Ethyl Corporation

Albemarle Corporation

Other

Albermarle Corporation

Albmarle Corporation

Bonnie G McKinnie

Paul F Ranken

Hassan Y Elnagar

Richard A Holub

Olan W Mitchell

David R Brackenridge

Gene C Robinson

Alvin E Harkins, Jr

Gary L Sharp

Alireza M Dadgar

Thanikavelu Manimaran

Everett M Marlett

Robert E Williams

Mark A Templeton

Saadat Hussain

Meng-Sheng Ao

Robert M Moore, Jr

Robert L Davis

Phillip R Beaver

William B Harrod

John Kirby Kendall

Warren B Kirsch

Tyson J Hall

Scott A Bottelberghe

Joseph H Miller

Daniel A Wood

J Todd Aplin

W Brian Harrod

Clinton R Parham

Steven R Alferi

Steven G Miller

Robert U Lyons

David E Raposa

A process for oxygen-initiated hydrobromination of propene to form a crude reaction mixture of 95 GC area % n-propyl bromide. The process includes feeding an oxygen-containing gas, propene and hydrogen bromide into a liquid phase mixture comprised of n-propyl bromide and hydrogen bromide. At least the oxygen-containing gas and the propene of the feed are fed subsurface to the liquid phase mixture and either (a) the oxygen-containing gas and the propene do not come together in the absence of hydrogen bromide or (b) the oxygen-containing gas and the propene come together only in a propene:oxygen molar ratio in the range of 145:1 to 180:1. Purification processes provide a propyl bromide product containing at least 99.7 GC area % n-propyl bromide. Also provided is a novel composition of enhanced thermal stability which comprises a mixture of n-propyl bromide and isopropyl bromide. The mixture has an n-propyl bromide content of at least 99.7 GC area %, and an isopropyl bromide content of no more than 0.05 GC area %. The mixture, if subjected to storage in a closed chemically inert container at 60&#xb0; C. for at least 480 hours, has an APHA color of 10 or less while the mixture is devoid of any added stabilizer component.

Processes for production and purification of normal propyl bromide

Certain substituted phenolic compounds when used with or without 1,2-epoxides as the sole stabilizer components are very effective in stabilizing n-propyl bromide (NPB). In a standard commercially important 60&#xb0; C. stability test, representative substituted phenolic compounds used pursuant to this invention, can enable NPB to pass the test even though present at levels of about 50 ppm (wt/wt) or less in NPB containing no other stabilizer additive component. In fact, amounts as low as 1 ppm have been found effective with various substituted phenolic compounds. In addition, it has been found that one of the preferred stabilizers of this invention&#x2014;2,6-di-tert-butyl-p-cresol&#x2014;even though higher boiling than NPB, left inconsequential amounts of residue at least throughout the range of 1 to 30 ppm (wt/wt). Also, it has been found that certain other preferred stabilizers of this invention can provide synergistically improved stability in passing the 60&#xb0; C. stability test when used with at least one 1,2-epoxide, notably butylene oxide.

Stabilized propyl bromide compositions

High assay reaction-derived decabromodiphenylethane product is produced and provided. The process comprises feeding diphenylethane, a partially brominated diphenylethane, or both subsurface into the liquid phase of a reaction mixture formed from components comprising excess liquid bromine and aluminum-based Lewis acid bromination catalyst. The temperature of the reaction mixture, the catalyst concentration in the excess bromine in the reaction mixture, and the feed time are coordinated in the processes to produce high assay reaction-derived decabromodiphenylethane product. Ways of effecting such coordination are described.

Preparation and provision of high assay decabromodiphenylethane

Bromine is scrubbed from a gaseous mixture of bromine and hydrogen bromide by passing the mixture into a mixture formed from (i) diphenylethane and/or partially brominated diphenylethane with average bromine number less than about 2 and (ii) a catalytic quantity of iron and/or iron halide in which the halogen atoms are bromine atoms and/or chlorine atoms. Component (i) is brominated, and during such bromination, the mixture is kept hot enough to melt the organics to provide a liquid phase in the scrubber. Gaseous mixtures of bromine and hydrogen bromide are formed in processes of the invention in which decabromodiphenylethane products are produced using the partially brominated diphenylethane as feed to the bromination, which is conducted using an aluminum-based catalyst. Effective ways of removing iron catalyst residues from partially brominated diphenylethane or from decabromodiphenylethane product are also described.

Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane

Bisphenol-A-bis(neopentylglycolphosphate) products of enhanced properties and processes for preparing them are described. One of the processes includes (a) mixing and reacting neopentyl glycol and bisphenol-A-bis(dichlorophosphate) in an inert polar organic solvent which (1) if mixed by itself with an equal volume of water at 25&#xb0; C., will form a separate phase, (2) the solvent by itself will dissolve at least about 10 wt % of bisphenol-A-bis(neopentylglycolphosphate) at a temperature in the range of 25 to 50&#xb0; C., and optionally but preferably (3) the solvent by itself can be completely vaporized at a temperature below about 180&#xb0; C.; (b) washing bisphenol-A-bis(neopentylglycolphosphate) product formed in a) while dissolved in inert organic solvent having such characteristics at least once with an aqueous alkaline washing solution; and (c) optionally but preferably, recovering bisphenol-A-bis(neopentylglycolphosphate) product from organic solvent having such characteristics. The reaction of (a) can be conducted in an inert non-polar solvent if that solvent is replaced by an inert polar organic solvent satisfying (1) and (2), and preferably (3). A solvent satisfying (1), (2), and (3) is used when (c) is conducted by distilling or vaporizing off the solvent to recover the bisphenol-A-bis(neopentylglycolphosphate) product as such. The product has a low acid number or a high thermal stability, and usually both.

Separation process

Process technology for selectively isomerizing vinylidene olefin to tri-substituted olefin is described. The vinylidene olefin, normally in admixture with other types of olefins, especially linear 1-olefins, is treated with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator. The contacting period, which can be a matter of minutes, is sufficient to selectively isomerize the vinylidene olefin to tri-substituted olefin. If the process is conducted properly, little if any hydrobromination occurs.

Isomerization of vinylidene olefins

In producing aqueous microbiocidal solutions by oxidation of a water-soluble alkali metal bromide, an intolerable loss of active halogen species has been found to occur during a 10-day period immediately after the product solution has been formed. Surprisingly, this loss has been found to result from an alcohol impurity in the alkali metal bromide used in the process. By eliminating or at least sharply reducing the amount of alcohol impurity in the reaction mixture, products are formed which do not undergo the intolerable loss of active halogen content during the 10-day period.

Stabilized active bromine biocidal solutions

Concentrated liquid biocide compositions are produced by: A) feeding (a) bromine atoms and chlorine atoms in the form of (i) one or more of BrCl, (ii) Br , and (iii) Cl into (b) water containing sulfamate anions, or feeding each of (a) and (b) into a reaction vessel, such that the numerical ratio of the total number of bromine atoms fed to the total number of chlorine atoms fed is in the range of about 0.7:1 to about 1.7:1; and B) providing enough alkali metal base in the mixture being formed in A) to keep the pH of such mixture in the range of about 7-11 during all or substantially all of the time feeding in A) is occurring, the amounts of (a) and (b) used being amounts that form an active-bromine-containing solution in which (i) the active bromine content is 50,000 ppm or more, and (ii) the atom ratio of nitrogen to active bromine originating from (a) and (b) is greater than about 0.93; and wherein if any sulfate is present in the solution as formed, the molar ratio of sulfate to sulfamate in the solution is less than about 0.2.

Concentrated aqueous bromine solutions and their preparation

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.

This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: (a) feeding to a reaction mass (i) bisphenol-A and (ii) a stream of gaseous bromine, the gaseous stream having a Reynold's No. .gtoreq.40,000; (b) the reaction mass containing from about 50 to about 20,000 ppm unreacted bromine and less than 20 wt % HBr; and (c) the reaction mass having precipitated therefrom tetrabromobisphenol-A, all of (a)(ii), (b) and (c) occurring during the bisphenol-A feed.

This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.

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Magnolia, AR, United States of America

Bonnie G McKinnie