Oxy Or -coo- Containing Reactant Patents (Class 568/460)
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Publication number: 20130190518Abstract: The present invention relates to a process for preparing a terpenoid derivative, the process comprising a metathesis of an olefin and a terpenoid, and to terpenoid derivatives prepared with said process.Type: ApplicationFiled: July 11, 2011Publication date: July 25, 2013Applicant: Ecole Nationale Superieure de Chimie de RennesInventors: Marc Mauduit, Frédéric Caijo, Christophe Crévisy
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Patent number: 8455698Abstract: The invention relates to a method for producing a mixture containing hydroxy- and aldehyde functional compounds by a cross-metathesis reaction of at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative with an olefinic compound having at least one hydroxy group and at least one C—C double bond, in the presence of a metathesis catalyst at a maximum temperature of 180° C.Type: GrantFiled: December 30, 2009Date of Patent: June 4, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker
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Patent number: 8394996Abstract: The invention relates to a method for producing aldehyde functional compounds by a cross-metathesis reaction of an olefinic compound having at least one hydroxy group and at least one C—C double bond with at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative, in the presence of a metathesis catalyst at a maximum temperature of 180° C. and in the presence of at least one reagent that acts as a protective group-forming compound in relation to the aldehyde group of the aldehyde functional compounds.Type: GrantFiled: January 12, 2010Date of Patent: March 12, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker, Peter Hannen, Martin Roos
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Publication number: 20120142972Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: ApplicationFiled: February 13, 2012Publication date: June 7, 2012Inventors: Andrew Thompson, Xiongzhi Zhang, Lonnie Robarge
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Patent number: 7271296Abstract: The invention relates to a process for preparing phytofluene of the formula I, where a) a phosphonium salt of the formula II is condensed with an aldehyde of the formula III in a Wittig reaction to give an acetal of the formula IV b) the condensation product of the formula IV is subjected to an acid-catalyzed acetal hydrolysis to give the aldehyde of the formula V c) and V is condensed in a further Wittig reaction with a phosphonium salt of the formula VI to give phytofluene where the radicals R1, R2 and R7, and X? and Y? have the meaning sated in the description.Type: GrantFiled: October 15, 2004Date of Patent: September 18, 2007Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 7247755Abstract: The present invention provides a process for producing an ?,?-bis(hydroxymethyl)alkanal represented by Formula (II): (wherein R represents an alkyl group, a cycloalkyl group, or an aryl group) which comprises reacting an aldehyde represented by Formula (I): R—CH2—CHO ??(I) (wherein R has the same meaning as defined above) with formaldehyde in the presence of a basic catalyst and a phase-transfer catalyst.Type: GrantFiled: July 22, 2004Date of Patent: July 24, 2007Assignee: Kyowa Hakko Chemical Co., Ltd.Inventors: Shinichi Konishi, Shingo Nakayama, Yukihiro Isogai, Tokuyuki Yoshimoto
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Patent number: 7045641Abstract: A process for preparing compounds of the formula I is described and entails converting a compound of the formula II by Wittig or Wittig-Horner reaction into a compound of the formula IV, where appropriate converting the compound of the formula IV by hydrolysis of the acetal function and Wittig or Wittig-Horner reaction into a compound of the formula VI and converting the compound of the formula IV or VI in two stages into the compound of the formula I. The radicals R1, R2 and R6 and k have the meaning indicated in the description. Novel intermediates are also described.Type: GrantFiled: January 6, 2003Date of Patent: May 16, 2006Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 6703527Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.Type: GrantFiled: May 21, 2002Date of Patent: March 9, 2004Assignee: Nikken Chemicals Co., Ltd.Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
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Patent number: 6610892Abstract: The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I which comprises a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III with an aldehyde of the formula IV in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V b) reducing the ester of the formula V to give an acetal alcohol of the general formula VI and c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I, where the substituents have the meaning defined in the description.Type: GrantFiled: March 12, 2002Date of Patent: August 26, 2003Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Publication number: 20020128519Abstract: The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I 1Type: ApplicationFiled: March 12, 2002Publication date: September 12, 2002Inventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 6175044Abstract: 3,7-Dimethyl-2,6-octadien-1-al of formula I is prepared continuously by: thermally cleaving, in the presence or absence of an acid catalyst, 3-methyl-2-buten-1-al diprenyl acetal of formula II: thereby eliminating 3-methyl-2-buten-1-ol of formula III and yielding cis/trans-prenyl 3-methylbutadienyl ether of formula IV: thermally rearranging the resultant butadienyl ether of formula IV thereby yielding 2,4,4-trimethyl-3-formyl-1,5-hexadiene of formula V: subsequently rearranging intermediate (V) thereby yielding citral product of formula I, which comprises: as the reaction proceeds, continuously distilling the reaction mixture thereby continuously removing prenol, which is formed by degradation of acetal II, and the intermediates of formula IV and V and any citral product which is formed during the reaction; and thermally rearranging said intermediates of formula IV and V at a temperature of 100-200° C.Type: GrantFiled: September 24, 1999Date of Patent: January 16, 2001Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Gerd Kaibel, Werner Aquila, G{umlaut over (u)}nter Wegner, Hartwig Fuchs
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Patent number: 6166262Abstract: Branched-chain olefins are prepared and used as feedstocks in the manufacture of detersive surfactants.Type: GrantFiled: October 13, 1998Date of Patent: December 26, 2000Assignee: The Procter & Gamble CompanyInventor: Daniel Stedman Connor
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Patent number: 5994592Abstract: The present invention relates to a process for producing 2,2'-bis(hydroxymethyl)alkanal and 2,2'-bis(hydroxymethyl)alkanoic acid as raw materials for dimethylol alkanoic acids or trimethylol alkanes, which are useful for the production of polyesters, polyurethanes, alkyd resins and the like, in an industrially advantageous manner.Type: GrantFiled: February 12, 1998Date of Patent: November 30, 1999Assignee: Nippon Kasei Chemical Company LimitedInventors: Toshiharu Yokoyama, Kouji Maeda
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Patent number: 5892129Abstract: A process for the preparation of 1,1,3-trialkoxypropane by acid-catalyzed reaction of acrolein with a C.sub.1 to C.sub.6 alcohol, which can be carried out well on a large scale and leads to a higher selectivity. The process involves (a) the reaction, in the presence of a solid acid catalyst which is insoluble in the reaction mixture, (b) a partial neutralization of the reaction mixture, using an amine or basic ion exchanger, and (c) specific recovery by distillation of the reaction mixture and recirculation of fractions containing useful materials; aqueous fractions containing recyclable useful materials are largely dehydrated by pervaporation prior to being recirculated.Type: GrantFiled: May 21, 1997Date of Patent: April 6, 1999Assignee: Degussa AktiengesellschaftInventors: Mathias Hoepp, Dietrich Arntz, Hans-Peter Ohlinger, Willi Hofen
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Patent number: 5886234Abstract: A process for producing a cyclic unsaturated aldehyde is herein disclosed which comprises the step of reacting a cyclic conjugated diene compound with an aldehyde represented by the general formula (I)R--CH.dbd.CH--CHO (I)wherein R is an alkyl group having 1 to 3 carbon atoms,in the presence of a solid acid catalyst in accordance with the Diels-Alder reaction.According to the process of the present invention, the cyclic unsaturated aldehydes useful as the raw materials of traction oils and the like can efficiently and industrially advantageously be produced through the Diels-Alder reaction at a low cost without causing the corrosion of an apparatus and without requiring any treatment after the reaction.Type: GrantFiled: December 22, 1997Date of Patent: March 23, 1999Assignee: Idemitsu Kosan Co., Ltd.Inventors: Takashi Ohno, Toshiyuki Tsubouchi
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Patent number: 5705706Abstract: 2-(Alkoxymethyl)acrolein of the formula ##STR1## is produced from acrolein, an alcohol ROH and formaldehyde, in one step, with a good yield being obtained. The acrolein is reacted with a substantially equimolar quantity of a source of formaldehyde in the presence of at least an equimolar quantity of the alcohol ROH and a catalytic quantity of a catalyst system based on a secondary amine and a mineral acid at a pH value of the reaction mixture in the range of 1 to less than 7.Type: GrantFiled: July 23, 1996Date of Patent: January 6, 1998Assignee: Degussa AktiengesellschaftInventors: Mathias Hoepp, Klaus Koehler, Dietrich Arntz
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Patent number: 5603813Abstract: Vinyl formate containing formic acid, acetaldehyde and water following synthesis is separated from formic acid and water in a first distillation stage and from acetaldehyde in a second stage to give pure vinyl formate.Type: GrantFiled: August 2, 1995Date of Patent: February 18, 1997Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Marc Heider, Jochem Henkelmann, Ralf-Thomas Rahn, Harald Rust
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Patent number: 5281713Abstract: There is provided a process for the manufacture of 2-alkoxymethylacrolein compounds via the reaction of an appropriate alcohol and acrolein in the presence of an acid and a trisubstituted amine to form an intermediate and the subsequent reaction of the intermediate with formaldehyde in the presence of an acid and a disubstituted amine. There is also provided a process for the manufacture of 3-alkoxymethylquinolines from 2-alkoxymethylacrolein.Type: GrantFiled: October 23, 1992Date of Patent: January 25, 1994Assignee: American Cyanamid CompanyInventors: Henry L. Strong, David A. Cortes, Zareen Ahmed
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Patent number: 5177265Abstract: An improved method for preparing citral in liquid phase from prenol and prenal, wherein, in a single reaction enclosure, the prenol and prenal are condensed in the presence of a mineral acid at a concentration of about 5.10.sup.-3 mole for one mole of prenal, 90 to 95% of the acid is neutralized, and once excess prenal and prenol is eliminated, the citral is distilled.Type: GrantFiled: October 31, 1991Date of Patent: January 5, 1993Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Jacques Chazal
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Patent number: 5177266Abstract: There is provided a process for the manufacture of 2-alkoxymethylacrolein compounds via the reaction of an appropriate alcohol and acrolein in the presence of an acid and a trisubstituted amine to form an intermediate and the subsequent reaction of the intermediate with formaldehyde in the presence of an acid and a disubstituted amine.Type: GrantFiled: December 20, 1991Date of Patent: January 5, 1993Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5138107Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: July 12, 1991Date of Patent: August 11, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5132475Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of a quaternary ammonium fluoride catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NF where R.sup.1, R.sup.2, and R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms.Type: GrantFiled: July 12, 1991Date of Patent: July 21, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5053552Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.Type: GrantFiled: June 14, 1990Date of Patent: October 1, 1991Assignee: Kuraray Company, Ltd.Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
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Patent number: 4933500Abstract: Citral is prepared from prenol and prenal by condensation to form an acetal followed by cracking, both operations being effected in the presence of a lithium halide (e.g. lithium chloride) as catalyst.Type: GrantFiled: May 15, 1989Date of Patent: June 12, 1990Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Jacques Chazal
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Patent number: 4892976Abstract: The process for the preparation of an aldehyde of formula R--CHO in which R is an alkyl group of C.sub.1 -C.sub.7 comprises according to the invention the reaction on an alkyl formate of formula H--COOR in which R has the meaning given above, of a gas constituted mainly by CO, in the presence of(a) a catalyst based on a metal chosen from among Rh, Ru, Ir, mixtures of them or a mixture of Rh and/or Ru and/or Ir with Co, Ni or Fe,(b) a promoter chosen from among iodides and mixtures of covalent compounds of iodine and a phosphine or a tertiary amine,(c) a solvent consisting of a cyclic N-alkyl amide.Type: GrantFiled: July 15, 1988Date of Patent: January 9, 1990Assignee: SollacInventors: Jean Cordier, Bernard Dussart, Francis Petit, Yves Castanet, Serge Melloul, Andre Mortreux
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Patent number: 4820876Abstract: Synthetic polyethylene wax having low molecular weight of 250 to 3000 and a density of 0.930 to 0.950 is prepared in a high pressure process at pressures of at least 800 bar using a carbonyl compound such as acetaldehyde as chain transfer agent. The resulting wax with incorporated CO has good compatibility in hot melt systems, and may be stripped to remove light ends, increase density and crystallinity and improve thermal stability.Type: GrantFiled: May 27, 1987Date of Patent: April 11, 1989Assignee: Exxon Research & Engineering Co.Inventors: Hugo J. C. Nuttens, Gerard Van Haeren
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Patent number: 4812593Abstract: Bifunctional compounds of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl of 1 to 6 carbon atoms, R.sup.2 and R.sup.3 may furthermore be hydrogen, R.sup.2 is furthermore alkoxy and R.sup.4 is hydrogen, alkyl of 1 to 6 carbon atoms or alkoxy, and a double bond may be present between carbon atoms 2 and 3, are prepared by converting a tetraalkoxyalkane or a dialkoxyalkanoate of the formulae ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the above meanings, in the presence of a catalyst, such as a zeolite, in particular one of the pentasil type, and/or a phosphate and/or phosphoric acid on a carrier.Type: GrantFiled: August 6, 1987Date of Patent: March 14, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4748279Abstract: A liquid sterlizing composition comprising the reaction product of a non-ionic surfactant, a gluteraldehyde and triethylene glycol.Type: GrantFiled: June 23, 1987Date of Patent: May 31, 1988Inventor: Reginald K. Whiteley
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Patent number: 4739111Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as zirconium butoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha. ,.beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.Type: GrantFiled: September 11, 1985Date of Patent: April 19, 1988Assignee: Exxon Research & Engineering Co.Inventor: Ji-Yong Ryu
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Patent number: 4617405Abstract: Alpha, beta carbonyl compounds are prepared from an acid anhydride selected from the group consisting of glutaric anhydride and 3-alkyl glutaric anhydride, and a beta-hydroxy carbonyl compound having the following chemical formula:R.sub.2 COH--CHR--CRO or R.sub.2 COH--CHR--CNwhere each R is any substitutent group.The process comprises: (a) reacting the acid anhydride and the beta-hydroxy carbonyl compound in the presence of a catalytically effective amount of an acid catalyst to form an ester; (b) reacting the ester in the presence of a catalytically effective amount of a base catalyst to form a alpha, beta-unsaturated carbonyl compound and a carboxylic acid; and (c) separating the alpha, beta-unsaturated carbonyl compound and the carboxylic acid.Type: GrantFiled: September 25, 1984Date of Patent: October 14, 1986Assignee: A. E. Staley Manufacturing CompanyInventors: Donald E. Kiely, Martin Seidman
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Patent number: 4560790Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as silicon ethoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha., .beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.Type: GrantFiled: August 8, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventor: Ji-yong Ryu
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Patent number: 4499308Abstract: Disclosed is the reaction acrolein or methacrolein with a mono- or dihydroxyalkane to produce a 3-alkoxypropionaldehyde or a 3-(hydroxyalkoxy)propionaldehyde in the case of acrolein; or to produce a 3-alkoxy-2-methylpropionaldehyde or a 3-(hydroxyalkoxy)-2-methylpropionaldehyde in the case of methacrolein, by contacting a mixture of the recited reactants with a particulate solid metallic catalyst comprising an alloy of palladium and cadmium.Type: GrantFiled: December 5, 1983Date of Patent: February 12, 1985Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw
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Patent number: 4447649Abstract: The invention is concerned with a novel process for the manufacture of citral from an N-oxide.Type: GrantFiled: September 27, 1982Date of Patent: May 8, 1984Assignee: Hoffmann-La Roche Inc.Inventor: Manfred W. Breuninger
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Patent number: 4400550Abstract: A process for the synthesis of (Z,Z)-11-13-hexadecadienal is disclosed, starting with undecylenic alcohol.Type: GrantFiled: February 12, 1982Date of Patent: August 23, 1983Assignee: Albany International Corp.Inventors: Clyde E. Bishop, Gary W. Morrow
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Patent number: 4313008Abstract: The S-enantiomer of 3-chloro-1,2-propanediol is prepared by reaction of a chlorodeoxy-D-saccharide having the partial structure. ##STR1## to cleave the glycol, reduce the aldehyde so formed to an alcohol, and hydrolyse the alcohol under mild acidic conditions.Type: GrantFiled: May 17, 1979Date of Patent: January 26, 1982Assignee: Tate & Lyle Ltd.Inventor: Haydn F. Jones
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Patent number: 4298762Abstract: Improved conversions of primary allylic and benzylic alcohols are obtained in an Oppenauer oxidation process, under Oppenauer oxidation conditions, by carrying out the oxidation employing furfural as the hydrogen acceptor. Primary alcohols to which the present invention relates are allylic alcohols substituted in at least the 2-position with a hydrocarbon radical and benzylic alcohols.Type: GrantFiled: December 5, 1979Date of Patent: November 3, 1981Assignee: SCM CorporationInventors: William J. Ehmann, Walter E. Johnson, Jr.
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Patent number: 4268444Abstract: A process for the preparation of polyene-aldehydes, derived from 2,6-dimethyl-2,4,6,8-nonatetraen-1-al by substitution in the 9-position, by means of the Wittig ylide synthesis. The process is based on the observation, contrary to all expectation, that on reacting 2,6-dimethyl-octa-2,4,6-triene-1,8-dial with an equimolar amount of an ylide, it is exclusively the 8-al group of the dialdehyde which reacts. This specificity of the reaction is of particular importance for the preparation of the food dye .beta.-apo-8'-carotinal.Type: GrantFiled: November 16, 1979Date of Patent: May 19, 1981Assignee: BASF AktiengesellschaftInventor: Hagen Jaedicke
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Patent number: 4233247Abstract: An improvement in a process for the preparation of 2,2-dimethylolalkanal of the formula ##STR1## where R denotes an optionally substituted aliphatic radical by reacting 2-alkylacrylaldehyde with formaldehyde in presence of water and a base, the improvement residing in employing an aldehyde of the formula ##STR2## wherein R has the meaning indicated above and a mol ratio of the same to formaldehyde of 1:8-30 at a temperature in the range from -10 to 100.degree. C.Type: GrantFiled: March 13, 1978Date of Patent: November 11, 1980Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz