Provided is a method of producing an acid halide solution that is useful in production of a polymerizable liquid-crystal compound. The method of producing an acid halide solution includes: a first step of reacting a specific dicarboxylic acid compound with a halogenating agent in a water-immiscible organic solvent in the presence of at least 1.1 equivalents and not more than 3.0 equivalents of an activator relative to the dicarboxylic acid compound to obtain a reaction liquid including a solution that contains an acid halide compound and an oily liquid that is immiscible with the solution containing the acid halide compound; and a second step of removing the oily liquid from the reaction liquid obtained in the first step to obtain a purified liquid containing the acid halide compound.

A naphthalenedicarboxylic acid dichloride production method includes causing a reaction between naphthalenedicarboxylic acid and a chlorinating agent at a reaction temperature of 20 C. or higher and 75 C. or lower in presence of a solvent including tetrahydrofuran. The causing a reaction in the naphthalenedicarboxylic acid dichloride production method is preferably performed in presence of N,N-disubstituted formamide.

A naphthalenedicarboxylic acid dichloride production method includes causing a reaction between naphthalenedicarboxylic acid and a chlorinating agent at a reaction temperature of 20 C. or higher and 75 C. or lower in presence of a solvent including tetrahydrofuran. The causing a reaction in the naphthalenedicarboxylic acid dichloride production method is preferably performed in presence of N,N-disubstituted formamide.

A naphthalenedicarboxylic acid dichloride production method includes causing a reaction between naphthalenedicarboxylic acid and a chlorinating agent at a reaction temperature of 20 C. or higher and 75 C. or lower in presence of a solvent including tetrahydrofuran. The causing a reaction in the naphthalenedicarboxylic acid dichloride production method is preferably performed in presence of N,N-disubstituted formamide.

The present disclosure provides a process for producing trifluoroiodomethane, the process comprising providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25 C. to about 400 C. to produce an intermediate product stream comprising trifluoroacetyl iodide, and reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature from about 200 C. to about 600 C. to produce a final product stream comprising the trifluoroiodomethane.

The present disclosure provides a process for producing trifluoroiodomethane, the process comprising providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25 C. to about 400 C. to produce an intermediate product stream comprising trifluoroacetyl iodide, and reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature from about 200 C. to about 600 C. to produce a final product stream comprising the trifluoroiodomethane.

Provided is a process for preparing 4-phenyl-1-butyric acid, comprising: reacting 4-phenyl-1-butanol with sodium chlorite, a nitroxyl radical catalyst and sodium hypochlorite in an organic solvent and a phosphate buffer; and quenching the reaction with sodium sulfite to produce 4-phenyl-1-butyric. Also provided is 4-phenyl-1-butyric acid prepared by such a process.

Provided is a process for preparing 4-phenyl-1-butyric acid, comprising: reacting 4-phenyl-1-butanol with sodium chlorite, a nitroxyl radical catalyst and sodium hypochlorite in an organic solvent and a phosphate buffer; and quenching the reaction with sodium sulfite to produce 4-phenyl-1-butyric. Also provided is 4-phenyl-1-butyric acid prepared by such a process.

Provided is a process for preparing 4-phenyl-1-butyric acid, comprising: reacting 4-phenyl-1-butanol with sodium chlorite, a nitroxyl radical catalyst and sodium hypochlorite in an organic solvent and a phosphate buffer; and quenching the reaction with sodium sulfite to produce 4-phenyl-1-butyric. Also provided is 4-phenyl-1-butyric acid prepared by such a process.

Provided is a method for industrially advantageously producing a fluorinated hydrocarbon (3). The disclosed method for producing a fluorinated hydrocarbon represented by formula (3) includes bringing into contact, in a hydrocarbon-based solvent, a secondary or tertiary ether compound represented by formula (1) below with an acid fluoride represented by formula (2) in the presence of lithium salt or sodium salt (in the formulae, R.sup.1 and R.sup.2 each represent a C.sub.1-3 alkyl, and R.sup.1 and R.sup.2 may be bonded to each other to form a ring structure; R.sup.3 represents a hydrogen atom, methyl, or ethyl; and R.sup.4 and R.sup.5 each represent methyl or ethyl).

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