US2070318A - Manufacture of alcohols - Google Patents
Manufacture of alcohols Download PDFInfo
- Publication number
- US2070318A US2070318A US41808A US4180835A US2070318A US 2070318 A US2070318 A US 2070318A US 41808 A US41808 A US 41808A US 4180835 A US4180835 A US 4180835A US 2070318 A US2070318 A US 2070318A
- Authority
- US
- United States
- Prior art keywords
- alcohol
- ester
- parts
- reduction
- cetyl
- 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 - Lifetime
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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
- C07C29/132—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
- C07C29/147—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 carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Definitions
- waxes we means the esters of monoor dihydric alcohols with high fatty acids (Holde, loc. cit. page 742).
- That primary alcohols may be obtained from the alkyl esters of the corresponding acids by reduction with sodium and anhydrous alcohol such as ethyl or amyl alcohol is well known (see, c. g.
- crude cetyl alcohol (which is the alcohol obtained by the reduction of cetyl palmitate) is used as the reagent for interaction with the alkali metal.
- a further advantage of our new process is thatthe necessity of separating and recovering a dif-' ferent alcohol is avoided and hence there is a considerable simplification and economy of time and labour.
- Example 1 120 parts of spermacetl, 121 parts of dry cetyl a reflux condenser. The air in the vessel is then displaced by nitrogen and to the creamy mass is slowly added with stirring 400 parts of water.
- the mixture is boiled and allowed to settle.
- Example 2 53.2 parts of coconut oil, 93 parts of dodecyl alcohol and 160 parts of xylene are dissolved together and added gradually during two hours to a stirred suspension of 22.5 parts of sodium in 230 parts of xylene already heated to 100-402 C. in a vessel fitted with a reflux condenser. The reaction mixture is then worked up as in Example 1.
- a process for the production of a high molecular weight aliphatic alcohol by reduction of an ester of a high molecular weight aliphatic organic acid comprising reacting said ester with alkali metal and a hydrolytic ,alcohol, said hydrolytic alcohol being identical with the alcohol produced by the said reduction of said ester and corresponding to the acid constituent of said ester.
- a process for the production of a long chain aliphatic alcohol by reduction of an ester of a long chain fatty acid comprising reacting said ester with alkali metal and a hydrolytic alcohol, said hydrolytic alcohol being identical with the alcohol produced by the said reduction of said ester and corresponding to the acid constituent of said ester.
- a process for the production of a high molecular weight alcohol comprising reacting an ester of a high molecular weight acid with alkali metal and a high molecular weight alcohol, said alcohol corresponding to the acid constituent of said ester.
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Patented Feb. 9, 1937 srarss PATENT @FFECE MANUFACTURE OF ALOQHGLS Reginald John Rosser and Herbert Swarm, Manchester, England, assignors to Imperial Chemical Industries Limited, a corporation of Great Britain No Drawing. Application September 23, 1935, Serial No. 41,808. In Great Britain September 4 Claims.
see Holde, Kohlenwasserstofiole und Fette, 6th
Edition, Berlin, 1924, pp. 598-611) By waxes we means the esters of monoor dihydric alcohols with high fatty acids (Holde, loc. cit. page 742).
That primary alcohols may be obtained from the alkyl esters of the corresponding acids by reduction with sodium and anhydrous alcohol such as ethyl or amyl alcohol is well known (see, c. g.
Bouveault and Blane, British specification No. 14758/03). The reaction has also been carried out in a medium comprising an inert compound such as toluene or xylene (Levene and Allen, -J. Biol. Chem. 1916, 27, 435).
It has been observed that the ester tends to suffer hydrolysis, and thus escape reduction. To overcome this it has been proposed to reduce under pressure.
We have now found that when the same long chain aliphatic alcohol as is produced as reduction product is usedxas reagent improved yields are obtained, and theinvention consists in a reduction by alkali metal and alcohol of fatty oils or waxes wherein the alcohol corresponding to the fatty acid of the fatty oil or wax is used as the reagent.
Thus, in reducing spermaceti (chiefly cetyl palmitate), crude cetyl alcohol, (which is the alcohol obtained by the reduction of cetyl palmitate) is used as the reagent for interaction with the alkali metal.
A further advantage of our new process is thatthe necessity of separating and recovering a dif-' ferent alcohol is avoided and hence there is a considerable simplification and economy of time and labour.
The invention is illustrated but not limited by the following examples in which the-parts are by weight.
Example 1 120 parts of spermacetl, 121 parts of dry cetyl a reflux condenser. The air in the vessel is then displaced by nitrogen and to the creamy mass is slowly added with stirring 400 parts of water.
The mixture is boiled and allowed to settle. The
lower aqueous layer is then removed and the xylene andcetyl alcohol mixture, which forms the upper oily layer, is subjected to steam distillation. The xylene passes over first with steam. Later, using superheated steam cetyl alcohol distills. This solidifies on cooling and isseparated. The weight of cetyl alcohol obtained is 217.8 parts gross. This is 96.8 parts net, i. e. 80% of theory calculated on the weight of spermaceti used.
Example 2 53.2 parts of coconut oil, 93 parts of dodecyl alcohol and 160 parts of xylene are dissolved together and added gradually during two hours to a stirred suspension of 22.5 parts of sodium in 230 parts of xylene already heated to 100-402 C. in a vessel fitted with a reflux condenser. The reaction mixture is then worked up as in Example 1.
We claim:
1. A process for the production of a high molecular weight aliphatic alcohol by reduction of an ester of a high molecular weight aliphatic organic acid comprising reacting said ester with alkali metal and a hydrolytic ,alcohol, said hydrolytic alcohol being identical with the alcohol produced by the said reduction of said ester and corresponding to the acid constituent of said ester.
2. A process for the production of a long chain aliphatic alcohol by reduction of an ester of a long chain fatty acid comprising reacting said ester with alkali metal and a hydrolytic alcohol, said hydrolytic alcohol being identical with the alcohol produced by the said reduction of said ester and corresponding to the acid constituent of said ester.
3. A process for the production of a high molecular weight alcohol comprising reacting an ester of a high molecular weight acid with alkali metal and a high molecular weight alcohol, said alcohol corresponding to the acid constituent of said ester.
4. 'A process for the production of cetyl alcohol comprising reacting cetyl palmitate with alkali metal and cetyl alcohol.
REGINALD JOHN ROSSER. HERBERT SWANN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2070318X | 1934-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2070318A true US2070318A (en) | 1937-02-09 |
Family
ID=10897631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US41808A Expired - Lifetime US2070318A (en) | 1934-09-28 | 1935-09-23 | Manufacture of alcohols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2070318A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2460969A (en) * | 1946-06-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for producing higher molecular alcohols |
| US2530042A (en) * | 1947-03-11 | 1950-11-14 | Innovations Chimiques Sinnova | Separating higher molecular alcohols from the soaps obtained in the preparation of the same |
| US2607806A (en) * | 1941-07-02 | 1952-08-19 | Innovations Chimiques Sinnova | Process for the manufacture of alcohol of high molecular weight |
-
1935
- 1935-09-23 US US41808A patent/US2070318A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2607806A (en) * | 1941-07-02 | 1952-08-19 | Innovations Chimiques Sinnova | Process for the manufacture of alcohol of high molecular weight |
| US2460969A (en) * | 1946-06-28 | 1949-02-08 | Innovations Chimiques Sinnova | Method for producing higher molecular alcohols |
| US2530042A (en) * | 1947-03-11 | 1950-11-14 | Innovations Chimiques Sinnova | Separating higher molecular alcohols from the soaps obtained in the preparation of the same |
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