General Electric Company

Sabic Innovative Plastics IP B.v.

John Yaw Ofori

Eric James Pressman

Grigorii Lev Soloveichik

Kirill Vladimirovich Shalyaev

Bruce Fletcher Johnson

James Lawrence Spivack

James Norman Cawse

Richard Anthony Battista

Ben Purushotam Patel

Ryan Christopher Mills

Eric Douglas Williams

Donald Wayne Whisenhunt, Jr

Ganesh Kailasam

Marsha Mottel Grade

Jonathan Lloyd Male

Ben Purushatom Patel

Larry Neil Lewis

Eugene Pauling Boden

Alberto Nisoli

Angel Sanchez Gonzalez

Donald Wayne Whisenhunt

Julia L Lee

John E Hallgren

Sheldon J Shafer

Ignacio Vic Fernandez

Timothy Leigh Chuck

Peter John Bonitatebus, Jr

Phillip Oscar Moreno

Ben Purushtotam Patel

Unexpected corrosion of downstream sections of a dialkyl carbonate manufacturing apparatus has been traced to alkyl chloroformate impurities, which slowly decompose to yield hydrochloric acid. An improved process and apparatus for dialkyl carbonate synthesis reduce corrosion by physically removing or chemically decomposing the alkyl chloroformate impurities within the corrosion-resistant upstream sections of the apparatus. The alkyl chloroformate may be decomposed by passing it through a passageway at a temperature of about 30&#xb0; C. to about 130&#xb0; C. for a time of about 0.5 hour to about 10 hours. The passageway may include one or more holding vessels or a tubular section that promotes plug flow.

Method and apparatus for preparing a dialkyl carbonate, and its use in the preparation of diaryl carbonates and polycarbonates

Unexpected corrosion of downstream sections of a dialkyl carbonate manufacturing apparatus has been traced to alkyl chloroformate impurities, which slowly decompose to yield hydrochloric acid. An improved process and apparatus for dialkyl carbonate synthesis reduce corrosion by physically removing or chemically decomposing the alkyl chloroformate impurities within the corrosion-resistant upstream sections of the apparatus.

A method for brominating hydroxyaromatic compounds to form products, such as p-bromophenol, is disclosed. The method uses elemental bromine as the brominating agent and comprises contacting a hydroxyaromatic compound with bromine and oxygen in the presence of metal catalyst. Suitable catalysts include elemental copper, copper compounds, and compounds of Group IV&#x2013;VIII transition metals.

Bromination of hydroxyaromatic compounds

Brominated hydroxyaromatic compounds such as p-bromophenol are prepared by contacting a hydroxyaromatic compound with oxygen and a bromine source such as hydrogen bromide or an alkali metal or alkaline earth metal bromide in an acidic medium, in the presence of elemental copper or a copper compound as catalyst. The brominated product of this reaction may be converted alternately to a dihydroxyaromatic compound such as hydroquinone by hydrolyses, or a dihydroxybiphenyl compound such as 4,4'-dihydroxybiphenyl by reductive coupling.

Bromination of hydroxyaromatic compounds and further conversion to dihydroxyaromatic compounds

A method for preparing and isolating dihydroxybiaryl compounds, such as 4,4'-dihydroxybiphenyl, is disclosed. The alkali metal salt of the dihydroxybiaryl compound is protonated with the monohydroxyaryl halide compound initially used in the reductive coupling reaction which produced the alkali metal salt. In addition, the alkali metal salt of the monohydroxyaryl halide compound is produced by the process, which can then be recycled as the base and monohydroxyaryl halide in a further reductive coupling reaction to form the alkali metal salt of the dihydroxybiaryl compound.

Process for the recovery of dihydroxybiaryl compounds

A method for preparing hydroxyaromatic compounds brominated in the para-position, such as p-bromophenol, is disclosed. The method yields overall high process selectivity through isomeric equilibration and separation of the brominated products, thereby eliminating the need for high para selectivity in the products of catalytic oxybromination reactions of hydroxyaromatic compounds using oxygen, a bromine source, and an acidic medium in the presence of a metal catalyst. Furthermore, the invention provides an efficient method for recycling the metal catalyst, as well as reagents used in the bromination, to further reactions.

Method for preparation of para-brominated hydroxyaromatic compounds

A method is described for the simultaneous preparation of p-bromophenols and p-benzoquinones, intermediates useful in the preparation of hydroquinones and 4,4&prime;-dihydroxybiphenyls, respectively. Hydroquinones and 4,4&prime;-dihydroxybiphenyls are useful monomers for the preparation of a variety of polymers. The method also comprises reducing the p-benzoquinone to its corresponding hydroquinone in the presence of the p-bromophenol. Limiting the amount of HBr present in the reaction mixture was shown to control the amount of benzoquinone produced. The method also allows for the recycling of many of the reagents used, thereby reducing the cost of producing each monomer.

Method for preparing hydroquinones and dihydroxybiphenyl compounds from mixtures of bromophenols and benzoquinones

A method for economically producing aromatic carbonates from aromatic hydroxy compounds is disclosed which in one embodiment comprises the steps of: (i) contacting at a temperature sufficient to keep the mixture molten at least one aromatic hydroxy compound with a catalyst composition comprising the following and any reaction products thereof: (A) at least one Group 8, 9, or 10 metal or a compound thereof; (B) at least one salt; (C) at least one metal co-catalyst; and (D) optionally, at least one activating solvent; (ii) optionally heating the mixture at atmospheric pressure to a temperature above that sufficient to keep the mixture molten; (iii) pressurizing the mixture with carbon monoxide; (iv) optionally heating the mixture under pressure of carbon monoxide to a temperature above that sufficient to keep the mixture molten; (v) optionally maintaining the mixture under pressure of carbon monoxide for a time period; (vi) introducing oxygen to the mixture to a desired concentration of oxygen in carbon monoxide; (vii) starting gas flow to the mixture at a desired concentration of oxygen and carbon monoxide; (viii) optionally maintaining gas flow for a time period at less than a desired ultimate temperature for the mixture; and (ix) optionally heating the mixture to a desired ultimate temperature under flow of gases.

Method for producing aromatic carbonates

The present invention is directed to a method for reactivating a deactivated carbonylation catalyst composition previously used in a carbonylation reaction involving an aromatic hydroxy compound, carbon monoxide and oxygen, so that the re-activated catalyst composition is effective at carbonylating an aromatic hydroxy compound in a subsequent oxidative carbonylation reaction.

Method for reactivating a catalyst composition

Hydroxyaromatic compounds such as phenol are carbonylated with oxygen and carbon monoxide in the presence of a catalyst system comprising a Group VIIIB metal, preferably palladium; an iodide salt, preferably sodium iodide; and at least one organic bisphosphine such as 1,3-bis(diphenylphosphino)propane or 1,4-bis(diphenylphosphino)butane. The catalyst system also preferably contains a compound of cerium or lead.

Catalyst composition and method for producing diaryl carbonates, using bisphosphines

A process for catalytic production of diaryl carbonates by oxidative carbonylation of aromatic hydroxy compounds with carbon monoxide and oxygen achieves water removal during reaction by a process comprising the steps of: removing a liquid stream from an oxidative carbonylation reaction mixture in a reaction vessel and transferring the stream to a disengagement vessel, transferring a stream from the disengagement vessel to a flash vessel and subjecting the liquid stream to reduced pressure, and returning at least a portion of dried liquid stream to the reaction vessel. Typical catalyst systems for oxidative carbonylation contain (A) at least one Group 8, 9, or 10 metal having an atomic number of at least 44 or a compound thereof; (B) at least one guanidinium salt or onium salt; (C) at least one metal co-catalyst; and (D) at least one base.

Process for the production of diaryl carbonates

A method is disclosed for recovering a substantially water-soluble solvent from a reaction mixture comprising at least about 35% by weight aromatic hydroxy compound, which comprises the steps of: (i) extracting a reaction mixture at least once with aqueous acid wherein the solvent remains substantially in the organic phase; and (ii) recovering solvent from the organic phase.

Method for recovery of catalyst components

A process for catalytic production of diaryl carbonates by oxidative carbonylation of aromatic hydroxy compounds with carbon monoxide and oxygen achieves water removal during reaction by a process comprising the steps of: removing a liquid stream from an oxidative carbonylation reaction mixture in a reaction vessel, subjecting the liquid stream to reduced pressure, and returning at least a portion of dried liquid stream to the reaction vessel. Typical catalyst systems for oxidative carbonylation contain (A) at least one Group 8, 9, or 10 metal having an atomic number of at least 44 or a compound thereof; (B) at least one alkali metal salt; (C) at least one metal co-catalyst; (D) at least one activating organic solvent; and (E) optionally, at least one base.

The present invention is directed to a method for reducing the percent decomposition of an aromatic carbonate in a first reaction mixture comprising the aromatic carbonate, the method comprising the step of adding at least one decomposition-reducing additive to the first reaction mixture, so as to produce a second reaction mixture in which the percent of the aromatic carbonate present in the second reaction mixture after a predetermined amount of time is greater than the percent of the aromatic carbonate that would be present in the first reaction mixture in the absence of adding the decomposition-reducing additive, after the same predetermined amount of time.

Method for reducing carbonate decomposition in reaction mixtures

A method and catalyst system for economically producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the present invention provides a method of carbonylating aromatic hydroxy compounds by contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system that includes a catalytic amount of an inorganic co-catalyst containing lead and a catalytic amount of an inorganic co-catalyst containing titanium. In various alternative embodiments, the carbonylation catalyst system can include an effective amount of a palladium source and an effective amount of a halide composition. Further alternative embodiments can include catalytic amounts of various inorganic co-catalyst combinations.

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Niskayuna, NY, United States of America

John Yaw Ofori