Acyclic Patents (Class 568/594)
  • Patent number: 5783732
    Abstract: 2:2 mixed orthocarbonates of the formula ##STR1## wherein R.noteq.R' and wherein R and R' are --C(NO.sub.2).sub.3, --CF(NOb.2).sub.2, --CF.sub.2 (NO.sub.2), --C(NO.sub.2).sub.2 CH.sub.3, --CH(NO.sub.2)CH.sub.3, --CH(NO.sub.2)CH.sub.3, --CH.sub.2 (NO.sub.2), --CF.sub.3, or --CF.sub.2 CF.sub.3, and methods of preparation.Additionally, orthoformates of the formula ##STR2## wherein R is --C(NO.sub.2).sub.2 CH.sub.3, --CF.sub.2 (NO.sub.2), --CH(NO.sub.2)CH.sub.3, and --CH.sub.2 (NO.sub.2), and methods of preparation.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: July 21, 1998
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: William H. Gilligan
  • Patent number: 5672779
    Abstract: The present invention provides a compound represented by the formula: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group or a C.sub.1 -C.sub.6 alkyl group which may be substituted with at least one halogen atom; and A' represents a hydrogen atom or a protecting group for a hydroxyl group. The compound is useful in the preparation of esters which can be used to control insect pests.
    Type: Grant
    Filed: May 1, 1996
    Date of Patent: September 30, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
  • Patent number: 5631406
    Abstract: Dichloroformals of the formula(RCH.sub.2 O).sub.2 CCl.sub.2wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.su), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, or --CF.sub.2 CF.sub.3. These dichloroformals are prepared by reacting the corresponding thionocarbonate of the formula(RCH.sub.2 O).sub.2 C.dbd.S,wherein R is as defined above, with sulfuryl chloride in the presence of a Friedel-Craft catalyst (e.g., AlCl.sub.3 or TiCl.sub.4). Another method is to react the thionocarbonate with chlorine gas in the presence of a polar additive such as 2,2,2-trifluoroethanol or acetonitrile. These energetic dichloroformals are useful as explosive and propellant ingredients and as intermediates in the synthesis of other energetic explosive and propellant ingredients.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: May 20, 1997
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: William H. Gilligan
  • Patent number: 5565585
    Abstract: A new and practical method for synthesizing heterocyclic polyhydroxylated alkaloids using enzymatic aldol condensation and catalytic intramolecular reductive amination is disclosed.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: October 15, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Chi-Huey Wong, Richard L. Pederson, Yi-Fong Wang
  • Patent number: 5550299
    Abstract: Ortho esters of the structure ##STR1## wherein R.sub.1 and R.sub.2 are different or the same alkyl moieties and can be a saturated, unsaturated, branched, unbranched or cyclic alkyl moiety of 1-3 carbon atoms, are prepared by first anhydrously reacting hydrogen cyanide or a hydrogen cyanide derivative with a secondary alkanol and hydrogen chloride in the presence of an inert organic solvent. Upon the formation of the resulting imino ether hydrochloride, more secondary alkanol is added to form the ortho esters (I). 1,1-Dialkoxycycloalkanes of the structure ##STR2## wherein R.sub.1 and R.sub.2 correspond to R.sub.1 and R.sub.2 of structure (I), and n is an integer from 4 to 9, are prepared by reacting with the imino ether hydrochloride more secondary alkanol and a cycloalkanone having 5 to 10 carbon atoms.
    Type: Grant
    Filed: October 24, 1994
    Date of Patent: August 27, 1996
    Assignee: Huls America Inc.
    Inventors: Chitoor S. Subramaniam, Thomas V. John, David Colvin, George W. Bitler
  • Patent number: 5527969
    Abstract: A process for preparing acetaldehyde diethyl acetal is provided which involves:reacting acetaldehyde with ethanol in the presence of an acid catalyst and in the presence of an entrainer having a boiling point of from 25.degree. to 75.degree. C.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: June 18, 1996
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Moustafa El-Chahawi
  • Patent number: 5449836
    Abstract: A process for the preparation of vitamin A which preferably comprises bringing cyclogeranyl sulphone into contact with a C.sub.10 aldehyde acetal, halogenating the derivative obtained and then removing the halogen group and the sulphone, removing the acetal group and isomerizing the retinal obtained to the desired configuration. Also disclosed are compounds useful as intermediates in the synthesis of vitamin A and processes for preparation of these intermediate compounds.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: September 12, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Pierre Chabardes
  • Patent number: 5399778
    Abstract: Ketals of longer-chain or branched alcohols are prepared from dimethyl ketals or their ketones by reaction of the dimethyl ketals and the alcohols at high temperatures of 150.degree. to 180.degree. C. in the presence of acid catalysts. The enol ethers and mixed ketals which are separated by distillation are added to the next reaction batch and also react to form the target product. The starting material, dimethyl ketal, may also be formed during the reaction from the ketone and trimethyl orthoformate.
    Type: Grant
    Filed: October 19, 1993
    Date of Patent: March 21, 1995
    Assignee: Huls Aktiengesellschaft
    Inventors: Klaus-Dieter Steffen, Josef Metz
  • Patent number: 5393867
    Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of a palladium(O) catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, m/(n+m) is greater than 0.30 and up to 0.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Falling: Stephen N.
  • Patent number: 5362918
    Abstract: A process for producing acetaldehyde dimethylacetal comprising reacting acetaldehyde and methanol in the presence of an acid catalyst is disclosed, in which the reaction is carried out in a part of a rectification tower while conducting rectification to withdraw the water by-produced from the bottom of the tower and to recover a distillate containing the acetaldehyde dimethylacetal produced from the top of the tower. The distillate is subjected to azeotropic distillation in the presence of n-hexane or cyclohexane to separate methanol as an azeotrope with n-hexane or cyclohexane and a small amount of the acetaldehyde dimethylacetal and to recover high purity acetaldehyde dimethylacetal as a bottom.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: November 8, 1994
    Assignee: Showa Denko K.K.
    Inventors: Toshiyuki Aizawa, Hitoshi Nakamura, Kunitoshi Wakabayashi, Tetsuo Kudo, Hiroyuki Hasegawa
  • Patent number: 5350878
    Abstract: This invention provides 1) novel reactive fluorinated compounds derived from a specified class of telomers or cotelomers of fluoroolefins; and 2) stable products and stable polymers thereof obtained by reaction or polycondensation of the novel reactive fluorinated compounds with specified classes of hydrogenated aliphatic, alicyclic, aromatic reactive compounds, telechelic oligomers and block polymers wherein said stable products and polymers contain hetero atoms such as oxygen, sulfur or nitrogen and are characterized by high thermal and chemical resistance.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: September 27, 1994
    Assignee: Dow Corning Corporation
    Inventor: Gerardo Caporiccio
  • Patent number: 5290912
    Abstract: The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: March 1, 1994
    Assignee: Asahi Glass Company Ltd.
    Inventors: Takashi Watabe, Hiromitsu Takeyasu, Shigeyuki Kozawa
  • Patent number: 5254744
    Abstract: Oligomeric formal diols are prepared by coupling segments of poly(tetramethylene ether) glycols, each having a molecular weight of 650-3000, with formaldehyde in the presence of a granular acidic catalyst, to yield poly(tetramethylene ether) formal glycols of 1,400-12,000 molecular weight.Oligomeric formal diols of a second type can also be prepared by coupling with formaldehyde segments of poly(tetramethylene ether) glycols mixed with segments of other polymeric glycols, as for example polyethylene oxide glycol of 200 molecular weight, to yield poly(ether formal) glycols of substantially higher molecular weight than either of the starting polyether glycols, and having properties significantly different from the parent polyether glycols that may affect the performance as soft or elastomeric segments of derived polyurethanes, polyetheresters, and polyureas.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: October 19, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: John F. Neumer
  • Patent number: 5155281
    Abstract: A method of preparing dichloroformals of the formula(RCH.sub.2 O).sub.2 CCl.sub.2by reaction of one mole of a thionocarbonate of the formula(RCH.sub.2 O).sub.2 C.dbd.Swith two moles of benzenesulfenyl chloride, chlorobenzenesulfenyl chloride, r methanesulfenyl chloride wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.sub.2), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, or --CF.sub.2 CF.sub.3. These energetic dichloroformals are useful as explosive and propellant ingredients and as intermediates in the synthesis of other energetic explosive and propellant ingredients.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: October 13, 1992
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, William H. Gilligan
  • Patent number: 5132465
    Abstract: Primary alcohols may be oxidized to the corresponding aldehydes using non-toxic oxidizing agents such as tert-butyl hydroperoxide (TBHP) in the presence of a transition metal phthalocyanine catalyst. Representative catalysts include ferrous phthalocyanine and chloroferric phthalocyanine. Under some conditions, 1,1-dialkoxyalkanes may be co-produced with the aldehydes. 1,1-Dialkoxyalkanes are protected aldehydes and find utility in solvents.
    Type: Grant
    Filed: April 23, 1991
    Date of Patent: July 21, 1992
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 5051153
    Abstract: Methylal cannot be completely separated from methylene chloride by conventional distallation or rectification because of the maximum boiling azeotrope. Methylal can be readily separated from methylene chloride by extractive distillation. Typical effective agents are n-butyl acetate, diisobutyl ether and 4-methyl-2-pentanone.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: September 24, 1991
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 4982011
    Abstract: Ether/ether-alcohol rich compositions are produced by hydrogenating hydroformylation reaction products, separating an ether/ether-alcohol containing mixture from the hydrogenation product, and catalytically hydrogenating such mixture at 200.degree.-250.degree. C. and 30-100 atmospheres. The crude product is then reflux distilled to separate the ether/ether-alcohol rich compositions from lighter and heavier ends.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: January 1, 1991
    Assignee: Exxon Research and Engineering Co.
    Inventor: Jean A. A. Hanin
  • Patent number: 4908477
    Abstract: Organic iodine compounds are separated from carbonylation products of methanol, methyl acetate and dimethyl ether and from mixtures of such carbonylation products by a process wherein the iodine compounds are removed by liquid phase extraction with a non-aromatic hydrocarbon.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: March 13, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
  • Patent number: 4851569
    Abstract: Methyl formate is produced continuously by reacting methanol in the liquid phase with molecular oxygen in the presence as catalyst of a soluble chromium compound which can be deliberately added or can result from corrosion of a reaction vessel fabricated in stainless steel or other chromium-containing metal alloy. Initiation of the oxidation can be accomplished by feeding a material more susceptible to oxidation than methanol, either with or without methanol, and optionally in the presence of a soluble chromium compound.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: July 25, 1989
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, John Pennington
  • Patent number: 4841075
    Abstract: A method of preparing an acetal or ketal from a corresponding aldehyde or ketone is disclosed. A hydrous oxide of an element of Group IV of the Periodic Table is used as a catalyst, and the aldehyde or ketone is caused to react with an alcohol. The hydrous oxide can be obtained by partially dehydrating a hydroxide of the corresponding element. The method does not require an acid catalyst and is applicable to a carbonyl compound which is not stable in acids.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: June 20, 1989
    Assignee: Japan Tobacco, Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi, Hideyuki Kuno
  • Patent number: 4792637
    Abstract: A process for the synthesis of vinyl ethers of formula ##STR1## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or a primary, secondary or tertiary alkyl group,R.sub.3 is a hydrogen, a primary alkyl, phenyl, or substituted phenyl group, orR.sub.2 and R.sub.3, taken together, represent a polymethylene chain containing from 3 to 10 carbon atoms wherein one or more hydrogens can be replaced by methyl or ethyl groups, andR is a primary, secondary or tertiary alkyl group, which comprises reacting a suitably selected dioxolane derivative of formula II ##STR2## wherein R.sub.1, R.sub.2, and R.sub.3 are as defined above, andR.sub.4, R.sub.5, R.sub.6, and R.sub.7, each independently, represent hydrogen or an alkyl group, with a boric acid ester of formula IIIB(OR).sub.3 IIIwhereinR is as defined above, in the vapor phase, at a temperature comprised between 100.degree. and 400.degree. C., and in the presence of an acidic heterogeneous catalyst.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: December 20, 1988
    Assignee: Enichem Anic SpA
    Inventors: Giuseppe Messina, Mario D. Moretti, Salvatore R. Sanna, Giovanni Soma, Pier G. Cabras
  • Patent number: 4775447
    Abstract: The process for the acid-catalyzed reaction of acetone with methanol to form 2,2-dimethoxypropane may be significantly improved if a stoichiometric ratio of methanol/acetone is employed in the initial reaction.Of particular advantage is the use of stoichiometric amounts of reactants in order to (1) avoid the expense of using an excess of either reactant, and (2) facilitate the removal of the 2,2-dimethoxypropane as an azeotrope with the methanol, thereby avoiding costly and complex product recovery methods.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: October 4, 1988
    Assignee: Sun Refining and Marketing Company
    Inventors: Chao-Yang Hsu, Paul E. Ellis, Jr.
  • Patent number: 4769497
    Abstract: A new method of synthesis of a 2,2-dialkoxy-propane e.g. 2,2-dimethoxy-propane, is described through reaction of a cyclic ketal, e.g. 2,2-dimethyl-(1,3)-dioxolane, with a boric acid alkyl ester, e.g. boric acid trimethyl ester, in the presence of an acidic catalyst. The reaction may be carried out either in liquid or in vapor phase. In the latter case, heating of the thus obtained intermediate mixture to the reflux temperature should follow the catalytic step.
    Type: Grant
    Filed: June 23, 1987
    Date of Patent: September 6, 1988
    Assignee: Enichem Anic S.p.A.
    Inventors: Giuseppe Messina, Mario D. Moretti, Gavino Sanna, Salvatore R. Sanna, Giovanni Soma
  • Patent number: 4749816
    Abstract: A process for preparing an acetal or a ketal comprises contacting an olefin with an alcohol at elevated temperature in the presence of a dihydrocarbyl peroxide and a catalyst comprising palladium and a copper compound. The process is preferably carried out in the presence of an amine which is unable to coordinate to the catalyst.
    Type: Grant
    Filed: May 20, 1987
    Date of Patent: June 7, 1988
    Assignee: British Petroleum Co. p.l.c.
    Inventor: Andrew R. Lucy
  • Patent number: 4743401
    Abstract: A process for converting an allylic ether to its corresponding acetal is disclosed. In this process an allylic ether is contacted with an organic hydroxy compound and a catalytically effective amount of a cobalt compound to produce the corresponding acetal.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: May 10, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventors: Biau-Hung Chang, Ronnie M. Hanes
  • Patent number: 4740273
    Abstract: A process for purifying diethoxymethane from a mixture containing ethanol and, optionally, water. The process involves the addition of an amount of water, DEM, or an appropriate mixture of any two or three of water, DEM and ethanol that is effective in moving the mixture into the two liquid phase region on an equilibrium tie-line which crosses the critical distillation boundary without the need for additional azeotrope-forming agents such as cyclohexane.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventors: Daniel L. Martin, Peter W. Raynolds
  • Patent number: 4683343
    Abstract: Heavy organic by-products obtained by hydroformylating olefins and hydrogenating the crude product to obtain higher alcohols, and their steam cracked derivatives, have been found useful as viscosity modifiers and low temperature property improvers in flexible PVC compositions.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: July 28, 1987
    Assignee: Exxon Research & Engineering Co.
    Inventors: Jean A. Hanin, Pierre E. Verrier
  • Patent number: 4658069
    Abstract: 9-methoxy-7-nonenal may be isomerized in the presence of methanol and ruthenium chloride to provide 1,1,9,9-tetramethoxynonane. The rates of reaction are increased by pre-formation of 1,1,9-trimethoxy-7-nonene and removal of the water generated prior to conducting the isomerization reaction.
    Type: Grant
    Filed: July 2, 1985
    Date of Patent: April 14, 1987
    Assignee: National Distillers and Chemical Corporation
    Inventors: Ronnie M. Hanes, William D. Baugh
  • Patent number: 4628113
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising cobalt in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: December 9, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4613411
    Abstract: Diethoxymethane (ethylal), prepared by reacting formaldehyde with ethanol, may be recovered from the product mixture in substantially pure form by first distilling off an azeotrope comprising ethanol and diethoxymethane, adding a selected solvent to the azeotrope which will form an azeotrope with the ethanol, distilling off said latter azeotrope and recovering the substantially pure diethoxymethane.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: September 23, 1986
    Assignee: Sun Refining and Marketing Company
    Inventors: Chao-Yang Hsu, Paul E. Ellis, Jr.
  • Patent number: 4579980
    Abstract: An ether compound is advantageously produced by an ether exchange reaction of a different ether compound and a hydroxy group containing compound in the presence of a heteropoly acid or an acidic salt thereof as the catalyst. The catalyst is novel and is extremely effective to the present process and brings about less by-products compared to other processes or other catalysts.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: April 1, 1986
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Kiyoshi Kogoma, Norio Sone, Takashi Tobita, Masahiro Shiozaki
  • Patent number: 4579979
    Abstract: A method of preparation for acetals utilizing saturated or unsaturated aldehydes, in particular, the preparation of dimethylacetals of acetaldehyde, acrolein and methacrolein. The production of the acetal takes place in a liquid phase in the presence of a solid acid catalyst, such as a strongly acidic ion exchange resin or zeolite. The conversion mixture is extracted by means of water and by means of water insoluble organic solvents. There is obtained not only the desired acetals, but in addition also the unconverted initial quantities of the starting materials by a simple method and with very good yields.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: April 1, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Dietrich Arntz, Michael Kraft, Gunter Prescher
  • Patent number: 4574158
    Abstract: Trioxane and other acetals are purified by contact with an alkali metal hydroxide and phase transfer catalyst followed by isolation in a purified form. This reaction provides acetals sufficiently pure for polymerization to high molecular weight.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: March 4, 1986
    Assignee: Conoco Inc.
    Inventor: Jeff T. Fenton
  • Patent number: 4536585
    Abstract: It is disclosed that a Pd-Tl alloy catalyst is used in making acetals and acetalic ethers from alcohols and saturated or unsaturated aldehydes, and to make cyclic acetals and cyclic acetalic ethers when reacting with diols.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: August 20, 1985
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw
  • Patent number: 4518785
    Abstract: Novel malondialdehyde tetraalkylacetals and the preparation of malondialdehyde tetraalkylacetals by reacting alkyl formates, oxiranes and alkyl vinyl ethers in the presence of a halide of boron, antimony(V), iron(III), tin(II or IV) and/or zinc.The malondialdehyde tetraalkylacetals obtainable by the process of the invention are valuable starting materials for the preparation of dyes, pest control agents and pharmaceuticals.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: May 21, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eckhardt, Klaus Halbritter, Wolfgang Rohr
  • Patent number: 4504422
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4504421
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: March 12, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4501705
    Abstract: An acetal is produced at a high yield and a high selectivity by contacting an olefin and an alcohol with each other in the presence of (a) a nitrite, (b) a platinum group metal or the salts thereof and (c) a halide at a high reaction rate without requirement of any troublesome operations for the separation, recovery and regeneration of the catalyst.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: February 26, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Akira Iwayama, Takashi Umezu
  • Patent number: 4491676
    Abstract: Described herein is a process for rapidly obtaining a stable freeze point depressed aqueous solution comprising a dialdehyde and an aliphatic monohydroxyl alcohol and/or polyhydroxyl alcohol by adding thereto a catalytic amount of a strong acid. Also included herein is a method for liberating the dialdehyde in the aqueous solution by dilution with water and the addition of a catalytic amount of a strong acid.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: January 1, 1985
    Assignee: Union Carbide Corporation
    Inventors: Robert G. Eagar, Jr., Gerald J. Murphy
  • Patent number: 4469887
    Abstract: To produce methacrylic acid, firstly, isobutyraldehyde is acetalized. The resultant acetal is cleaved into the isobutenyl ether and alcohol. The isobutenyl ether is oxidized with molecular oxygen or an oxygen-containing gaseous mixture in the presence of an alkaline solution at temperatures of 30.degree.-70.degree. C. to obtain the epoxide. This epoxide is hydrolyzed to the .alpha.-hydroxyisobutyraldehyde. The latter is then oxidized with concentrated or fuming nitric acid at temperatures of 20.degree.-110.degree. C. to produce .alpha.-hydroxyisobutyric acid, and methacrylic acid is obtained therefrom by splitting off water.
    Type: Grant
    Filed: October 26, 1982
    Date of Patent: September 4, 1984
    Assignee: Chemische Werke Huels, AG
    Inventors: Rudolf Brockhaus, Hans-Jurgen Franke
  • Patent number: 4460767
    Abstract: A process is disclosed for production of a sugar ketal, which comprises reacting a sugar with a ketone in the presence of (A) (1) copper, or an oxide, hydroxide or salt thereof and (2) hydrogen chloride or hydrogen bromide, or (B) cupric chloride or cupric bromide, said catalyst system being very effective in a small amount. The formation of unfavorable by-products can be reduced to a trace amount. The process offers the objective ketal in improved yields, and an industrially advantageous process.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: July 17, 1984
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Koichi Matsumura, Tetsuya Aono
  • Patent number: 4440892
    Abstract: The invention relates to pharmaceutical compositions containing, as an active ingredient, a water-soluble polyester or polycarbonate based on one or more polyetherglycols of Formula (I) as defined in the specification. Also included in the invention is the use of said compositions for their tumor-inhibiting action.
    Type: Grant
    Filed: June 25, 1981
    Date of Patent: April 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard D. Wolf, Bruno Bomer, Robert Bierling
  • Patent number: 4408069
    Abstract: A homogeneous catalytic process for the conversion of methanol to methyl acetate. The process comprises contacting CO with methanol in the presence of a catalytically effective amount of an iron-cobalt carbonyl complex of the formula M[FeCo.sub.3 (CO).sub.12 ] or M[CoFe.sub.3 (CO).sub.13 ] where M is hydrogen or a cation and an iodide promoter, heating the resultant mixture at temperatures of from 100.degree. to 250.degree. C. at pressures of from 5 to 100 MPa.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: October 4, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventor: Gerald Doyle
  • Patent number: 4393252
    Abstract: Ethylene glycol is prepared by reacting methanol and an organic peroxide of the formula R--O--O--R.sub.1, wherein R and R.sub.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms, in the presence of a minor amount of a basic material. Preferably, formaldehyde is present as a reactant in the presence of water. The presence of the basic material reduces the hydrogen ions which are formed and thus reduces the amount of methylal produced.
    Type: Grant
    Filed: March 26, 1982
    Date of Patent: July 12, 1983
    Assignee: Redox Technologies, Inc.
    Inventor: John Kollar
  • Patent number: 4385965
    Abstract: In a process for recovering pure methylal from methanol-methylal mixtures, which can optionally contain still further compounds, the separation conducted in a rectification device comprising two rectifying columns. In the first rectifying column, the mixture to be separated is rectified under a pressure lower than that in the second column, into a methylal-rich, methanol-poor distillate, and into a practically methylal-free, methanol-rich sump product. The methylal-rich distillate of the first rectification is then separated in a second rectifying column, operated under a higher pressure than the first rectification column, into a compound stream containing methanol and methylal, which is then recycled to the first rectifying column, and into pure methylal as the sump product.
    Type: Grant
    Filed: January 26, 1982
    Date of Patent: May 31, 1983
    Assignee: Chemische Werke Huls A.G.
    Inventors: Wolfgang H. E. Muller, Manfred Kaufhold
  • Patent number: 4331612
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: July 16, 1980
    Date of Patent: May 25, 1982
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase
  • Patent number: 4313893
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: February 2, 1982
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase
  • Patent number: 4301090
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt carbonyl and a polyamine promoter ligand. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: November 17, 1981
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase
  • Patent number: 4280011
    Abstract: The use of acetals as aldehyde generators in foodstuff applications is disclosed.
    Type: Grant
    Filed: April 5, 1978
    Date of Patent: July 21, 1981
    Assignee: Hercules Incorporated
    Inventor: Robert S. DeSimone
  • Patent number: 4278819
    Abstract: Improved process for the production of acetaldehyde dimethyl acetal by reacting methanol with carbon monoxide and hydrogen in the presence of a cobalt-containing catalyst, halogen or a halide as promoter and a 3-valent phosphorus compound as ligand using a nickel compound as a co-catalyst.
    Type: Grant
    Filed: April 2, 1980
    Date of Patent: July 14, 1981
    Assignee: Union Rheinische Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Joachim Korff, Max Fremery, Johannes Zimmermann