Objects of the present invention are to provide a novel dehydrogenation reaction catalyst, to provide a method that can produce a ketone, an aldehyde, and a carboxylic acid with high efficiency from an alcohol, and to provide a method for efficiently producing hydrogen from an alcohol, formic acid, or a formate, and they are accomplished by a catalyst containing an organometallic compound of Formula (1). ##STR00001##

Objects of the present invention are to provide a novel dehydrogenation reaction catalyst, to provide a method that can produce a ketone, an aldehyde, and a carboxylic acid with high efficiency from an alcohol, and to provide a method for efficiently producing hydrogen from an alcohol, formic acid, or a formate, and they are accomplished by a catalyst containing an organometallic compound of Formula (1). ##STR00001##

A compound of formula (I)

or a compound of formula (II)
wherein, for each of the compound of formula (I) and the compound of formula (II), R.sup.1 denotes a CH.sub.2OH group, R.sup.2 denotes a CHO group or a CH.sub.2OH group, and R.sup.3 and R.sup.4, independently of one another, denote a C.sub.1-C.sub.4 alkyl group.

##STR00001##

##STR00002##

A compound of formula (I)

or a compound of formula (II)
wherein, for each of the compound of formula (I) and the compound of formula (II), R.sup.1 denotes a CH.sub.2OH group, R.sup.2 denotes a CHO group or a CH.sub.2OH group, and R.sup.3 and R.sup.4, independently of one another, denote a C.sub.1-C.sub.4 alkyl group.

##STR00001##

##STR00002##

Embodiments of the invention are directed to cooling compounds and cooling compositions having a unique cooling perception, as well as various edible, potable, and/or cosmetic products containing one or more cooling compounds having a general Formula (I): wherein Q is selected from CR.sup.1R.sup.2 or CH-CH(CH.sub.2OR.sup.8)CH.sub.2OR.sup.9; wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of CHO, CO.sub.2H; CH.sub.2CH.sub.2OH; CHR.sup.10OR.sup.11, and CHR.sup.10OR.sup.12; wherein R.sup.8 and R.sup.9 are independently H, or in combination form a spiroacetal or spiroketal moiety; wherein each R.sup.10 is independently H or CH.sub.3; wherein R.sup.11 and R.sup.12 are independently selected from H, substituted or unsubstituted C1 to C6 alkyls, substituted or unsubstituted cycloalkyls, substituted or unsubstituted alkaryls, substituted or unsubstituted aryls or heteroaryls, and substituted or unsubstituted acyls, or wherein R.sup.11 and R.sup.12 in combination form a spiroketal or a spiroacetal moiety; wherein R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are independently selected from H, CH.sub.3, and CH.sub.2CH.sub.3; and wherein R.sup.7 is selected from H, iso-propyl, isopropenyl, and sec-butyl; with the proviso that R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are not all H.

##STR00001##

Embodiments of the invention are directed to cooling compounds and cooling compositions having a unique cooling perception, as well as various edible, potable, and/or cosmetic products containing one or more cooling compounds having a general Formula (I): wherein Q is selected from CR.sup.1R.sup.2 or CH-CH(CH.sub.2OR.sup.8)CH.sub.2OR.sup.9; wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of CHO, CO.sub.2H; CH.sub.2CH.sub.2OH; CHR.sup.10OR.sup.11, and CHR.sup.10OR.sup.12; wherein R.sup.8 and R.sup.9 are independently H, or in combination form a spiroacetal or spiroketal moiety; wherein each R.sup.10 is independently H or CH.sub.3; wherein R.sup.11 and R.sup.12 are independently selected from H, substituted or unsubstituted C1 to C6 alkyls, substituted or unsubstituted cycloalkyls, substituted or unsubstituted alkaryls, substituted or unsubstituted aryls or heteroaryls, and substituted or unsubstituted acyls, or wherein R.sup.11 and R.sup.12 in combination form a spiroketal or a spiroacetal moiety; wherein R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are independently selected from H, CH.sub.3, and CH.sub.2CH.sub.3; and wherein R.sup.7 is selected from H, iso-propyl, isopropenyl, and sec-butyl; with the proviso that R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are not all H.

##STR00001##

Process for preparing the dialdehyde of vinylcyclohexene.

Process for preparing the dialdehyde of vinylcyclohexene.