Polyalkylol Substituted Alkane (e.g., Pentaerythritol, Trimethylolethane, Ect.) Patents (Class 568/853)
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Patent number: 6077964Abstract: A process is described for the production of at least one C.sub.4 compound selected from butane-1,4-diol, .gamma.-butyrolactone and tetrahydrofuran, which includes the step of hydrogenation in the vapour phase of maleic anhydride in the presence of a heterogeneous hydrogenation catalyst, which process comprises:(a) contacting a vaporous stream containing maleic anhydride vapour, water vapour, and carbon oxides in an absorption zone with a high boiling organic solvent having a boiling point at atmospheric pressure which is at least about 30.degree. C.Type: GrantFiled: November 12, 1998Date of Patent: June 20, 2000Assignee: BASF AktiengesellschaftInventors: Michael William Marshall Tuck, Michael Anthony Wood, Andrew George Hiles
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Patent number: 6077980Abstract: A process for producing a polyhydric alcohol which comprises subjecting formaldehyde and a specific aliphatic aldehyde to an aldol condensation reaction in the presence of a base catalyst, and then subjecting the resultant reaction product to a crossed Cannizzaro reaction, while separating 2-alkenal formed as a byproduct during the aldol condensation reaction, prior to the completion of the crossed Cannizzaro reaction. Also a process for producing a polyhydric alcohol which comprises reacting formaldehyde with a 2-alkenal, such as that obtained in the aldol condensation reaction, in the presence of a base catalyst, then subjecting the resultant reaction product and a specific aliphatic aldehyde to an aldol condensation reaction, and subsequently subjecting the resultant reaction product to a crossed Cannizzaro reaction. The processes provide a polyhydric alcohol in high selectivity with a minimum excess of formaldehyde, without substantially by-producing a 2-alkenal.Type: GrantFiled: July 17, 1998Date of Patent: June 20, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Teruyuki Ninomiya, Toshio Watanabe, Takaki Ikebe, Atsushi Iwamoto
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Patent number: 6034285Abstract: High quality trimethylolalkane can be easily and efficiently produced at a high yield through a reaction between n-alkanal and formaldehyde in the presence of tertiary amine and water, in which a reaction mixture obtained aster the reaction is heated so that a salt of tertiary amine with formic acid produced as a by-product is decomposed into hydrogen and carbon dioxide and/or water and carbon monoxide, and tertiary amine; and the tertiary amine distilled from the reaction mixture is reused in producing trimethylolalkane.Type: GrantFiled: October 20, 1998Date of Patent: March 7, 2000Assignee: Koei Chemical Company, LimitedInventors: Kenji Doi, Takuhiko Jinno, Ayao Moriyama, Michiaki Matsuura
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Patent number: 6034284Abstract: High quality trimethylolalkane can be easily and efficiently produced at a high yield through a reaction between n-alkanal and formaldehyde in the presence of tertiary amine and water, in which a reaction mixture obtained after the reaction is heated up to a temperature at which a salt of tertiary amine with formic acid produced as a by-product can be thermally dissociated so as to distill tertiary amine and water from the reaction mixture, and a formate of trimethylolalkane produced in the distillation of tertiary amine and contained in a residue is reacted with water, ammonia, primary amine or secondary amine; and the tertiary amine distilled from the reaction mixture is reused in producing trimethylolalkane.Type: GrantFiled: October 20, 1998Date of Patent: March 7, 2000Assignee: Koei Chemical Company, LimitedInventors: Kenji Doi, Takuhiko Jinno, Ayao Moriyama, Shingo Uji
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Patent number: 6018074Abstract: A process for the preparation of polyalcohols comprises the stages:(a) Reaction of an alkanal or ketone with formaldehyde in aqueous solution in the presence of a tertiary amine, to form a formates containing polyalcohol product mixture,(b) removal of water, excess tertiary amine, excess formaldehyde(c) heating of remaining mixture from (b) with removal of further formaldehyde and tertiary amine with formation of the formates of the polyalcohol,(d) transfer of tertiary amine removed from stage (b) and/or from stage (c), to synthesis stage (a) and/or to the subsequent transesterification stage (e),(e) transesterification of the resulting formates of the polyalcohol from stage (c) with an alcohol of the formula ROH in the presence of a transesterification catalyst to give polyalcohols and formates of the formula ##STR1## where R is a hydrocarbon radical, preferably alkyl of 1-6, particularly preferably 1-2, carbon atoms, and(f) isolation of the polyalcohols.Type: GrantFiled: October 5, 1998Date of Patent: January 25, 2000Assignee: BASF AktiengesellshcaftInventors: Detlef Kratz, Achim Stammer, Tom Witzel, Martin Brudermuller
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Patent number: 6008418Abstract: 1,6-Hexanediol is prepared from a carboxylic acid mixture comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols which is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol by water extraction of the reaction mixture, by esterification of the acids and hydrogenation whereina) the monocarboxylic and dicarboxylic acids present in the aqueous dicarboxylic acid mixture are reacted with a low molecular weight alcohol to give the corresponding carboxylic esters,b) the resulting esterification mixture is freed of excess alcohol and low boilers in a first distillation stage,c) the bottoms are fractionated in a second distillation stage to give an ester fraction essentially free of 1,4-cyclohexanediols and a fraction comprising at least the major part of the 1,4-cyclohexanediols,d) the ester fraction essentially free of 1,4-cyclohexanediols is catalytically hydrogenated ande) in a pure distillation stage, 1,6-hexanediol is isolated from the hydrogenaType: GrantFiled: August 28, 1998Date of Patent: December 28, 1999Assignee: BASF AktiengesellschaftInventors: Karl Gerhard Baur, Rolf Fischer, Rolf Pinkos, Frank Stein, Harald Rust, Boris Breitscheidel
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Patent number: 5976202Abstract: Reaction products of polyolefins having predominantly a terminal double bond and a number average molecular weight of from 250 to 10,000, which possess an aliphatic hydrocarbon skeleton which is straight-chain or carries C.sub.1 -C.sub.4 -alkyl side chains, with from 1 to 10 mol, per equivalent of double bond, of one or more vinyl esters I ##STR1## are obtainable by reacting the stated polyolefins with the vinyl esters I in the presence of a free radical initiator at from 80 to 200.degree. C., it being possible for these reaction products subsequently to have been hydrolyzed to the corresponding alcohols or converted into the corresponding amines by reductive amination with amines II ##STR2## .Type: GrantFiled: July 20, 1995Date of Patent: November 2, 1999Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Helmut Mach, Harald Schwahn, Hans-Joachim Muller, Wolfgang Reif, Thomas Ruhl
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Patent number: 5948943Abstract: Disclosed is a process for acquiring crude trimethylolpropane (TMP) of low reacted color. TMP is generally prepared by the condensation of n-butyraldehyde and formaldehyde in an alkali solution. The mixture is then concentrated and placed through an extractor. It has been found that a high concentration of low color TMP is present in the extractor and may by obtained by taking a slip stream of hot organic/water/TMP from the extractor and allowing the mixture to cool and phase separate. Upon separation of the phases, TMP generally having an acid wash color of about or less than 5 GU is recovered from the water phase. Disclosed is use of a single and multistage extractor.Type: GrantFiled: October 16, 1997Date of Patent: September 7, 1999Assignee: Celanese International CorporationInventors: Carolyn Supplee, Rodolfo W. Laurel, George C. Seaman
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Patent number: 5859263Abstract: The present invention relates to a continuous process for preparing levulinic acid from starch in a reactive extrusion process. In a preferred embodiment, the extrusion takes place in a twin-screw extruder having a plurality of temperature zones wherein the starch slurry is preconditioned, extruded, filter pressed, reboiled, vacuum distilled, condensed, centrifuged, whereby the waste effluent from the centrifugation is reprocessed upstream to the preconditioning stage.Type: GrantFiled: August 14, 1996Date of Patent: January 12, 1999Assignee: Board of Regents University of Nebraska LincolnInventors: Viswas M. Ghorpade, Milford A. Hanna
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Patent number: 5853458Abstract: A solvent composition comprising a glycol, a potassium carboxylate and a neopentyl alcohol having improved dehydrating capacity and reduced absorbency for aliphatic and aromatic hydrocarbons.Type: GrantFiled: August 18, 1997Date of Patent: December 29, 1998Assignee: Gavlin Associates, IncInventors: Gilbert Gavlin, Boris Goltsin
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Patent number: 5841002Abstract: An aldolisation process is disclosed for converting an aldehyde or mixture of aldehydes, such as iso-butyraldehyde and formaldehyde, to a desired polyhydroxy alcohol or glycol, such as neopentyl glycol. Aldolisation is effected in a stirred tank reactor using an alkali catalyst, such as sodium hydroxide. An aldolisation intermediate product is converted to the desired polyhydroxy alcohol or glycol by a hydrogenation or cross-Cannizzaro reaction step. The product is recovered and an aqueous catalyst-containing phase is recycled to the aldolisation zone. At least a portion of this catalyst recycle stream is purged to control the build up of cross-Cannizzaro products in the recycle stream. The purge stream is treated electrolytically to obtain an aqueous catalyst-containing solution for recycle to the aldolisation zone and an effluent stream comprising volatile organic materials and being substantially free from alkali catalyst.Type: GrantFiled: September 27, 1996Date of Patent: November 24, 1998Assignee: Davy Process Technology LimitedInventors: George Edwin Harrison, Arthur James Reason
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Patent number: 5763690Abstract: Trimethylolpropane of high purity is efficiently made by mixing the aldol reaction product of formaldehyde and n-butyraldehyde with at least about 20 wt % of a lower alcohol prior to hydrogenation. The alcohol addition also promotes hydrogenolysis of by-product esters at pressures below 3000 psig and allows recovery of high purity product by simple distillation.Type: GrantFiled: August 2, 1996Date of Patent: June 9, 1998Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
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Patent number: 5741956Abstract: A process for the preparation of pentaerythritol, comprising reacting formaldehyde, acetaldehyde and sodium hydroxide and acidification with formic acid. These steps take place in a reactor with supplies of formaldehyde, sodium hydroxide, acetaldehyde and formic acid and at the end the solution formed is evacuated to a buffer tank of larger capacity than the reactor. In the reactor new reactions and acidifications are successively reinitiated by new supplies. In the first place a formaldehyde solution is added, followed by simultaneous but separate additions of sodium hydroxide solution and acetaldehyde, forming a reaction mixture in such a way that the flowrates of the solutions vary with the time and that the temperature at which the reactions are conducted also varies with the time. The outflow from the buffer tank is constant and continuous.Type: GrantFiled: November 26, 1996Date of Patent: April 21, 1998Assignee: Patentes y NovedadesInventor: Lluis Eek
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Patent number: 5731479Abstract: Optically active alcohols are prepared by reducing optically active carboxylic acids with hydrogen in the presence of ruthenium catalysts.Type: GrantFiled: December 5, 1995Date of Patent: March 24, 1998Assignee: Bayer AktiengesellschaftInventor: Stefan Antons
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Patent number: 5663450Abstract: This invention encompasses a substantially homogeneous lipid chemoattractant released from stressed mammalian tissue which is a neutral lipid which is acid labile and stable to base and is stable in boiling water. This lipid recruits macrophages but not neutrophils to stressed tissue. The invention also encompasses a method for detecting injured tissue by detecting the presence of the above described lipid chemoattractant in body fluids such as urine, serum and saliva. The invention also includes a method for reducing recruitment of macrophages to injured tissue by reducing the amount of the above lipid chemoattractant or by blocking the interaction of this lipid chemoattractant with its macrophage binding site. The addition of this lipid chemoattractant to injured skin tissue promotes healing.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: CV TherapeuticsInventors: George F. Schreiner, Louis G. Lange, III
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Patent number: 5635588Abstract: Disclosed herein is a process wherein glycerol, glycidol or 2,2-dimethyl-1,3-dioxolane-4-methanol is polymerized in the presence of an acid zeolite having an average pore size of at least 0.6 nanometer at 150.degree.-250.degree. C. At least 50 wt. % of cyclic polymers are obtained.Type: GrantFiled: December 20, 1995Date of Patent: June 3, 1997Assignee: Unichema Chemie B.V.Inventors: Johan I. Eshuis, Johannes A. Laan, Ronald P. Potman
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Patent number: 5635542Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.Type: GrantFiled: June 16, 1995Date of Patent: June 3, 1997Assignee: Bayer AktiengesellschaftInventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel
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Patent number: 5618985Abstract: The invention relates to a novel, technically simple but efficient and high-yield process for the preparation of 2-n-butyl-2-ethyl-1,3-propane diol from 2-ethyl hexanal and formaldehyde by using a basic alkali metal hydroxide or earth alkali metal hydroxide catalyst. In the process according to the invention, cationic or neutral phase transfer catalysts are additionally used for promoting the reaction. The correct choice of the sources of the initial material components is also essential. 2-n-butyl-2-ethyl-1,3-propane diol is used, for example, in the paint industry in the preparation of pulverous paints.Type: GrantFiled: May 1, 1995Date of Patent: April 8, 1997Assignee: Neste OyInventors: Kari Kulmala, Kjell Ankner, Lea Rintala
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Patent number: 5583270Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of productiong 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: June 23, 1994Date of Patent: December 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5567810Abstract: Compounds, compositions and methods for inhibiting gene expression are disclosed. The compounds comprise oligonucleotide sequences of from about 9 to about 200 bases having a diol at either or both termini. Preferred diols are polyalkyleneglycols, preferably polyethyleneglycols. Pharmaceutical compositions comprising the compounds and a physiologically acceptable carrier and methods of inhibiting gene expression in mammals comprising administering such compounds are also provided. Methods for inhibiting nuclease cleavage of compounds are also provided.Type: GrantFiled: May 31, 1995Date of Patent: October 22, 1996Assignee: Sterling Drug, Inc.Inventors: Alexander L. Weis, Fred T. Oakes, Frederick H. Hausheer, Paul F. Cavanaugh, Jr., Patricia S. Moskwa
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Patent number: 5532417Abstract: Neopentyl glycol is made from isobutyraldehyde and formaldehyde. The formaldehyde may be in the form of paraformaldehyde or aqueous formaldehyde. The aldol reaction product is mixed with a lower alcohol prior to hydrogenation to promote hydrogenolysis and allow recovery of high purity product by simple distillation. In a less preferred mode, the alcohol may be added after hydrogenation, resulting in a smaller improvement over previous processes.Type: GrantFiled: August 2, 1993Date of Patent: July 2, 1996Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
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Patent number: 5498734Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.Type: GrantFiled: July 30, 1993Date of Patent: March 12, 1996Assignee: University of NebraskaInventor: Reuben D. Rieke
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Patent number: 5449841Abstract: A process for reducing the level of metal ions and/or metal compounds in a polyoxyalkylene monool or polyol having a number average molecular weight of above 500-25000 by bringing the monool or polyol into contact with an extracting compound which is a polyol or a polyol mixture having a number average molecular weight of at most 500 and being immiscible with the polyoxyalkylene monool or polyol, mixing the extracting compound and the polyoxyalkylene monool or polyol, allowing the extracting compound and the polyoxyalkylene monool or polyol to separate and removing the extracting compound.Type: GrantFiled: October 12, 1994Date of Patent: September 12, 1995Assignee: Imperial Chemical Industries PLCInventor: Patrick M. G. Goegebeur
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Patent number: 5426206Abstract: Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.Type: GrantFiled: November 24, 1993Date of Patent: June 20, 1995Assignee: The Regents of the University of CaliforniaInventors: Michael E. Jung, Derin C. D'Amico
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Patent number: 5395989Abstract: Disclosed is a process for producing neopentyl glycol which comprises hydrogenating hydroxypivaldehyde in the presence of a catalyst comprising copper, zinc and zirconium.The catalyst has a high catalytic activity and a long service lifetime.Type: GrantFiled: April 14, 1993Date of Patent: March 7, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mikio Yoneoka, Kumiko Watabe, Gen Matsuda
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Patent number: 5371242Abstract: Abstract of the Disclosure: Products of the reduction of 4-hydroxybutyric acid derivatives of the formula IIa ##STR1## where one of A and B is methylene and the other is cyclopropylidene, or of C.sub.1 --C.sub.4 --alkyl esters (IIb) or lactones (IIc) of these acids IIa, are prepared by hydrogenating the compounds IIa or IIb or IIc catalytically using hydrogen in the presence of a heterogeneous hydrogenation catalyst, giving novel compounds which can be used to prepare polymers.Type: GrantFiled: August 23, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Werner Schnurr, Norbert Goetz, Thomas Kuekenhoehner
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Patent number: 5345004Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of producing 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: December 8, 1993Date of Patent: September 6, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5300708Abstract: A process for the catalytic hydrogenation of organic compounds in the gas phase. The reaction product-containing circulating gas leaving the hydrogenation reactor is compressed without prior cooling, and is then used to heat the starting materials in a superheater to the reaction temperature. The circulating gas stream is further cooled in a hot-gas heat exchanger by cold reactants in a counter-current manner; as a result, substantially all the reaction product condenses out leaving recycle gas. After addition of fresh gas and starting material, the recycle gas is returned via a purification column to the hydrogenation reactor.Type: GrantFiled: June 23, 1993Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hofs, Thomas Muller
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Patent number: 5245003Abstract: Provided are certain novel fluid ternary glycol mixtures. Also provided is an improved process for preparing polyesters comprised of residues of the glycols which comprise the fluid ternary glycol/water mixtures.Type: GrantFiled: January 23, 1992Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventor: Larry K. Johnson
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Patent number: 5233100Abstract: A process for producing an alcohol from a fatty acid ester, a fatty acid triglyceride or a fatty acid by continuously catalytically reducing the starting material in the presence of a hydrogenation catalyst is disclosed. In the process of the present invention, two reactors (i.e., the main reactor located upstream and the after reactor located downstream) being located in series are employed. In the process of the present invention, two reactors are employed and the temperatures thereof are individually controlled, whereby the conversion ratio is elevated while suppressing the formation of hydrocarbon and aldehyde by-products. Thus, an alcohol of extremely high quality and high purity can be produced. Further, the process of the present invention makes it possible to omit any post-treatment for eliminating the by-products. Furthermore, the active life of the hydrogenation catalyst can be remarkably prolonged by using three reactors (i.e., the guard reactor, the main reactor and the after reactor).Type: GrantFiled: December 27, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Atsuhito Mori, Takahiro Kawakami, Kunizo Hashiba, Kiyoshi Tsukada
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Patent number: 5233099Abstract: A process for producing an alcohol by continuously passing a fatty acid ester, a fatty acid triglyceride or a fatty acid through a hydrogenation catalyst to thereby produce the aimed alcohol through catalytic reduction is disclosed, wherein the employed reactor is a fixed bed reactor in which the liquid phase and the gas phase are continuously passed together in descending parallel flows through the hydrogenation catalyst fixed in the reactor; and at least one cooling mean for cooling the reaction system is provided at a position in the vertical direction of the reactor. According to the process of the present invention with the use of a fixed bed reactor, an alcohol, which has extremely high qualities and a high purity and is contaminated with little hydrocarbon and aldehyde by-products, can be produced. The process of the present invention further makes it possible to omit the post-treatment for eliminating the by-products.Type: GrantFiled: December 24, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Kunizo Hashiba, Takahiro Kawakami
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Patent number: 5214182Abstract: A process is disclosed for the cogeneration of ethylene glycol and dimethyl carbonate by reacting methanol and ethylene carbonate in the presence of a heterogeneous, phosphine-bound polymer catalyst. Dimethyl carbonate and ethylene glycol are generated in greater than 98% selectivity.Type: GrantFiled: July 1, 1991Date of Patent: May 25, 1993Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5210337Abstract: Rhenium has been found to be formaldehyde resistant catalyst and is thus useful in the catalytic hydrogenation of carbonyls, acetals and esters to alcohols when the reaction medium contains formaldehyde as a reactant or impurity. Also, rhenium is a useful catalyst in the hydrogenolysis of acylic acetals to alcohols.Type: GrantFiled: March 28, 1990Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventor: Jerry A. Broussard
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Patent number: 5185478Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and cadmium or yttrium oxide; then hydrogenating the resulting reaction mixture containing hydroxypivaldehyde and at least about 20% 3-hydroxy-2,2-dimethylpropylhydroxypivalate.Type: GrantFiled: April 16, 1992Date of Patent: February 9, 1993Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach
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Patent number: 5149861Abstract: Trialkylamines and methyl formate are recovered from reaction mixtures obtained in the preparation of trimethylolalkanes by reaction of n-alkanals with from 2.2 to 4.5 moles of formaldehyde in aqueous solution in the presence of from 0.6 to 3 mole of trialkylamine, each quantity based on 1 mole of alkanal, and subsequent hydrogenation in a process wherein the crude reaction mixturea) is heated to from 100.degree. to 200.degree. C.Type: GrantFiled: March 1, 1991Date of Patent: September 22, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Peter Hettinger, Leopold Hupfer, Juergen Paetsch, Heribert Deck, Heinz Auer, Erwin Brunner
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Patent number: 5146012Abstract: Neopentyl glycol is made from isobutyraldehyde and paraformaldehyde; the aldol reaction product is directly mixed with a lower alcohol for hydrogenolysis.Type: GrantFiled: June 28, 1991Date of Patent: September 8, 1992Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
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Patent number: 5144088Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and one or more oxides of elements of Groups IB, IVA, IVB, VA, VB, VIB and VIII of the periodic table; then hydrogenating the resulting hydroxypivaldehyde-containing product.Type: GrantFiled: April 26, 1991Date of Patent: September 1, 1992Assignee: Aristech Chemical CorporationInventors: Jeffrey S. Salek, Joseph Pugach
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Patent number: 5136096Abstract: The bis-homotris compounds 4-amino-4-[1-(3-hydroxypropyl)]-1,7-heptanediol and 4-[1-(3-aminopropyl)]-4-[1-(3-hydroxypropyl)]-1, 7-heptanediol, and organic synthetic methods for their preparation are described. Unique multifunctional aminotriols, as well as their percursors, quaternary nitroalkanes are disclosed as building blocks for unimolecular micelles, as well as new series of cascade polymers. The quaternary nitro compounds which are disclosed allow the synthesis of a new aminotriol containing a quaternary carbon.Type: GrantFiled: March 26, 1991Date of Patent: August 4, 1992Assignee: University of South FloridaInventors: George R. Newkome, Charles N. Moorefield
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Patent number: 5072058Abstract: A process for the preparation of 2,2-dimethylpropane-1,3-diol by an addition reaction between isobutyraldehyde and formaldehyde in the presence of tertiary amines as the catalyst, hydrogenation of the reaction mixture, and subsequent distillation. Before the distillation, formaldehyde is added to the hydrogenation product to remove unwanted basic impurities.Type: GrantFiled: December 21, 1990Date of Patent: December 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Georg Dambkes, Peter Lappe, Franz Thonnessen, Helmut Springer
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Patent number: 5064928Abstract: The present invention provides an isocyanate prepolymer prepared by reacting an organic di-isocyanate with an unsaturated alcohol dimer having 16 to 24 carbon atoms and/or a hydrogen addition product of the unsaturated alcohol dimer and a process for preparing the same.Type: GrantFiled: March 27, 1990Date of Patent: November 12, 1991Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Mitsuo Kase, Kazue Tsuyuzaki, Yoichi Kawasaki, Shunji Arimoto
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Patent number: 5041283Abstract: A cosmetic composition comprising a long-chain alkyltrimethylol is disclosed. The alkyltrimethylol is represeneted by the formula (I): ##STR1## wherein R is a linear or branched, saturated or unsaturated alkyl group having 8-22 carbon atoms. The composition is applied to various types of cosmetic and exhibits superior extendibility when applied, imparts a non-sticky, fresh feeling upon use, and provides an excellent moisture-retaining effect.Type: GrantFiled: September 8, 1989Date of Patent: August 20, 1991Assignee: Kao CorporationInventors: Katsumi Kita, Tetsuo Uno, Shinichi Masuda, Kazuyuki Yahagi, Kazuhiro Tashiro
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Patent number: 5037936Abstract: Described are crystalline block copolymers displaying high glass transition temperatures, excellent mechanical properties, excellent chemical and thermal stability, and good melt processability. These block polymers contain segments of crystalline poly(aryl ether ketones).Type: GrantFiled: April 24, 1989Date of Patent: August 6, 1991Assignee: Amoco CorporationInventors: Robert A. Clendinning, James E. Harris, George T. Kwiatkowski, Lee P. McMaster, Markus Matzner, Paul A. Winslow
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Patent number: 5024772Abstract: A process for producing 2,2-dimethyl-3-hydroxypropyl-2,2-dimethyl-3-hydroxypropionate (HPN) and neopentyl glycol (NP) blends from a neopentyl glycol production by-product stream containing neopentyl glycol, hydroxypivalic acid, and HPN using an acid catalyst.Type: GrantFiled: July 10, 1989Date of Patent: June 18, 1991Assignee: BASF CorporationInventors: Laurance R. Thurman, Joseph P. Dowd, Kathy J. Fischer
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Patent number: 4996375Abstract: Novel methyl carbinol derivatives of Vitamin E and a method for their manufacture.Type: GrantFiled: April 24, 1989Date of Patent: February 26, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4935555Abstract: In a process for the production of neopentyl glycol by hydrogenation of the aldol product of formaldehyde and isobutyraldehyde, an improvement comprises the wiped-film evaporator treatment of a saponified NPG-containing mixture. The process results in a very pure product and also eliminates the need for the addition of steam to the crude NPG, thus saving the cost of energy for removing the water from the NPG.A further yield improvement is achieved by extracting NPG from the caustic residue with isobutyraldehyde and water. The isobutyraldehyde selectively recovers the NPG while the water selectively removes the caustic. The isobutyraldehyde and NPG are then conveniently recycled to the aldol reaction zone.Type: GrantFiled: November 25, 1988Date of Patent: June 19, 1990Inventors: Carole L. Elias, Marvin C. Fields
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Patent number: 4935488Abstract: Novel trimethylolheptanes having three highly reactive hydroxyl groups are provided. They are useful as raw materials for the production of polyesters for use in or as raw materials or modifiers for paints, inks, adhesives, coating compositions and molding resins. Uses for the trimethylolheptanes are also provided.Type: GrantFiled: April 20, 1989Date of Patent: June 19, 1990Assignee: Kurary Company, Ltd.Inventors: Toshihiro Omatsu, Yasuo Tokitoh, Noriaki Yoshimura, Masao Ishida, Makoto Yano, Koji Hirai, Yoichi Matsumoto, Keiji Kubo
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Patent number: 4933473Abstract: A process for production of neopentyl glycol by hydrogenation of hydroxypivaldehyde in the presence of a Pt-Ru-W catalyst. This catalyst exhibits high activity and selectivity, and further has a long life. Neopentyl glycol is an important intermediate for use in production of a wide variety of chemicals.Type: GrantFiled: April 21, 1989Date of Patent: June 12, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Teruyuki Ninomiya, Tomiyoshi Furuta, Seiji Kita, Yoshimi Fujii
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Patent number: 4918247Abstract: Preparation of 2,2-dimethylpropanediol-1,3 by the aldol addition of isobutyraldehyde and formaldehyde using tri-n-propylamine as a catalyst, followed by hydrogenation of the reaction mixture, and subsequent distillation of the hydrogenation product in the presence of isobutanol and water.Type: GrantFiled: May 26, 1989Date of Patent: April 17, 1990Assignee: Ruhrchemie AktiengesellschaftInventors: Norbert Breitkopf, Wolfgang Hofs, Heinz Kalbfell, Franz Thonnessen, Peter Lappe, Helmut Springer
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Patent number: 4851592Abstract: A process for producing neopentyl glycol is disclosed which comprises reacting isobutyraldehyde and formaldehyde in the presence of a trialkylamine catalyst to form a condensation reaction product comprising hydroxypivaldehyde, followed by hydrogenation of the hydroxypivaldehyde in a hydrogen gas sparged reactor in the presence of a Raney nickel catalyst. This process minimizes unwanted by-products, and does not have to be carried out under high pressure as do certain prior art methods.Type: GrantFiled: October 27, 1987Date of Patent: July 25, 1989Assignee: Eastman Kodak CompanyInventor: Don L. Morris
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Patent number: H918Abstract: Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.Type: GrantFiled: October 5, 1988Date of Patent: May 7, 1991Assignee: The United States of America as represented by the United States Department of EnergyInventors: Mark A. Andrews, Stephen A. Klaeren