Process for making tricyclodecenyl esters

Abstract

A process for making tricyclodecenyl esters is disclosed. A C2-C4 carboxylic acid and a dicyclopentadiene react in the presence of triflic acid under conditions effective to produce the ester. The process gives tricyclodecenyl esters in good yield while avoiding the need to use a large excess of the carboxylic acid. The process efficiently provides fragrance-quality tricyclodecenyl esters from technical grade dicyclopentadienes and / or recycled carboxylic acids.

Description

field of invention

[0001] This invention relates to a process for the preparation of tricyclodecenyl esters. Said esters are derived from dicyclopentadiene compounds and are valuable perfume ingredients. Background of the invention

[0002] Tricyclodecenyl esters, especially C derived from dicyclopentadiene 2 -C 4 Esters, are ubiquitous fragrance ingredients in detergents, shampoos, deodorants, hard surface cleaners and other applications. The most common tricyclodecenyl ester, which is prepared by reacting dicyclopentadiene with acetic acid, is tricyclodecenyl acetate or "TCDA". Such products with a sweet, anise-like aroma are sold by several companies, including, for example, International Flavors & Fragrances ( ), Quest( ), Millennium Specialty Chemicals (Navacet TM ) and Symrise ( ).

[0003] Tricyclodecenyl esters are typically produced by the acid-catalyzed addition of the corresponding carboxylic acids (acetic, propionic, butyric, isobutyric) to dicyclopent...