Addition Reaction of the Mono and Sesquiterpen Hydrocarbons with C1-C4 Alcohols in the Presence of Synthetic Zeolitest

Abstract

Addition reaction of sabinene ( 1 ), isolimonene ( 2 ), r-terpinene ( 3 ), humulene ( 4), p-caryophyllene ( 5 ) and longicyclene ( 6 ) with alcohols (C1C4) in the presence of forei gn synthetic zeolites was studied, In the 300 series zeolites (HSZ-330 HUA, HSZ-340 HUA, HSZ-360 HUA), 1-alkoxy-1-p-menthene ( 9 )(11), 4-alkoxy-2-p-menthene (12)(15) and 1-alkoxy-3-p-menthene (16)(18) were obtained from ( 1 ), ( 2 ) and ( 3 ) as main products, respectively. In methanol and ethanol with 300 series (HSZ-330 HUA, HSZ-360 HUA) or 600 series zeolites (HSZ-620 HOA, HSZ-640 HOA), the addition of ( 4 ) and ( 5 ) gave 8-alkoxy-1, 4, 4, 8-tetramethy1-1, 5-cycloundecadiene (19), (20) and 1-alkoxy-4, 4, 8-trimethyltricyclo[6.3.1.02.5]dodecane (22), (23), respectively, with high selectivity. In methanol and 1-propanol with HSZ-360 HUA synthetic zeolite, 11-methoxy-1, 2, 6, 6-tetramethyltricyclo[5.3.1.02.8] undecane (28) and 8-propoxy-3, 3, 7, 9-tetramethyltricyclo[5.4.0.02.8]undecane (32) were obtained with high selectivity from ( 6 ). These compounds were evalua ted on the basis of their odor; ( 9 ), (22) especially emitted an odor that would qualify them for use as flavor materials. t Studies on the Reaction of Terpenes in the Presenec e of Synthetic Zeolites. XXI.