Ishihara Sangyo Kaisha, Ltd.

Nissan Chemical Industries Limited

Isao Yokomichi

Kanichi Fujikawa

Ryohei Takahashi

Ryuzo Nishiyama

Nobuyuki Sakashita

Yasuhiro Tsujii

Takahiro Haga

Itaru Shigehara

Shigeyuki Nishimura

Kuniaki Nagatani

Sinzo Someya

Rikuo Nasu

Toshio Nakajima

Tadaaki Toki

Kazuyuki Maeda

Terumasa Komyoji

Mikio Miyaji

Shinzo Someya

Kiyoshi Ota

Toru Koyanagi

Fumio Kimura

Takao Awazu

Norifusa Matsuo

Kouji Hayashi

Junichi Kawashima

Akio Mohri

Takeo Yamada

Minoru Ikeda

Takeo Kaji

A trifluoromethylpyridine selected from the group consisting of .alpha.-trifluoromethylpyridine, .gamma.-trifluoromethylpyridine, a bis(trifluoromethyl)pyridine and chlorides thereof which have 1 to 3 chlorine atoms in its pyridine nucleus is produced by reacting a pyridine derivative selected from the group consisting of .alpha.-picoline, .gamma.-picoline and a lutidine with chlorine and anhydrous hydrogen fluoride at a temperature of 300.degree. to 600.degree. C. in a vapor phase in the presence of a diluent and a catalyst comprising a fluoride of a metallic element selected from the group consisting of aluminum, chromium, iron, nickel, manganese, cobalt and copper.

Process for producing trifluoromethylpyridines

A trifluoromethyl-2-(thio)pyridone compound having the formula: ##STR1## wherein X represents a hydrogen atom or a halogen atom, Y.sub.1 and Y.sub.2 each represents a hydrogen atom, a halogen atom or a trifluoromethyl group, and Z represents an oxygen atom or a sulfur atom, in which either Y.sub.1 or Y.sub.2 represents a trifluoromethyl group, and when X and Y.sub.2, or X and Y.sub.1 represent a hydrogen atom at the same time, then Z represents a sulfur atom, and a process for preparing the same.

Trifluoromethyl-2-pyridinone or pyridinthione compounds and process for

5,6-Dichloro-.beta.-trifluoromethylpyridine or 2,5,6-trichloro-.beta.-trifluoromethylpyridine is produced by reacting 6-chloro-.beta.-trifluoromethylpyridine or 2,6-dichloro-.beta.-trifluoromethylpyridine with chlorine gas to chlorinate the 5-position of pyridine nucleus thereof:

Process for producing 5-chloro-.beta.-trifluoromethylpyridines

A pyridine derivative having the formula ##STR1## wherein X.sup.2 and Y.sup.2 represents hydrogen atom or chlorine atom is produced by reacting a pyridine compound having the formula ##STR2## wherein X.sup.1 and Y.sup.1 represent hydrogen atom or chlorine atom, with chlorine and anhydrous hydrogen fluoride by a vapor phase reaction in the presence of a catalyst at a temperature of 250.degree. to 600.degree. C. using as the catalyst a fluoride of a metal selected from the group consisting of copper, vanadium, tin, bismuth, zirconium, magnesium, barium, zinc, calcium, potassium and sodium.

Process for producing a .beta.-trifluoromethylpyridine

A phenoxybutyltriazole compound represented by the following formula (I): ##STR1## wherein X is a halogen atom, a phenyl group or a 5-trifluoromethylpyridine-2-yloxy group; Y is a halogen atom or a trifluoromethyl group; Q is a &gt;C.dbd.O group or a &gt;CH--OH group; A is a &gt;CH-- group or a nitrogen atom; and m and n are each an integer of 0 to 2, or a salt thereof, which is useful as an active ingredient for agricultural and horticultural fungicides, is disclosed. A process for producing the compound of the formula (I) is also disclosed.

Phenoxybutyltriazole compound, agricultural and horticultural fungicidal

An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150.degree. to 250.degree. C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.

Process for producing 1,3,5-triaminobenzene

1,3,5,-Trichlorobenzene is produced by chlorinating 1,3,5-trihalobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom. The gaseous 1,3,5-halobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom is brought into contact with chlorine gas at a molar ratio of 0.5 to 3.0 of the stoichiometric amount of chlorine required for said conversion, in a vapor phase at a temperature of 280.degree. to 500.degree. C.

Process for producing 1,3,5-trichlorobenzene

A 2-substituted-5-trifluoromethylpyridine compound represented by Formula (I): ##STR1## wherein X is a hydrogen atom or a halogen atom, and Y is a cyano group or a carboxy group, provided that Y is a cyano group, then X is a halogen atom, or a salt thereof, and a process for the production of the same. This compound is useful as an intermediate for the production of various fine chemicals.

2-Substituted-5-trifluoromethylpyridines and process for producing the

A novel compound, 2-amino-trifluoromethyl-halogenopyridine, is provided, which is prepared by amination of a 2-halogeno-trifluoromethyl-halogenopyridine or by halogenation of 2-amino-trifluoromethylpyridine. This compound is useful as an intermediate for synthesis of agricultural chemicals and medicines.

2-Amino-3-chloro-5-trifluoromethylpyridine

1-Bromo-3,5-dichlorobenzene is produced in high efficiency by a special isomerization of monobromodichlorobenzene in the presence of an aluminum halide and separating the object product and recycling a residue. 1-Bromo-3,5-dichlorobenzene is useful intermediates for various agricultural chemicals, dyes and medicines.

Process for producing 1-bromo-3,5-dichlorobenzene

.alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the '4-trifluoromethylphenoxy group' of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.

Herbicidal compound, herbicidal composition containing the same, and

This is a process for recovering bromine from a waste liquid formed in the production of an aniline derivative by ammonolysis of a nuclear substituted bromobenzene derivative with a halogen atom or a functional group. The waste liquid is first subjected to chlorine treatment in alkaline region to remove most part of ammonia and aniline derivatives, and then it is subjected to chlorine treatment in acidic region to recover bromine. The process does not involve danger of explosion accidents and can be smoothly operated.

Process for recovering bromine from waste liquid

.alpha.[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the '4-trifluoromethylphenoxy group' of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.

Pyridine derivatives having a trifluoromethyl group at .beta.-position thereof are produced by reacting .beta.-picoline with chlorine and hydrogen fluoride in a vapor phase at high temperature for a short time. The reaction condition can be mild and the yield of the object compound is increased by reacting them in the presence of a specific metal fluodie. The pyridine derivatives useful as starting materials for agricultural chemicals and medicines can be continuously obtained by a simple reaction at high yield.

Growing community of inventors

Moriyama, Japan

Isao Yokomichi