Basf Aktiengesellschaft

Horst Scheuermann

Hans-Joachim Opgenorth

Albert Hettche

Helmut Hoch

Axel Nissen

Harald Laas

Wolfgang Mach

Dieter Schneider

Ulrich Jersak

Renate Elisabeth Hell

Guenter Hansen

Georg Zeidler

Wolfgang Schulte

Hans J Kolbinger

Hans-Richard Mueller

Dietmar Augart

Walter Stilz

Helmut Gorth

Polyazo dyes which in the form of the free acids correspond to the general formula I ##STR1## where D is the radical of a diazo component, or a radical of the formula ##STR2## n is 0 or 1, R.sup.1 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, carboxyl, trifluoromethyl, methylsulfonyl, ethylsulfonyl or hydroxysulfonyl,

Trisazo or tetrakisazo dyes containing a heterocyclic group

The novel compound (3-nitro-4-methyl)-phenyl chloroformate is prepared by reacting (4-methyl)-phenyl chloroformate with nitric acid in the presence of sulfuric acid. The novel compound (3-nitro-4-methyl)-phenyl chloroformate is a valuable starting material for the preparation of dyes and crop protection agents and in particular is an intermediate for the preparation of 3-nitro-4-methylphenol, which is reduced to 3-amino-4-methylphenol.

(3-Nitro-4-methyl)-phenyl chloroformate and its preparation

A process for the preparation of an indolenine of the formula ##STR1## where R, X and Y are conventional substituents, by thermal rearrangement of a compound of the formula ##STR2## to give a compound of the formula ##STR3## and cyclization of this compound in the presence of an acid catalyst.

Preparation of indolenines

A process for the preparation of an indolenine of the general formula I ##STR1## where R, R.sup.1 and R.sup.2 are aliphatic radicals and R.sup.1 and R.sup.2 may also be linked and the ring A may be additionally substituted, wherein a compound of the formula II ##STR2## is heated in the presence of a Lewis acid and of a halide. The products are valuable starting compounds for the preparation of dyes.

Halobenzenes are manufactured by (a) a one-vessel reaction of anilines with halogenating agents to give haloanilines, followed by reaction of the mixture thus obtained with alkanols and nitrosylating agents in the presence of water and acid at not less than 35.degree. C. or (b) the corresponding reaction of a haloaniline which has been manufactured in the above manner or by some other method and has been isolated from its reaction mixture. The products are starting materials for the manufacture of drugs, dyes and pesticides.

Manufacture of substituted halobenzenes

N',N'-disubstituted N-(2-cyanophenyl)-formamidines are manufactured by reacting isatoic anhydrides with ammonia and then with a mixture of acid halides and formamides. The N-(2-cyanophenyl)-formamidines which may be manufactured by the process of the invention are valuable starting materials for the manufacture of dyes, crop protection agents and drugs.

Manufacture of N-(2-cyanophenyl)-formamidines

Compounds of the formula: ##STR1## in which one R is identical with or different from the other R and each is alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cycloalkyl, aralkyl, aryl, N,N-dialkylaminoalkyl or quaternized N,N-dialkylaminoalkyl; A is ##STR2## or ##STR3## R.sup.1 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, aralkyl, aryl or heteroaryl;

N-Acylaminonaphthalimides

Dimethylaminobenzenesulfonates are manufactured by reacting nitrobenzenesulfonates with formaldehyde and hydrogen in the presence of a hydrogenation catalyst containing a metal of atomic number from 24 to 29 and of phosphoric acid and water at a pH of from 2 to 3.5, at from 50 to 150.degree. C, under a pressure of at least 40 bars, with a residence time of from 1 to 15 minutes. The products are starting materials for the synthesis of dyes, especially of rhodamine dyes, oxazine dyes and reactive dyes, and also of pharmaceuticals and pesticides.

Manufacture of dimethylaminobenzenesulfonates

Process for the production of benzothiazoles from N-arylsubstituted thioureas by oxidative ring closure characterized by the use of chlorine as oxidizing agent and by the presence of catalytic amounts of bromine. Yield and quality of the benzothiazoles obtained are very good.

Manufacture of benzothiazoles

Compounds of the naphthalimide series which in the dissolved condition exhibit a characteristic blue, violet or bluish violet fluorescence, and a process for their production. The compounds are outstandingly suitable for the optical brightening of synthetic fibers.

Naphthalimide compounds and optical brighteners

Arylamines are manufactured by reacting alcohols with amines in the presence of phosphorus-III compounds. The arylamines I manufactured by the process of the invention are intermediates for the manufacture of crop protection agents, optical brighteners, especially amino-coumarin derivatives, and dyes, especially of the xanthene, pyronine, rhodamine, oxazine, azo, triphenylmethane and diphenylmethane series.

Manufacture of arylamines

Halonitrobenzenes are manufactured by reacting halonitroanilines with alkanols and nitrosating agents in the presence of water and an acid at not less than 35.degree. C. The products are starting materials for the manufacture of pharmaceuticals, dyes and pesticides.

Manufacture of halonitrobenzenes

Bisstyryl-substituted aryl compounds of the formula (I): ##STR1## where X is arylene and R.sup.1 and R.sup.5 are substituents common to the dye art. The compounds are useful as optical brighteners, particularly for acrylonitrile polymers, and give excellent whitening having good fastness properties.

Bisstyrylaryl compounds

Dyes of the formula ##STR1## wherein A is --O--, --S-- or --CH=CH-- and X and Z are substituents, obtained from the corresponding 2-iminocoumarines by reaction with a compound of the formula ##STR2## The dyes give brilliant yellow to red shades on textile material, particularly polyesters and acrylonitrile polymers.

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Ludwigshafen, Germany

Horst Scheuermann