Disclosed herein are embodiments of a method for making fuels and feedstocks from readily available alcohol starting materials. In some embodiments, the method concerns converting alcohols to carbonyl-containing compounds and then condensing such carbonyl-containing compounds together to form oligomerized species. These oligomerized species can then be reduced using by-products from the conversion of the alcohol. In some embodiments, the method further comprises converting saturated, oligomerized, carbonyl-containing compounds to aliphatic fuels.

Disclosed herein are embodiments of a method for making fuels and feedstocks from readily available alcohol starting materials. In some embodiments, the method concerns converting alcohols to carbonyl-containing compounds and then condensing such carbonyl-containing compounds together to form oligomerized species. These oligomerized species can then be reduced using by-products from the conversion of the alcohol. In some embodiments, the method further comprises converting saturated, oligomerized, carbonyl-containing compounds to aliphatic fuels.

The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)-isomers of 6,10,14-trimethylpentadeca-5,9,13-trien-2-one or 6,10,14-trimethylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.

The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)-isomers of 6,10,14-trimethylpentadeca-5,9,13-trien-2-one or 6,10,14-trimethylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.

The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)-isomers of 6,10,14-trimethylpentadeca-5,9,13-trien-2-one or 6,10,14-trimethylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.

The present invention addresses the problem of providing a novel compound capable of imparting a highly appealing floral and verdant scent, and a flavor composition and/or fragrance composition containing the same. This compound is a racemic or optically active compound represented by general formula (1).

##STR00001##

In formula (1), the solid and dotted double line indicates a double bond or a single bond, the definition of Y is the same as described in the specification, and * represents an asymmetric carbon atom.

The present invention addresses the problem of providing a novel compound capable of imparting a highly appealing floral and verdant scent, and a flavor composition and/or fragrance composition containing the same. This compound is a racemic or optically active compound represented by general formula (1).

##STR00001##

In formula (1), the solid and dotted double line indicates a double bond or a single bond, the definition of Y is the same as described in the specification, and * represents an asymmetric carbon atom.

To provide a novel method for producing a halogenated acrylic acid derivative.

A compound represented by the formula (1):

##STR00001##

(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2):

##STR00002##

the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):

CHXYZ(3)

(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4):

##STR00003##

and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5):

##STR00004##

To provide a novel method for producing a halogenated acrylic acid derivative.

A compound represented by the formula (1):

##STR00001##

(wherein each of R.sup.1 and R.sup.2 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom, or R.sup.1 and R.sup.2 together form a ring, R.sup.3 is a monovalent group capable of being desorbed by R.sup.3OH removal reaction, and each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom or a monovalent group essentially containing a carbon atom) and having a boiling point of at most 500 C., is subjected to R.sup.3OH removal reaction in a vapor phase in the presence of a solid catalyst to obtain an ethene derivative represented by the formula (2):

##STR00002##

the ethene derivative represented by the formula (2) and a halogenated methane represented by the formula (3):

CHXYZ(3)

(wherein each of X, Y and Z which are independent of one another, is a halogen atom) are reacted in the presence of a basic compound and a phase transfer catalyst, to obtain a cyclopropane derivative represented by the formula (4):

##STR00003##

and the cyclopropane derivative represented by the formula (4) is reacted by heating in a liquid phase or in a vapor phase to obtain a halogenated acrylic acid ester derivative represented by the formula (5):

##STR00004##

The present invention relates to a method for the production of 2-substituted 4-hydroxy-4-methyltetrahydropyrans from the acid-catalyzed reaction of 3-methylbut-3-ene-1-ol with an aldehyde, a stable odoriferous quality being achieved and avoiding off-odors that interfere with the odor sensation.