Halcon International, Inc.

Olav Torgeir Onsager

Peter L Szecsi

Ethylene glycol is prepared by the reaction of ethylene, molecular oxygen and water in the presence of an iodine catalyst and in the presence of a copper co-catalyst or promoter.

Process for producing ethylene glycol

Acrylonitrile is dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is Zn or Co, X is an anion derived from an alkyl or aryl sulfonic acid or from a carboxylic acid containing at least two carbon atoms which is substituted by at least one of the groups, --F, --Cl, --Br, --I and --CN in the .alpha.--C-position relative to the acid group and n is a number equal to the valence of the metal M divided by the number of acid equivalents of X and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoamine of the formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are the same or different and each is an alkyl, cycloalkyl, benzyl or aryl radical; or (2) a tertiary di- or poly-functional amine which contains at least two Lewis Base nitrogen groups separated from each other by at least one carbon atom and which are (a) N-disubstituted amino groups wherein each N-substituent is the same or different and is an alkyl, cycloalkyl, benzyl or aryl radical, or (b) N-heterocyclic groups containing 3 to 20 carbon atoms; or (3) an N-substituted heterocyclic amine containing 3 to 20 carbon atoms in the heterocyclic ring wherein the N-substituent is an alkyl, cycloalkyl, benzyl or aryl radical.

Dimerization process

Ethylene glycol is prepared in an oxidation zone by the reaction of ethylene, molecular oxygen, and water in the presence of an iodine source to produce a liquid reaction product which is separated into a lower-boiling portion, a glycol fraction and a higher-boiling portion and the higher-boiling portion is recycled to the oxidation zone together with part of the lower-boiling portion.

Preparation of ethylene glycol

Derivatives of the .alpha.,.beta.-unsaturated carboxylic acids are dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is zinc, aluminum, titanium, vanadium, iron, or cobalt, X is a halide and n is a number equal to the valence of the metal M and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoaryl amine of the formula, ##EQU1## wherein R.sup.1 and R.sup.2 are the same or different and each is an alkyl group or a cycloalkyl group with at least one of R.sup.1 and R.sup.2 containing at least two carbon atoms; or (2) a tertiary monobenzyl amine of the formula, ##EQU2## wherein R.sup.3 and R.sup.4 are the same or different and each is an alkyl or cycloalkyl radical; or (3) a tertiary di- or poly-functional amine which contains at least two Lewis Base nitrogen groups which are separated from each other by at least one carbon atom, and are (a) N-disubstituted amino groups wherein each N-substituent is the same or different and is an alkyl, cycloalkyl, benzyl, aryl radical or (b) N-heterocyclic groups containing 3 to 20 carbon atoms; or (4) an N-substituted heterocyclic amine wherein the N-substituent is an alkyl, benzyl, cycloalkyl or aryl radical.

Dimerization method

Acrylonitrile is dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is Zn or Co, X is an anion derived from an alkyl or aryl sulfonic acid or from a carboxylic acid containing at least two carbon atoms which is substituted by at least one of the groups, --F, --Cl, --Br, --I and --CN in the .alpha.-C-position relative to the acid group and n is a number equal to the valence of the metal M divided by the number of acid equivalents of X and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoamine of the formula ##EQU1## wherein R.sup.1, R.sup.2, and R.sup.3 are the same or different and each is an alkyl, cycloalkyl, benzyl or aryl radical; or (2) a tertiary di- or poly-functional amine which contains at least two Lewis Base nitrogen groups separated from each other by at least one carbon atom, and which are (a) N-disubstituted amino groups wherein each N-substituent is the same or different and is an alkyl, cycloalkyl, benzyl or aryl radical, or (b) N-heterocyclic groups containing 3 to 20 carbon atoms; or (3) an N-substituted heterocyclic amine containing 3 to 20 carbon atoms in the heterocyclic ring wherein the N-substituent is an alkyl, cycloalkyl, benzyl or aryl radical.

Acrylonitrile is dimerized by reaction in the presence of a catalyst consisting essentially of (a) at least one metal compound of the formula M(X).sub.n wherein M is magnesium, chromium or manganese, X is a halide and n is a number equal to the valence of the metal M and (b) at least one nitrogen-containing Lewis Base which is (1) a tertiary monoamine of the formula ##EQU1## wherein R.sup.1, R.sup.2, and R.sup.3 are the same or different and each is an alkyl, cycloalkyl, benzyl or aryl radical; or (2) a tertiary di- or poly-functional amine which contains at least two Lewis Base nitrogen groups separated from each other by at least one carbon atom, and which are (a) N-disubstituted amino groups wherein each N-substituent is the same or different and is an alkyl, cycloalkyl, benzyl or aryl radical, or (b) N-heterocyclic groups containing three to 20 carbon atoms; or (3) an N-substituted heterocyclic amine containing three to 20 carbon atoms in the heterocyclic ring wherein the N-substituent is an alkyl, cycloalkyl, benzyl or aryl radical.

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Suffern, NY, United States of America

Olav Torgeir Onsager