GB932670A - Improvements in or relating to vinylation of tertiary alcohols - Google Patents
Improvements in or relating to vinylation of tertiary alcoholsInfo
- Publication number
- GB932670A GB932670A GB3663960A GB3663960A GB932670A GB 932670 A GB932670 A GB 932670A GB 3663960 A GB3663960 A GB 3663960A GB 3663960 A GB3663960 A GB 3663960A GB 932670 A GB932670 A GB 932670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary
- alcohol
- acetylene
- magnesium
- catalyst
- 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
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
- C07C43/16—Vinyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A catalyst for the conversion of tertiary alcohols to their vinyl ethers by reaction with acetylene (see Group IV(b)) comprises an alkali metal alkoxide promoted with an oxide of an alkaline earth metal or of magnesium.ALSO:Vinyl ethers of tertiary alcohols are prepared by reacting together, in the liquid phase at a temperature of from 100 DEG C. to 250 DEG C. and at an elevated pressure of up to 500 p.s.i.g. in the presence of a catalyst comprising an alkali metal alkoxide and an oxide of an alkaline earth metal or of magnesium, acetylene and a tertiary alcohol of formula <FORM:0932670/IV(a)/1> wherein the R groups may be the same or different and represent alkyl, aryl, aralkyl, alkaryl or cycloalkyl radicals or two R groups together with the tertiary carbon atom form a cycloalkyl group. The alkoxide catalyst may be derived from any primary, secondary or tertiary alcohol. An inert solvent may be present. In Examples (1) and (3) potassium is reacted with excess tertbutanol and the resultant solution of potassium tert-butoxide is charged into an autoclave together with calcium oxide; acetylene is introduced under pressure and the product contains more than 90% tert-butyl vinyl ether. Examples (2) and (4) are similar but use, respectively, magnesium and barium oxides in place of calcium oxide. In Example (5) a ,a -dimethylbenzyl vinyl ether is prepared from a ,a -dimethylbenzyl alcohol by the method of Example (1); a comparative example omits the calcium oxide. Other specified alcohols are triphenyl methanol, 1,1-dimethyln-butanol, 1,1-dimethyl (p-methylbenzyl) alcohol, 1-methyl-cyclohexanol, dihydro-a -terpineol and 1,1,2,2-tetramethyl propanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85005859A | 1959-11-02 | 1959-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB932670A true GB932670A (en) | 1963-07-31 |
Family
ID=25307161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3663960A Expired GB932670A (en) | 1959-11-02 | 1960-10-25 | Improvements in or relating to vinylation of tertiary alcohols |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1194407B (en) |
| GB (1) | GB932670A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3358041A (en) * | 1965-10-22 | 1967-12-12 | Air Reduction | Preparation of vinyl ethers and catalyst therefor |
| US7518021B2 (en) * | 2002-10-25 | 2009-04-14 | Daicel Chemical Industries, Ltd. | Aromatic vinyl ether compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10048696A1 (en) * | 2000-09-30 | 2002-04-11 | Basf Ag | Tertiary divinyl ether compounds for use as comonomers or crosslinkers in plastics production or as reactive diluents in coatings, obtained by base-catalysed reaction of a tertiary di-alcohol with an acetylene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR724955A (en) * | 1930-10-30 | 1932-05-06 | Ig Farbenindustrie Ag | Process for the production of vinyl ethers |
| FR952158A (en) * | 1946-08-29 | 1949-11-10 | Distillers Co Yeast Ltd | Improvement in the manufacture of vinyl ethers |
| US2615050A (en) * | 1947-09-24 | 1952-10-21 | Koppers Co Inc | Vinyl ethers |
-
1960
- 1960-10-25 GB GB3663960A patent/GB932670A/en not_active Expired
- 1960-10-27 DE DEH40795A patent/DE1194407B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3358041A (en) * | 1965-10-22 | 1967-12-12 | Air Reduction | Preparation of vinyl ethers and catalyst therefor |
| US7518021B2 (en) * | 2002-10-25 | 2009-04-14 | Daicel Chemical Industries, Ltd. | Aromatic vinyl ether compounds |
| US7732645B2 (en) | 2002-10-25 | 2010-06-08 | Daicel Chemical Industries, Ltd. | Aromatic vinyl ether compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1194407B (en) | 1965-06-10 |
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