Preparing By Alcoholysis, Hydrolysis Or Saponification Of An Ester Patents (Class 568/858)
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Patent number: 4519875Abstract: Ethylene glycol is purified, particularly for fiber-grade applications, by removal of the residual ethylene carbonate from which the glycol was derived. The effluent from a reactor in which ethylene carbonate is hydrolyzed to ethylene glycol is distilled to produce a lower-boiling fraction comprising substantially ethylene glycol and water and a higher-boiling fraction comprising substantially ethylene glycol, higher glycols, and concentrated in hydrolysis catalyst. The higher-boiling fraction is recirculated to reflux against the lower-boiling product, thereby essentially completing the hydrolysis of unreacted ethylene carbonate thereby reducing the ethylene carbonate content of the ethylene glycol to very low levels suitable for fiber-grade applications.Type: GrantFiled: May 9, 1984Date of Patent: May 28, 1985Assignee: The Halcon SD Group, Inc.Inventors: Mitchell Becker, Howard M. Sachs
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Patent number: 4508927Abstract: A process for preparation of glycols in which the vapor remaining after the partial condensation of a conventional ethylene oxide stripper overhead vapor stream is contacted with an aqueous solution of ethylene carbonate to recover ethylene oxide. No water need be removed from the enriched ethylene carbonate stream. Carbon dioxide is added and ethylene carbonate is formed by reaction at about 50.degree. to 200.degree. C. and 5 to 150 kg/cm.sup.2 gauge in the presence of a suitable catalyst, preferably about 0.5-20 wt % of an organic phosphonium halide. After stripping off unreacted components, the ethylene carbonate is hydrolyzed to glycols in the presence of the same carbonation catalyst and at temperatures in the range of about 100.degree. to 200.degree. C. and pressures of about 5 to 150 kg/cm.sup.2 gauge. Optionally, ethylene oxide and ethylene carbonate may be co-produced.Type: GrantFiled: August 2, 1983Date of Patent: April 2, 1985Assignee: The Halcon SD Group, Inc.Inventors: Vijay S. Bhise, Harold Gilman
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Patent number: 4480123Abstract: A process for preparing diacyloxyalkadienes of the formula ##STR1## where R.sup.1 to R.sup.6 are each hydrogen or a hydrocarbon radical, which contain one or more hydrocarbon radicals having one or more non-conjugated double bonds, by reacting an aliphatic triene of the formula ##STR2## in which R.sup.1 to R.sup.6 have the same meanings given above with a carboxylic acid of the formulaR.sup.7 -COOHin which R.sup.7 has the same meaning given above, in the presence of a catalyst which contains palladium, platinum or salts of these metals and in the presence of oxygen.Type: GrantFiled: July 25, 1983Date of Patent: October 30, 1984Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz
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Patent number: 4479021Abstract: There is described a continuous process for producing 1,2-alkanediols of the formula ##STR1## in which R is an alkyl group having 3-6 carbon atoms, by reaction of a 1-alkene of the formulaR--CH.dbd.CH.sub.2in which R is as defined above, with formic acid and hydrogen peroxide, and subsequent saponification of the formed alkanediol monoformate, which process is performed in several consecutive reaction stages.The 1,2-alkanediols of the above formula obtainable by the process are intermediates for the production of pesticides.Type: GrantFiled: August 30, 1983Date of Patent: October 23, 1984Assignee: Ciba-Geigy CorporationInventors: Heinz Issler, Rudolf Maul
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Patent number: 4415747Abstract: This process is concerned with the reductive coupling of .alpha.-halo ethers and/or .alpha.-halo esters to make ethylene glycol derivatives by carrying out the reductive coupling process in the presence of an iron compound having iron in an oxidation state of zero.Type: GrantFiled: September 29, 1981Date of Patent: November 15, 1983Assignee: Union Carbide CorporationInventor: Leonard Kaplan
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Patent number: 4413140Abstract: A solvent comprising at least one aromatic hydrocarbon and/or halogenated paraffin is used in a liquid extraction process for extracting diesters from mixtures comprising diesters, the corresponding monoesters and acids, diols and water.Type: GrantFiled: April 26, 1977Date of Patent: November 1, 1983Assignee: Phillips Petroleum CompanyInventor: George B. Fozzard
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Patent number: 4404410Abstract: An improved process for the preparation of 2,3-dimethyl-2,3-butanediol is disclosed wherein hydrogen peroxide and 2,3-dimethylbutene are reacted with formic acid at 50.degree. to 70.degree. C. while stirring, the 2,3-dimethylbutene and hydrogen peroxide being introduced into the formic acid simultaneously but separately. The diol can be obtained by hydrolysis of the pinacol monoformate formed.Type: GrantFiled: June 10, 1981Date of Patent: September 13, 1983Assignee: Ruhrchemie AktiengesellschaftInventors: Boy Cornils, Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
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Patent number: 4400559Abstract: Ethylene glycol is prepared by a process in which ethylene oxide is extracted from an aqueous solution with near-critical or super-critical carbon dioxide. Thereafter an ethylene oxide--carbon dioxide--water mixture is contacted with a catalyst to form ethylene carbonate, which is then hydrolyzed to ethylene glycol in the presence of the same catalyst. The ethylene glycol is separated as product and the carbon dioxide and the catalyst are recycled.Type: GrantFiled: June 14, 1982Date of Patent: August 23, 1983Assignee: The Halcon SD Group, Inc.Inventor: Vijay S. Bhise
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Patent number: 4301077Abstract: Oxygenated C.sub.4 hydrocarbons, such as maleic anhydride, are hydrogenated to tetrahydrofuran and/or 1,4-butanediol by a process comprising contacting the hydrocarbon with hydrogen at hydrogenation conditions in the presence of less than 25 wt. % water, based on the weight of the hydrocarbon, and a ruthenium-containing hydrogenation catalyst, such as the catalyst of the formulaRu Ni Co Zn.sub.0.4.Type: GrantFiled: December 22, 1980Date of Patent: November 17, 1981Assignee: Standard Oil CompanyInventors: Frederick A. Pesa, Anne M. Graham
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Patent number: 4298758Abstract: Propylene glycol and dipropylene glycol diesters are prepared by reacting dichloropropyl ethers with a carboxylic acid salt, e.g., sodium acetate, and the corresponding carboxlyic acid, e.g., acetic acid. The by-product sodium chloride is insoluble in the acetic acid and easily separated from the reaction mixture. The diesters can be hydrolyzed to their respective glycols.Type: GrantFiled: February 11, 1980Date of Patent: November 3, 1981Assignee: The Dow Chemical CompanyInventors: Frank T. Cook, Donald G. Prier
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Patent number: 4297506Abstract: An organic ester is produced by conversion of an organic halide employing excess alkali metal carboxylate. A resultant reaction mass including solids comprised of alkali metal halide is obtained containing occluded in the solids portion an amount of otherwise difficult-to-recover desired ester product. At least a portion of said solids is recycled to the conversion whereby to prevent further occlusion of desired product. In an embodiment of the invention, potassium acetate salt is recycled for reuse.Type: GrantFiled: January 8, 1980Date of Patent: October 27, 1981Assignee: Phillips Petroleum Co.Inventor: Kiplin D. Cowan
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Patent number: 4283579Abstract: A process for producing a diol by reacting an acetic ester of butanediol or butenediol with methanol, which comprises (a) continuously feeding to a first reaction-distilling column from its upper part a liquid acetic ester of butanediol or butenediol, while continuously feeding methanol to said column from its lower part, to bring both feeds into counter current gas-liquid contact in the presence of an acidic or a basic catalyst, to allow both feeds to react, and withdrawing from the bottom a bottom stream comprising a diol as major constituent, (b) continuously feeding to a hydrolyzer the distillate obtained from said first reaction-distilling column containing methyl acetate as major constituent, thus bringing said distillate into contact with water or steam in the presence of an acidic catalyst to hydrolyze the methyl acetate, (c) then continuously feeding the hydrolysis product thus obtained from the hydrolyzer to a second distilling column, withdrawing a methyl acetate-containing methanol stream from theType: GrantFiled: September 6, 1979Date of Patent: August 11, 1981Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Hiroshi Oka
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Patent number: 4283580Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene carbonate to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.Type: GrantFiled: September 19, 1979Date of Patent: August 11, 1981Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Hiroshi Odanaka, Minoru Saotome, Toshihiko Kumazawa
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Patent number: 4281197Abstract: Porous polyurethane solids such as open cell polyurethane foams are rapidly heated and hydrolytically decomposed into separate polyol component and diamine component by contacting the porous solids with saturated steam in a heated vacuum chamber. Separation of high quality liquid polyol and diamine is achieved.Type: GrantFiled: October 6, 1980Date of Patent: July 28, 1981Assignee: Ford Motor CompanyInventor: Fred G. Oblinger
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Patent number: 4273934Abstract: 3-Hydroxy-2,2,4-trimethylpentyl isobutyrate is prepared by reaction of isobutyraldehyde in the presence of an alkaline earth metal hydroxide and of carboxylic acids or the corresponding salts, under specific conditions in respect of reaction time and proportion and concentration of the hydroxide suspension. The product is a starting material for the preparation of dyes, pesticides, adhesives and surface coatings.Type: GrantFiled: April 17, 1979Date of Patent: June 16, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Hans-Juergen Foerster
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Patent number: 4272455Abstract: A method for the formation of monoalkyleneglycols, monoalkanolamines and alkylenediamines, comprising the steps of: (a) reacting ammonia or ammonium carbonate with an alkylenecarbonate to form a carbamate, (b) heating the carbamate to form a monoalkyleneglycol, an alkyleneurea and a 2-oxazolidinone, (c) further reacting the alkyleneurea and the 2-oxazolidinone with ammonium hydroxide to form ammonia or ammonium carbonate, a monoalkanolamine, and an alkylenediamine, (d) separating the ammonia or ammonium carbonate, the monoalkyleneglycol, the alkylenediamine, and the monoalkanolamine, and (e) recycling the ammonia or ammonium carbonate to reaction step (a).Type: GrantFiled: December 26, 1979Date of Patent: June 9, 1981Assignee: The Dow Chemical CompanyInventors: Frank T. Cook, Daniel W. Baugh, Jr., Robert V. Chambers, Jr.
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Patent number: 4268447Abstract: A process for producing simultaneously tetrahydrofuran and 1,4-butanediol in any desired proportion which comprises (a) reacting the acetic ester of 1,4-butanediol with a theoretical or smaller quantity, based on said acetic ester, of water (preferably 0.2-0.Type: GrantFiled: December 12, 1979Date of Patent: May 19, 1981Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Hiroshi Oka
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Patent number: 4262139Abstract: A process for the preparation of butenediol diacetate by reacting butadiene with oxygen and acetic acid or with a compound which liberates acetic acid under the reaction conditions, over a solid catalyst which contains a platinum metal and one or more elements of main group 5 or 6, in the presence of butanediol diacetate, butanediol monoacetate, butanediol or a mixture of these, and the use of the butenediol diacetate, thus obtained, to prepare butane-1,4-diol by hydrogenating and then hydrolyzing the diacetate.Type: GrantFiled: October 22, 1979Date of Patent: April 14, 1981Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Hans-Martin Weitz, Rolf Schnabel
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Patent number: 4260814Abstract: A process for the preparation of bromoalkyl esters and vicinal glycol esters which comprises thermally decomposing at temperatures of from 100.degree. C. to 200.degree. C. a bis(2-bromoalkyl)tellurium dicarboxylate compound of the formula ##STR1## wherein at least one R is hydrogen or R is a methyl group and R' is hydrogen or an alkyl group having 1 to 3 carbon atoms in the presence of an aliphatic monocarboxylic acid selected from formic, acetic, propionic or butyric acid employed as solvent and to facilitate solvolysis in the reaction to give in addition to the bromoalkyl ester, the vicinal glycol ester. An inert acetonitrile solvent may be employed alone to give predominately the bromoalkyl ester or an admixture with the acid may be employed. Oxygen is preferably employed with the carboxylic acid solvent to provide an increase in the mole ratio of vicinal glycol ester to the bromoalkyl ester produced.Type: GrantFiled: July 23, 1979Date of Patent: April 7, 1981Assignee: Atlantic Richfield CompanyInventors: Jar-lin Kao, Ming N. Sheng
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Patent number: 4258208Abstract: A process for the preparation of 2-bromoalkyl esters and vicinal glycol esters which comprises thermally decomposing at temperatures of from 100.degree. C. to 200.degree. C. an organic bromoalkyl tellurium compound selected from 2-bromoalkyltellurium tribromide or bis(2-bromoalkyl)tellurium dibromide, wherein the alkyl group is ethyl, propyl or butyl, in a carboxylic acid having from 1 to 4 carbon atoms which is employed as solvent as well as to supply the ester moiety to the esters produced. The esters may be converted to the respective glycol with water or an aqueous base.Type: GrantFiled: July 23, 1979Date of Patent: March 24, 1981Assignee: Atlantic Richfield CompanyInventors: Jar-lin Kao, Ming N. Sheng
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Patent number: 4251673Abstract: An organic ester e.g. 1,4-diacetoxybutane is hydrolyzed with an alkali metal or an alkaline earth metal hydroxide to a corresponding alcohol, the reaction being rapidly effected by having present a hydroxyl-containing compound. In a preferred embodiment, the hydroxyl-containing compound to be present is the very compound to be produced e.g. 1,4-butanediol is to be produced from 1,4-diacetoxybutane and there is present during the reaction of hydrolysis an earlier produced 1,4-butanediol.Type: GrantFiled: July 3, 1979Date of Patent: February 17, 1981Assignee: Phillips Petroleum CompanyInventors: Harold W. Mark, William V. Childs
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Patent number: 4239910Abstract: In a process for the manufacture of butenediol-dicarboxylic acid esters by reacting butadiene with oxygen and a carboxylic acid in the presence of a noble metal catalyst containing platinum or palladium, the carboxylic acid is added to the reaction mixture in the form of the ester of the acid with a low molecular weight aliphatic alcohol such as methanol and the reaction is carried out under conditions under which the ester undergoes hydrolysis, or the hydrolysis is carried out before the main reaction. This enables the carboxylic acid obtained on further processing of the butenediol esters to be recycled.Type: GrantFiled: March 18, 1977Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Platz, Juergen Hartig
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Patent number: 4239911Abstract: Alkylene glycol dicarboxylates are obtained by reacting carboxylic acid esters of monohydric or polyhydric aliphatic short-chain alcohols with an olefin and oxygen in the presence of a catalyst, a hydrolyzing agent and water.Type: GrantFiled: May 24, 1977Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Juergen Hartig
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Patent number: 4237324Abstract: Alkylene glycols are produced from alkylene carbonates by hydrolysis in the presence of water at temperatures of from about 80.degree. to about 200.degree. C. Catalysts, such as alumina, are employed at temperatures from 80.degree. to about 150.degree. C. and only slightly greater than the stoichiometric amount of water is employed to allow the most efficient use of the process.Type: GrantFiled: January 22, 1979Date of Patent: December 2, 1980Assignee: The Dow Chemical CompanyInventors: Dale A. Raines, Oliver C. Ainsworth
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Patent number: 4233230Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.Type: GrantFiled: May 4, 1978Date of Patent: November 11, 1980Assignee: Rhone-Poulenc IndustriesInventor: Jean Otton
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Patent number: 4164616Abstract: Halogen, e.g., bromine, and a conjugated diene, e.g., butadiene, are reacted in vapor phase, the reacted mass condensed and contacted with alkali metal acetate dissolved or dispersed in an acid, e.g., potassium acetate in glacial acetic acid, thus causing a reaction of formed dibromobutene-2 with the acetate to form diacetoxy-2-butene. The latter is hydrogenated to the corresponding diacetoxylated alkane. The diacetoxy alkane is hydrolyzed to the dihydroxy alkane, e.g., 1,4-butanediol. Alternately, the diacetoxy alkene can be hydrolyzed and the hydrogenation then conducted.Type: GrantFiled: January 17, 1978Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: William V. Childs
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Patent number: 4156685Abstract: A process is disclosed in which hydrolysis and cyclization of an acetate ester of a 1,4-diol are carried out in separate reaction zones in the pressure of a solid acid catalyst and unreacted acetate ester recovered from each of the reaction zones is supplied to another zone thereby producing a hydrofuran and a 1,4-diol in any proportion.Type: GrantFiled: July 27, 1978Date of Patent: May 29, 1979Assignee: Mitsubishi Chemical Industries LimitedInventors: Yasuo Tanabe, Jun Toriya, Ikuo Kasahara, Ken Shiraga
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Patent number: 4152525Abstract: Disclosed is a method of recovering butadiene gas from an acetoxylation process which method comprises steps: (a) contacting a butadiene-containing gas with acetic acid to effect the absorption of butadiene in acetic acid, (b) recycling the acetic acid containing butadiene to the acetoxylation process, (c) contacting the waste gas containing acetic acid from step (a) with water to effect the absorption of acetic acid in water and (d) recycling the water containing acetic acid to hydrolysis step of the acetoxylation product.Type: GrantFiled: January 30, 1975Date of Patent: May 1, 1979Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Yasuo Tanabe, Jun Toriya, Ikuo Kasahara
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Patent number: 4122291Abstract: Production of an alken-2-ol-1, or of an alken-2-ol-1 and an alkanol-1 from the corresponding alken-3-ol-1 is described. The above compound or compounds can be produced with good selectivity by converting an alken-3-ol-1 to the boric acid ester, and, then, contacting the ester with a palladium catalyst in the presence of hydrogen or, alternatively, by carrying out the latter-mentioned step under conditions favorable to the formation of said boric acid ester and, thereafter, subjecting the reaction product to solvolysis.Type: GrantFiled: June 6, 1977Date of Patent: October 24, 1978Assignee: Kuraray Co., Ltd.Inventors: Sunao Kyo, Tsumoru Renge, Hidetsugu Tanaka
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Patent number: 4117250Abstract: A continuous process for hydrolyzing alkylene carbonates according to specific procedure whereby the akylene glycol obtained is essentially free of polymeric glycols and contains minimum amounts of dimeric glycols.Type: GrantFiled: December 22, 1977Date of Patent: September 26, 1978Assignee: Union Carbide CorporationInventors: Robert Dean Foster, Thomas Arthur Maliszewski, Joseph Alton Sims, Jr., Glenn Alfred Taylor
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Patent number: 4091039Abstract: In the preparation of an alkylene glycol such as ethylene glycol by hydrolysis of the corresponding aliphatic acid ester, the improvement which comprises hydrolyzing the ester in a distillation column, taking to a condenser as overhead a vaporous mixture of water and aliphatic acid from the hydrolysis column, which immiscible stream is mixed with vapors of a water immiscible aliphatic ketone in the condenser, condensing the mixture and conducting the condensate to a settling tank where an upper ketone phase containing extracted aliphatic acid and a lower aqueous phase is formed, recycling the aqueous phase to the hydrolysis column, feeding the ketone phase to a distillation column where the ketone is distilled off and returned to the condenser, and separating essentially anhydrous aliphatic acid from the bottom of the distillation column.Type: GrantFiled: April 26, 1977Date of Patent: May 23, 1978Assignee: Suntech, Inc.Inventor: Edward Scheibel
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Patent number: 4087453Abstract: A process for recovering monomeric glycols and glycerine from polyoxyalkylene glycols and polyglycerines which comprises heating the polymeric compounds together with a lower saturated mono-carboxylic acid, containing from 2 to 4 carbon atoms such as acetic acid, in the presence of a strong acid, e.g. sulfuric acid, or a strong acid cation exchange resin. The product, which is the diester of the monomeric glycol or the triester of glycerine, is recovered and subsequently hydrolyzed to obtain the desired monoglycol or glycerine product. If it is desired to obtain the ester itself, the latter step of hydrolyzing can be omitted.Type: GrantFiled: June 18, 1976Date of Patent: May 2, 1978Assignee: The Dow Chemical CompanyInventors: Fred A. Sherrod, William L. Howard, Joanne D. Burger