A true GB1122090A (en) | 1968-07-31 |
Family
ID=23928642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39530/66A Expired GB1122090A (en) | 1965-09-07 | 1966-09-05 | Oxidation of paraffins to secondary aliphatic alcohols |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3375265A (en) |
| BE (1) | BE686456A (en) |
| DE (1) | DE1593424A1 (en) |
| GB (1) | GB1122090A (en) |
| NL (1) | NL6612501A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2140252A1 (en) * | 1995-01-11 | 2000-02-16 | Repsol Quimica Sa | Process for obtaining short and long fibres and their chemically cross-linked fabrics by centrifugation, drawing or extrusion of sols obtained by the controlled hydrolysis of metal alkoxide solutions |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524893A (en) * | 1967-12-22 | 1970-08-18 | Texaco Inc | Secondary alcohol manufacture |
| US3622647A (en) * | 1969-09-11 | 1971-11-23 | Texaco Inc | Manufacture of alkene from alkane via boron esters |
| ATE492553T1 (en) * | 2005-06-13 | 2011-01-15 | Basf Se | METHOD FOR THE SYNTHESIS OF ORGANO-OXAZABOROLIDINES |
| US10479748B2 (en) | 2017-11-30 | 2019-11-19 | Cambridge Enterprise Limited | Oxidation of C1-9-alkanes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB939534A (en) * | 1960-11-09 | 1963-10-16 | Ici Ltd | Improvements in and relating to the preparation of oxidation products of hydrocarbons |
| GB1035624A (en) * | 1961-12-07 | 1966-07-13 | Ici Ltd | Improvements in and relating to the preparation of alcohols |
| NL273572A (en) * | 1962-01-15 | |||
| US3232704A (en) * | 1962-03-21 | 1966-02-01 | Exxon Research Engineering Co | Process for recovering boric acid |
-
1965
- 1965-09-07 US US485564A patent/US3375265A/en not_active Expired - Lifetime
-
1966
- 1966-09-05 DE DE19661593424 patent/DE1593424A1/en active Pending
- 1966-09-05 GB GB39530/66A patent/GB1122090A/en not_active Expired
- 1966-09-05 BE BE686456D patent/BE686456A/xx unknown
- 1966-09-06 NL NL6612501A patent/NL6612501A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2140252A1 (en) * | 1995-01-11 | 2000-02-16 | Repsol Quimica Sa | Process for obtaining short and long fibres and their chemically cross-linked fabrics by centrifugation, drawing or extrusion of sols obtained by the controlled hydrolysis of metal alkoxide solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| US3375265A (en) | 1968-03-26 |
| NL6612501A (en) | 1967-03-08 |
| BE686456A (en) | 1967-03-06 |
| DE1593424A1 (en) | 1970-07-30 |
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