Preparing From Ethylenically Unsaturated Compound Patents (Class 568/850)
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Patent number: 11505743Abstract: The present invention provides a chemical solution which has an excellent dissolving ability for a transition metal-containing substance and can realize excellent smoothness of a portion to be treated. Furthermore, the present invention provides a method of treating a substrate. The chemical solution according to an embodiment of the present invention is used for removing a transition metal-containing substance on a substrate. The chemical solution contains one or more kinds of specific hypochlorous acids selected from the group consisting of hypochlorous acid and a salt thereof and contains one or more kinds of specific anions selected from the group consisting of ClO3? and Cl?. In a case where the chemical solution contains one kind of the specific anion, the content of one kind of the specific anion is 5 ppb by mass to 1% by mass with respect to a total mass of the chemical solution.Type: GrantFiled: March 4, 2021Date of Patent: November 22, 2022Assignee: FUJIFILM CorporationInventors: Nobuaki Sugimura, Tomonori Takahashi, Hiroyuki Seki
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Patent number: 11466209Abstract: The present invention provides a chemical solution which has an excellent dissolving ability for a transition metal-containing substance and can realize excellent smoothness of a portion to be treated. Furthermore, the present invention provides a method of treating a substrate. The chemical solution according to an embodiment of the present invention is used for removing a transition metal-containing substance on a substrate. The chemical solution contains one or more kinds of specific hypochlorous acids selected from the group consisting of hypochlorous acid and a salt thereof and contains one or more kinds of specific anions selected from the group consisting of ClO3? and Cl?. In a case where the chemical solution contains one kind of the specific anion, the content of one kind of the specific anion is 5 ppb by mass to 1% by mass with respect to a total mass of the chemical solution.Type: GrantFiled: March 4, 2021Date of Patent: October 11, 2022Assignee: FUJIFILM CorporationInventors: Nobuaki Sugimura, Tomonori Takahashi, Hiroyuki Seki
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Patent number: 10590054Abstract: There are provided methods and systems to form propylene chlorohydrin by hydrolysis of dichloropropane in presence of Lewis acid and to further form propylene oxide from the propylene chlorohydrin.Type: GrantFiled: May 29, 2019Date of Patent: March 17, 2020Assignee: Calera CorporationInventors: Michael Joseph Weiss, Kyle Self, Thomas A Albrecht, Margarete K Leclerc
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Patent number: 9365480Abstract: A process for the manufacture of an alkenone comprising the steps of: (a) providing a halogenated precursor of the alkenone and (b) subjecting at least a fraction of the halogenated precursor of step (a) to a thermolysis reaction to form a reaction mixture comprising the alkenone and a hydrogen halide wherein the hydrogen halide is removed from the reaction mixture by cyclonic separation is described.Type: GrantFiled: August 20, 2013Date of Patent: June 14, 2016Assignee: SOLVAY SAInventors: Max Josef Braun, Stefan Palsherm
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Patent number: 8404905Abstract: The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon by-products or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon by-products and chloroacetone is less than 2000 ppm throughout any stage of the said process.Type: GrantFiled: January 31, 2011Date of Patent: March 26, 2013Assignee: Dow Global Technologies LLCInventors: William J. Kruper, Tina Arrowood, Bruce M. Bell, John Briggs, Robert M. Campbell, Bruce D. Hook, Anh Nguyen, Curt Theriault, Ralf Fitschen
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Publication number: 20120209033Abstract: Methods and systems for the preparation of chlorohydrins are described herein. The method includes introducing a liquid stream into a high shear device, wherein the liquid stream has an aqueous phase; introducing a gas stream into the high shear device, wherein the gas stream has an olefin gas; forming a dispersion in the high shear device, the dispersion comprising gas bubbles dispersed in the liquid stream; and reacting at least a portion of the dispersion to produce chlorohydrin.Type: ApplicationFiled: April 24, 2012Publication date: August 16, 2012Applicant: H R D CorporationInventors: Abbas HASSAN, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20110207970Abstract: Methods and systems for the preparation of chlorohydrins are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins into the chlorinating phase. The high shear device may allow for lower reaction temperatures and pressures and may also reduce chlorination time.Type: ApplicationFiled: February 22, 2011Publication date: August 25, 2011Applicant: H R D CORPORATIONInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7317131Abstract: The catalysts of formula (II): [Ru(L)m(L?)wXY], wherein X and Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, m is 1 or 2, w is 1 when m is 1 and w is 0 when m is 2, L is a phosphino-amine or phosphino-imine bidentate ligand and L? a diphosphine, are useful for the hydrogenation of substrates having a carbon-hetero atom double bond.Type: GrantFiled: September 11, 2001Date of Patent: January 8, 2008Assignee: Firmenich SAInventors: Valentin Rautenstrauch, René Challand, Raphaël Churlaud, Robert Harold Morris, Eric Brazi, Hubert Mimoun, Kamaluddin Abdur-Rashid
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Patent number: 7186868Abstract: The invention pertains to a hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, followed by a third step of recycling the solution to the reactor.Type: GrantFiled: December 16, 2003Date of Patent: March 6, 2007Assignee: Shell Oil CompanyInventors: Eit Drent, Jacoba Catherina Lucia Johanna Suykerbuyk
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Patent number: 7157609Abstract: A process of producing propylene chlorohydrin using a reactor having a one-way flow reaction area and a circulating flow reaction area which are connected in series. In this process, a propylene-containing gas is supplied to an aqueous solution of chlorine in the one-way flow reaction area to carry out at least part of a propylene chlorohydrin forming reaction so as to form a reaction mixture fluid containing propylene chlorohydrin and propylene and/or chlorine. The above reaction mixture fluid discharged from this reaction area is supplied to the circulating flow reaction area as at least part of a make-up medium, a propylene-containing gas and/or chlorine are/is supplied as required to continue the reaction in the circulating flow reaction area so as to obtain a reaction solution having a desired content of propylene chlorohydrin, and part of the reaction solution is extracted.Type: GrantFiled: May 21, 2003Date of Patent: January 2, 2007Assignee: Tokuyama CorporationInventors: Hiroki Tanaka, Yoji Mizushima, Yoshikazu Kodama, Tomoaki Fujii, Manabu Kamamoto, Koujiro Miyazaki
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Patent number: 6982355Abstract: A process is disclosed for making high value olefins and alcohols from synthesis gas as well as a process for an improved yield of alpha-olefins from synthesis gas. The process for hydroformulation of olefins is also provided.Type: GrantFiled: August 23, 2004Date of Patent: January 3, 2006Assignee: Syntroleum CorporationInventor: Armen N. Abazajian
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Patent number: 6878852Abstract: A process for the hydrogenation, using molecular hydrogen (H2) of a catalytic system, wherein the catalytic system includes a base and a complex of formula (II): Ru(P2N2)Y2??(II) wherein Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and P2N2 is a tetradentate diimino-diphosphine ligand.Type: GrantFiled: November 11, 2001Date of Patent: April 12, 2005Assignee: Firmenich SAInventors: Valentin Rautenstrauch, Raphaël Churlaud, Robert Harold Morris, Kamaluddin Abdur-Rashid
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Patent number: 6838576Abstract: A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.Type: GrantFiled: October 23, 2003Date of Patent: January 4, 2005Assignee: 3M Innovative Properties CompanyInventors: Markus A. Wicki, Kent E. Nielsen
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Patent number: 6743955Abstract: Methods for continuously producing 2,3-dichloro-1-propanol (2,3-DCH) and epichlorohydrin in high yields and in a stabel manner for a long time are disclosed. In a method where allyl alcohol is chorinated in a hyrochloric acid solution and the reaction solution is introduced into a degassing tower to release hydrogen chloride and 2,3-DCH is obtained from the remaining solution, the concentraton of chlorine in the reaction mixture to be introduced into the degassing tower is maintaining to 0.015 g/ml or less and/or the partial pressure of chlorine gas in the reactor immediately before the degassing tower to 0.08 MPa or less, by monitoring and/or the partial pressure of chlorine gas in the reactor immediately before the degassing tower to 0.Type: GrantFiled: December 16, 2002Date of Patent: June 1, 2004Assignee: Showa Denko K.K.Inventors: Toshitaka Hiro, Kazuhiro Sakurai
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Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
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Patent number: 6573409Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.Type: GrantFiled: May 19, 2000Date of Patent: June 3, 2003Assignee: The Nutrasweet CompanyInventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
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Patent number: 6479708Abstract: A process is provided for catalyzing an organic reaction to form a reaction product by placing reactants and a catalyst for the organic reaction, the catalyst of a metal complex and at least one ligand soluble within one of the phases of said aqueous biphasic system, within an aqueous biphasic system including a water phase, a dense phase fluid, and a surfactant adapted for forming an emulsion or microemulsion within the aqueous biphasic system, the reactants soluble within one of the phases of the aqueous biphasic system and convertible in the presence of the catalyst to a product having low solubility in the phase in which the catalyst is soluble; and, maintaining the aqueous biphasic system under pressures, at temperatures, and for a period of time sufficient for the organic reaction to occur and form the reaction product and to maintain sufficient density on the dense phase fluid, the reaction product characterized as having low solubility in the phase in which the catalyst is soluble.Type: GrantFiled: November 18, 1999Date of Patent: November 12, 2002Assignee: The Regents of the University of CaliforniaInventors: Gunilla B. Jacobson, William Tumas, Keith P. Johnston
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Patent number: 6388124Abstract: There is disclosed a dihalo-compound of formula (1): wherein X1 and X2 represent different halogen atoms, R represents a hydrogen atom or a protective group for a hydroxyl group, and a process for producing vitamin A derivative via a sulfone derivative of formula (5): wherein Ar represents an optionally substituted aryl group, and R represents the same as defined above.Type: GrantFiled: January 26, 2001Date of Patent: May 14, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko
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Patent number: 6333420Abstract: Allyl alcohol and chlorine are reacted in a gaseous phase to efficiently produce dichloropropanol and, using the dichloropropanol so produced, epichlorohydrin is efficiently produced.Type: GrantFiled: June 8, 2000Date of Patent: December 25, 2001Assignee: Showa Denko K.K.Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami
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Patent number: 6051742Abstract: A process for hypochlorinating unsaturated alpha-olefins to produce chlorohydrins which comprises forming a microemulsion of water and an unsaturated alpha-olefin and then adding an oxidant to the microemulsion under conditions sufficient to form the chlorohydrins. The microemulsion is formed by adding a non-nucleophilic surfactant and, optionally, a co-surfactant, to the mixture of water and unsaturated alpha-olefin.Type: GrantFiled: December 14, 1998Date of Patent: April 18, 2000Assignee: The Dow Chemical CompanyInventors: Daniel P. Green, John Klier, Christopher J. Tucker, Michael S. Ferritto
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Patent number: 6043400Abstract: This invention is a process for preparing chlorohydrins by reacting a chlorinating species, such as hypochlorous acid, with at least one unsaturated organic compound, such as propylene or butylene, at a pH of greater than 6.0. The chlorinating species is formed in a first step by reacting a source of chlorine, such as Cl.sub.2 gas, with an aqueous pH adjusting source, such as aqueous NaOH.Type: GrantFiled: December 30, 1996Date of Patent: March 28, 2000Assignee: The Dow Chemical CompanyInventor: Edward M. Jorge
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Patent number: 5981818Abstract: A novel process is provided which integrates the cracking of hydrocarbon containing feedstocks with the olefins purification and olefins derivative process utilizing dilute olefin feedstocks.Type: GrantFiled: October 18, 1996Date of Patent: November 9, 1999Assignee: Stone & Webster Engineering Corp.Inventors: David Purvis, Richard H. Mc Cue
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Patent number: 5962744Abstract: A process comprising subjecting at least one compound containing at least one carbon--carbon double bond or at least one carbon--carbon triple bond, hydrogen and carbon monoxide, to a hydrocarbonylation reaction in supercritical carbon dioxide, in the presence of a Group VIII transition metal catalyst precursor, and a phosphite ligand.Type: GrantFiled: March 27, 1998Date of Patent: October 5, 1999Assignees: The Research Foundation of State University of New York, Mitsubishi Chemical CorporationInventors: Iwao Ojima, Hisao Urata
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Patent number: 5929292Abstract: A production method which comprises reacting one or more feedstock compounds to form a desired compound having a boiling point higher than the feedstock compounds, wherein the reaction is carried out under reflux in a distillation column portion of a reactor provided with the distillation column.Type: GrantFiled: June 6, 1997Date of Patent: July 27, 1999Assignee: Asahi Glass Company Ltd.Inventors: Toru Shimoyama, Kazuya Oharu, Toru Ueno, Seisaku Kumai
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Patent number: 5874650Abstract: A process for the preparation of 4,4,4-trichlorobutan-1-ol which comprises reacting allyl alcohol with chloroform in the presence of a radical initiator. Preferably the allyl alcohol is added incrementally to the chloroform over the period of the reaction.Type: GrantFiled: July 8, 1997Date of Patent: February 23, 1999Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5728376Abstract: The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.Type: GrantFiled: April 25, 1995Date of Patent: March 17, 1998Assignee: Cornell Research Foundation, Inc.Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
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Patent number: 5532389Abstract: A process of preparing alkylene oxides comprises steps of: (1) optionally forming a hypochlorite solution; (2) contacting chlorine with a solution of a hypochlorite below about 60.degree. C., and a pH of less than about 5.5, with sufficient micromixing to achieve a product hypochlorous acid in a yield of at least about 80 percent; (3) separating at least a portion the hypochlorous acid from an aqueous metal chloride solution wherein the solution is sprayed as droplets; (4) distilling the remaining liquid phase; (5) absorbing the hypochlorous acid and dichlorine monoxide in low-chlorides water to produce a low-chlorides aqueous hypochlorous acid solution; (6) contacting the low-chlorides aqueous hypochlorous acid solution with an olefin in a continuous process to form a olefin chlorohydrin; (7) optionally contacting the olefin chlorohydrin with a base to form a alkylene oxide and a salt solution; and (8) optionally separating the alkylene oxide from the salt solution.Type: GrantFiled: September 9, 1994Date of Patent: July 2, 1996Assignee: The Dow Chemical CompanyInventors: David L. Trent, George J. Quarderer, Kim G. Bargeron, Douglas C. Greminger, David J. Koranek, Erik J. Stewart, Curtis N. Swisher, Cheryl A. Tirtowidjojo, Danil Tirtowidjojo
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Patent number: 5523425Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.Type: GrantFiled: December 21, 1994Date of Patent: June 4, 1996Assignee: The Dow Chemical CompanyInventors: Gunther A. Pech, Werner J. Witzl
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Patent number: 5523495Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallylcarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.Type: GrantFiled: February 13, 1995Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Company LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5486627Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.Type: GrantFiled: December 2, 1994Date of Patent: January 23, 1996Assignee: The Dow Chemical CompanyInventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
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Patent number: 5382716Abstract: Mixtures of isomeric decyl alcohols obtained by hydroformylation of butadiene to produce aldehyde mixtures, condensation of the aldehyde mixtures, isolated from the reaction product, to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified using phthalic acid, gives a mixture of isomeric decyl phthalates which are plasticizers having excellent cold properties.Type: GrantFiled: March 23, 1993Date of Patent: January 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5258558Abstract: Solid solutions of magnesium oxide-aluminum oxide related to hydrotalcite and what previously has been referred to as synthetic hydrotalcites, have been prepared with a surface area in excess of 250 m.sup.2 /g, especially at low Mg/Al atom ratios. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C.Type: GrantFiled: May 18, 1992Date of Patent: November 2, 1993Assignee: UOPInventors: Blaise J. Arena, Jennifer S. Holmgren
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Patent number: 5227541Abstract: A process for purifying 2,3-dichloro-1-propanol is disclosed, which comprises introducing a chlorination reaction mixture obtained by chlorination of allyl alcohol in a hydrochloric acid aqueous solution in a reactor, to a degassing tower, where hydrogen chloride is released, returning the hydrogen chloride to the chlorination reactor, cooling the residual liquid to separate into an aqueous layer and an oily layer, and returning the aqueous layer to the chlorination reactor while recovering 2,3-dichloro-1-propanol from the oily layer, wherein said oily layer is introduced to a first distillation tower, where hydrogen chloride, part of the produced 2,3-dichloro-1-propanol, and other low-boiling components are recovered as a distillate, cooling the distillate to separate it into an aqueous layer and an oily layer, returning the aqueous layer of the distillate to the chlorination reactor, and recovering 2,3-dichloro-1-propanol from the oily layer of the distillate and a high-boiling fraction of the first distillType: GrantFiled: November 25, 1992Date of Patent: July 13, 1993Assignee: Showa Denko K.K.Inventors: Toshio Mori, Hiromitu Nojima, Koji Kudo, Tatsuharu Arai
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Patent number: 4985594Abstract: Process for the preparation of fluorinated carboxylic acid fluoridesFluorinated carboxylic acid fluorides of the Formula I ##STR1## can be prepared from fluorinated vinyl ethers of the Formula II ##STR2## by heating the vinyl ethers to a temperature of 100.degree. to 350.degree. C.Perfluorinated carboxylic acids and derivatives thereof can be prepared from the carboxylic acid fluorides by secondary reactions, for example hydrolysis, esterification or aminolysis.Type: GrantFiled: August 3, 1989Date of Patent: January 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Heinz Strutz
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Patent number: 4957986Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.Type: GrantFiled: December 15, 1989Date of Patent: September 18, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry N. Cripps
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Patent number: 4696726Abstract: A continuous process for the production of dichlorohydrin by the reaction of allyl chloride, water and chlorine having substantially lower energy requirements than conventional processes, wherein the reaction mixture is subjected to reverse osmosis to concentrate the dichlorohydrin and to provide a permeate stream substantially free of dichlorohydrin, which permeate stream is recycled to the reaction.Type: GrantFiled: July 14, 1986Date of Patent: September 29, 1987Assignee: Shell Oil CompanyInventors: George C. Blytas, F. Norman Grimsby, John F. Scamehorn
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Patent number: 4681977Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: June 27, 1985Date of Patent: July 21, 1987Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4598162Abstract: Novel, liquid mixtures of isomeric aldehydes and alcohols are described in the C.sub.11 -C.sub.16 carbon range, the compounds being characterized by a main carbon branched at the position and moderate additional branching in most isomers; the aldehyde mixtures are prepared by an economic route from olefins involving oxo and aldol reaction with the reaction conducted in such a way as to give a high percentage of aldolable product, and preferably with a base catalyzed aldol reaction conducted under conditions to make high conversions attainable. The aldehyde mixtures can be hydrogenated to alcohols and converted to novel ethoxylates or sulfate compositions suitable for use as biodegradable detergents; or hydrogenated and oxidized to novel carboxylic acid compositions also suitable for detergent use.Type: GrantFiled: November 4, 1983Date of Patent: July 1, 1986Assignee: Monsanto CompanyInventors: Denis Forster, George F. Schaefer, George E. Barker
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Patent number: 4560811Abstract: Novel methods for making chlorohydrins are provided using a Lewis acid catalyst with an olefin and peroxy compound or where an enantiomer is desired, a Lewis acid catalyst in combination with a chiral alcohol, particularly glycol, and a combination of a peroxy compound and alkenol. In certain situations, an epoxide may be employed.Type: GrantFiled: January 18, 1984Date of Patent: December 24, 1985Assignee: Massachusetts Institute of TechnologyInventors: Karl B. Sharpless, Roy A. Johnson
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Patent number: 4496777Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a water soluble salt of an amphoteric metal; in particular, a salt of tin, aluminum, zinc, zirconium, magnesium, or titanium, which provides a pH of from 2 to 5 under reaction conditions.Type: GrantFiled: November 9, 1983Date of Patent: January 29, 1985Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4479020Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a metal selected from Group II-A, II-B, III-A, III-B, IV-A, IV-B, or V-A of the Periodic Table. The use of such metals improves the production of halohydrin.Type: GrantFiled: November 12, 1982Date of Patent: October 23, 1984Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4374277Abstract: Described are branched chain C.sub.11 aldehydes and alcohols, processes for producing same by (i) first dimerizing isoamylene(2-methyl-2-butene) to form a mixture of diisoamylenes and (ii) reacting the resulting mixture or separated components thereof with carbon monoxide and hydrogen by means of an oxo reaction, as well as methods for augmenting or enhancing the aroma of perfumes, colognes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of the thus produced C.sub.11 branched chain aldehydes and alcohol compositions of matter. Also described are perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, hair preparations, deodorant compositions and bleaching compositions containing such products thus produced.Type: GrantFiled: September 25, 1981Date of Patent: February 15, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, John H. Geiger, Jr.
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Patent number: 4322355Abstract: An improvement in the reaction of olefin with aldehyde, and optionally, carboxylic acid, in the liquid phase in the presence of a catalytically effective amount of strong acid to provide a 1,3-difunctional compound or a mixture of 1,3-difunctional compounds is provided by carrying out the aforesaid reaction in the further presence of a co-catalyst selected from the group consisting of antimony oxide, bismuth oxide, antimony salt, bismuth salt and mixtures thereof.Type: GrantFiled: April 15, 1980Date of Patent: March 30, 1982Assignee: National Distillers & Chemical Corp.Inventors: David Horvitz, William D. Baugh
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4293717Abstract: Aldehydes and diols are prepared by reacting an olefine with hydrogen peroxide in the presence of a Group Va or VIa metal compound, such as molybdenum-(III)-acetylacetonate.Type: GrantFiled: February 5, 1979Date of Patent: October 6, 1981Assignee: Bayer AktiengesellschaftInventors: Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk