Synthesis of vinyl esters
AssigneeAllied Colloids Limited
InventorDavid Farrar
Life of this patent
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Abstract
A vinyl ester of the formula R.sup.3 COOR.sup.4 where R.sup.3 is CH.sub.2 .dbd.CH-- or CH.sub.2 .dbd.C.CH.sub.3 -- and R.sup.4 contains at least four carbon atoms and is selected from alkyl, cycloalkyl and aminoalkyl is conducted by reaction of an ester R.sup.3 COOR.sup.1, where R.sup.1 is C.sub.1-3 alkyl, with metal alcoholate formed from an alcohol R.sup.4 OH and titanium, aluminum, zirconium, calcium or magnesium in the absence of water or reactive alcohol.
Claims13
A process for making an ester of the formula R.sup.3 COOR.sup.4, where R.sup.3 is CH.sub.2 .dbd.CH-- or CH.sub.2 .dbd.CCH.sub.3 -- and R.sup.4 contains at least four carbon atoms and is selected from alkyl, cycloalkyl and aminoalkyl, by reaction from a compound formula R.sup.3 COOR.sup.1, where R.sup.1 is C.sub.1-3 alkyl, in the presence of metal alcoholate formed from an alcohol R.sup.4 OH, and in which the metal alcoholate provides the groups R.sup.4 utilized in forming the ester and reacts with the compound R.sup.3 COOR.sup.1, the reaction is conducted in the substantial absence of water or reactive alcohol and the metal is selected from titanium, aluminum, zirconium, calcium and magnesium;
- and wherein the metal alcoholate formed in the reaction is removed from the resulting reaction product mixture and reacted with excess alcohol R.sup.4 OH, in the substantial absence of compound R.sup.3 COOR.sup.1, the metal alcoholate thus formed is recycled to the reaction.
A process for making an ester of the formula R.sup.3 COOR.sup.4, where R.sup.3 is CH.sub.2 .dbd.CH-- or CH.sub.2 .dbd.CCH.sub.3 -- and R.sup.4 contains at least four carbon atoms and is selected from alkyl, cycloalkyl and aminoalkyl, by reaction from a compound formula R.sup.3 COOR.sup.1, where R.sup.1 is C.sub.1-3 alkyl, in the presence of metal alcoholate formed from an alcohol R.sup.4 OH, and in which the metal alcoholate provides the groups R.sup.4 utilised in forming the ester and reacts with the compound R.sup.3 COOR.sup.1, the reaction is conducted in the substantial absence of water or reactive alcohol and the metal is selected from titanium, aluminium, zirconium, calcium and magnesium, and the reaction is carried out in the sequential steps:
- (A) the reaction is conducted between (a) the metal alcoholate formed from the alcohol R.sup.4 OH and (b) an excess of the ester R.sup.3 COOR.sup.1, to form a mixture containing the ester R.sup.3 COOR.sup.4, unreacted ester R.sup.3 COOR.sup.1 and metal alcoholate that has at least partially been converted to an alcoholate formed from the alcohol R.sup.1 OH,
- (B) alcoholate is separated from the reaction mixture and the ester R.sup.3 COOR.sup.4 is recovered from the reaction mixture and the ester R.sup.3 COOR.sup.1 is recycled for use in step A,
- (C) the separated alcoholate is reacted, in the substantial absence of ester R.sup.3 COOR.sup.1, with excess alcohol R.sup.4 OH to give alcohol R.sup.1 OH and alcoholate formed from the alcohol R.sup.4 OH,
- (D) this alcoholate is separated and recycled for use in step A, and alcohol R.sup.4 OH is recovered and recycled for use in step C.
Dependencies are inferred from the claim text.