Huels Aktiengesellschaft

Chemische Werke Huls Aktiengesellschaft

Chemische Werke Huels Aktiengesellschaft

Chemische Werke Huls Aktiengesellchaft

Friedrich-Wilhelm Kupper

Heinz-Werner Voges

Roland Streck

Wolfgang H Muller

Alfred Oberholz

Richard Schaaf

Werner Patzold

Karl-Heinz Nordsiek

Bernhard Stutzel

Hans-Jurgen Haage

Wolfgang Schroder

Alfred Wieland

Helmut Schwesig

Walter Trautmann

Ulrich Reichert

Gunter Padberg

A method of manufacturing orthosubstituted alkylphenols, employing a catalyst of increased activity, by reacting phenol or 2-alkylphenols with 2-alkyl-1-alkenes and/or 2-aryl-1-alkenes in the liquid phase, optionally in the presence of inert diluents and/or an excess of the alkene, wherein the reaction is carried out in the presence of modified aluminum-containing catalysts obtained by adding small amounts of polyhalophenols, each having at least 3 like or unlike halogen substituents from the group of the elements fluorine, chlorine, and bromine, serving as cocatalysts, to known aluminum trisphenolate catalysts, wherein the molar ratio between the cocatalysts and the aluminum compound is in the range 0.5:1-8:1. The invention also relates to the catalyst for manufacturing the ortho-alkylated phenols, which catalyst is comprised of the (2-alkyl)phenol undergoing alkylation, an organoaluminum compound, and a polyhalophenol as the (or a) cocatalyst.

Method of manufacturing ortho-substituted alkylphenols, and catalyst

The invention relates to a method of cyclooligomerization of 3-hydroxy-1-alkynes having 4-20 C atoms, particularly cyclooligomerization of 3-methyl-1-butyne-3-ol to yield 1,3,5-tris(.alpha.-hydroxyisopropyl)-benzene, with the aid of nickel-containing catalysts formed from a nickel compound, a phosphite of an ortho-substituted phenol, and an organoaluminum compound of formula

Method for the cyclooligomerization of 3-hydroxy-1 alkynes

For producing 2,6-di-tert-butylphenol and products therefrom, utilizing small quantities of aluminum tris-(2-tert-butylphenolate as a catalyst by reaction of 2-tert-butylphenol with isobutene in the liquid phase, the reaction is performed in the presence of diluents such as liquid saturated aliphatic or cycloaliphatic hydrocarbons, C.sub.5 -C.sub.16 alkenes of formula R.sub.1 --CH.dbd.CH.sub.2 or R.sub.2 --CH.dbd.CH--R.sub.3, C.sub.5 to C.sub.12 cycloalkenes, which contain no branching on the C.dbd.C-bond, excess isobutene or mixtures thereof, at temperatures of 0.degree. C. to 80.degree. C., pressures of 0.1 to 11 bars and catalyst amounts of 0.005 to 5 mol %, based on 2-tert-butylphenol. High conversions are obtained with few undesirable trialkylated products.

Process for the production of 2,6-di-tert-butylphenol

Useful for the stabilization of polymers, especially polypropylene and polyethylene are esters of 3-tert-butyl or 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane) carboxylic acids with oxethylates of bis-(4- or 2-hydroxyphenyl) alkanes, oxides, sulfides or sulfones, with oxethylates of tris-(4-hydroxyphenyl) alkanes, or with oxethylates of 1,3,5-tris-(4-hydroxyphenyl isopropylidene) aryls, the oxethylate preferably comprising a hydroxyethoxy group substituted for each hydroxyl group.

Esters of 3-tert-butyl or 3-tert-butyl-5-alkyl-4-hydroxylphenyl(alkane)

Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl (alkane) carboxylic acids with oxyethylates of polythiols are useful as stabilizers for polymers, especially for polyethylene and polypropylene.

Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl

Esters of 3-tert-butyl- and 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane) carboxylic acids of Formula I ##STR1## with oxethylates of polyhydroxyaromatics of 2-6 hydroxy groups of general Formulae II and III, containing 1-6 oxethylate units, ##STR2## with X=(CH.sub.2).sub.q OH

Molding compositions based on polyvinyl chloride contain as the component imparting impact resistance homo- and copolymeric acrylic acid esters of oxethylates of phenol or of substituted phenols, wherein the difference of the indices of refraction n.sub.D.sup.20 (at least 20.degree. C., measured with the Na D line) between the basic polymer and the component imparting impact resistance at most is .+-.0.01; optionally copolymers with other acrylic acid esters can also be used in the molding compositions. The latter are inexpensive to manufacture and, besides transparency and weatherability, also have impact resistance.

Transparent, impact-resistant molding compositions based on polyvinyl

Impact-resistant modified styrene polymers having the characteristics: molecular weight M.sub.v 150,000 to 170,000; gel content exceeding 22%; degree of swelling of 11.5 to 13.5 and a mean gel particle diameter of 1.7 to 4.5 microns are produced by continuously polymerizing a styrene solution of polybutadiene, possibly in the presence of diluents, by means of a cascade consisting of at least three continuous stirred tank reactors, at rising temperatures and in the presence of organic peroxide initiators. The process steps are carried out as follows:

Production of impact-resistant styrene polymers

Vulcanizable polyalkenamer molding compositions comprising: (a) a polyoctenamer having an extensively cyclic structure with a trans-content of 50-70% and a reduced specific viscosity of 0.8-1.7 (dl./g.); and (b) conventional elastomer vulcanizing agents and additives have improved flow properties suitable for thermoplastic molding techniques together with mechanical properties in the vulcanizate comparable to SBR rubber.

Vulcanizable molding compositions

7,8-Epoxy-2-methyloctadecane is economically prepared by a metathesis reaction of 7-methyl-1-octene and 1-dodecene to form 2-methyl-7-octadecene which is then epoxidized to give the desired product.

Process for the preparation of 7,8-epoxy-2-methyloctadecane

Higher alkenes with a double bond in the 9-position, e.g. 9-tricosene and/or 9-heneicosene, are economically prepared by a metathesis reaction of suitable alkene starting materials.

Process for the preparation of 9-tricosene and 9-heneicosene

A process for the production of cyclopentene free of C.sub.5 -diene impurities, which comprises metathetically reacting cis,cis-cyclodecadiene-(1,6) with a catalytic amount of a metathesis catalyst comprising a support material and an oxide of an element of Group VI A or VII A of the Periodic Table, at a reaction temperature of from 0.degree.C up to the temperature at which said catalyst decomposes, for a period of time sufficient to form said cyclopentene.

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Marl, Germany

Friedrich-Wilhelm Kupper