Nissan Chemical Industries Limited

Norio Tanaka

Masatoshi Baba

Tsutomu Nawamaki

Eiichi Oya

Takuya Kakuta

Takashi Ikai

Shigeomi Watanabe

Yasuo Kondo

Hideaki Suzuki

Kenzo Fukuda

Masatoshi Ohnari

Koichi Nishio

Yoshihisa Watanabe

Yasuo Fukue

Makoto Ishikawa

Koichi Suzuki

Isao Hashiba

Masataka Hatanaka

Takasi Ikai

Kenichi Mizusawa

Masaji Matsunaga

Hideo Suzuki

Yoshihiro Kudo

Jun Satow

Yasuyuki Nakajima

Shinichiro Takigawa

Hiroyuki Kousaka

Masakazu Taniguchi

Shuzo Shinke

Yoshiyuki Kusuoka

Yoshio Kamiya

Shigeru Futamura

Yasuhisa Sugiyama

Kouichi Masahashi

Takashi Kitabayashi

There is provided a process for stereoselectively producing E-form of 3-acyloxyacrylonitrile compound (3) or Z-form which comprises reacting 3-oxopropionitrile compound (1) with an acid chloride (2), characterized in that the reaction is conducted with removal of hydrogen chloride, or by using an organic base or an inorganic base, to thereby regulate the stereostructure of the product; a process for producing the compound (1) characterized by reacting acetonitrile compound (5) with an aromatic ester compound (6) by use of an alkali metal alkoxide in a hydrocarbon solvent while removing alcohol formed as a by-product by azeotropic distillation in a separating tank; and a process for isomerizing E-form of 3-acyloxyacrylonitrile compound to Z-form thereof by use of an organic base. 

Process for producing acrylonitrile compound

A novel process for the preparation of benzonitrile compounds useful for herbicides or their intermediates is provided. A process for the preparation of compounds of the formula (1), characterized in comprising reacting a compound of the formula (1,) with one or more cyanides selected from potassium cyanide, sodium cyanide and zinc cyanide in the presence of a metallic catalyst.

Process for the preparation of benzonitrile compounds

The present invention provides a method for modifying melamine derivatives that can produce N-substituted melamine derivatives by introducing a substituent group to melamine or N-substituted melamine derivatives. The method is characterized by heating melamine or an N-substituted melamine derivative and an alcohol in the presence of a mixed catalyst comprising a hydrogenation catalyst and a dehydrogenation catalyst and hydrogen to allow reaction or heating melamine or an N-substituted melamine derivative and an alcohol in the presence of a hydrogenation catalyst and hydrogen with addition/coexistence of a metal to allow reaction. The compound groups obtained by introducing a substituent group to the amino group of melamine derivative with an alcohol by the method of the present invention can be used widely as intermediates of fine chemicals such as various agricultural chemicals, medicines, dyes, paints, etc. and as various resin materials and flame retardant materials.

Method for modifying melamine derivatives

Method of alkylating triazine derivatives

Method for modifying 1,3,5-triazine derivatives

A process for the separation of phenyluracil compounds is provided. The process according to the present invention comprises treating with a weakly-basic substance a mixture of a halogenophenyluracil compound (I) and a cyanophenyluracil compound (II): ##STR1## wherein X is a hydrogen or fluorine atom, Y is a chlorine or bromine atom, and R is an alkyl group containing 1 to 3 carbon atoms, to separate the compounds (I) and (II).

Process for the separation of phenyluracil compounds

Method of alkylating of triazine derivatives

A process for producing a heterocyclic tertiary amine of the formula (III): ##STR1## wherein A is a nitrogen atom or C-R.sup.5, B is a nitrogen atom or C-R.sup.6,  is a single bond or a double bond, and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom, an acyl group, a halogen atom, a cyano group, etc., provided that two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may together form a 3-membered, 4-membered, 5-membered or 6-membered aliphatic ring, a heterocyclic rig or aromatic ring, and R.sup.7 is a C.sub.1-6 alkyl group which may be substituted, etc., which process comprises reacting a heterocyclic secondary amine of the formula (I): ##STR2## wherein A, B, , R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with an alkylating agent of the formula (II):

N-alkylation of heterocyclic, aromatic amines

A pyrazole derivative having the formula ##STR1## is disclosed; the groups A, B, Q, V, W, X, Y, and Z are defined in the description.

Benzoic acid derivatives useful as intermediates for the preparation of

A process for producing substituted benzoic acids represented by General Formula II: ##STR1## wherein Q represents a member selected from the group consisting of hydrogen, halogen atoms, --CN, --NO.sub.2, --COOH, --COOR.sub.1, --COR.sub.1, --SR.sub.1, --SO.sub.2 R.sub.1 and --OR.sub.2 ; and Y and Z each represents a member selected from the group consisting of halogen atoms, --CN, --NO.sub.2, --COOH, --COOR.sub.1, --COR.sub.1, --SR.sub.1, --SO.sub.2 R.sub.1 and --OR.sub.2 (in which R.sub.1 represents an alkyl group containing 1 to 10 carbon atoms; and R.sub.2 represents an alkyl group containing 1 to 10 carbon atoms or a phenyl group which may be substituted), which comprises oxidizing a substituted toluene represented by General Formula I: ##STR2## wherein W represents a member selected from the group consisting of hydrogen, halogen atoms, --CH.sub.3, --CN, --NO.sub.2, --COOH, --COOR.sub.1, --COR.sub.1, --SR.sub.1, --SO.sub.2 R.sub.1 and --OR.sub.2 ; and Y and Z have the same meanings as defined above with an oxygen-containing gas in the presence of a metal compound catalyst.

Substituted benzoic acids

A substituted benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, cyano, nitro or halogen; X.sub.2 is --L--OR.sub.1 (wherein L is C.sub.1 -C.sub.4 alkylene or C.sub.1 -C.sub.4 alkylidene, and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl), --L--O--L--OR.sub.1 (wherein L and R.sub.1 are as defined above), --L--S(O).sub.n --R.sub.2 (wherein L is as defined above, R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, and n is an integer of 0, 1 or 2), --L--O--COR.sub.2 (wherein L and R.sub.2 are as defined above), --L--NR.sub.1 R.sub.3 (wherein L and R.sub.1 are as defined above, and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl), --COOR.sub.1 (wherein R.sub.1 is as defined above) or --COO--L--O--R.sub.1 (wherein L and R.sub.1 are as defined above), provided that when X.sub.1 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl, X.sub.2 is not --COOR.sub.1 ; X.sub.3 is trifluoromethyl, C.sub.1 -C.sub.3 alkoxy, halogen, cyano, nitro or --S(O).sub.n R.sub.4 (wherein n is as defined above, and R.sub.4 is C.sub.1 C.sub.3 alkyl); X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; X.sub.5 is hydrogen or fluorine; and each of Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; or a salt thereof.

Substituted benzoyl derivatives and selective herbicides

A process for producing a 4-benzoyl-5-hydroxylpyrazole of the formula III: ##STR1## which comprises reacting carbon monoxide and a 5-hydroxypyrazole of the formula II: ##STR2## with a substituted benzene of the formula I: ##STR3## in the presence of a base and a catalyst of Group VIII of the Periodic Table.

Substituted benzenes useful as intermediates

An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;

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Funabashi, Japan

Norio Tanaka