Chemische Werke Huls Aktiengesellschaft

Huels Aktiengesellschaft

Chemische Werke Huels Aktiengesellschaft

Huls Aktiengesellschaft

Manfred Zur Hausen

Werner Otte

Werner Fuhrmann

Manfred Kaufhold

Josef Disteldorf

Werner Hubel

Rudolf Nehring

Erhard Lange

Gunter Kriebel

Wilfried Krix

Rudolph Nehring

Werner Neumann

A method of producing aliphatic and cycloaliphatic diols by catalytic hydrogenation of dicarboxylic acid esters by the use of a copper chromite catalyst in which the copper content (calculated as CuO) is 40-47 wt. %, and the chromium content (calculated as Cr.sub.2 O.sub.3) is 40-47 wt. %, and barium is also present in the amount of up to 10 wt. % (calculated as BaO) under mild temperature and pressure conditions is disclosed. The method produces diols without the formation of high boiling materials and does not require purification of the product diols by overhead distillation.

Method of producing aliphatic and cycloaliphatic diols by catalytic

A process for the manufacture of phthalic anhydride by oxidation in the gas phase of an o-xylol naphthalene mixture. By producing a solution of 1 to 80 parts by mass naphthalene in 99 to 20 parts by mass o-xylol at a temperature of 0.degree. to 80.degree. C., storing the solution at that temperature, heating the solution only shortly prior to the reaction to 110.degree. to 180.degree. C., atomizing the heated solution into a hot airflow, passing the heated solution over metal oxide catalysts in the gas phase and collecting phthalic anhydride product, a problem-free manufacture of phthalic anhydride is attained.

Manufacture of phthalic anhydride by gas phase oxidation of a mixture of

C.sub.1 -- to C.sub.6 -N-alkylpyrrolidones are produced from succinic anhydride and C.sub.1 -- to C.sub.6 -N-alkylamines or C.sub.1 -- to C.sub.6 --N-alkylsuccinimides. They are hydrogenated in the presence of a Ni hydrogenation catalyst containing from about 0.1-3% of one or several alkaline earth oxides and/or iron oxide and/or chromium oxide, at temperatures of from about 180.degree.-250.degree. C. and under pressures of at least about 100 bar. Preferably, a Ni catalyst is utilized which contains a total of 1.5-2% alkaline earth oxides, iron oxide and chromium oxide.

Process for the production of C.sub.1 -- to C.sub.6 -N-alkylpyrrolidones

2- and 4-tert-butylcyclohexanols are produced having high proportions of cis-isomers, by hydrogenating the corresponding tert-butylphenols in the presence of Pd and Ru catalysts in two stages under hydrogen pressures of above 200 bar and at temperatures of 70.degree.-280.degree. C. In the first stage, a Pd catalyst is employed, and a Ru catalyst is used in the second stage.

Process for the production of 2- and 4-tert-butylcyclohexanols with high

A process for producing polyalkylpiperidylamines of the formula (I): ##STR1## wherein R.sub.1 is hydrogen or a C.sub.1 -C.sub.12 alkylradical; R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkylradicals or R.sub.2 and R.sub.3, taken together, are --(CH)--.sub.a or --CH.sub.2 --NR.sub.1 --C(R.sub.5,R.sub.6)--CH.sub.2 --; R.sub.4 is a C.sub.2 -C.sub.18 alkylene radical, which is unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl; a C.sub.5 -C.sub.12 cycloalkylene radical, which is unsubstituted or is methyl-substituted; a cycloalkylene radical of the formula ##STR2## where the cyclohexyl rings are unsubstituted or are methyl-substituted; or groups of the formula --(CH.sub.2).sub.k --X--[CH.sub.2).sub.m --X]--.sub.n (CH.sub.2).sub.p --, where X is --O--, --NH--, --NR.sub.5 and R.sub.5 and R.sub.6 are each a C.sub.1 -C.sub.5 alkyl radical and a is 4 or 5, k is 2 or 3, n is 0-3 and p is 2 or 3; which process involves reductively alkylating an alkylated 4-aminopiperidine of the formula (II): ##STR3## with a difunctional alcohol of the formula HO--R.sub.4 --OH, wherein R.sub.1 and R.sub.4 have the above definitions.

Process for the production of polyalkylpiperidylamines

In a process for the production of neopentyl glycol comprising high-pressure hydrogenating a crude hydroxypivalaldehyde, containing the monoisobutyric acid ester of neopentyl glycol as an impurity, in the liquid phase over a barium-activated copper chromite catalyst, an improvement comprises hydrogenating the crude hydroxypivalaldehyde in the presence of 3-8% of water, and in two stages, wherein, in the first stage, the temperature is 120.degree.-160.degree. C. and the charge of hydrogenation starting material is 0.05-1.0 liter/liter of catalyst . h., and in the second stage, the temperature is 170.degree.-200.degree. C. and the charge of hydrogenation starting material is 0.05-1.0 liter/liter of catalyst . h., whereby there is obtained neopentyl glycol having a degree of purity of above 98% as determined by gas chromatographic analysis.

Two stage hydrogenation to make neopentyl glycol

The oxo process wherein propene is hydroformylated and then distilled to separate n-butyraldehyde, iso-butyraldehyde, n-butanol, iso-butanol, n-butyl formate, iso-butyl formate and distillation residues having an acid number of about 80 to 130 is improved by adding to the distillation residues molar to twice molar amounts, relative to the acid content, of n-butanol, isobutanol or mixtures thereof, carrying out an esterification in the presence of catalytically active amounts of sulphonic acids at temperatures from about 50.degree. to 200.degree. C., separating off the water of reaction, distilling the esterification reaction product and hydrogenating the distillate thereof.

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Marl, Germany

Manfred Zur Hausen