GB798541A - New primary alcohols - Google Patents
New primary alcoholsInfo
- Publication number
- GB798541A GB798541A GB1719755A GB1719755A GB798541A GB 798541 A GB798541 A GB 798541A GB 1719755 A GB1719755 A GB 1719755A GB 1719755 A GB1719755 A GB 1719755A GB 798541 A GB798541 A GB 798541A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- mixture
- catalyst
- dimerization
- hexene
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
Abstract
The invention comprises the new primary alcohols 3-ethylheptanol-1 and 3-ethylhexanol-1 and mixtures comprising 3-ethylhexanol-1 and 3-methylheptanol-1. The compounds or compositions may be prepared by the dimerization of butene-1 or of a propylene and butene-1 mixture followed by carbonylation and hydrogenation of the dimerization product. The dimerization of butene-1 gives 2-ethyl-hexene-1 which on carbonylation and hydrogenation gives 3-ethyl-heptanol-1. A mixture of propylene and butylene on dimerization gives 2-methylpentene-1, 2-ethyl-hexene-1 and a mixture of 2-methyl-hexene-1 and 2-ethyl-pentene-1 and on carbonylation and hydrogenation these give 3-methyl-hexanol-1, 3-ethyl-heptanol-1 and a mixture comprising 3-methyl-heptanol-1 and 3-ethyl-hexanol-1 respectively. The dimerization takes place in the presence of one or more aluminium alkyl compounds, such as aluminium tri-ethyl, at elevated temperature in a sealed vessel and may be carried out batchwise or continuously. The dimer product is carbonylated in the presence of a cobalt catalyst by a mixture of carbon monoxide and hydrogen at superatmospheric pressure and temperature. The product is freed from carbon monoxide and is hydrogenated at elevated temperature and pressure in the presence of cobalt retained from the carbonylation or in the presence of a hydrogenation catalyst such as copper-zinc oxide. The cobalt catalyst may be added as an organic compound soluble in the reactants or as a catalyst on a support such as kieselguhr. In the examples: (a) a mixture of propylene and butene-1 is dimerized in the presence of a mixture of aluminium tripropyl, aluminium tributyl and decahydronaphthalene, to give a mixture of 2-methyl-pentene-1, 2-methylhexene-1, 2-ethyl-pentene-1 and 2-ethyl-hexene-1; the co-dimer heptenes are carbonylated in the presence of a cobalt-on-kieselguhr catalyst and the product is hydrogenated to give a mixture of 3-ethyl hexanol-1 and 3-methyl heptanol-1; (b) 2-ethyl-hexene-1 obtained by the dimerization of butene-1 as in (a) is carbonylated in the presence of a cobalt naphthenate catalyst and the product is hydrogenated using a copper-zinc oxide catalyst to give 3-ethyl-heptanol-1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1719755A GB798541A (en) | 1955-06-15 | 1955-06-15 | New primary alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1719755A GB798541A (en) | 1955-06-15 | 1955-06-15 | New primary alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB798541A true GB798541A (en) | 1958-07-23 |
Family
ID=10090947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1719755A Expired GB798541A (en) | 1955-06-15 | 1955-06-15 | New primary alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB798541A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| EP0958267A1 (en) | 1996-11-26 | 1999-11-24 | Shell Internationale Researchmaatschappij B.V. | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US6222077B1 (en) | 1996-11-26 | 2001-04-24 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| JP2017510545A (en) * | 2014-01-13 | 2017-04-13 | パーデュ リサーチ ファンデーション | Method for synthesizing chiral 1-alkanol |
-
1955
- 1955-06-15 GB GB1719755A patent/GB798541A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| EP0958267A1 (en) | 1996-11-26 | 1999-11-24 | Shell Internationale Researchmaatschappij B.V. | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6222077B1 (en) | 1996-11-26 | 2001-04-24 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US7781390B2 (en) | 1996-11-26 | 2010-08-24 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US7871973B1 (en) | 1996-11-26 | 2011-01-18 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US7888307B2 (en) | 1996-11-26 | 2011-02-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| JP2017510545A (en) * | 2014-01-13 | 2017-04-13 | パーデュ リサーチ ファンデーション | Method for synthesizing chiral 1-alkanol |
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