Preparing From An Acetal Or Ketal Patents (Class 568/691)
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Patent number: 8933275Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing acetylene as an intermediate stream to form a stream having oxygenates. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to oxygenates through subsequent reactors.Type: GrantFiled: June 11, 2013Date of Patent: January 13, 2015Assignee: UOP LLCInventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Patent number: 8791307Abstract: A process of producing ?,?-unsaturated ethers includes pyrolyzing an acetal represented by Formula (2) below in a gas phase in the presence of a catalyst and a compound having at least one hydrogen atom capable of hydrogen bonding to produce an ?,?-unsaturated ether represented by Formula (3) below: R1R2CH—CR3(OR4)2??(2) R1R2C?C—R3(OR4)??(3) In Formulae (2) and (3), R1, R2 and R3 are each independently a hydrogen atom, an alkyl group, an alkenyl group or an aryl group; R4 is an alkyl group, an alkenyl group or an aryl group; the plurality of R4 in Formula (2) may be the same or different from each other.Type: GrantFiled: November 6, 2008Date of Patent: July 29, 2014Assignee: Showa Denko K.K.Inventors: Yoshikuni Okumura, Hiroto Kouka, Takanori Aoki
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Publication number: 20140058135Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing acetylene as an intermediate stream to form a stream having oxygenates. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to oxygenates through subsequent reactors.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Publication number: 20100261936Abstract: A process of producing ?,?-unsaturated ethers includes pyrolyzing an acetal represented by Formula (2) below in a gas phase in the presence of a catalyst and a compound having at least one hydrogen atom capable of hydrogen bonding to produce an ?,?-unsaturated ether represented by Formula (3) below: R1R2CH—CR3(OR4)2??(2) R1R2C?C—R3(OR4)??(3) In Formulae (2) and (3), R1, R2 and R3 are each independently a hydrogen atom, an alkyl group, an alkenyl group or an aryl group; R4 is an alkyl group, an alkenyl group or an aryl group; the plurality of R4 in Formula (2) may be the same or different from each other.Type: ApplicationFiled: November 6, 2008Publication date: October 14, 2010Applicant: SHOWA DENKO K.K.Inventors: Yoshikuni Okumura, Hiroto Kouka, Takanori Aoki
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Patent number: 7728181Abstract: Disclosed is a method for producing an ?,?-unsaturated ether efficiently and stably for a long time. In the method for producing an ?,?-unsaturated ether, an acetal is thermally decomposed in the presence of a catalyst containing an apatite represented by any of the following formula (1)-(4) (M)5?y(HZO4)y(ZO4)3?y(X)1?y??(1) (M)5?y(HPO4)y(PO4)3?y(X)1?y??(2) (M)5?y+2n(HZO4)y(ZO4)3?y(X)1?y(SiO4)n??(3) (M)5?y+m(HZO4)y(ZO4)3?y(X)1?y(CO3)m??(4).Type: GrantFiled: January 26, 2007Date of Patent: June 1, 2010Assignee: Showa Denko K.K.Inventors: Hiroto Kouka, Yoshikuni Okumura
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Publication number: 20090227818Abstract: Disclosed is a method for producing an ?,?-unsaturated ether efficiently and stably for a long time. In the method for producing an ?,?-unsaturated ether, an acetal is thermally decomposed in the presence of a catalyst containing an apatite represented by any of the following formulae (1)-(4).Type: ApplicationFiled: January 26, 2007Publication date: September 10, 2009Applicant: SHOWA DENKO K.K.Inventors: Hiroto Kouka, Yoshikuni Okumura
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Publication number: 20090054697Abstract: The present invention provides a method for producing an unsaturated ether compound represented by general formula (2) below, the method comprising reacting an acetal represented by general formula (1) below in the presence of an aliphatic or aromatic sulfonic acid and an organic base having a total carbon number of 3 to 7. (In the formulae, R1, R2, and R3 may be the same or different and each represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, or R1 and R2 form cycloalkyl together with the adjacent carbon atom.Type: ApplicationFiled: April 26, 2006Publication date: February 26, 2009Applicant: KYOWA HAKKO CHEMICAL CO., LTD.Inventors: Ryo Numazaki, Katsuhiro Ito, Hiroshi Matsuoka, Iwao Hotta
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Publication number: 20040199026Abstract: A process is described for the production of ethers, typically terahydrofuran, by reaction of a corresponding organic feed material selected from dicarboxylic acids and/or anhydrides, monoesters of dicarboxylic acids and/or anhydrides, diesters of dicarboxylic acids and/or anhydrides, lactones, and mixtures of two or more thereof in the presence of hydrogen which comprises the steps of: (a) supplying a stream comprising the organic feed material to a first vaporisation zone and contacting said feed with cycle gas comprising hydrogen such that at least a portion of the feed material is vaporised by and into the cycle gas; (b) supplying at least a portion of the cycle gas and the vaporised feed material to a first reaction zone comprising catalyst and operating under reaction conditions to allow hydrogenation and dehydration to occur; (c) recovering from the first reaction zone an intermediate product stream comprising unreacted feed material, cycle gas, desired product(s), and any co-products and by-products;Type: ApplicationFiled: April 28, 2004Publication date: October 7, 2004Inventors: David Mark Sutton, Andrew George Hiles, Graham Reed, John Anthony Stannard
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Patent number: 6660890Abstract: A process for the heterogeneous and enantioselective hydrogenation of prochiral organic &agr;-keto compounds with platinum as the catalyst in the presence of a soluble or immobilized chiral aromatic nitrogen base with at least one basic nitrogen atom adjacent to stereogenic carbon atoms, whereby prochiral &agr;-ketoacetals are hydrogenated to optically active &agr;-hydroxyacetals.Type: GrantFiled: December 19, 2001Date of Patent: December 9, 2003Assignee: Solvias AGInventor: Martin Studer
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Patent number: 6566559Abstract: Process for the production of unsaturated ethers, in particular isopropenyl methyl ether (IPM), by pyrolysis of a ketal-containing or acetal-containing mixture, in particular dimethoxypropane (DMP), in the liquid phase in the presence of an organic carboxylic acid, according to the following reaction scheme: wherein R1=H or alkyl with 1-8 C atoms; R2=H, CH3—, C2H5—, or Cl—; R3=alkyl with 1-8 C atoms; R4=H, CH3—, C2H5—, or C3H7—, and R1 and R4 may be joined to form a 5-, 6-, or 7-membered ring. DMP is produced by the process from acetone and methanol by reaction in an acidic heterogeneous ion exchanger, the product being isolated by extraction with aqueous alkaline solution. In particular the process involves combining the IPM reaction product with the DMP reaction product, which permits the execution of a stable recycling process in which the methanol-containing streams of the IPM and DMP stages can be simultaneously extracted.Type: GrantFiled: June 1, 2001Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Steffen Krill, Stephan Kretz, Volker Häfner, Georg Markowz
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Publication number: 20020042543Abstract: Process for the production of unsaturated ethers, in particular isopropenyl methyl ether (IPM), by pyrolysis of a ketal-containing or acetal-containing mixture, in particular dimethoxypropane (DMP), in the liquid phase in the presence of an organic carboxylic acid, according to the following reaction scheme: 1Type: ApplicationFiled: June 1, 2001Publication date: April 11, 2002Inventors: Steffen Krill, Stephan Kretz, Volker Hafner, Georg Markowz
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Patent number: 6235944Abstract: The present invention relates to a general synthesis for producing secondaryalkoxy-1-alkenes in commercial quantities in good yields by reacting cyclic and acyclic ketones and the corresponding alcohol with a secondary alkyl orthoformate ester in the presence of an acid catalyst, a Lewis acid, ferric chloride being preferred, and recovering the produce as a liquid of high purity.Type: GrantFiled: January 21, 1999Date of Patent: May 22, 2001Assignee: Creanova Inc.Inventors: Thomas V. John, Chitoor S. Subramaniam, Zheng Wang, Richard J. Kucera, Jr.
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Patent number: 6211416Abstract: Enol ethers of the formula I where R1 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical which may carry further substituents which do not react with acetylenes or allenes, and the radicals R, independently of one another, are hydrogen or aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, which may be bonded to one another to form a ring, and m is 0 or 1, are prepared by reacting an acetal or ketal of the formula II with an acetylene or allene of the formula III or IV where R and R1 have the abovementioned meanings, in the gas phase at elevated temperatures in the presence of a zinc- or cadmium- and silicon- and oxygen-containing heterogeneous catalyst.Type: GrantFiled: December 6, 1999Date of Patent: April 3, 2001Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Heinz Etzrodt, Udo Rheude
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Patent number: 5990360Abstract: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CHO [I], wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH-C (CH.sub.3).dbd.CH-OR.sup.1 [II], wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CH (OR.sup.1)(OR.sup.2) [III] to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus manufactured .gamma.Type: GrantFiled: May 12, 1998Date of Patent: November 23, 1999Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
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Patent number: 5767325Abstract: A process for the preparation of enol ethers of the general formula I ##STR1## in which R.sup.1,R.sup.2,R.sup.3,R.sup.4,R.sup.5 denote C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl, or C.sub.7 -C.sub.20 phenylalkyl,R.sup.2,R.sup.3,R.sup.4 denote hydrogen, aryl, cyano, --COOR.sup.5, C.sub.1 -C.sub.12 alkyl monosubstituted to trisubstituted or interrupted by --COOR.sup.5, --C.dbd.O, cyano, or C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 alkyl monosubstituted to trisubstituted by --COOR.sup.5, --C.dbd.O, cyano, or C.sub.1 -C.sub.12 alkyl, or C.sub.7 -C.sub.20 phenylalkyl andR.sup.2 and R.sup.4 or R.sup.3 and R.sup.4 together form a C.sub.3 -C.sub.10 alkylene chain or a C.sub.2 -C.sub.20 alkylidene chain, from acetals or ketals.Type: GrantFiled: November 22, 1996Date of Patent: June 16, 1998Assignee: BASF AktiengesellschaftInventors: Jurgen Schroder, Stefan Bock, Klaus Ebel
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Patent number: 5723687Abstract: A process is described for the joint production of ethers and hydrocarbons with a high octane number starting from C.sub.4 hydrocarbon cuts containing isobutene, by oligomerization with acid catalysts, in the presence of primary alcohols selected from methanol or ethanol in such a quantity as to have a molar ratio primary alcohols/isobutene in the feeding of between 0.2 and 0.7, preferably operating at a reaction temperature of between 30.degree. and 100.degree. C. and at feeding space velocities of less than 20 h.sup.-1.Type: GrantFiled: May 15, 1996Date of Patent: March 3, 1998Assignee: Snamprogetti S.p.A.Inventors: Mario Marchionna, Francesco Ancillotti, Marco Di Gerolamo
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Patent number: 5576465Abstract: A process for preparing unsaturated ethers of the formula (1) ##STR1## from acetals or ketal of the formula (2) ##STR2## is improved by heating the acetals or ketals at from 100.degree. to 250.degree. C. in a high-boiling, branched carboxylic acid and obtaining the unsaturated ether as a distillate. The process, which is insensitive to contaminants, gives the unsaturated ether in high yields.Type: GrantFiled: June 2, 1995Date of Patent: November 19, 1996Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 5449844Abstract: The present invention relates to a new method of condensing polyenic compounds wherein a compound having the formula III ##STR1## is condensed with a compound having the formula IV ##STR2## under the influence of a Lewis acid or a protic acid. R.sub.1 through R.sub.7 represent alkyl or alkenyl groups, A' is preferably chlorine, B is preferably a hydroxyl group, and n' is 0 to 10. The invention also relates to novel intermediates for use in the preparation of Vitamins A and E produced by means of the new method.Type: GrantFiled: November 27, 1992Date of Patent: September 12, 1995Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Jean-Erick Ancel, Bienayme, Hugues, Lucette Duhamel, Pierre Duhamel
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Patent number: 5446210Abstract: A process for the production of polyol ethers comprising the steps ofA) reacting a mixture of at least one polyol and at least one carbonyl compound of the formulaR.sup.1 --CO--R.sup.2 (I)in which R.sup.1 and R.sup.2 independently of one another represent hydrogen or aliphatic hydrocarbon radicals containing 1 to 22 carbon atoms and 0, 1, 2, or 3 double bonds, with hydrogen at an elevated temperature in the presence of a hydrogenation catalyst which is insoluble in the reaction mixture; andB) removing the polyol ether-containing reaction product from the catalyst.Type: GrantFiled: January 21, 1994Date of Patent: August 29, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Udo Hees, Georg Assman, Fritz Schuster
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Patent number: 5354911Abstract: A process for the preparation of ethers of the formula R.sup.1 --CR.sup.2 .dbd.CH--O--R.sup.3, in which R.sup.1 and R.sup.3 are each a radical having 1 to 6 carbon atoms and R.sup.2 is hydrogen or a radical having 1 to 2 carbon atoms, by reaction of a diacetal of the formula R.sup.1 --CHR.sup.2 --CH(--O--R.sup.3).sub.2 in the presence of a catalyst composed of an acid and an amine at elevated temperature in the liquid phase. The unsaturated ether of the above-mentioned formula is formed from the diacetal with elimination of an alcohol R.sup.3 --OH.Type: GrantFiled: January 7, 1994Date of Patent: October 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Peter Lappe, Helmut Springer
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Patent number: 5130435Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: August 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 5100852Abstract: Catalytic dealkoxylation of gem-dialkoxy compounds for synthesizing vinyl ethers is disclosed. Zeolites of the mordenite or ZSM5 type with an Na.sub.2 O/Al.sub.2 O.sub.3 molar ratio of 1:1.05 (.+-.0.25) are used as catalysts.Type: GrantFiled: February 25, 1988Date of Patent: March 31, 1992Assignee: Degussa AktiengesellschaftInventors: Dietrich Arntz, Michael Baacke, Peter Kleinschmit, Guenter Prescher
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Patent number: 4960954Abstract: Enol ethers of the general formula I ##STR1## are prepared by eliminating the radical R.sup.4 OH from acetals or ketals of the formula II ##STR2## where the substituents R.sup.1 and R.sup.2 are each independently of the other hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 -cycloalkenyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted aryl or C.sub.7 -C.sub.16 aralkyl,R.sup.3 is --CR.sup.5 (OR.sup.4).sub.2, --COOR.sup.4 or --COR.sup.4,R.sup.4 is C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.5 is hydrogen or C.sub.1 -C.sub.8 -alkyl,in a process which comprises performing the reaction in the presence of phosphoric acid and/or phosphates on a carrier material and/or phosphates and/or zeolites as catalysts.Type: GrantFiled: March 27, 1989Date of Patent: October 2, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Walter Himmele
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Patent number: 4891451Abstract: Vinyl ethers of the formula (I) ##STR1## where R.sup.1 to R.sup.3 are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, halogen-substituted alkyl, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, alkenylaryl, aralkyl or aralkenyl radical of 6 to 16 carbon atoms, halogen-substituted aryl or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, may form a cycloalkane, cycloalkene or heterocyclic structure, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by a process in which an alcohol is eliminated from an acetal or ketal of the formula (II) ##STR2## where R.sup.1 to R.sup.4 have the above meanings, in the presence of borosilicate and/or iron silicate zeolites as catalysts.Type: GrantFiled: June 30, 1988Date of Patent: January 2, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4792637Abstract: 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: GrantFiled: July 17, 1987Date of Patent: December 20, 1988Assignee: Enichem Anic SpAInventors: Giuseppe Messina, Mario D. Moretti, Salvatore R. Sanna, Giovanni Soma, Pier G. Cabras
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Patent number: 4469887Abstract: 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: GrantFiled: October 26, 1982Date of Patent: September 4, 1984Assignee: Chemische Werke Huels, AGInventors: Rudolf Brockhaus, Hans-Jurgen Franke
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Patent number: 4396782Abstract: A process for producing .alpha.,.beta.-unsaturated alkenyl ethers by cleavage of acetals in the gas phase and in the presence of a catalyst, the catalyst used being calcium oxide, the acetal cleavage being performed in the temperature range of 200.degree. to 300.degree. C. and the process being carried out preferably in a simple distilling apparatus.Type: GrantFiled: January 7, 1982Date of Patent: August 2, 1983Assignee: Ciba-Geigy CorporationInventors: Sameer H. Eldin, Milos Rusek
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Patent number: 4317925Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.Type: GrantFiled: July 25, 1979Date of Patent: March 2, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
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Patent number: 4131739Abstract: Cyclic acetals are rearranged to form isomeric carboxylic acid esters according to the following formula: ##STR1## wherein R is an alkyl, alkenyl, or aromatic moiety containing 1 to 12 carbon atoms;AndR' is an alkyl or alkenyl moiety containing 1 to 12 carbon atoms;In the presence of a catalyst consisting of a metal selected from the group Ru, Rh, Pd, Os, Ir or Pt supported on carbon.Type: GrantFiled: July 11, 1977Date of Patent: December 26, 1978Assignee: Eastman Kodak CompanyInventor: Don L. Morris