Higher alkyl esters of cyanoacetic acid
AssigneeCreanova Inc.
InventorsThomas V. John, Chitoor S. Subramaniam, Mark Whipkey
Life of this patent
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Abstract
C3-12 alkyl, substituted alkyl, alkenyl and cycloalkyl cyanoacetates are prepared by an efficient and simplified one-step process in which a small molar excess of the corresponding alcohol, i.e., C3-12 alkyl, substituted alkyl, alkenyl or cycloalkenyl alcohol is reacted with crystalline cyanoacetic acid, or a concentrated aqueous solution of cyanoacetic acid, in the presence of an acid catalyst, such as, for example, methanesulfonic acid, p-toluenesulfonic acid, sulfuric acid and phosphoric acid at a temperature in the range of from about 60° C. to about 150° C., in accordance with the following reaction: CNCH2COOH+R—OH→(cat)CNCH2COOR+H2O (I) where R is a C3-12 alkyl, substituted alkyl, alkenyl or cycloalkyl.
Claims17
An improved process for preparing a C3-12 alkyl, substituted alkyl, alkenyl and cycloalkyl cyanoacetate product, which process comprises:
- esterifying a C3-12 alkyl, substituted alkyl, alkenyl or cycloalkyl alcohol by reaction with cyanoacetic acid in the presence of an acid catalyst in a reaction zone in accordance with reaction
- CNCH2COOH+R—OH→(cat)CNCH2COOR+H2O (I),
- wherein R is a C3-12 alkyl, substituted alkyl, alkenyl or cycloalkyl, and
- where the improvement comprises:
- (a) combining the cyanoacetate acid in crystalline form with the alcohol in a ratio from about 1:1.1 to about 1:4;
- (b) heating the reaction mixture of step (a);
- (c) removing the by-product water from the reaction mixture by distillation until the esterification reaction is substantially complete and substantially all of the water has been removed from the reaction zone;
- (d) removing the remaining alcohol from the reaction zone by distillation;
- and
- (e) recovering the cyanoacetate product.
Dependencies are inferred from the claim text.