Process for preparing mixtures containing 8,9-epithio-1-p-menthene

A process for preparing a composition of matter including as a major proportion the compound defined according to the structure:

• ##STR111## comprising the step of reacting the compound having the structure:
• ##STR112## with an alkali metal thiocyanate having the structure:
• ##STR113## according to the reaction:
• ##STR114## wherein M represents alkali metal in the presence of a phase transfer catalyst, said phase transfer catalyst having the general formula:
• ##STR115## wherein at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is C.sub.6 -C.sub.14 aryl, C.sub.6 -C.sub.10 aralkyl, C.sub.6 -C.sub.20 alkyl, C.sub.6 -C.sub.14 alkaryl and C.sub.6 -C.sub.20 alkenyl and the other of R.sub.2, R.sub.3 and R.sub.4 is alkyl selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, 1-butyl, 2-butyl, 1-methyl-2-propyl, 1-pentyl and 1-octyl and Z.sup.- is an anion selected from the group consisting of chloride, bromide and hydroxide, the reaction temperature varying from about 45.degree. C. up to about 85.degree. C.;
• the pressure of reaction varying from one atmosphere up to 10 atmospheres;
• the mole ratio of alkali metal thiocyanate:epoxide varying from about 8:1 down to about 1:1;
• the said alkali metal thiocyanate being dissolved in water with the alkali metal thiocyanate being in a concentration of between 10% and 50% in said water.