Abstract: An alcohol such as methanol is reacted with carbon monoxide in a liquid reaction medium containing a rhodium catalyst stabilized with an iodide salt, especially lithium iodide, along with alkyl iodide such as methyl iodide and alkyl acetate such as methyl acetate in specified proportions. With a finite concentration of water in the reaction medium the product is the carboxylic acid instead of, for example, the anhydride. The present reaction system not only provides an acid product of unusually low water content at unexpectedly favorable reaction rates but also, whether the water content is low or, as in the case of prior-art acetic acid technology, relatively high, is characterized by unexpectedly high catalyst stability; i.e., it is resistant to catalyst precipitation out of the reaction medium.
Type:
Grant
Filed:
January 7, 1991
Date of Patent:
September 1, 1992
Assignee:
Hoechst Celanese Corporation
Inventors:
Brad L. Smith, G. Paull Torrence, Adolfo Aguilo, James S. Alder
Abstract: The present invention relates to a process for the purification of 4-acetoxystyrene from a crude product mixture comprising 4-acetoxystyrene and typically 5 or more contaminants in substantial amount.The crude product mixture is purified by melt crystallization by cooling the mixture to a temperature ranging from about +8.degree. C. to about -50.degree. C., whereby at least a first portion of the mixture is crystallized; removing the liquid remaining from contact with the crystallized first portion of the mixture; and, subsequently slowly heating the crystallized first portion, while simultaneously removing liquid which forms due to the heating, whereby impurities contained in the liquid which forms are removed from the crystallized first portion.Surprisingly, despite the large number of contaminants present, and use of the process to purify crude product mixtures containing as little as 50% by weight 4-acetoxystyrene, purities as high as 99.
Type:
Grant
Filed:
August 30, 1990
Date of Patent:
August 4, 1992
Assignee:
Hoechst Celanese Corporation
Inventors:
Jack Chosnek, George E. Beck, Donna L. Keene, Siegbert Rittner, Volker Hautzel
Abstract: 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.
Abstract: 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.
Type:
Grant
Filed:
December 13, 1990
Date of Patent:
June 9, 1992
Assignee:
Hoechst Celanese Corporation
Inventors:
Olan S. Fruchey, Graham N. Mott, John R. Durrwachter
Abstract: 1,3-Propanediol is manufactured by the hydration of acrolein in an aqueous solution over a fully hydrated, alumina-bound zeolite with a pore size >5 angstroms to form 3-hydroxypropanal and hydrogenation of the 3-hydroxypropanal typically in an aqueous solution in the presence of a nickel catalyst.
Type:
Grant
Filed:
July 24, 1991
Date of Patent:
March 3, 1992
Assignee:
Hoechst Celanese Corporation
Inventors:
Jerry D. Unruh, Debra A. Ryan, Ioan Nicolau
Abstract: This invention pertains to the addition of an alkyl alcohol to an alkyl acrylate to form alkyl 3-alkoxy propanoate catalyzed by a strong acid catalyst. The process has sepcific application in the addition of ethanol to ethyl acrylate to form ethyl 3-ethoxy propanoate.
Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
Type:
Grant
Filed:
July 26, 1990
Date of Patent:
December 10, 1991
Assignee:
Hoechst Celanese Corporation
Inventors:
Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium, a phosphine, and a lower-alkyl iodide or .beta.-hydroxy lower-alkyl iodide.
Abstract: An alcohol such as methanol is reacted with carbon monoxide in a liquid reaction medium containing a rhodium catalyst stabilized with an iodide salt, especially lithium iodide, along with alkyl iodide such as methyl iodide and alkyl acetate such as methyl acetate in specified proportions. With a finite concentration of water in the reaction medium the product is the carboxylic acid instead of, for example, the anhydride. The present reaction system not only provides an acid product of unusually low water content at unexpectedly favorable reaction rates but also, whether the water content is low or, as in the case of prior-art acetic acid technology, relatively high, is characterized by unexpectedly high catalyst stability; i.e., it is resistant to catalyst precipitation out of the reaction medium.
Type:
Grant
Filed:
May 25, 1990
Date of Patent:
June 25, 1991
Assignee:
Hoechst Celanese Corporation
Inventors:
Brad L. Smith, G. Paull Torrence, Adolfo Aguilo', James S. Alder
Abstract: A method is provided for the production of 2,2-diorgano-1-indanones, e.g., 2,2-dimethyl-1-indanone, by reacting an alcohol which is the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)carbinol, e.g., 2-methyl-1-phenyl-1-propanol, with carbon monoxide in the presence of a Lewis acid catalyst, e.g., hydrogen fluoride, with any substituents on the phenyl group of the alcohol being hydroxy or organo. The foregoing reaction is preferably integrated with the preparation of the feed alcohol by reducing the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)ketone, e.g., isobutyrophenone, with a reducing agent containing available hydrogen, e.g., sodium borohydride, or with hydrogen gas in the presence of a hydrogenation catalyst.
Abstract: An alcohol such as methanol is reacted with carbon monoxide in a liquid reaction medium containing a rhodium catalyst stabilized with an iodide salt, especially lithium iodide, along with alkyl iodide such as methyl iodide and alkyl acetate such as methyl acetate in specified proportions. With a finite concentration of water in the reaction medium the product is the carboxylic acid instead of, for example, the anhydride. The present reaction system not only provides an acid product of unusually low water content at unexpectedly favorable reaction rates but also, whether the water content is low or, as in the case of prior-art acetic acid technology, relatively high, is characterized by unexpectedly high catalyst stability; i.e., it is resistant to catalyst precipitation out of the reaction medium.
Type:
Grant
Filed:
June 3, 1986
Date of Patent:
March 19, 1991
Assignee:
Hoechst Celanese Corporation
Inventors:
Brad L. Smith, G. Paull Torrence, Adolfo Aguilo', James S. Alder
Abstract: A method is provided for separating hydrogen fluoride (HF) from a mixture comprising HF complexed with an aromatic ketone in which the keto carbon atom is directly bonded to an aromatic ring carbon atom, e.g., 4-isobutylacetophenone, by adding a carboxylic acid anhydride, e.g., acetic anhydride, to the mixture while maintaining the mixture at conditions sufficient to sustain a reaction between the anhydride and the HF to form the corresponding acyl fluoride, e.g., acetyl fluoride, and carboxylic acid, e.g., acetic acid, and separating the acyl fluoride from the mixture. The method is conveniently carried out in a stripping column near the top of which the mixture comprising aromatic ketone and HF is fed and below which the anhydride is fed. Between these feed points, the uncomplexed HF is stripped from the mixture, while below the anhydride feed point or points, the anhydride reacts with the complexed HF to form the acyl fluoride which is stripped from the mixture, and the carboxylic acid.
Type:
Grant
Filed:
December 4, 1989
Date of Patent:
February 5, 1991
Inventors:
Thomas A. Curtis, Timothy R. Ryan, Daniel D. Lindley
Abstract: Polyunsaturated compounds useful in radiation curable compositions are made by reacting p-vinylphenol and a polyisocyanate in the ratio of one mole of p-vinylphenol for each isocyanate group of the polyisocyanate.
Abstract: The invention provides a process for the production of C.sub.1 to C.sub.5 alkyl nitrite by forming an aqueous solution of C.sub.1 to C.sub.5 alkyl alcohol an alkali metal nitrite; cooling it; then slowly adding a hydrohalic acid solution while it is stirring; the reaction temperature is maintained in the range of from about -10.degree. C. to about 10.degree. C. until the reaction is substantially complete; and the two formed phases are separated in a separatory funnel.
Abstract: Black acid or the sulfuric acid residue obtained in the manufacture of ethyl acrylate by reaction of ethylene and acrylic acid in the presence of sulfuric acid is heated and distilled in a distillation zone in the presence of a solvent to form an overhead mixture comprising an organic phase containing ethyl acrylate and solvent, and an aqueous phase containing water, solvent and acrylic acid. The aqueous phase is recycled to the distillation zone for recovery of additional acrylic acid value from the organic phase.
Type:
Grant
Filed:
May 7, 1990
Date of Patent:
November 6, 1990
Assignee:
Hoechst Celanese Corporation
Inventors:
Brad L. Smith, Adolfo Aguilo, Cecil D. Homer, Jr.
Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
Type:
Grant
Filed:
August 2, 1988
Date of Patent:
October 23, 1990
Inventors:
Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
Abstract: Poly(4-hydroxystyrene) is prepared by aqueous suspension polymerization of 4-acetoxystyrene monomer followed by hydrolysis with ammonium hydroxide.
Abstract: A process for preparing a stable 4-hydroxyacetophenone oil by mixing 4-hydroxyacetophenone with an aqueous hydroxylamine salt in the absence of added caustic, at a temperature of 50.degree.-100.degree. C., for about 10-60 minutes and then cooling the same is disclosed.
Abstract: There are provided novel copolymers of a p-mercaptostyrene ester, e.g., the acetate, with at least one comonomer selected from the group consisting of styrene, N-methylmaleimide, maleic anhydride and p-acetoxystyrene. These copolymers may be hydrolyzed to produce corresponding copolymers of p-mercaptostyrene with at least one comonomer selected from the group consisting of styrene, N-methylmaleimide, maleic acid and p-vinylphenol. The copolymers have application as heavy metal sequestering agents in various forms and structures.
Type:
Grant
Filed:
May 4, 1989
Date of Patent:
May 29, 1990
Assignee:
Hoechst Celanese Corporation
Inventors:
Mohammad Aslam, Richard Vicari, Kenneth G. Davenport
Abstract: Polymers of 4-acetoxystyrene in finely divided particulate form are suspended in water, and while in suspension are hydrolyzed to polymers of 4-hydroxystyrene using aqueous nitrogen bases. Such polymers are useful in photoresists, as protective coatings for metal, in the manufacture of epoxy resins and epoxy resin curing agents.