Halogen Containing Reactant Patents (Class 568/490)
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Patent number: 9024076Abstract: 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: GrantFiled: July 18, 2012Date of Patent: May 5, 2015Assignee: Northwestern UniversityInventors: Justin M. Notestein, Nicholas J. Schoenfeldt, Andrew W. Korinda
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Publication number: 20140296578Abstract: 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: ApplicationFiled: July 18, 2012Publication date: October 2, 2014Applicant: Northwestern UniversityInventors: Justin M. Notestein, Nicholas J. Schoenfeldt, Andrew W. Korinda
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Publication number: 20140228579Abstract: 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: ApplicationFiled: September 11, 2013Publication date: August 14, 2014Applicant: Brock UnviersityInventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
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Publication number: 20120288445Abstract: 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: ApplicationFiled: April 13, 2012Publication date: November 15, 2012Applicant: The University of ManchesterInventor: Christian PRENANT
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Patent number: 8030526Abstract: 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: GrantFiled: June 22, 2009Date of Patent: October 4, 2011Assignee: Brookhaven Science Associates, LLCInventors: Jacob Matthew Hooker, Matthias Schonberger, Hanno Schieferstein, Joanna S. Fowler
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Patent number: 7977515Abstract: 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: GrantFiled: July 1, 2010Date of Patent: July 12, 2011Inventor: John E. Stauffer
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Patent number: 7790933Abstract: 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: GrantFiled: November 3, 2009Date of Patent: September 7, 2010Inventor: John E. Stauffer
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Publication number: 20090317880Abstract: 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: ApplicationFiled: June 22, 2009Publication date: December 24, 2009Applicant: BROOKHAVEN SCIENCE ASSOCIATES, LLCInventors: Jacob Matthew Hooker, Mathias Schonberger, Hanno Schieferstein, Joanna S. Fowler
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Publication number: 20080274046Abstract: 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: ApplicationFiled: February 20, 2008Publication date: November 6, 2008Inventor: Christian Prenant
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Patent number: 7161050Abstract: 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: GrantFiled: August 19, 2003Date of Patent: January 9, 2007Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen Stucky, Peter Ford
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Patent number: 7161030Abstract: 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: GrantFiled: July 31, 2003Date of Patent: January 9, 2007Assignee: Solvay Solexis S.p.A.Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
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Patent number: 7084308Abstract: 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: GrantFiled: July 29, 2005Date of Patent: August 1, 2006Inventor: John E. Stauffer
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Patent number: 7053238Abstract: 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: GrantFiled: July 15, 2004Date of Patent: May 30, 2006Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
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Patent number: 6984759Abstract: 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: GrantFiled: July 31, 2003Date of Patent: January 10, 2006Assignee: Solvay Solexis S.p.A.Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
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Patent number: 6822123Abstract: 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: GrantFiled: April 2, 2003Date of Patent: November 23, 2004Inventor: John E. Stauffer
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Publication number: 20040199025Abstract: 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: ApplicationFiled: April 2, 2003Publication date: October 7, 2004Inventor: John E. Stauffer
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Patent number: 6713655Abstract: 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: GrantFiled: February 12, 2003Date of Patent: March 30, 2004Inventors: Aysen Yilmaz, Gurkan Atinc Yilmaz, Ivan M. Lorkovic, Galen D. Stucky, Peter C. Ford, Eric McFarland, Jeffrey H. Sherman
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Publication number: 20030125585Abstract: 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: ApplicationFiled: February 12, 2003Publication date: July 3, 2003Inventors: Aysen Yilmaz, Gurkan Atinc Yilmaz, Ivan M. Lorkovic, Galen D. Stucky, Peter C. Ford, Eric McFarland, Jeffrey H. Sherman
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Publication number: 20020161265Abstract: 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 2Type: ApplicationFiled: June 7, 2002Publication date: October 31, 2002Inventors: Reinhard Sommerlade, Hansjorg Grutzmacher, Souad Boulmaaz
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Patent number: 6403838Abstract: 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: GrantFiled: September 27, 2001Date of Patent: June 11, 2002Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
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Patent number: 6399835Abstract: 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: GrantFiled: April 6, 2000Date of Patent: June 4, 2002Assignee: Bromine Compounds Ltd.Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
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Patent number: 6198006Abstract: 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: GrantFiled: March 16, 1999Date of Patent: March 6, 2001Assignee: Roche Vitamins Inc.Inventor: Werner Bonrath
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Patent number: 6191313Abstract: 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: GrantFiled: March 29, 1999Date of Patent: February 20, 2001Assignee: Roche Vitamins Inc.Inventor: Werner Bonrath
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Patent number: 5994593Abstract: 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: GrantFiled: September 17, 1998Date of Patent: November 30, 1999Assignee: The NutraSweet CompanyInventors: Indra Prakash, Zhi Guo
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Patent number: 5977415Abstract: 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: GrantFiled: August 20, 1998Date of Patent: November 2, 1999Assignee: The NutraSweet CompanyInventors: Indra Prakash, Zhi Guo
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Patent number: 5905175Abstract: 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: GrantFiled: May 20, 1998Date of Patent: May 18, 1999Assignee: The NutraSweet CompanyInventors: Zhi Guo, Indra Prakash
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Patent number: 5679869Abstract: 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: GrantFiled: December 5, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Rolf Fischer, Joachim Wulff-Doring, Michael Hesse
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Patent number: 5639919Abstract: 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: GrantFiled: June 7, 1995Date of Patent: June 17, 1997Assignee: Rhone-Poulenc Nutrition AnimaleInventor: Hugues Bienayme
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Patent number: 5563235Abstract: 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: GrantFiled: January 16, 1996Date of Patent: October 8, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5512652Abstract: 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: GrantFiled: February 14, 1995Date of Patent: April 30, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5426240Abstract: 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: GrantFiled: July 7, 1994Date of Patent: June 20, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5414140Abstract: 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: GrantFiled: January 21, 1992Date of Patent: May 9, 1995Assignee: E. I. du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5414139Abstract: 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: GrantFiled: March 15, 1994Date of Patent: May 9, 1995Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
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Patent number: 5321166Abstract: 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: GrantFiled: February 18, 1993Date of Patent: June 14, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Hans Hilpert
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Patent number: 5248832Abstract: 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: GrantFiled: May 20, 1992Date of Patent: September 28, 1993Assignee: Imperial Chemical Industries PLCInventor: Stanley A. Lee
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Patent number: 5196608Abstract: 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: GrantFiled: December 2, 1991Date of Patent: March 23, 1993Assignee: Duphar International Research B.V.Inventors: Gerrit J. Lagerweij, Cornelis Bakker, Monique E. A. De Bruin-Van Der Flier
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Patent number: 5059716Abstract: 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: GrantFiled: August 8, 1990Date of Patent: October 22, 1991Assignee: Bayer AktiengesellschaftInventors: Winfried Joentgen, Helmut Fiege
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Patent number: 5015780Abstract: 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: GrantFiled: January 16, 1990Date of Patent: May 14, 1991Assignee: Ciba-Geigy CorporationInventors: Heinz Steiner, Hans Tobler
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Patent number: 5008462Abstract: 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: GrantFiled: November 8, 1989Date of Patent: April 16, 1991Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Makoto Ishizuka, Takashi Wakasugi
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Patent number: 4983776Abstract: 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: GrantFiled: April 27, 1989Date of Patent: January 8, 1991Assignee: Societe AtochemInventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
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Patent number: 4847424Abstract: 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: GrantFiled: February 25, 1988Date of Patent: July 11, 1989Assignee: Japan Tobacco Inc.Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
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Patent number: 4837366Abstract: 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: GrantFiled: September 3, 1987Date of Patent: June 6, 1989Assignee: Central Glass Company, LimitedInventors: Katsuyoshi Murata, Toru Nakazora, Takashi Isago
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Patent number: 4825003Abstract: 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: GrantFiled: September 11, 1987Date of Patent: April 25, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hiroshi Ono, Takaharu Kasuga, Shinji Kiyono, Yoshihiro Fujita
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Patent number: 4760196Abstract: 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: GrantFiled: May 8, 1987Date of Patent: July 26, 1988Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto
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Patent number: 4745229Abstract: 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: GrantFiled: February 13, 1987Date of Patent: May 17, 1988Assignee: Kuraray Company Ltd.Inventors: Junzo Otera, Shigeaki Suzuki, Takashi Onishi, Yoshiji Fujita
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Patent number: 4691062Abstract: 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: GrantFiled: October 22, 1986Date of Patent: September 1, 1987Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Gunter Prescher, Klaus Kohler
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Patent number: 4638091Abstract: 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: GrantFiled: February 11, 1985Date of Patent: January 20, 1987Assignee: Imperial Chemical Industries PLCInventor: Roy D. Bowden
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Patent number: 4613702Abstract: 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: GrantFiled: May 15, 1985Date of Patent: September 23, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Philippe Leconte
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Patent number: 4605749Abstract: 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: GrantFiled: June 20, 1985Date of Patent: August 12, 1986Assignee: State of Israel, Prime Minister's Office, Atomic Energy CommissionInventors: Ouri Buchman, Ilan Pri-Bar
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Patent number: 4602105Abstract: 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: GrantFiled: March 26, 1984Date of Patent: July 22, 1986Assignee: Shell Oil CompanyInventor: Eit Drent