Albemarle Corporation

Ethyl Corporation

Albmarle Corporation

Si Group, Inc.

Hassan Y Elnagar

Joe D Sauer

Mahmood Sabahi

Bonnie G McKinnie

Richard A Holub

Vincent James Gatto

Ronny W Lin

Christopher J Nalepa

Arcelio J Malcolm

Robert L Davis

Bruce C Peters

Dustin H Thomas

Edgar E Spielman, Jr

Meng-Sheng Ao

Thanikavelu Manimaran

Robert H Allen

Jamie R Strickler

Chi Hung Cheng

K Pushpananda Senaratne

Ralph W Magin

J Robert Adams, Jr

Alvin E Harkins, Jr

Robert C Herndon

Felix M Orihuela

Noel H Brantley

Jonathan N Howarth

John F Balhoff

Kestutis A Keblys

Richmond M Starrett

William S Pickrell

Chi-Hung Cheng

Steven R Alferi

J Robert Adams

Robert M Moore

This invention provides a process for the N-halogenation of at least one 5-hydrocarbyl hydantoin and/or at least one 5,5-dihydrocarbyl hydantoin. The process comprises concurrently feeding into a reaction zone (i) water, inorganic base, and 5,5-dimethylhydantoin, these being fed separately and/or in any combination(s), (ii) a separate feed of a brominating agent, and (iii) a separate feed of a chlorinating agent, in proportions such that during all or substantially all of the time the concurrent feeding is occurring halogenation of the 5-hydrocarbyl hydantoin and/or 5,5-dihydrocarbyl hydantoin occurs and resultant halogenated product precipitates in the liquid phase of an aqueous reaction mixture, and in which the pH of the liquid phase is continuously or substantially continuously maintained in the range of about 2.0 to about 8.0 during all or substantially all of the time the concurrent feeding is occurring. Also provided by this invention is a composition of matter which is a halogenated 5-hydrocarbyl hydantoin or a halogenated 5,5-dihydrocarbyl hydantoin, which is a mixture of the 1,3-dibromo-, 1,3-dichloro-, and/or N,N'-bromochloro-species of the halogenated hydantoin.

Process for producing N-halogenated hydantoins

This invention relates to novel macromolecular amine-phenolic compositions having oxidation inhibition characteristics that are exhibited when added to organic material normally susceptible to oxidative degradation in the presence of air or oxygen, such as petroleum products, synthetic polymers, and elastomeric substances.

Macromolecular amine-phenolic antioxidant compositions, process technology thereof, and uses thereof

This invention relates to novel macromolecular compositions having oxidation inhibition characteristics that are exhibited when added to organic material normally susceptible to oxidative degradation in the presence of air or oxygen, such a petroleum products, synthetic polymers, and elastomeric substances.

Alkylated heterocyclic reaction products useful as antioxidants

A novel manufacturing process is described for producing hindered phenolic alkyl esters, which may be useful as antioxidants. This process simplifies catalyst neutralization and removal during the preparation of hindered phenolic esters. Compositions that comprise the hindered phenolic esters produced according to these methods are also described.

Preparation of sterically hindered hydroxyphenylcarboxylic acid esters

Propargyl bromide is effectively stabilized against shock or thermal decomposition by use therewith of an environmentally acceptable inert liquid solvent that forms an azeotrope with propargyl bromide.

Stabilization and use of propargyl bromide

The process enables highly effective N-halogenation of a compound having one or more halogenatable amido or imido functional groups in the molecule. The process involves, for example, concurrently feeding into a reactor (i) water, inorganic base, and the compound to be N-halogenated, e.g., a hydantoin, and a feed of (ii) a brominating agent and/or a chlorinating agent. The proportions of these feeds are such that the pH is kept within the range of ca. 5.5-8.5 (preferably 6.5-8.5, and most preferably 6.8-7.2) and one or more of the amido or imido nitrogen atoms is substituted by a bromine or chlorine atom. A feature of the process is that it can be conducted at elevated temperatures as high as about 90&deg; C. without appreciable thermal decomposition of reactants or product. The resultant product continuously precipitates in high yield and purity. Moreover, products can be produced that are very pale yellow to almost pure white in appearance. Further, the process has been found capable of producing 1,3-dibromo-5,5-dimethylhydantoin with far larger particle sizes than previously produced on a commercial basis.

Process for producing N-halogenated organic compounds

Among the enhanced properties of the 1,3-dibromo-5,5-dimethylhydantoins described are their larger average particle sizes, their compactibility even though devoid of a binder, their excellent free-flowing and low-dust properties, and their more appealing aesthetic qualities, as compared to previously known 1,3-dibromo-5,5-dimethylhydantoins. These novel 1,3-dibromo-5,5-dimethylhydantoins can be produced, for example, by concurrently feeding (i) an aqueous solution or slurry formed from an inorganic base and 5,5-dimethylhydantoin, and (ii) a brominating agent, in proportions such that each nitrogen atom is substituted by a bromine atom, thereby forming product which precipitates in an aqueous reaction mixture. The pH of the reaction mixture is maintained in the range of about 5.5 to about 8.5.

1,3-dibromo-5,5-dimethylhydantoin of enhanced properties

Aromatic substrates are Ar-brominated in high yield and selectivity by reacting the substrate with a brominating agent in the presence of at least about 0.19 gram per mmol of substrate of a zeolite catalyst which has an absorbed water content of no greater than about 7.5 weight percent.

Selective bromination of aromatic compounds

This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br,during the feed of bisphenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.

Process for the preparation of tetrabromobisphenol-A

This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br,during the feed of bis-phenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.

This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features the addition of bisphenol-A to a reaction mass containing unreacted Br.sub.2 and 30 to 85 wt % water and an alcohol solvent, the reaction mass being at a relatively high temperature.

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Baton Rouge, LA, United States of America

Hassan Y Elnagar