Huels Aktiengesellschaft

Chemische Werke Huels Aktiengesellschaft

Huls Aktiengesellschaft

Miles Inc.

Werner Otte

Rudolf Nehring

Manfred Zur Hausen

Manfred Kaufhold

Klaus Burzin

Gary F Allen

Jorg Dorffel

Erhard Lange

Friedrich Heinrich

George H Schmelzer

Guenther K Bub

The present invention is directed to a process for the catalytic hydrogenation of a starting material containing 4,4'-diamino-diphenylmethane (4,4'-MDA) or its mixtures with 2,4'-diamino-diphenylmethane, 2,2'-diamino-diphenylmethane and/or higher ring compounds of the diphenylmethane series to a hydrogenation product having a trans-trans isomer content of 4,4'-diamino-dicyclohexylmethane (4,4'-HMDA) of about 15 to 40 weight percent, based on the diamine content of the hydrogenated product, by continuously hydrogenating in at least one fixed bed reactor at a temperature of about 100.degree. to 190.degree. C. and a pressure of about 50 to 350 bar in the presence of a ruthenium catalyst on a catalyst support having a BET surface area of about 70 to 280 m.sup.2 /g and an average pore diameter d.sub.p of about 10 to 320 .ANG., the catalyst being prepared by impregnating the catalyst support to a penetration depth of at least about 50 .mu.m with a soluble ruthenium compound in an amount sufficient to provide a catalyst containing about 0.1 to 5 weight percent ruthenium and subsequently reducing the soluble ruthenium compound to ruthenium.

Process for the production of 4,4'-diamino-dicyclohexylmethane with a

A process for the preparation of 5-chloro-2-pentanone starting from a ketal of a levulinic ester, followed by hydrogenation, and then reaction with hydrochloric acid. The process involves first purifying the ketal of the levulinic ester by distillation, making the hydrogenation catalysts for the ketal alkaline, and reacting the 3-(2-methyl-1,3-dioxolan-2-yl)propan-1-ol formed in this hydrogenation with hydrochloric acid to obtain 5-chloro-2-pentanone.

Process for the preparation of 5-chloro-2-pentanone

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

For the selective production of hydroxymethylcyclopropane, cyclopropanecarboxylic acid esters are hydrogenated in the presence of a Zn chromite catalyst in the sump phase or trickling phase under a hydrogen pressure of 200-320 bar and at temperatures of 200.degree.-350.degree. C. Preferably, cyclopropanecarboxylic acid esters are used, the alcohol component of which contains 1-10, especially 1-8 carbon atoms.

Process for the production of hydroxymethylcyclopropane

A method of producing cyclohexyl compounds by catalytic hydrogenation of benzyl compounds, particularly acetophenone, whereby the benzyl compounds are hydrogenated in the presence of a catalyst comprising Ru and a support, with said benzyl compounds being in a slurry or a trickling liquid phase, at a hydrogen pressure of 200-350 bar, particularly 250-320 bar, and a temperatures of from 80.degree. to about 160.degree. C., particularly 100.degree.-130.degree. C., wherewith the catalyst contains Ru in the amount of, in particular, 0.1-1 wt. %.

Method of producing cyclohexyl compounds

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 naphtha-soluble, hydrogenated C.sub.1-4 -alkyl C.sub.6-10 -aryl ketone/formaldehyde resin, having an oxygen content of at least 6% by weight and a softening point of at least 70.degree. C. can be produced by a process comprising the step of hydrogenating a C.sub.1-4 -alkyl C.sub.6-10 -aryl ketone/formaldehyde resin under a hydrogen pressure of at least 200 bar and a temperature of 140.degree.-300.degree. C., in the presence of a nickel, palladium, palladium/copper or palladium/nickel catalyst. These resins are useful, for example, as additives to improve the hardness of varnishes and other coatings.

Naphtha-soluble, hydrogenated alkyl aryl ketone/formaldehyde resins and

Aliphatic ethers of hydroxymethylcyclododecane of the general formula ##STR1## wherein R is a saturated or unsaturated aliphatic hydrocarbon residue of 1-4 carbon atoms, are valuable odoriferous substances possessing a long-lasting, intense woodsy scent with a balsam note of great richness.

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Dorsten, Germany

Werner Otte