Phenols (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/716)
  • Patent number: 4744921
    Abstract: The present invention is directed toward a method for preparing Group II metal overbased sulfurized alkylphenols. In particular, the present invention employs a sulfurization catalyst in the preparation of Group II metal overbased sulfurized alkylphenols. Use of a sulfurization catalyst in this preparation results in a product generally characterized as having lower crude sediment, a higher Total Base Number and lower viscosity than a similar product prepared without using a sulfurization catalyst.
    Type: Grant
    Filed: October 21, 1986
    Date of Patent: May 17, 1988
    Assignee: Chevron Research Company
    Inventor: Thomas V. Liston
  • Patent number: 4740330
    Abstract: The aromatic hydroxyl groups of aromatic hydroxyl-containing compounds can be allylated to greater than 95% conversion by reacting the alkali metal salt of said aromatic hydroxyl-containing compounds with an allyl halide such as allyl chloride in the presence of a polar aprotic solvent such as dimethylformamide. These compounds are useful in preparing epoxy resins containing a low halogen content.
    Type: Grant
    Filed: September 3, 1986
    Date of Patent: April 26, 1988
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Zeng-kun Liao
  • Patent number: 4731491
    Abstract: Liquefaction of lignin by hydrogenolysis in the presence of a catalytic composition of metal sulfides which are prepared in situ and in the presence of a lower aliphatic alcohol affords substantially increased yields of monophenols. When methanol is used in the presence of a catalyst which is a mixture of the sulfides of divalent iron, copper, and tin the total monophenols can be as high as 65% with the total cresols being about 45%. Phenol, which is used as a liquefying solvent, can itself be formed in good yield when lignin tar is used as the liquefying solvent. This affords the opportunity of conducting the liquefaction in a continuous fashion using two stages of reaction.
    Type: Grant
    Filed: January 22, 1986
    Date of Patent: March 15, 1988
    Assignee: UOP Inc.
    Inventors: Peter Urban, Dusan J. Engel
  • Patent number: 4691057
    Abstract: The reaction of alkali metal with aromatic hydroxy compounds is promoted by inclusion of an alcohol in the reaction mixture. The alkali metal aryloxide formed can be reacted with phosphonitrilic chloride polymers to make polyaryloxyphosphazenes.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 1, 1987
    Assignee: Ethyl Corporation
    Inventor: Allan A. Eisenbraun
  • Patent number: 4683344
    Abstract: A process for the preparation of a pulverulent organomagnesium compound involves bringing together into intimate admixture a particulate hydroxyl functional material with an organomagnesium-containing material. The process is conducted at a temperature below the melting point of the hydroxyl functional material but at a temperature sufficient to convert at least a portion of the hydroxyl functional material to the pulverulent organomagnesium compound. The aforesaid organomagnesium compounds are useful as intermediates in generating anionic sites for anionic polymerization.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Robert B. Hodek, Jerome A. Seiner
  • Patent number: 4668760
    Abstract: A process comprising synthesizing a liquid crystal polyester consisting essentially of recurring moieties of formulas: ##STR1## and moiety III or IV wherein III is ##STR2## wherein the mole ratio of moiety II to moiety III, when present, is 1:4 to 2:1 and wherein the mole ratio of moiety II to moiety IV, when present, is 2:8 to 1:9 and devolatilizing said liquid crystal polyester prior to shaping such polyester into an article and then shaping said devolatilized polyester into said article.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: May 26, 1987
    Assignee: Owens-Corning Fiberglass Corp.
    Inventors: Edwin Boudreaux, Jr., David M. Lee, David A. Hutchings, Gloria M. Sieloff, G. Fred Willard
  • Patent number: 4661637
    Abstract: Disclosed is a process for converting solid metal phenates to phenols and hydroxides of the metals of the phenates by treating the phenates with steam at a temperature from about 250.degree. C. to about 450.degree. C.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: April 28, 1987
    Assignee: Exxon Research and Engineering Company
    Inventor: Charles G. Scouten
  • Patent number: 4657707
    Abstract: The invention relates to a process for the preparation of aromatic hydroxy compounds, starting from the corresponding halogenated aromatic compounds and replacing the halogen atom or atoms by the hydroxyl group. The process comprises converting the halogenated aromatic compound into the hydroxy compound by treatment with concentrated sulfuric acid, with the addition of an aldehyde and at elevated temperature.The aromatic hydroxy compounds are used as intermediates, for example for the manufacture of disperse and vat dyes.
    Type: Grant
    Filed: May 22, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Muller, Maurice Grelat
  • Patent number: 4647704
    Abstract: Hydrocracking of lignin in the presence of a supported tungsten-nickel catalyst affords phenolic compounds in higher yield and with greater selectivity then previously obtainable. Mildly acidic supports, such as alumina, alumina-silica, aluminum phosphate, and silica-aluminum phosphate, have been found to be particularly effective. When the hydrocracking is done in the presence of water, a lower aliphatic alcohol, or a Lewis acid such as ferrous chloride, increased yields of both cresols and C.sub.6 -C.sub.8 and C.sub.6 -C.sub.9 phenolics are obtained.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: March 3, 1987
    Assignee: UOP Inc.
    Inventors: Dusan J. Engel, Karl Z. Steigleder
  • Patent number: 4634771
    Abstract: There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: January 6, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
  • Patent number: 4603226
    Abstract: A stable creosote product is prepared from which little or no sludge heel settles and which does not require heat to be applied to prevent settling out of solids. The stable product is obtained by a method that mechanically reduces the particle size or the salts that form upon cooling below the limpid point. The layer of salt which settles on the bottom of the beaker is then mechanically broken and homogenized. The fine salts which had previously settled and were homogenized, did not resettle but remained relatively evenly dispersed throughout the mixture and remained dispersed even after prolonged periods of uninterrupted standing. The salts are not allowed to settle before homogenizing. Little or no heel formation was detected in the creosote in which the settled and material was homogenized as described.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: July 29, 1986
    Assignee: Allied Corporation
    Inventors: George H. Collingwood, Gail L. Erickson, Howard L. Simon, Roger L. Haley, Bill E. Sparling
  • Patent number: 4600765
    Abstract: Melt spinnable, liquid crystal aromatic polyesters which are optically anisotropic in the melt phase are provided.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: July 15, 1986
    Assignee: Owens-Corning Fiberglas Corporation
    Inventors: David M. Lee, David A. Hutchings, Gloria M. Sieloff, G. Fred Willard
  • Patent number: 4599462
    Abstract: Novel composites or solid solutions made from heretofore immiscible chemical components and methods for making such composites or solid solutions. A wall of a deposition cell is cooled to a temperature within the range of about -273.degree. C. to about -20.degree. C. A solid host component and one or more guest components are vaporized and codeposited onto the cold wall of the deposition cell so as to form a solid solution. The resultant solid solutions are stable at room temperature and often at much higher temperatures. The present invention also provides methods for modifying the surface structure of solid materials.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: July 8, 1986
    Assignee: University of Utah
    Inventor: Josef Michl
  • Patent number: 4595489
    Abstract: Disclosed is a process for recovering phenols from phenol-containing streams having at least a sufficient amount of water. The stream is contacted with a metal composition comprised of one or more oxides and/or hydroxides of metals capable of forming a metal phenate with the phenols of the stream. The resulting metal phenates are separated from the stream and are treated with steam at a temperature from about 250.degree. C. to about 450.degree. C., thereby producing phenols, and hydroxides of the metals of the phenate.
    Type: Grant
    Filed: July 22, 1985
    Date of Patent: June 17, 1986
    Assignee: Exxon Research and Engineering Co.
    Inventor: Charles G. Scouten
  • Patent number: 4593129
    Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4585897
    Abstract: A process for hydration and condensation of acetylene in a crude acetylene stream containing water in the presence of a zirconia-alumina catalyst containing water to prepare aliphatic, aromatic and oxygenated compounds suitable for use as high octane liquid water fuels and as octane improvers for motor fuels is disclosed.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: April 29, 1986
    Assignee: Standard Oil Company (Indiana)
    Inventors: Ellis K. Fields, Mark L. Winzenburg, David A. De Marco
  • Patent number: 4577046
    Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: March 18, 1986
    Assignee: University of New Mexico
    Inventors: Mark D. Hylarides, Fred A. Mettler, Jr.
  • Patent number: 4570024
    Abstract: An aromatic hydrocarbon in which at least one hydrogen atom on the ring is substituted by a group selected from the class consisting of unsubstituted or lower alkyl-substituted tricyclo[5.2.1.0.sup.2,6 ]dec-3-yl, tricyclo[5.2.1.0.sup.2,6 ]dec-4-yl, tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-4-yl and tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-5-yl groups, or its hydrogenation product.The compound is prepared by reacting an aromatic hydrocarbon having at least one hydrogen atom on the ring with a compound selected from the group consisting of unsubstituted or lower alkyl-substituted tricyclo[5.2.1.0.sup.2,6 ]dec-3-ene and tetracyclo[6.2.1.1.sup.3,6.0.sup.2,7 ]dodec-4-ene in the presence of a Friedel-Crafts catalyst, or hydrogenating the thus-obtained compound in the presence of a hydrogenation catalyst.The compound is useful as an additive for adhesives.
    Type: Grant
    Filed: May 7, 1985
    Date of Patent: February 11, 1986
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kinya Mizui, Masami Takeda, Yoshimi Ozaki, Ryosuke Tomita
  • Patent number: 4554388
    Abstract: This invention relates to a process for isomerization and transalkylation of alkylphenols and for phenol-derivatives in the presence of a catalyst comprising ironoxide (s) and at least one additional oxide and in the case of 2,4,6-trimethylphenol and 2,4-dimethylphenol as alkylphenol feed, of ironoxide (s) or of a catalyst comprising ironoxide (s) and at least one additional oxide.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: November 19, 1985
    Assignee: Rheinische Braunkohlenwerke Aktiengesellschaft
    Inventors: Karl-Heinz Keim, Joachim Korff
  • Patent number: 4554309
    Abstract: Thermoplastic polymer exhibiting improved heat resistance comprised of the polymerized reaction products of (i) a carbonate precursor, and (ii) at least one dihydric phenol represented by the general formula ##STR1## wherein: R is independently selected from alkyl radicals;R.sup.1 is independently selected from monovalent hydrocarbon radicals;X is selected from cycloalkylidene radicals containing from 8 to about 16 ring carbon atoms;each n is two; andm represents a whole number having a value of from 0 up to the number of replaceable hydrogen atoms present on X.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: November 19, 1985
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4551563
    Abstract: A method is provided for making polymethylated phenols, such as 2,3,5-trimethylphenol and 2,3,5,6-tetramethylphenol from a mixture of isophorone and methanol. Catalytic demethanation of isophorone and methanation of the resulting product is achieved by contacting the mixture of isophorone and methanol with the calcination residue of a mixture of magnesium carbonate and/or magnesium hydroxide and a manganese compound at elevated temperatures.
    Type: Grant
    Filed: May 24, 1984
    Date of Patent: November 5, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4546207
    Abstract: Anhydrous di-(alkali metal) (especially disodium) salts of dihydroxyaromatic compounds such as bisphenol A are prepared by first contacting the solid dihydroxyaromatic compound with an aqueous alkali metal hydroxide solution so as to convert it into the solid di-(alkali metal) salt or hydrate thereof and subsequently separating the solid salt or hydrate from the aqueous system and removing water therefrom, typically by mixing the same with an organic liquid and removing water, including water of hydration, by evaporation. The organic liquid is preferably one such as toluene or o-dichlorobenzene in which water and the anhydrous di-(alkali metal) salt are substantially insoluble. The process may be operated in batch or continuous fashion.
    Type: Grant
    Filed: July 23, 1984
    Date of Patent: October 8, 1985
    Assignee: General Electric Company
    Inventors: Ashok K. Mendiratta, Subhas K. Sikdar
  • Patent number: 4535187
    Abstract: The aldol condensation of acetone to isophorone and mesityl oxides in high conversions and efficiencies is achieved by a catalyst comprising a calcined calcium salt deposited on an alumina support.
    Type: Grant
    Filed: December 21, 1983
    Date of Patent: August 13, 1985
    Assignee: Union Carbide Corporation
    Inventors: Anthony J. Papa, Steven W. Kaiser
  • Patent number: 4533765
    Abstract: This invention pertains to a process for preparing polyhydroxy aromatic compounds by reacting an alkali metal hydroxide with a hydroxymononuclear aromatic compound, e.g., phenol or resorcinol. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably nickel, or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The polyhydroxy aromatic compound is then formed by adding a protonating agent to the reaction product, with the protonating agent liberating the hydroxy compound from the salt.
    Type: Grant
    Filed: December 7, 1983
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, George B. DeLaMater
  • Patent number: 4533763
    Abstract: This invention pertains to a process for preparing hydroxy mononuclear aromatic compounds by reacting an alkali metal hydroxide with a mononuclear aromatic compound, e.g., benzene, xylene or toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The hydroxy mononuclear aromatic compound is then formed by adding a protonating agent to the resulting reaction product, with the protonating agent liberating the hydroxy compound from the salt.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: August 6, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Barton Milligan, George B. DeLaMater
  • Patent number: 4529556
    Abstract: The invention bis((aryl)vinyl)benzenes wherein the aryl and benzene moieties may be substituted, and the vinyl carbon alpha to the central benzene ring may be further substituted with an aliphatic group.
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: July 16, 1985
    Assignee: The Dow Chemical Company
    Inventor: Kenneth J. Bruza
  • Patent number: 4518807
    Abstract: A process for the production of a basic alkaline earth metal phenate is disclosed. The process comprises reacting a phenol, a dihydric alcohol, and an alkaline earth metal agent selected from alkaline earth metal oxides and hydroxides to achieve the addition of the alkaline earth metal to the phenol, wherein water is added to the reaction system in an amount of from 0.01 to 10 mols per mol of the alkaline earth metal agent. This basic alkaline earth metal phenate is useful as an additive for lubricating oils and fuel oils.
    Type: Grant
    Filed: August 10, 1983
    Date of Patent: May 21, 1985
    Assignee: Maruzen Oil Co., Ltd.
    Inventors: Takashi Hori, Sanae Ueda, Yoshihiro Kojima
  • Patent number: 4514577
    Abstract: Phenols having an unsubstituted ortho-position are benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst especially gamma alumina at a temperature sufficient to maintain the reactants in the vapor phase.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: April 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Allen H. Filbey, Henry G. Braxton, Jr., Bernard R. Meltsner
  • Patent number: 4503270
    Abstract: A method is provided for producing 2,3,6 trimethylphenol by rearrangement of 2,4,6 trimethylphenol in the presence of an aluminum based catalyst, such as AlCl.sub.3, and an acid upon heating the mixture to a temperature within the range of 80.degree. C. to 150.degree. C.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: March 5, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4503269
    Abstract: An improvement in a process for the isomerization of cresols may be obtained by effecting the isomerization reaction of a cresol in the presence of a crystalline aluminosilicate zeolite catalyst and added hydrogen. The added hydrogen will provide stability and longer life to the catalyst as well as a more stable selectivity to the desired isomers. The isomerization reaction is effected at temperatures ranging from about 250.degree. to about 450.degree. C. and pressures ranging from 2 to about 75 atmospheres in the presence of added hydrogen, said hydrogen being present in a mole ratio in the range of from about 1:1 to about 10:1 moles of hydrogen per mole of cresol.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: March 5, 1985
    Assignee: UOP Inc.
    Inventors: Dusan J. Engel, Thomas P. Malloy, James P. Shoffner
  • Patent number: 4499312
    Abstract: A process is disclosed for separating 3,5-xylenol or 3,4-xylenol from other closely boiling polymethylated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with the xylenol over other related phenolics in the mixture. The preferentially-formed complex of the xylenol may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of the xylenol.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: February 12, 1985
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4496774
    Abstract: A process is disclosed for separating nitrated phenolic compounds from other nitrated and unnitrated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-nitrated derivatives, or a mixture of two isomeric nitrated phenols or cresols or a mixture of mono- and dinitrated phenols or cresols.
    Type: Grant
    Filed: July 23, 1984
    Date of Patent: January 29, 1985
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4492806
    Abstract: Anhydrous alkali metal (especially sodium) salts of hydroxyaromatic compounds, particularly bisphenols such as bisphenol A, are prepared by forming a solution of the hydroxyaromatic compound in a solvent mixture comprising a relatively high boiling non-polar organic liquid such as toluene or o-dichlorobenzene and an alkanol containing up to about 4 carbon atoms, preferably methanol; contacting said solution with an aqueous solution of a substantially stoichiometric amount of alkali metal hydroxide; and removing substantially all volatile materials from the reaction mixture by evaporation. The product thus obtained is a slurry of the anhydrous alkali metal salt in the non-polar liquid.
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: January 8, 1985
    Assignee: General Electric Company
    Inventors: Ashok K. Mendiratta, Wayne F. Morgan
  • Patent number: 4484011
    Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.
    Type: Grant
    Filed: December 2, 1983
    Date of Patent: November 20, 1984
    Assignee: Eastman Kodak Company
    Inventor: Dale E. Van Sickle
  • Patent number: 4476330
    Abstract: Conversion, e.g. dehydration of aliphatic organic oxygenates having up to about 6 carbon atoms by contact with a crystalline aluminosilicate zeolite, preferably ZSM-5, having a silica to alumina ratio substantially greater than 10, at a temperature of about 70.degree. to 1400.degree. F., depending upon the exact nature of the reactant and product.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: October 9, 1984
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: 4469901
    Abstract: A process is disclosed for separating 5-isopropyl-m-cresol from other isopropylated m-cresols by treating a mixture of the isopropylated m-cresols with a metal halide salt. The metal halide salt preferentially forms a complex with 5-isopropyl-m-cresol over other related closely-boiling isopropylated m-cresols in the mixture. The preferentially-formed complex of 5-isopropyl-m-cresol may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, 5-isopropyl-m-cresol. The process is particularly suitable for isolating 5-isopropyl-m-cresol from closely-boiling isomers, and di-isopropylated m-cresols.
    Type: Grant
    Filed: January 3, 1984
    Date of Patent: September 4, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4460799
    Abstract: This invention relates to a process for the selective preparation of ortho-hydroxybenzyl alcohols and, in particular, ortho-hydroxybenzyl alcohol. According to the invention, the reaction of a phenol with an aldehyde in an initially anhydrous medium and in the presence of a catalytic amount of a metal phenate, results in the selective production of ortho-hydroxybenzyl alcohols.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: July 17, 1984
    Assignee: Isover Saint-Gobain
    Inventors: Robert Perrin, Roger Fugier
  • Patent number: 4410737
    Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid phase in an acid solvent medium which is at least partially aqueous and which comprises halide ions, in the presence of a Group VIII noble metal catalyst, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 18, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Georges Cordier
  • Patent number: 4410739
    Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid organic phase and in the presence of a nobel metal catalyst and a Lewis acid, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 18, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Georges Cordier
  • Patent number: 4410738
    Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid phase in an acid solvent medium which is at least partially aqueous, in the presence of a Group VIII noble metal catalyst and at least one Group 1b to 5a heavy metal, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 18, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Georges Cordier
  • Patent number: 4394526
    Abstract: Para-cresol is separated from a mixture comprising meta-cresol and various other methylated and ethylated phenols by preferentially complexing the para-cresol with one or more anhydrous or dehydrated inorganic salts selected from the group consisting of calcium bromide, lithium bromide, manganese bromide and magnesium chloride. The anhydrous inorganic salt is added to the phenolic mixture in an amount to give a mole ratio of salt to para-cresol in the mixture in the range of about 0.5 mole to one to about 1.5 mole to one. The para-cresol and salt form a complex and the complex is removed from the mixture of methylated and ethylated phenols. Then the complex is decomposed to recover the para-cresol and salt; the recovered salt may be recycled to complex with more para-cresol.
    Type: Grant
    Filed: September 26, 1980
    Date of Patent: July 19, 1983
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4381413
    Abstract: A process for converting anisoles to ortho-methylated phenolic products in high selectivity is disclosed. The process comprises passing methoxybenzene, o-methylmethoxybenzene, 2,6-dimethylmethoxybenzene, or mixtures thereof, over gamma-alumina in the presence of an effective amount of water at a temperature in the range of about 225.degree. to about 295.degree. C.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: April 26, 1983
    Assignee: Conoco Inc.
    Inventor: John R. Dodd
  • Patent number: 4375566
    Abstract: A process for producing selectively o-alkylated phenols wherein an anisole having at least one ortho positioned hydrogen atom is contacted with a mixed oxide catalyst in the vapor phase.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: March 1, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Motoo Kawamata, Kazushi Ohshima, Mitsuo Onofusa, Akihide Kudoh, Makoto Kotani, Takeshi Tsuda
  • Patent number: 4370257
    Abstract: A process for producing a magnesium containing support for titanium comprising contacting magnesium metal, a halogenated hydrocarbon and a compound represented by the formula X'.sub.m C(OR').sub.4-m wherein X' is a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.10 alkyl, aryl, cycloalkyl or halogenated alkyl, aryl, cycloalkyl group, R' is a C.sub.1 -C.sub.20 alkyl, aryl or cycloalkyl group and m is 0, 1 or 2 to form a magnesium-containing solid represented by the formula R'OMgX and thereafter contacting the magnesium-containing solid with a Lewis base or a compound which can form an ester such as benzoyl chloride and a titanium compound such as titanium tetrachloride. The obtained magnesium supported titanium composition is useful as a catalyst component in combination with a co-catalyst organoaluminum compound for the polymerization of olefins.
    Type: Grant
    Filed: August 11, 1980
    Date of Patent: January 25, 1983
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Masafumi Imai, Hiroshi Ueno, Naomi Inaba, Makoto Yoda, Shozo Wada
  • Patent number: 4328368
    Abstract: A method if provided for continuously hydrolyzing urethane foam in a vertically oriented hydrolysis reactor. In a preferred practice, a bed of foam particles is formed in the reactor. Superheated steam is flowed continuously upward through the bed at a temperature and rate such that only the foam particles then adjacent the bottom of the reactor are hydrolyzed and the bulk of the bed is not fluidized. Unreacted steam heats the unhydrolyzed foam. Liquid hydrolysis products are drained as they are formed to prevent hydrolysis-impeding liquid saturation of unhydrolyzed particles.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: May 4, 1982
    Assignee: General Motors Corporation
    Inventors: Robert J. Salloum, Clifford C. Duff
  • Patent number: 4319050
    Abstract: A homogeneous catalytic process for the decarbonylating of formate esters to alcohols and carbon monoxide. The process comprises contacting formate esters of the formula HCOOR where R is C.sub.1 -C.sub.10 aliphatic, C.sub.7 -C.sub.14 araliphatic or C.sub.6 -C.sub.10 aryl with a copper complex of the formula Cu(L)X where L is CO, phosphine or phosphite and X is the anion of an acid in an inert atmosphere at temperatures of from about 100.degree. to 300.degree. C.
    Type: Grant
    Filed: February 13, 1981
    Date of Patent: March 9, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventor: Gerald Doyle
  • Patent number: 4278816
    Abstract: Phenols and thiophenols are produced by reacting the corresponding diphenyl ether compound with hydrogen sulfide in contact with an absorptive catalyst, such as charcoal, activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 300.degree. to about 900.degree. C. are employed.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: July 14, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Kyung-sup Shim
  • Patent number: 4271317
    Abstract: The invention relates to alkylborane complexes with aromatic amines of the formula: ##STR1## in which R.sup.1 and R.sup.2 are the same or different (1-4C)-alkyl radicals, or together with the adjacent nitrogen atom are morpholino, piperidino or pyrrolidino radicals; R.sup.3 and R.sup.4 are independently selected from hydrogen, (1-4C)-alkyl, (1-4C)-alkoxy, di-(1-4C)-alkylamino, morpholino, piperidino and pyrrolidino; thexyl stands for 1,1,2-trimethylpropyl; and n is the integer 1 when R.sup.3 and R.sup.4 are other than nitrogen containing radicals, or the integer 1 or 2 when one of R.sup.3 and R.sup.4 is a nitrogen containing radical, or the integer 1, 2 or 3 when both R.sup.3 and R.sup.4 are nitrogen containing radicals.The complexes are more stable than thexylborane tetrahydrofuran complex, but are sufficiently reactive to be valuable as hydroborating and reducing agents.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: June 2, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventors: Andrew Pelter, David J. Ryder
  • Patent number: 4260808
    Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: April 7, 1981
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: T101601
    Abstract: Novel phenolic cyan dye-forming couplers contain in the 2-position a p-cyanophenylureido group. These couplers are useful in photographic emulsions, elements and processes.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: March 2, 1982
    Inventor: Philip T. S. Lau