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

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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).

The invention relates to a process for preparing chloroacetaldehyde acetals of monohydric, dihydric or higher-functionality aliphatic alcohols, in which the chloroacetaldehyde acetal is obtained from an aqueous chloroacetaldehyde solution in the presence of the alcohol to be acetalized and an acid catalyst by azeotropic removal of water with the aid of a solvent, wherein the solvent is a halogenated solvent.

The invention relates to a process for preparing chloroacetaldehyde acetals of monohydric, dihydric or higher-functionality aliphatic alcohols, in which the chloroacetaldehyde acetal is obtained from an aqueous chloroacetaldehyde solution in the presence of the alcohol to be acetalized and an acid catalyst by azeotropic removal of water with the aid of a solvent, wherein the solvent is a halogenated solvent.

The present invention relates to a process for preparing a haloalkyl alkoxymethyl ether compound (1B), wherein X.sup.1 represents a halogen atom, and R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, the process comprising the steps of converting a haloalkyl alkoxymethyl ether compound of the following general formula (1A), wherein X.sup.1 and R.sup.1 are as defined above, into a nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl, of the following general formula (2A), wherein M.sup.1A represents Li, MgZ.sup.1A, CuZ.sup.1A, or CuLiZ.sup.1A, Z.sup.1A represents a halogen atom or a 4-alkoxymethoxy-1-methylbutyl group, and R.sup.1 is as defined above, and subsequently subjecting the nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl (2A), to a nucleophilic addition reaction with propylene oxide of the following formula (3) to obtain 6-hydroxy-4-methylheptyl alkoxymethyl ether compound of the following general formula (4), wherein R.sup.1 is as defined above, and subjecting the 6-hydroxy-4-methylheptyl alkoxymethyl ether compound (4) to a halogenation reaction to form the aforesaid haloalkyl alkoxymethyl ether compound (1B).

##STR00001##

The present invention relates to a process for preparing a haloalkyl alkoxymethyl ether compound (1B), wherein X.sup.1 represents a halogen atom, and R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, the process comprising the steps of converting a haloalkyl alkoxymethyl ether compound of the following general formula (1A), wherein X.sup.1 and R.sup.1 are as defined above, into a nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl, of the following general formula (2A), wherein M.sup.1A represents Li, MgZ.sup.1A, CuZ.sup.1A, or CuLiZ.sup.1A, Z.sup.1A represents a halogen atom or a 4-alkoxymethoxy-1-methylbutyl group, and R.sup.1 is as defined above, and subsequently subjecting the nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl (2A), to a nucleophilic addition reaction with propylene oxide of the following formula (3) to obtain 6-hydroxy-4-methylheptyl alkoxymethyl ether compound of the following general formula (4), wherein R.sup.1 is as defined above, and subjecting the 6-hydroxy-4-methylheptyl alkoxymethyl ether compound (4) to a halogenation reaction to form the aforesaid haloalkyl alkoxymethyl ether compound (1B).

##STR00001##

A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a 2,2-difluoroacetaldehyde-alcohol composite system in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the 2,2-difluoroacetaldehyde-alcohol composite system formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a 2,2-difluoroacetaldehyde-alcohol composite system in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the 2,2-difluoroacetaldehyde-alcohol composite system formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a 2,2-difluoroacetaldehyde-alcohol composite system in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the 2,2-difluoroacetaldehyde-alcohol composite system formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a 2,2-difluoroacetaldehyde-alcohol composite system in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the 2,2-difluoroacetaldehyde-alcohol composite system formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.