August 22, 2011

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The following patent record is from the CAplusSM database.


Patent Number: US 7985870
Title: Process for the manufacture of substituted 2-cyanocinnamic esters
Inventor(s): DSM IP Assets B. V., Neth.
Patent Assignee(s): Sumitomo Chemical Company, Limited, Japan
Source: PCT Int. Appl., 16 pp. CODEN: PIXXD2
Language: Enlgish

Claimed is a process for the manufacture of cyanocinnamic esters I [R1 = H,alkyl, alkoxy; R2 = H, alkyl, phenyl; R3 = alkyl] wherein a cyanoacetic ester is reacted with a carbonyl compound in the presence of an organic solvent, a C3-C6 monocarboxylic acid, and an ammonium compound with the proviso that the molar ratio of the cyanoacetic ester to the carbonyl compound is in a range of about 0.65 to 0.9.  2-Cyano-3,3-diarylacrylic esters are UV absorbers for plastics and cosmetics.  Thus, a mixture of 2-ethylhexyl cyanoacetate (EHCA) 62.2 g (0.32 mol), benzophenone (BP) 81 g (0.45 mol) (molar ratio EHCA:BP = 0.71:1), ammonium acetate 27.7 g (0.36 mol), propionic acid 81 g (1.1 mol), and heptane 81 g in a flask is heated under stirring; when the temperature reaches 110 degrees C, a mixture of propionic acid, water, and heptane is distilled off over 5 h at normal pressure; heptane is returned to the flask; then the reactant is cooled to 90 degrees C, and hot water 100 mL is added to the reaction mixture; the mixture is kept at 85 degrees C for 10 min and transferred to a funnel for separation; to a flask equipped with a column 256 g of crude 2-ethylhexyl 2-cyano-3,3-diphenylacrylate solution is added; rectification is carried out at 1 mbar; 2-ethylhexyl 2-cyano-3,3-diphenylacrylate is distilled out at 210 degrees C (vapor); after distillation, light yellow 2-ethylhexyl 2-cyano-3,3-diphenylacrylate is obtained; the yield of the product is 93.09% (based on EHCA) or 98.38% (based on BP).  In anther example, the optimal molar ratio of ammonium acetate to benzophenone is 0.8.

View the full-text U.S. patent from USPTO.

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