Hoechst Celanese Corporation

Other

Celanese Gmbh

Graham N Mott

James R Sounik

Charles B Hilton

Ahmed M Tafesh

Joseph A McDonough

John R Durrwachter

B Frank Wood

Werner H Mueller

Mohammad Aslam

Kenneth G Davenport

Brad L Smith

Michael Meier

Edward G Zey

Varadaraj Elango

Mark A Murphy

Charlet R Lindley

Gary L Moss

Joel D Hendricks

Olan S Fruchey

Thomas S Johnson

The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.

Process for preparing 4-hydroxyphenylmethylcarbinol

The present invention provides a unique and novel way of producing polyhydroxystyrene which comprises the steps of (a) heating 4-hydroxyacetophenone under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable palladium catalyst and a basic material and for a sufficient period of time to form 4-hydroxyphenylmethylcarbinol; (b) heating 4-hydroxyphenylmethylcarbinol under suitable conditions of temperature and pressure and for a sufficient period of time to form said polyhydroxystyrene.

Process for preparing vinylphenol polymers & copolymers

The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and for a sufficient period of time to form HPMC.

The present invention provides a unique and novel way of producing vinyl phenols such as poly(4-hydroxystyrene) (PHS). In this new process, 4-hydroxyphenylmethylcarbinol (HPMC) is heated under suitable conditions of temperature and pressure and for a sufficient period of time to form the poly (4-hydroxystyrene) (PHS).

Process for preparing poly(4-hydroxystyrene)

The present invention provides a unique and novel way of producing polyhydroxystyrene which comprises the steps of (a) heating 4-hydroxyacetophenone under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable palladium catalyst and for a sufficient period of time to form 4-hydroxyphenylmethylcarbinol; (b) heating 4-hydroxyphenylmethylcarbinol under suitable conditions of temperature and pressure and for a sufficient period of time to form said polyhydroxystyrene.

Process for preparing vinylphenol polymers and copolymers

A process for the preparation of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone by reacting nitrosyl chloride with a mixture of 4-hydroxyacetophenone and a strong acid catalyst such as hydrogen chloride is disclosed. The nitrosyl chloride is introduced as a gas into the reactor to contact 4-hydroxyacetophenone and said acid catalyst dissolved in a solvent therein.

Process for preparing

This invention provides a process for directly preparing arylethylamines and their salts from (.alpha.-halo-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst. The process is illustrated by conversion of 4-hydroxy-(.alpha.-chloro-.alpha.-oximino)acetophenone to Tyramine hydrochloride: ##STR1##

Process for the preparation of arylethylamines and substituted

This invention provides a process for directly preparing hydrohalide salts of arylethylamines from (.alpha.-chloro-.alpha.-oximino)acetophenones. The process involves hydrogenation in presence of a transition metal catalyst in an organic acid in substantial absence of moisture. The process is illustrated by conversion of 4-hydroxy (.alpha.-chloro-.alpha.-oximino)acetophenone to Tyramine hydrochloride: ##STR1##

Arylalkylamines (as the hydrochloride salt), e.g. tyramine hydrochloride, are prepared by hydrogenating substituted or unsubstituted aryl-.alpha.-oximinoalkyl ketones, e.g. p-hydroxyisonitroacetophenone, in either in an aqueous reaction medium comprising hydrochloric acid, essentially without the presence of a lower alkyl alcohol in said reaction medium, or in an aqueous reaction medium comprising water, hydrochloric acid, and a lower alkyl alcohol, wherein the alcohol comprises less than about 90% by volume of the reaction medium. A substituent on the aryl portion of the aryl-.alpha.-oximinoalkyl ketone must be on a position which activates the aromatic ring.

Process for the preparation of arylalkylamines and substituted

A method is provided for the preparation of ibuprofen by carbonylating 1-(4'-isobutylphenyl)ethanol (IBPE) with carbon monoxide comprising initially a reaction mixture comprising IBPE, ibuprofen and a catalyst for the carbonylation with carbon monoxide under conditions to initiate the reaction, and continuing to feed carbon monoxide to the composition to produce the desired yield of ibuprofen. Preferably the catalyst comprises palladium and a monodentate phosphine ligand. The presence of ibuprofen in the feed composition when the reaction is initiated with CO makes it possible to obtain high selectivities to ibuprofen with substantially complete conversion of IBPE at much shorter reaction times than if no ibuprofen is present initially.

Method for producing ibuprofen

Compositions of matter, which are mono-, di- or tri-acrylate esters of 1,1,1-trishydroxyphenylethane and a method for the production of such esters by acrylating 1,1,1-tris(4'-hydroxyphenyl)ethane.

Acrylate esters of 1,1,1-trishydroxyphenylethane

Substituted phenethanol ethers are prepared by the catalytic reduction of corresponding substituted phenylglyoxal acetals. The catalytic reduction is carried out by reacting a substituted phenylglyoxal acetal with hydrogen in the presence of an acid catalyst and a metal catalyst. Certain substituted phenylglyoxal acetals, and more particularly, 4-hydroxyphenylglyoxal dialkyl acetals are prepared by reacting 4-hydroxyacetophenone with a primary or a secondary alkyl alcohol in the presence of a hydrogen ion (H+) source and a nitrosonium ion (NO+) source.

Process for preparing phenethanol ethers by the reduction of

The present invention provides a method for producing a hydroxyaromatic ketoacetal from a hydroxyaromatic methylketone. The invention further provides a method for producing a hydroxyaromatic ketoaldehyde from a hydroxyaromatic ketoacetal. The hydroxyaromatic ketoaldehyde can be further reacted to form a hydantoin, which hydantoin can be hydrolyzed to produce a hydroxyphenylglycine.

Formation of hydroxyaromatic ketoacetal from a hydroxyaromatic

A method is provided for preparing aromatic acetamides comprising reacting an aryl methyl ketone containing the same number of carbon atoms as the aromatic acetamide, with sulfur and ammonia under substantially anhydrous conditions. The method is particularly useful for the preparation of 4-hydroxyphenylacetamide from 4-hydroxyacetophenone.

Preparation of aromatic acetamides from aryl methyl ketones

A method is provided for the preparation of ibuprofen by carbonylating 1-(4'-isobutylphenyl)ethanol (IBPE) with carbon monoxide in an acidic aqueous medium, e.g. containing at least 10% of water based on the weight of IBPE initially added, at a temperature of at least about 10.degree. C. and a carbon monoxide pressure of at least about 500 psig, and in the presence of (1) a catalyst complex consisting essentially of a palladium compound in which the palladium has a valence of zero to 2 and is complexed with at least one monodentate phosphine ligand miscible with the organic phase of the reaction medium, the phosphorus/palladium mole ratio in said palladium compound and ligand being at least about 2:1 when the palladium/IBPE mole ratio is such that palladium=1 and IBPE=10,000 or more; (2) dissociated hydrogen ions from an acid which is substantially completely ionizable in dilute aqueous solution such that the mole ratio of hydrogen ions to IBPE added to the reaction zone is at least about 0.15; and, (3) dissociated halide ions such that the mole ratio of halide ions to IBPE added to the reaction zone is at least about 0.15. Advantageously, a hydrogen halide is the source of hydrogen ions and halide ions. The carbonylation is preferably integrated with a method of producing IBPE from isobutylbenzene wherein the latter compound is subjected to Friedel-Crafts reaction with an acetylating agent to produce 4-isobutylacetophenone, which is then reduced with hydrogen in the presence of a hydrogenation catalyst, or with a reducing agent containing available hydrogen, to obtain IBPE. The palladium catalyst complex can be precipitated from an organic phase of the carbonylation reaction which typically includes the ibuprofen product. The precipitated catalyst complex can be recycled without further treatment.

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Corpus Christi, TX, United States of America

Graham N Mott