GB828371A - Alkyl 3-alkoxypropionates - Google Patents
Alkyl 3-alkoxypropionatesInfo
- Publication number
- GB828371A GB828371A GB15519/57A GB1551957A GB828371A GB 828371 A GB828371 A GB 828371A GB 15519/57 A GB15519/57 A GB 15519/57A GB 1551957 A GB1551957 A GB 1551957A GB 828371 A GB828371 A GB 828371A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methane
- dialkoxy
- ketene
- weight
- ether complex
- 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
- 125000000217 alkyl group Chemical group 0.000 title abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 2
- -1 methyl methoxy, ethyl ethoxy Chemical group 0.000 abstract 2
- QLCJOAMJPCOIDI-UHFFFAOYSA-N 1-(butoxymethoxy)butane Chemical compound CCCCOCOCCCC QLCJOAMJPCOIDI-UHFFFAOYSA-N 0.000 abstract 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyl 3-alkoxy propionates are prepared by contacting a symmetrical dialkoxy methane with ketene under substantially anhydrous conditions at a temperature in the range of from 10 DEG to 60 DEG C. and in the presence, as catalyst, of not more than 5% by weight of BF3 based on the dialkoxy methane. Generally a molar ratio of ketene : dialkoxy methane of from 0.5 : 1 to 0.9 : 1 is used. The catalyst may be present in the form of its diethyl ether complex. Suitably, the ketene is bubbled into the dialkoxy methane, if desired under elevated pressure. The reacted mixture is then neutralized and fractionally distilled to recover the ester. Examples describe the conversion of dimethoxy methane, diethoxy methane and di-n-butoxy methane into methyl methoxy, ethyl ethoxy and butyl butoxy propionates. Di-isopropoxy- and diisobutoxy methanes are also mentioned. Comparative experiments show the reduction in yield obtained by operating at -5 DEG to 0 DEG C. The first Provisional Specification describes the reaction of ketene with dialkoxy methanes under substantially anhydrous conditions in the presence of at least 5% by weight of a BF3/diethyl ether complex based on the dialkoxy methane at temperatures of, for example, - 5 DEG to 40 DEG C. The second Provisional Specification specifies for the same reaction the use of not more than 5% by weight of the BF3-ether complex based on the dialkoxy methane and of temperatures above about 300 DEG C. U.S.A. Specification 2,436,286 is referred to.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15519/57A GB828371A (en) | 1957-05-16 | 1957-05-16 | Alkyl 3-alkoxypropionates |
| FR1195579D FR1195579A (en) | 1957-05-16 | 1958-05-03 | Preparation of esters with alkoxy substituent |
| US734103A US2910503A (en) | 1957-05-16 | 1958-05-09 | Alkyl 3-alkoxypropionates |
| DED28106A DE1154083B (en) | 1957-05-16 | 1958-05-13 | Process for the preparation of ª‰-alkoxypropionic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15519/57A GB828371A (en) | 1957-05-16 | 1957-05-16 | Alkyl 3-alkoxypropionates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB828371A true GB828371A (en) | 1960-02-17 |
Family
ID=10060562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15519/57A Expired GB828371A (en) | 1957-05-16 | 1957-05-16 | Alkyl 3-alkoxypropionates |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2910503A (en) |
| DE (1) | DE1154083B (en) |
| FR (1) | FR1195579A (en) |
| GB (1) | GB828371A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4827021A (en) * | 1988-03-07 | 1989-05-02 | Eastman Kodak Company | Process for the preparation of alkyl 3-alkoxypropionates |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067798B (en) * | 1958-08-04 | 1959-10-29 | Wacker Chemie Gmbh | Process for the preparation of beta-alkoxycarboxylic acid esters |
| US4785133A (en) * | 1987-10-05 | 1988-11-15 | Eastman Kodak Company | Process for the preparation of alkyl 3-alkoxypropionates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2436286A (en) * | 1945-11-09 | 1948-02-17 | Du Pont | Alkoxy-substituted esters |
-
1957
- 1957-05-16 GB GB15519/57A patent/GB828371A/en not_active Expired
-
1958
- 1958-05-03 FR FR1195579D patent/FR1195579A/en not_active Expired
- 1958-05-09 US US734103A patent/US2910503A/en not_active Expired - Lifetime
- 1958-05-13 DE DED28106A patent/DE1154083B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4827021A (en) * | 1988-03-07 | 1989-05-02 | Eastman Kodak Company | Process for the preparation of alkyl 3-alkoxypropionates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1195579A (en) | 1959-11-18 |
| DE1154083B (en) | 1963-09-12 |
| US2910503A (en) | 1959-10-27 |
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