Implementations of a method of forming a wax ether composition may include: providing a batch of lipids, drying the batch of lipids, and cooling the batch of lipids. The method may also include dosing, with a catalyst, the batch of lipids at 0.1% to 0.3% by weight of the batch of lipids and dissolving the catalyst in the batch of lipids to form a homogenous solution. The method may include adding at least a molar equivalent of a hydrogen donor to the homogenous solution. The method may include sealing and maintaining the homogenous solution and hydrogen donor under atmospheric pressure under reflux until a chemical reaction between the homogenous solution and the hydrogen donor forms a product comprising an ether.

Implementations of a method of forming a wax ether composition may include: providing a batch of lipids, drying the batch of lipids, and cooling the batch of lipids. The method may also include dosing, with a catalyst, the batch of lipids at 0.1% to 0.3% by weight of the batch of lipids and dissolving the catalyst in the batch of lipids to form a homogenous solution. The method may include adding at least a molar equivalent of a hydrogen donor to the homogenous solution. The method may include sealing and maintaining the homogenous solution and hydrogen donor under atmospheric pressure under reflux until a chemical reaction between the homogenous solution and the hydrogen donor forms a product comprising an ether.

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound.

There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2-X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2=CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound.

There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2-X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2=CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

A process for obtaining a mixture of C4-C8 and C9-C18 alkyl monoether of saccharide, comprising: a) a first step of acetalization or trans-acetalization of a saccharide or of a mixture of saccharides with a C4-C8 aliphatic aldehyde or the acetal thereof, b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a) of the saccharide or mixture of saccharides with a C9-C18 aliphatic aldehyde or the acetal thereof, c) a step of catalytic hydrogenolysis of the saccharide acetals obtained, and d) a step of recovery of a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers. The invention further relates to a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers and the use thereof as a surfactant.

A process for obtaining a mixture of C4-C8 and C9-C18 alkyl monoether of saccharide, comprising: a) a first step of acetalization or trans-acetalization of a saccharide or of a mixture of saccharides with a C4-C8 aliphatic aldehyde or the acetal thereof, b) a second consecutive or simultaneous step of acetalization or trans-acetalization of the product obtained in a) of the saccharide or mixture of saccharides with a C9-C18 aliphatic aldehyde or the acetal thereof, c) a step of catalytic hydrogenolysis of the saccharide acetals obtained, and d) a step of recovery of a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers. The invention further relates to a mixture of C4-C8 and C9-C18 alkyl saccharide monoethers and the use thereof as a surfactant.

Implementations of a method of forming a wax ether composition may include: providing a batch of lipids, drying the batch of lipids, and cooling the batch of lipids. The method may also include dosing, with a catalyst, the batch of lipids at 0.1% to 0.3% by weight of the batch of lipids and dissolving the catalyst in the batch of lipids to form a homogenous solution. The method may include adding at least a molar equivalent of a hydrogen donor to the homogenous solution. The method may include sealing and maintaining the homogenous solution and hydrogen donor under atmospheric pressure under reflux until a chemical reaction between the homogenous solution and the hydrogen donor forms a product comprising an ether.

Implementations of a method of forming a wax ether composition may include: providing a batch of lipids, drying the batch of lipids, and cooling the batch of lipids. The method may also include dosing, with a catalyst, the batch of lipids at 0.1% to 0.3% by weight of the batch of lipids and dissolving the catalyst in the batch of lipids to form a homogenous solution. The method may include adding at least a molar equivalent of a hydrogen donor to the homogenous solution. The method may include sealing and maintaining the homogenous solution and hydrogen donor under atmospheric pressure under reflux until a chemical reaction between the homogenous solution and the hydrogen donor forms a product comprising an ether.

The invention is directed to methods of producing alkoxylated or hydroxylated terpenes comprising the steps of continuously passing a solution comprising an alcohol in combination with a terpene over an acidic resin catalyst in a packed bed reactor in order to yield a product, as well as compounds that are the products of the methods described herein.

The invention is directed to methods of producing alkoxylated or hydroxylated terpenes comprising the steps of continuously passing a solution comprising an alcohol in combination with a terpene over an acidic resin catalyst in a packed bed reactor in order to yield a product, as well as compounds that are the products of the methods described herein.