Synthesis of a hydrocarbylvinylphosphonic acid hydrocarbyl ester
US6429329B1 · kind B1 · utility
Assignee
Inventors
Key dates
| Filing date | Sep 9, 1996 |
| Grant date | Aug 6, 2002 |
| Priority date | — |
| Expiry date | May 30, 2020 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F9/4006
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the synthesis of a hydrocarbylvinyl-1-phosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester, which utilizes: (a) the base catalyzed addition (preferably using a nonnucleophilic strong organic base) of a hydrocarbyl phosphite, such as a dialkyl phosphite containing no more than about eight carbon atoms in either of its alkyl groups, to an aldehyde or methyl ketone, such as a phenyl ketone, as exemplified by acetophenone, to form a hydrocarbyl 1-hydroxy-1-hydrocarbylphosphonate, such as a dialkyl 1-hydroxy-1-phenylalkylphosphonate compound; (b) the acid-catalyzed esterification (preferably acetylation) of the compound from (a) with an acid anhydride to form an acylated intermediate; and (c) the removal of carboxylic acid (preferably at a temperature of from about 50° C. to about 215° C. under reduced or atmospheric pressure) from the intermediate from (b) to form the desired hydrocarbylvinylphosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.