The invention relates to a method for (I) producing a carboxylic ester of formula (I). Said method comprises the steps of: a) bringing an organosilane/borane of formula Si or B into contact with CO.sub.2, in the presence of a catalyst and an electrophilic compound of formula (III), the groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Y, and M′ being as defined in claim 1; and optionally b) recovering the compound of formula (I) produced.

##STR00001##

Provided is a method for resolution of formula 4-[4-dimethylamino-1-(4-fluorophenyl)-1-hydroxylbutyl]-3-hydroxy-methyl benzonitrile as an enantiomer thereof, comprising the following steps: a salt of (S)-4-[4-dimethylamino-1-(4-fluorophenyl)-1-hydroxylbutyl]-3-hydroxymethyl benzonitrile with a resolving agent D-(+)di-p-toluoyl tartaric acid was crystallized in a resolving solvent; the method is characterized in that the resolving solvent is an ether solvent. Also provided is a new crystal form of the resolved intermediate.

Provided is a method for resolution of formula 4-[4-dimethylamino-1-(4-fluorophenyl)-1-hydroxylbutyl]-3-hydroxy-methyl benzonitrile as an enantiomer thereof, comprising the following steps: a salt of (S)-4-[4-dimethylamino-1-(4-fluorophenyl)-1-hydroxylbutyl]-3-hydroxymethyl benzonitrile with a resolving agent D-(+)di-p-toluoyl tartaric acid was crystallized in a resolving solvent; the method is characterized in that the resolving solvent is an ether solvent. Also provided is a new crystal form of the resolved intermediate.

The invention provides a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat or light, a high clearing point (or a high maximum temperature), a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a small dielectric anisotropy, a suitable elastic constant and a good compatibility with other liquid crystal compounds, a liquid crystal composition including this compound, and a liquid crystal display device containing this composition. The invention provdes a compound represented by formula (1):

##STR00001##

where R.sup.1 and R.sup.2 is alkyl having 1 to 20 carbons or the like; one of L.sup.1 and L.sup.2 is both hydrogens, and the other is both fluorines; Z.sup.1 and Z.sup.2 are independently a single bond, —COO—, —OCO—, —OCH.sub.2—, —CH.sub.2O—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2CH.sub.2—, —CH═CH—, —C≡C— or the like.

The invention provides a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat or light, a high clearing point (or a high maximum temperature), a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a small dielectric anisotropy, a suitable elastic constant and a good compatibility with other liquid crystal compounds, a liquid crystal composition including this compound, and a liquid crystal display device containing this composition. The invention provdes a compound represented by formula (1):

##STR00001##

where R.sup.1 and R.sup.2 is alkyl having 1 to 20 carbons or the like; one of L.sup.1 and L.sup.2 is both hydrogens, and the other is both fluorines; Z.sup.1 and Z.sup.2 are independently a single bond, —COO—, —OCO—, —OCH.sub.2—, —CH.sub.2O—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2CH.sub.2—, —CH═CH—, —C≡C— or the like.

A plasticizer composition, a resin composition and methods of preparing the same are disclosed. The compositions and methods comprise a terephthalate-based material, which has two alkyl groups bound to a diester group, and a dibenzoate-based material. The compositions and methods have a weight ratio of the terephthalate-based material to the dibenzoate-based material of 99:1 to 1:99.

A plasticizer composition, a resin composition and methods of preparing the same are disclosed. The compositions and methods comprise a terephthalate-based material, which has two alkyl groups bound to a diester group, and a dibenzoate-based material. The compositions and methods have a weight ratio of the terephthalate-based material to the dibenzoate-based material of 99:1 to 1:99.

A process for production of C.sub.4 to C.sub.15 esters by the esterification of a carboxylic acid or anhydride with a C.sub.4 to C.sub.15 alcohol including forming a reaction mixture of the acid or anhydride and the C.sub.4 to C.sub.15 alcohol including a stoichiometric excess of the alcohol is provided.

A process for production of C.sub.4 to C.sub.15 esters by the esterification of a carboxylic acid or anhydride with a C.sub.4 to C.sub.15 alcohol including forming a reaction mixture of the acid or anhydride and the C.sub.4 to C.sub.15 alcohol including a stoichiometric excess of the alcohol is provided.

A process for production of C.sub.4 to C.sub.15 esters by the esterification of a carboxylic acid or anhydride with a C.sub.4 to C.sub.15 alcohol including forming a reaction mixture of the acid or anhydride and the C.sub.4 to C.sub.15 alcohol including a stoichiometric excess of the alcohol is provided.