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Lorenz Heiss

Klaus-Dieter Hammer

Martin Hille

Gunter Gerigk

Klaus Uhl

Klaus Fischer

A process for preparing 4,4'-bis-benz-ox(-thi,-imid)-azol-2-yl-stilbenes of the formula ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 may be the same or different from each other and denote hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, chlorine, bromine, nitro or sulfo and X denotes oxygen, sulfur or NH, which comprises reacting a (4-chloromethyl)-iminobenzoic acid alkyl ester of the formula ##STR2## wherein R denotes C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxyethyl, or HCl salts thereof, with o-aminophenol, o-aminothiophenol or o-phenylene diamine and reacting the resulting 2-benz-ox(-thi,-imid)-azolyl-4-chloromethyl-benzenes with potassium hydroxide or sodium hydroxide in a polar aprotic solvent.

Process for preparing 4,4-bis-benz-ox(-thi,-imid)-azol-2-yl-stilbenes

A process for preparing stilbenedicarbonitrile by dimerizing o- or p-cyanobenzyl chloride in a polar aprotic solvent in the presence of an excess of alkali metal hydroxide powder. Stilbenedicarbonitriles are precursors for the preparation of fluorescent brighteners of the bisbenzoxazolylstilbene class.

Process for preparing stilbenedicarbonitriles

A process for the preparation of 4,4'-bis[benz(ox, othi or imid)azol-2-yl]stilbenes of the formula ##STR1## in which R, R.sup.1, R.sup.2 and R.sup.3 are identical or different and denote hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, chlorine, bromine, nitro or sulfo and X denotes oxygen, sulfur or NH, by reacting alkyl (4-halomethyl)iminobenzoates of the formula ##STR2## or their HCl or HBr salts, R denoting C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxyethyl and X denoting Cl or Br, with o-aminophenol, o-aminothiophenol or o-phenylenediamine and allowing the 2-benz(ox, othi or imid)azol-4-ylhalomethylbenzenes obtained thereby to react with an approximately equivalent amount of sodium tert.-butylate. The stilbene compounds obtained thereby are used as optical brighteners.

Process for the preparation of 4,4'-bis[benz(ox, othi or

New alkyl (4-halomethyl)iminobenzoates of the formula ##STR1## and their HCl or HBr salts, R denoting C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxyethyl and X denoting Cl or Br. These compounds are prepared by reaction of p-cyanobenzyl chloride or p-cyanobenzyl bromide with a C.sub.1 -C.sub.4 -alcohol or C.sub.1 -C.sub.4 -alkoxyethanol in the presence of hydrogen chloride or bromide. The new imines serve as intermediate products, inter alia for the preparation of optical brighteners of the bisbenzoxazolylstilbene class.

Imines of alkyl 4-halomethylbenzoates

A shaped article, especially a tube-shaped article, including a chemically modified cellulose hydrate and water which comprises:

Shaped article comprising cellulose hydrate which is chemically modified

Process for the preparation of trans, trans-muconic acid by reacting a glyoxalacetal with ketene in the presence of an acid catalyst and hydrolyzing the .beta., .beta.'-dialkoxy-adipic acid-alkylester formed with alkali. By this new process trans, trans-muconic acid is easily obtained in better yield, which compound is an important intermediate for the production of 1,4-naphthalene-dicarboxylic acid esters.

Process for the preparation of trans, trans-muconic acid

Process for the preparation of 1,4-naphthodinitrile, by reacting o-phenylene-diacetonitrile with a glyoxalbisaldimine. By this process the 1,4-naphthodinitrile is easily obtained in a one-step process. This compound is an important intermediate for the production of 1,4-naphthalene-dicarboxylic acid.

Process for the preparation of 1,4-naphthodinitrile

Compounds of the formula ##EQU1## IN WHICH R.sub.1 is alkyl, alkenyl, or alkylpheyl, R.sub.2 is a bivalent aromatic radical, and R.sub.3 is an alkylene, alkenylene, or alkylphenylene radical and A.sup.(.sup.-) stands for a halogen atom, are used as demulsifiers and corrosion inhibiting agents in crude oil refining.

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