Halogen Containing Reactant Patents (Class 568/490)
  • Patent number: 9024076
    Abstract: Embodiments include an alkane oxidation catalyst having a support modified with a carboxylate group. The carboxylate group is functionalized with a manganese complex selected from the group consisting of [(C6H12N3R3)Mn(OCH3)3]Z, [(C6H12N3R3)Mn2O3]Z2, [(C6H15N3)Mn4O6]Z4. Each R is independently an alkyl group having 1 to 3 carbons, and each Z is independently PF6?, ClO4?, or Br?.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 5, 2015
    Assignee: Northwestern University
    Inventors: Justin M. Notestein, Nicholas J. Schoenfeldt, Andrew W. Korinda
  • Publication number: 20140296578
    Abstract: Embodiments include an alkane oxidation catalyst having a support modified with a carboxylate group. The carboxylate group is functionalized with a manganese complex selected from the group consisting of [(C6H12N3R3)Mn(OCH3)3]Z, [(C6H12N3R3)Mn2O3]Z2, [(C6H15N3)Mn4O6]Z4. Each R is independently an alkyl group having 1 to 3 carbons, and each Z is independently PF6?, ClO4?, or Br?.
    Type: Application
    Filed: July 18, 2012
    Publication date: October 2, 2014
    Applicant: Northwestern University
    Inventors: Justin M. Notestein, Nicholas J. Schoenfeldt, Andrew W. Korinda
  • Publication number: 20140228579
    Abstract: The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
    Type: Application
    Filed: September 11, 2013
    Publication date: August 14, 2014
    Applicant: Brock Unviersity
    Inventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
  • Publication number: 20120288445
    Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.
    Type: Application
    Filed: April 13, 2012
    Publication date: November 15, 2012
    Applicant: The University of Manchester
    Inventor: Christian PRENANT
  • Patent number: 8030526
    Abstract: Isotopically labeled formaldehyde (*C§H2O) is prepared from labeled methyl iodide (*C§H3I) by reaction with an oxygen nucleophile having a pendant leaving group. The mild and efficient reaction conditions result in good yields of *C§H2O with little or no *C isotopic dilution. The simple, efficient production of 11CH2O is described. The use of the 11CH2O for the formation of positron emission tomography tracer compounds is described. The reaction can be incorporated into automated equipment available to radiochemistry laboratories. The isotopically labeled formaldehyde can be used in a variety of reactions to provide radiotracer compounds for imaging studies as well as for scintillation counting and autoradiography.
    Type: Grant
    Filed: June 22, 2009
    Date of Patent: October 4, 2011
    Assignee: Brookhaven Science Associates, LLC
    Inventors: Jacob Matthew Hooker, Matthias Schonberger, Hanno Schieferstein, Joanna S. Fowler
  • Patent number: 7977515
    Abstract: A process is disclosed for the synthesis of formaldehyde from methane starting with the oxychlorination of methane to produce methylene chloride. Hydrolysis of methylene chloride yields the product formaldehyde. Gaseous formaldehyde is condensed for shipment. Byproduct chloroform and carbon tetrachloride are recovered and hydrogenated to provide additional methylene chloride.
    Type: Grant
    Filed: July 1, 2010
    Date of Patent: July 12, 2011
    Inventor: John E. Stauffer
  • Patent number: 7790933
    Abstract: A process is disclosed for the synthesis of formaldehyde from methane starting with the oxychlorination of methane to produce methylene chloride. Hydrolysis of methylene chloride yields the product formaldehyde. Byproduct chloroform and carbon tetrachloride are recovered and hydrogenated to provide additional methylene chloride.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: September 7, 2010
    Inventor: John E. Stauffer
  • Publication number: 20090317880
    Abstract: Isotopically labeled formaldehyde (*C§H2O) is prepared from labeled methyl iodide (*C§H3I) by reaction with an oxygen nucleophile having a pendant leaving group. The mild and efficient reaction conditions result in good yields of *C§H2O with little or no *C isotopic dilution. The simple, efficient production of 11CH2O is described. The use of the 11CH2O for the formation of positron emission tomography tracer compounds is described. The reaction can be incorporated into automated equipment available to radiochemistry laboratories. The isotopically labeled formaldehyde can be used in a variety of reactions to provide radiotracer compounds for imaging studies as well as for scintillation counting and autoradiography.
    Type: Application
    Filed: June 22, 2009
    Publication date: December 24, 2009
    Applicant: BROOKHAVEN SCIENCE ASSOCIATES, LLC
    Inventors: Jacob Matthew Hooker, Mathias Schonberger, Hanno Schieferstein, Joanna S. Fowler
  • Publication number: 20080274046
    Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO ??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.
    Type: Application
    Filed: February 20, 2008
    Publication date: November 6, 2008
    Inventor: Christian Prenant
  • Patent number: 7161050
    Abstract: A reactant selected from the group consisting of alkanes, alkenes, alkynes, dienes, and aromatics is reacted with a halide selected from the group including chlorine, bromine, and iodine to form a first reaction product. The first reaction product is reacted with a solid oxidizer to form a product selected from the group including olefins, alcohols, ethers, and aldehydes, and spent oxidizer. The spent oxidizer is oxidized to form the original solid oxidizer and the second reactant which are recycled.
    Type: Grant
    Filed: August 19, 2003
    Date of Patent: January 9, 2007
    Assignees: GRT, Inc., The Regents of the University of California
    Inventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen Stucky, Peter Ford
  • Patent number: 7161030
    Abstract: Hydrofluoroethers of formula: T-CFX?—O—Rf—CFX-T???(II) wherein: T=CH3; X, X?, equal to or different from each other, are selected between F, CF3; T00?=F, Cl, H, C1–C3 perfluoroalkyl, CH3, CH2OH, COCl, CHO, CO2H; Rf is a perfluoroalkylene or a perfluoropolyoxyalkylene and respective preparation process by reduction with hydrogen in the presence of a platinum catalyst supported on metal fluorides of the corresponding compounds with at least one —COCl end group.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: January 9, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
  • Patent number: 7084308
    Abstract: A process is provided for the manufacture of formaldehyde from methyl bromide. In the process, methyl bromide is oxidized with air over a catalyst to give formaldehyde and hydrogen bromide. In a preferred embodiment of the invention, a mixture of two different catalysts are employed, one to promote hydrolysis of methyl bromide to methyl alcohol and the other to promote the oxidation of methyl alcohol to formaldehyde.
    Type: Grant
    Filed: July 29, 2005
    Date of Patent: August 1, 2006
    Inventor: John E. Stauffer
  • Patent number: 7053238
    Abstract: A fluorinated polyvalent carbonyl compound is produced by an economically advantageous method from inexpensive materials without requiring a complicated synthetic process step. Namely, the present invention comprises reacting a polyvalent alcohol having at least two kinds of alcohol skeletons selected among a primary alcohol, a secondary alcohol and a tertiary alcohol, with an acid halide to obtain a polyvalent ester compound, fluorinating it in a liquid phase to obtain a perfluorinated polyvalent ester compound, and cleaving the ester bonds derived from primary and secondary alcohols in the perfluoropolyvalent ester compound to obtain a fluorinated polyvalent carbonyl compound.
    Type: Grant
    Filed: July 15, 2004
    Date of Patent: May 30, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
  • Patent number: 6984759
    Abstract: Process for the perfluoropolyether preparation having reactive end groups —CH2NH2, —CHO, —CH2OH, by reduction of the corresponding perfluoropolyethers having —CN, —COCl, —CHO end groups by using gaseous hydrogen in the presence of a catalyst constituted by Pd, Rh, or Ru, supported on solid metal fluorides, at a temperature from 20° C. to 150° C. and under a pressure between 1 and 50 atm.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: January 10, 2006
    Assignee: Solvay Solexis S.p.A.
    Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
  • Patent number: 6822123
    Abstract: A process is provided for the production of formaldehyde from methyl chloride. In the process methyl chloride is oxidized with air over a catalyst to give formaldehyde and hydrogen chloride. In a preferred embodiment of the invention, a mixture of two different catalysts is used, one catalyst to promote the hydrolysis of methyl chloride to methyl alcohol, and the other catalyst to oxidize the methyl alcohol so formed to formaldehyde. The reaction kinetics can be regulated by adjusting the proportion of the two catalysts in the mixture. In this manner, the release of heat from the reaction can be controlled and excessive temperatures in the catalyst mixture can be avoided.
    Type: Grant
    Filed: April 2, 2003
    Date of Patent: November 23, 2004
    Inventor: John E. Stauffer
  • Publication number: 20040199025
    Abstract: A process is provided for the production of formaldehyde from methyl chloride. In the process methyl chloride is oxidized with air over a catalyst to give formaldehyde and hydrogen chloride. In a preferred embodiment of the invention, a mixture of two different catalysts is used, one catalyst to promote the hydrolysis of methyl chloride to methyl alcohol, and the other catalyst to oxidize the methyl alcohol so formed to formaldehyde. The reaction kinetics can be regulated by adjusting the proportion of the two catalysts in the mixture. In this manner, the release of heat from the reaction can be controlled and excessive temperatures in the catalyst mixture can be avoided.
    Type: Application
    Filed: April 2, 2003
    Publication date: October 7, 2004
    Inventor: John E. Stauffer
  • Patent number: 6713655
    Abstract: Alcohols, ethers, aldehydes, and olefins are manufactured from alkanes by mixing an alkane and a halogen selected from the group including chlorine, bromine, and iodine in a reactor to form alkyl halide and hydrogen halide. The alkyl halide only or the alkyl halide and the hydrogen halide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal halide. The metal halide is oxidized to form original metal oxide and halogen, both of which are recycled.
    Type: Grant
    Filed: February 12, 2003
    Date of Patent: March 30, 2004
    Inventors: Aysen Yilmaz, Gurkan Atinc Yilmaz, Ivan M. Lorkovic, Galen D. Stucky, Peter C. Ford, Eric McFarland, Jeffrey H. Sherman
  • Publication number: 20030125585
    Abstract: Alcohols, ethers, aldehydes, and olefins are manufactured from alkanes by mixing an alkane and a halogen selected from the group including chlorine, bromine, and iodine in a reactor to form alkyl halide and hydrogen halide. The alkyl halide only or the alkyl halide and the hydrogen halide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal halide. The metal halide is oxidized to form original metal oxide and halogen, both of which are recycled.
    Type: Application
    Filed: February 12, 2003
    Publication date: July 3, 2003
    Inventors: Aysen Yilmaz, Gurkan Atinc Yilmaz, Ivan M. Lorkovic, Galen D. Stucky, Peter C. Ford, Eric McFarland, Jeffrey H. Sherman
  • Publication number: 20020161265
    Abstract: The invention relates to a process for the selective oxidation of alcohols to ketones or to aldehydes by means of an alkali hypohalite under alkaline conditions, which comprises carrying out the oxidation in the presence of a heterogeneous oxidation catalyst that is insoluble in the reaction medium and is selected from the group comprising the compounds of formula (I) 1 2
    Type: Application
    Filed: June 7, 2002
    Publication date: October 31, 2002
    Inventors: Reinhard Sommerlade, Hansjorg Grutzmacher, Souad Boulmaaz
  • Patent number: 6403838
    Abstract: A process for making 2,7-dimethyl-2,4,6-octatrien-1,8-dial starting form an allylic halide is described. The process steps include aldehyde protection, conversion to a sulfide, oxidation to an allylic sulfone followed by a Ramberg-Backlund reaction and hydrolysis.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: June 11, 2002
    Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
  • Patent number: 6399835
    Abstract: Processes for the electrophilic substitution of aromatic compounds, such as alkylation, with a desired substituent are disclosed. The processes include contacting the aromatic compound, a precursor of the desired substituent and an aqueous reagent containing zinc halide at elevated temperatures such as above 50° C.
    Type: Grant
    Filed: April 6, 2000
    Date of Patent: June 4, 2002
    Assignee: Bromine Compounds Ltd.
    Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
  • Patent number: 6198006
    Abstract: A process for the manufacture of citral is provided by the catalyzed rearrangement of dehydrolinalool to citral. The rearrangement is carried out in the presence of a molybdenum compound of the general formula MoO2X2 wherein X signifies an acetylacetonate or halide ion, and a dialkyl or diaryl sulphoxide as the catalyst system, in the presence of an organic acid having a pK value in the range of about 4.0 to about 6.5 and in an apolar aprotic organic solvent.
    Type: Grant
    Filed: March 16, 1999
    Date of Patent: March 6, 2001
    Assignee: Roche Vitamins Inc.
    Inventor: Werner Bonrath
  • Patent number: 6191313
    Abstract: A process for the manufacture of dihydrocitral, a valuable intermediate, through the catalyzed rearrangement of dihydrodehydrolinalool by carrying out the rearrangement in the presence of a molybdenum compound of the general formula MoO2X2 wherein X signifies an acetylacetonate or halide ion, and a dialkyl or diaryl sulphoxide as the catalyst system, in the presence of an organic acid having a pK value in the range of about 4.0 to about 6.5 and in an aprotic organic solvent.
    Type: Grant
    Filed: March 29, 1999
    Date of Patent: February 20, 2001
    Assignee: Roche Vitamins Inc.
    Inventor: Werner Bonrath
  • Patent number: 5994593
    Abstract: 3,3-Dimethylbutyraldehyde is synthesized via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane in the presence of water and a base and is purified via an aldehyde/bisulfite adduct.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: November 30, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 5977415
    Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor and vinyl chloride. The tert-butyl cation precursor is contacted with vinyl chloride in the presence of an inorganic acid, and the product is allowed to react with water to form 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: November 2, 1999
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Zhi Guo
  • Patent number: 5905175
    Abstract: 1-chloro-3,3-dimethylbutane is oxidized by dimethyl sulfoxide, in the presence of an effective amount of inorganic bromide or iodide, and in the present of an effective amount of base, to produce 3,3-dimethylbutyraldehyde.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: May 18, 1999
    Assignee: The NutraSweet Company
    Inventors: Zhi Guo, Indra Prakash
  • Patent number: 5679869
    Abstract: A process for preparing aldehydes of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylphenyl, C.sub.7 -C.sub.12 -phenylalkyl and R.sup.1 and R.sup.2 are joined together to form a 3-, 4-, 5-, 6- or 7-membered cycloaliphatic ring,R.sup.1 and R.sup.3 are each C.sub.1 -C.sub.4 -alkoxy, phenoxy, methylamino, dimethylamino or halogen, andR.sup.1 is additionally hydroxyl or aminocomprises reacting a carboxylic acid or ester of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, andR.sup.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.12 -alkylphenyl or C.sub.7 -C.sub.12 -phenylalkyl,with hydrogen in the gas phase at temperatures from 200.degree. to 450.degree. C. and pressures from 0.1 to 20 bar in the presence of a catalyst whose catalytically active mass comprises from 60 to 99.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: October 21, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schnurr, Rolf Fischer, Joachim Wulff-Doring, Michael Hesse
  • Patent number: 5639919
    Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids, corresponding to the following formula (I): ##STR1## in which X is a carbon atom; n is equal to 1 or 2; R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 11 carbon atoms or aryl, each alkyl and alkenyl may be linear, branched or cyclic, or R.sub.1 and R.sub.2 can together with the carbon atom to which they are attached form a cycloaliphatic compound which is optionally substituted; and R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms or alkenyl containing 2 to 10 carbon atoms, each alkyl or alkenyl being linear, or if containing sufficient numbers of carbon atoms, may also be branched or cyclic, or an aryl containing 6 to 10 carbon atoms, or any two of R.sub.4, R.sub.5, R.sub.6, R.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 17, 1997
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Hugues Bienayme
  • Patent number: 5563235
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: October 8, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5512652
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5426240
    Abstract: A process for producing dichloroacetaldehyde hydrate together with chloral from acetaldehyde or para-aldehyde. The process comprises a step of chlorinating acetaldehyde or para-aldehyde to obtain a chlorinated solution containing dichloroacetaldehyde as a major component, a step of distilling this chlorinated solution to obtain a distillate having a boiling point of 90.degree.-100.degree. C. and containing 50% or more of dichloroacetaldehyde, a step of adding water to this distillate, crystallizing dichloroacetaldehyde hydrate, and separating the crystals, and a step of chlorinating the remaining aldehyde components into chloral. The process enables dichloroacetaldehyde hydrate to be separated at a high purity and the raw materials to be utilized efficiently.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: June 20, 1995
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
  • Patent number: 5414140
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: May 9, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5414139
    Abstract: A process for manufacturing monochloroacetaldehyde trimer and chloral together by effectively utilizing a raw material acetaldehyde or para-aldehyde. The process comprises a step of chlorinating acetaldehyde or para-aldehyde to produce a chlorinated liquid of which the major component is monochloroacetaldehyde, a step comprising adding chloral to said chlorinated liquid and distilling the mixture to obtain a fraction of which the major components are monochloroacetaldehyde and chloral, a step of trimerizing monochloroacetaldehyde by reacting said fraction in the presence of a trimerization catalyst and separating the MCA trimer by filtration, and a step of chlorinating other fractions from said distillation step and the filtrate from said trimerization step to produce chloral. According to this process all raw material aldehydes and components derived from aldehydes which have not been consumed for the production of MCA trimer can be easily converted into chloral which is useful as an industrial chemical.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: May 9, 1995
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
  • Patent number: 5321166
    Abstract: A process for the manufacture of aldehydes by the catalytic reduction of carboxylic acid halides with hydrogen in the presence of an alkylene oxide.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: June 14, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Hans Hilpert
  • Patent number: 5248832
    Abstract: A process for the manufacture of trifluoroacetaldehyde, or a hydrate or hemiacetal thereof, which comprises reduction of an ester of trifluoroacetic acid with a borohydride reducing agent in a hydroxylic solvent to form trifluoroacetaldehyde hydrate or hemiacetal; whereafter if the free aldehyde is required, water or alcohol is removed from the hydrate or hemiacetal respectively using conventional procedures.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Stanley A. Lee
  • Patent number: 5196608
    Abstract: The present invention relates to the use of an allylchloride of the general formula ##STR1##wherein R is a C.sub.1 -C.sub.12 alkyl group or a C.sub.2 -C.sub.12 alkenyl group, which groups may be substituted with one or more substitutents selected from the group consisting of C.sub.1 -C.sub.4 alkoxy, halogen, unsubstituted phenyl and substituted phenyl; a (trihydrocarbyl)silyl group; a (dihydrocarbyl) (hydrocarbyloxy)silyl group; or a dihydropyran-2-yl group, a tetrahydropyran-2-yl group, a dihydrofur-2-yl group or a tetrahydrofur-2-yl group, which groups may be substituted with C.sub.1 -C.sub.6 alkyl;for preparing an aldehyde compound via an intermediate alcohol compound.The invention further relates to a new allylchloride.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: March 23, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Gerrit J. Lagerweij, Cornelis Bakker, Monique E. A. De Bruin-Van Der Flier
  • Patent number: 5059716
    Abstract: Aromatic and aliphatic aldehydes can be prepared from the corresponding aromatic or aliphatic carboxylic acids or the esters, anhydrides or halides thereof at elevated temperature by catalytic gas phase hydrogenation using hydrogen if use is made of a catalyst system composed of oxides of titanium and/or vanadium and of one or more co-metals, the co-metals being selected from the group consisting of chromium, molybdenum, cobalt, nickel, zinc, cadmium and copper.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Joentgen, Helmut Fiege
  • Patent number: 5015780
    Abstract: Dihalobutyraldehydes of formula I ##STR1## wherein X and Y are each independently of the other Cl or Br, are obtainable at high rates of conversion and with excellent selectivities by catalytic dehalogenation with hydrogen by carrying out the reaction with appropriate .alpha.,.alpha.-dihalobutyraldehydes in an organic aprotic solvent. The dihalobutyraldehydes are intermediates for the synthesis of herbicidal acyl cyclohexanediones.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Steiner, Hans Tobler
  • Patent number: 5008462
    Abstract: A method for preparing a monochloroacetaldehyde trimer in a high yield is here disclosed which comprises the steps of dissolving, in an organic solvent, a solution containing monochloroacetaldehyde as the main component, and then trimerizing monochloroacetaldehyde in the presence of sulfuric acid. The thus prepared monochloroacetaldehyde trimer can be heated at 120.degree. C. under atmospheric pressure to obtain pure monochloroacetaldehyde.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: April 16, 1991
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Makoto Ishizuka, Takashi Wakasugi
  • Patent number: 4983776
    Abstract: The invention relates to the synthesis of functional fluoro derivatives and more particularly that of perfluorinated aldehydes of the type R.sub.F -CHO where R.sub.F denotes a linear or branched perfluoroalkyl radical.A perfluoroalkyl iodide R.sub.F I is reacted over the zinc-copper metal couple, in the presence of a radical initiator, with an amide RCONR.sub.1 R.sub.2, R denoting a hydrogen atom or a methyl or ethyl radical, and each of R.sub.1 and R.sub.2 denoting a C.sub.1 -C.sub.4 alkyl radical.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: January 8, 1991
    Assignee: Societe Atochem
    Inventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
  • Patent number: 4847424
    Abstract: A carboxylic acid or its ester is reduced by formic acid in the presence of a hydrous metal oxide solid catalyst, to produce a corresponding aldehyde. Using this method, no harmful waste is by-produced, an aldehyde compound can be produced at relatively low cost, and the aldehyde produced can be easily recovered.
    Type: Grant
    Filed: February 25, 1988
    Date of Patent: July 11, 1989
    Assignee: Japan Tobacco Inc.
    Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
  • Patent number: 4837366
    Abstract: A group of polyfluoroaldehydes represented by 3,3,3-trifluoropropanal can be formed with very good selectivity by reacting polyfluoroalkenes represented by 3,3,3-trifluoropropene with water in the presence of a source of divalent palladium. A group of polyfluoroacetals represented by 1,1-dialkoxy-3,3,3-trifluoropropane can be formed with very good selectivity by reacting the same polyfluoroalkenes with an alcohol in the presence of a source of divalent palladium.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: June 6, 1989
    Assignee: Central Glass Company, Limited
    Inventors: Katsuyoshi Murata, Toru Nakazora, Takashi Isago
  • Patent number: 4825003
    Abstract: A process for the production of 2-chloropropionaldehyde from vinyl chloride, carbon monoxide and hydrogen which comprises using a rhodium compound and a trivalent organic phosphorus compound or the oxide of a trivalent organic phosphorus compound as a catalyst and carrying out the reaction under the co-existence of an acid the pka of which is in the range of 0.5-5, the oxide, hydroxide or a weak acid salt of an alkali metal or alkaline earth metal, or a buffer solution.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: April 25, 1989
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hiroshi Ono, Takaharu Kasuga, Shinji Kiyono, Yoshihiro Fujita
  • Patent number: 4760196
    Abstract: The inventive method is particularly advantageous for the preparation of an unsaturated alcohol or aldehyde by the reduction of a corresponding unsaturated carboxylic acid since the unsaturated double bond in the starting acid is not hydrogenated by the reaction of reduction. The method comprises first reacting the starting acid with an alkyl chloroformate to form an intermediate compound by the dehydrochlorination and the intermediate compound is then reduced by using sodium borohydride as the reducing agent. The proportion of the aldehyde to alcohol in the product mixture can be controlled by modifying the amount of the reducing agent and/or the reaction time.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: July 26, 1988
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 4745229
    Abstract: A process for preparing .alpha.,.beta.-unsaturated aldehydes of the general formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are independently a hydrogen atom, or an alkyl or alkenyl group with or without being substituted with a lower acyloxy group. The aldehyde of the general formula (I) is prepared by reaction between an allylic chloride of the following general formula (IIa) ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have, respectively, the same meanings as defined above, and an amine oxide selected from the group consisting of tri(lower alkyl)amine N-oxides of the formula,R.sub.3.sup.4 N.sup.+ O.sup.-,in which R.sup.4 represents a lower alkyl group having from 2 to 4 carbon atoms, and N-lower alkylmorpholine N-oxides of the following formula ##STR3## in which R.sup.5 represents a lower alkyl group having from 1 to 4 carbon atoms. Alternatively, the aldehyde of the formula (I) is obtained by reaction between an allylic chloride of the following general formula (IIb) ##STR4## in which R.sup.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: May 17, 1988
    Assignee: Kuraray Company Ltd.
    Inventors: Junzo Otera, Shigeaki Suzuki, Takashi Onishi, Yoshiji Fujita
  • Patent number: 4691062
    Abstract: 4-chloro-butanals of the formula ##STR1## where R is hydrogen or a straight or branched chain alkyl group of 1 to 4 carbon atoms are produced by reacting the corresponding 1,1-dimethoxy-4-hydroxybutane at a temperature between -20.degree. and +80.degree. C. in the presence of triphenylphosphine with carbon tetrachloride and hydrolyzing the 1,1-dimethoxy-4-chloro-butane obtained in acid medium.
    Type: Grant
    Filed: October 22, 1986
    Date of Patent: September 1, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Gunter Prescher, Klaus Kohler
  • Patent number: 4638091
    Abstract: A method for the preparation of a fluorinated amine of the formula: ##STR1## wherein X represents hydrogen or fluorine, R represents hydrogen, lower alkyl, difluoromethyl or trifluoromethyl and each of R.sup.1 and R.sup.2, independently, represents hydrogen or lower alkyl, which comprises reacting a carbonyl compound of the formula:XCF.sub.2 CORat an elevated temperature with a nitrogenous base of the formula: ##STR2## and hydrogen in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: January 20, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Roy D. Bowden
  • Patent number: 4613702
    Abstract: Aldehydes are facilely prepared in high yields by catalytically hydrocarbonylating an organic halide with gaseous admixture of hydrogen and carbon monoxide in the presence of a neutralizing agent for the hydrogen acid produced thereby, said hydrocarbonylation being carried out in an inert, liquid carboxylic acid reaction medium, i.e., a liquid carboxylic acid which is inert under the reaction conditions of temperature and pressure.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: September 23, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Philippe Leconte
  • Patent number: 4605749
    Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: August 12, 1986
    Assignee: State of Israel, Prime Minister's Office, Atomic Energy Commission
    Inventors: Ouri Buchman, Ilan Pri-Bar
  • Patent number: 4602105
    Abstract: A process for the preparation of alpha-haloalkylesters, wherein an acylhalide having the general formula ##STR1## in which R.sup.1 represents a substituted or unsubstituted hydrocarbyl group and Hal represents chlorine or bromine is contacted with hydrogen at elevated temperature and pressure in the presence of a catalytic system comprising at least one Group VIII element.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Shell Oil Company
    Inventor: Eit Drent