Disclosed is an industrial method for efficient production of an ,-difluoroaldehyde compound, which includes reaction of an ,-difluoroacetate with hydrogen gas (H.sub.2) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target ,-difluoroaldehyde compound with a high conversion rate and high selectivity.

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4). ##STR00001##

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4). ##STR00001##

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4). ##STR00001##

Provided herein are halogenated ether compounds of Formula (I), Formula (II), or Formula (III):

##STR00001##

Also provided are electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III) and electrochemical cells comprising electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III).

Provided herein are halogenated ether compounds of Formula (I), Formula (II), or Formula (III):

##STR00001##

Also provided are electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III) and electrochemical cells comprising electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III).

Method for preparing methyl formate and coproducing dimethyl ether by reacting a formaldehyde and methanol raw material (molar ratio range of 1:4 to 1:0.05) in a First Reaction Region at ranges from 50 C. to 100 C. with Catalyst A resulting in post-reaction material separated into Constituent I. Reacting Constituent I in a Second Reaction Region at ranges from 50 C. to 200 C. and from 0.1 MPa to 10 MPa with Catalyst B resulting in post-reaction material, which is separated into methyl formate, dimethyl ether and Constituent II. At least 1% of dimethyl ether is product, and recycling the rest to the First Reaction Region. Constituent II is recycled to the Second Reaction Region. Each component is gaseous phase and/or liquid phase, independently. The method shows long catalyst life, mild reaction condition, high utilization ratio of raw materials, continuous production and large scale industrial application potential.

Method for preparing methyl formate and coproducing dimethyl ether by reacting a formaldehyde and methanol raw material (molar ratio range of 1:4 to 1:0.05) in a First Reaction Region at ranges from 50 C. to 100 C. with Catalyst A resulting in post-reaction material separated into Constituent I. Reacting Constituent I in a Second Reaction Region at ranges from 50 C. to 200 C. and from 0.1 MPa to 10 MPa with Catalyst B resulting in post-reaction material, which is separated into methyl formate, dimethyl ether and Constituent II. At least 1% of dimethyl ether is product, and recycling the rest to the First Reaction Region. Constituent II is recycled to the Second Reaction Region. Each component is gaseous phase and/or liquid phase, independently. The method shows long catalyst life, mild reaction condition, high utilization ratio of raw materials, continuous production and large scale industrial application potential.

The invention relates to a process for the preparation of acetals from carbon dioxide. The invention also relates to a mixture of phosphorus containing ligands comprising least one polydentate ligand and at least one monodentate ligand. Further, the invention also relates to the use of mixtures comprising at least one polydentate ligand and at least one monodentate ligand in transition metal complexes for the preparation of acetals.

The invention relates to a process for the preparation of acetals from carbon dioxide. The invention also relates to a mixture of phosphorus containing ligands comprising least one polydentate ligand and at least one monodentate ligand. Further, the invention also relates to the use of mixtures comprising at least one polydentate ligand and at least one monodentate ligand in transition metal complexes for the preparation of acetals.