Carbon Monoxide Reactant (e.g., Carbonylation, Etc.) Patents (Class 568/428)
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Patent number: 12145903Abstract: An object of the present invention is to provide a method for producing 2,4-dialkylbenzaldehyde with excellent conversion rate and yield, and excellent regioselectivity for formylation, by allowing carbon monoxide to react on a starting material containing a specific m-dialkylbenzene in the presence of hydrogen fluoride and boron trifluoride. The method for producing 2,4-dialkylbenzaldehyde according to the present invention comprises a step of allowing carbon monoxide to react on a starting material containing m-dialkylbenzene represented by formula (1) in the presence of hydrogen fluoride and boron trifluoride for formylation at least at a position (a), wherein the starting material is a dialkylbenzene containing more than 90 mol % of m-dialkylbenzene represented by formula (1), and the number of moles of boron trifluoride relative to 1 mole of m-dialkylbenzene represented by formula (1) is 0.7 mol or more and 3.Type: GrantFiled: October 16, 2020Date of Patent: November 19, 2024Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Toru Shishimi, Tatsuya Utamura, Yutaka Matsuura, Shinichi Nagao
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Patent number: 10737993Abstract: The present invention provides a method for producing indancarbaldehyde, including a step of reacting indan with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a reaction liquid including indancarbaldehyde, wherein the indan includes an amine, and a content of the amine is less than 1000 ppm by mass.Type: GrantFiled: March 9, 2018Date of Patent: August 11, 2020Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventor: Tatsuya Utamura
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Patent number: 9567278Abstract: The present invention is a process for preparing a 4-alkylbenzaldehyde (para-alkylbenzaldehyde). An alkylbenzene, solvated in a solvent comprising at least one aliphatic solvent having in the range of 3 to 15 carbons, is reacted with carbon monoxide, in the presence of an aluminum halide and a hydrogen halide acid. Disproportionation is reduced and proportion of para-alkyl-benzaldehyde is increased with respect to other methods.Type: GrantFiled: March 13, 2014Date of Patent: February 14, 2017Assignee: ALBEMARLE CORPORATIONInventor: Tse-Chong Wu
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Publication number: 20150111991Abstract: There are provided a novel aromatic aldehyde compound capable of providing an epoxy resin coating film and an epoxy resin cured material satisfying all of the excellent surface property (smoothness, gloss), drying property, water resistance, transparency and adhesion, and an epoxy resin curing agent and an epoxy resin composition containing the aromatic aldehyde compound. The aromatic aldehyde has a branched alkyl group having 10 to 14 carbon atoms.Type: ApplicationFiled: May 17, 2013Publication date: April 23, 2015Applicant: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuharu Kitamura, Yutaka Matsuura, Hisayuki Kuwahara, Tomotaka Wada, Yuiga Asai
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Patent number: 8969627Abstract: A method for producing a 4,4?-diformyldiphenylalkane represented by the following formula (2), containing formylating a diphenylalkane represented by the following formula (1) with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride, in which the reaction temperature of the formylation is from ?50 to 5° C., from 5 to 30 mol of hydrogen fluoride is used per 1 mol of the diphenylalkane, and from 1.5 to 5 mol of boron trifluoride is used per 1 mol of the diphenylalkane: wherein R represents an alkanediyl group having from 1 to 6 carbon atoms, wherein R represents an alkanediyl group having from 1 to 6 carbon atoms.Type: GrantFiled: March 29, 2012Date of Patent: March 3, 2015Assignee: Mitsubishi Gas Chemical Company, IncInventor: Mitsuharu Kitamura
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Publication number: 20110180968Abstract: A method for making a carbon nanotube metal composite includes the following steps. A number of carbon nanotubes is dispersed in a solvent to obtain a suspension. Metal powder is added into the suspension, and then the suspension agitated. The suspension containing the metal powder is allowed to stand for a while. The solvent is reduced to obtain a mixture of the number of carbon nanotubes and the metal powder.Type: ApplicationFiled: October 15, 2010Publication date: July 28, 2011Applicants: TSINGHUA UNIVERSITY, HON HAI PRECISION INDUSTRY CO., LTD.Inventors: CHUN-HUA HU, CHANG-HONG LIU, SHOU-SHAN FAN
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Patent number: 7902405Abstract: 2,6-Dimethyl-1-naphthaldehyde having a ratio of the amount of 3,7-dimethyl-1-naphthaldehyde to the total amount of 2,6-dimethyl-1-naphthaldehyde and 3,7-dimethyl-1-naphthaldehyde of 30 mol % or less is particularly useful as optical functional materials, etc. The present invention provides a process for producing such 2,6-dimethyl-1-naphthaldehyde in an industrially advantageous manner. Specifically, in the process for producing 2,6-dimethyl-1-naphthaldehyde through formylation of 2,6-dimethylnaphthalene with carbon monoxide, formylation is performed in the presence of hydrogen fluoride in an amount of 5 to 100 times by mole and boron trifluoride in an amount of 0.5 to 3.5 times by mole, with respect to 2,6-dimethylnaphthalene, and at a reaction temperature of 35 to 70° C.Type: GrantFiled: October 19, 2007Date of Patent: March 8, 2011Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Mitsuharu Kitamura
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Patent number: 7777081Abstract: A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.Type: GrantFiled: May 8, 2007Date of Patent: August 17, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuharu Kitamura, Junya Nishiuchi, Norio Fushimi
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Patent number: 7740812Abstract: The present invention relates to a method and an apparatus for continuously separating aromatic dialdehyde from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene. The method for continuously separating aromatic dialdehyde includes the steps of congealing aromatic dialdehyde by cooling the gas-phase reaction mixture including the aromatic dialdehyde, which is obtained by gas-phase oxidation of dimethylbenzene, to 5-70° C. and separating the congealed aromatic dialdehyde from the remaining reaction mixture. Using the method and apparatus in accordance with the present invention, aromatic dialdehyde can be effectively and selectively separated from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene in high yield.Type: GrantFiled: June 2, 2008Date of Patent: June 22, 2010Assignee: LG Chem, Ltd.Inventors: Jong-Hyun Chae, Won-Ho Lee, Dong-Il Lee, Hyun-Kyung Yoon
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Publication number: 20100004488Abstract: 2,6-Dimethyl-1-naphthaldehyde having a ratio of the amount of 3,7-dimethyl-1-naphthaldehyde to the total amount of 2,6-dimethyl-1-naphthaldehyde and 3,7-dimethyl-1-naphthaldehyde of 30 mol % or less is particularly useful as optical functional materials, etc. The present invention provides a process for producing such 2,6-dimethyl-1-naphthaldehyde in an industrially advantageous manner. Specifically, in the process for producing 2,6-dimethyl-1-naphthaldehyde through formylation of 2,6-dimethylnaphthalene with carbon monoxide, formylation is performed in the presence of hydrogen fluoride in an amount of 5 to 100 times by mole and boron trifluoride in an amount of 0.5 to 3.5 times by mole, with respect to 2,6-dimethylnaphthalene, and at a reaction temperature of 35 to 70° C.Type: ApplicationFiled: October 19, 2007Publication date: January 7, 2010Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventor: Mitsuharu Kitamura
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Publication number: 20090118547Abstract: A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.Type: ApplicationFiled: May 8, 2007Publication date: May 7, 2009Inventors: Mitsuharu Kitamura, Junya Nishiuchi, Norio Fushimi
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Patent number: 7241925Abstract: In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.Type: GrantFiled: December 15, 2004Date of Patent: July 10, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Junya Nishiuchi, Mitsuharu Kitamura
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Patent number: 7154008Abstract: In the production of an alkylbenzaldehyde by a method comprising a step of preparing a solution of complex of a starting alkylbenzene and a hydrogen fluoride-boron trifluoride catalyst and a step of formylation by bringing the solution of complex into contact with carbon monoxide, an alkylbenzene having at least one primary alkyl group having two or more carbon atoms on its benzene ring is used as the starting alkylbenzene. The preparation of the solution of complex is carried out in the presence of an aliphatic or alicyclic saturated hydrocarbon having 6 to 10 carbon atoms which contains at least one tertiary carbon atom but contains no quaternary carbon atom. By the combined use of the specific alkylbenzene and the aliphatic or alicyclic saturated hydrocarbon, the disproportionation of the alkylbenzene is prevented and the alkylbenzaldehyde is produced at high yields.Type: GrantFiled: October 14, 2004Date of Patent: December 26, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Yoshihiro Shiokawa, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
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Patent number: 6984668Abstract: A liquid-phase chemical reaction medium comprises one or more reactants, optionally in the presence of a reaction product(s) and one or more solvents, diluents or other form of liquid carrier, a catalyst system comprising at least a metal or metal compound and optionally further compounds such as ligands or complexing agents; characterized in that the reaction medium further comprises a polymeric dispersant dissolved in said liquid carrier, said polymeric dispersant being capable of stabilizing a colloidal suspension of particles of said metal or metal compound within the liquid carrier. The presence of the polymeric dispersant enables metal formed by catalyst deactivation to be more easily recovered and recycled. Preferably, the polymeric dispersant has sufficiently acidic or basic functionality to stabilize the colloidal suspension of said metal or metal compound.Type: GrantFiled: August 2, 2000Date of Patent: January 10, 2006Assignee: Lucite International UK LimitedInventors: Graham Ronald Eastham, Raymond Anthony Hadden, David William Johnson
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Patent number: 6906207Abstract: Plastic additives which are useful as nucleating agents and which are especially useful for improving the optical properties of polymeric materials are provided. More particularly, this invention relates to certain alkyl (or alkoxy) substituted fluoro-benzylidene sorbitol acetals and polymer compositions thereof which may be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive fluorinated and alkylated benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspirant gel sticks.Type: GrantFiled: January 7, 2003Date of Patent: June 14, 2005Assignee: Milliken & CompanyInventors: John D. Anderson, Nathan A. Mehl
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Patent number: 6881866Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.Type: GrantFiled: July 9, 2003Date of Patent: April 19, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kinji Kato, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
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Patent number: 6806391Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system. The catalyst system includes (a) a source of Pt group metal cations, (b) a certain bidentate diphosphine composition.Type: GrantFiled: July 31, 2002Date of Patent: October 19, 2004Assignee: Shell Oil CompanyInventor: Eit Drent
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Publication number: 20040147787Abstract: The use of iodine as a primary oxidant for TEMPO provides a novel and selective method for oxidizing alcohols to their corresponding carbonyl compounds.Type: ApplicationFiled: January 5, 2004Publication date: July 29, 2004Inventor: Ross A Miller
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Publication number: 20040092776Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.Type: ApplicationFiled: July 9, 2003Publication date: May 13, 2004Inventors: Kinji Kato, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
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Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
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Patent number: 6673856Abstract: The present invention relates to improved alditol acetal compositions, in particular 1,3-2,4-di(benzylidene) sorbitol (DBS) or one of its alkylated derivatives. The improvement in these compositions is expressed in particular in terms of flow behavior and/or thermal stability. It is obtained by combining the alditol acetal with an additive selected from tocopherols, polyols and certain of their respective derivatives. These additives may act as binding or densifying agents and/or stabilizing agents or odor maskers. The alditol acetal and additive are advantageously combined by cold mixing, followed by granulation or compaction, also cold. The compositions of the invention, for example based on DBS or the methylated derivatives of DBS, are in the form of densified or compacted powders, granules, pellets, pastilles or extrudates. They are used in particular for preparing plastic or jellified materials or additives for these types of materials.Type: GrantFiled: September 22, 1999Date of Patent: January 6, 2004Assignee: Roquette FreresInventor: Léon Mentink
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Patent number: 6462242Abstract: Benzyl alcohols, particularly those which bear fluorine substituents or fluoroalkyl substituents on the benzyl ring, can be obtained by formylation of corresponding aryl bromides to form benzaldehydes and reduction of the latter using further formate, wherein the benzaldehydes formed do not have to be isolated.Type: GrantFiled: June 5, 2000Date of Patent: October 8, 2002Assignee: Bayer AktiengesellschaftInventors: Torsten Neugebauer, Albrecht Marhold
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Patent number: 6455739Abstract: 4-Fluorobenzaldehyde is produced by a commercially feasible process. The process comprises heating a mixture of fluorobenzene and a strong Lewis acid with dissolved hydrogen halide in an atmosphere of carbon monoxide at about 45 to about 100° C. and at a total pressure of about 150 psig up to the maximum pressure rating of the reactor. Formed is a reaction mass containing a Lewis acid complex of 4-fluorobenzaldehyde and at least a halobis(fluorophenyl)methane by-product. The complex is broken by quenching the reaction mass with a Lewis acid-solvating liquid to liberate 4-fluorobenzaldehyde. By-product halobis(fluorophenyl)methane is converted to di(fluorophenyl)methanol to avoid potential corrosion problems and formation of light sensitive color bodies in the recovered 4-fluorobenzaldehyde.Type: GrantFiled: September 7, 2001Date of Patent: September 24, 2002Assignee: Albemarle CorporationInventors: Steven G. Karseboom, Michael J. Turpie, Phillip R. Devrou, John F. Balhoff
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Patent number: 6429340Abstract: It is an object of the present invention to provide a production method of 2,4,5-trialkylbenzaldehyde from 1,2,4-tribenzaldehyde at low cost and safely. The present invention provides a production method of a 2,4,5-trialkylbenzaldehyde which comprises carbonylating a 1,2,4-trialkylbenzene with carbon monoxide in the presence of a catalyst, said catalyst comprising trifluoromethanesulfonic acid.Type: GrantFiled: September 27, 2001Date of Patent: August 6, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Bo-Qing Xu, Yasuo Ohnoki, Tsukasa Takahashi
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Publication number: 20020068841Abstract: A composition containing isomeric mixtures of arylaldehydes prepared from a mixed alkyl aromatic feedstock. A composition containing isomeric mixtures of dimethylbenzaldehydes prepared from a mixed xylene feedstock using a Gatterman-Koch type reaction. A composition of isomeric mixtures of tolualdehydes prepared from a toluene feedstock using a Gatterman-Koch type reaction.Type: ApplicationFiled: August 20, 2001Publication date: June 6, 2002Inventor: Ramzi Yanni Saleh
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Publication number: 20020062047Abstract: It is an object of the present invention to provide a production method of 2,4,5-trialkylbenzaldehyde from 1,2,4-tribenzaldehyde at low cost and safely.Type: ApplicationFiled: September 27, 2001Publication date: May 23, 2002Applicant: NIPPON SHOKUBAI CO., LTD.Inventors: Bo-Qing Xu, Yasuo Ohnoki, Tsukasa Takahashi
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Patent number: 6320083Abstract: A process for the carbonylation of alkyl aromatic compounds uses acidic ionic liquids. In one embodiment, the ionic liquid is intrinsically acidic, having an anion mole fraction of greater than 0.5. The ionic liquids include those comprised of a quaternary nitrogen-containing cation and a metal halide anion. The process provides for good conversion and selectivity in the production of the corresponding aromatic aldehyde compound.Type: GrantFiled: September 10, 1999Date of Patent: November 20, 2001Assignee: ExxonMobil Chemical Co.Inventor: Ramzi Yanni Saleh
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Patent number: 6303827Abstract: Alkyl aromatic compounds are converted to alkyl aromatic aldehydes by a carbonylation reaction. The carbonylation catalyst can be a high boiling point carbonylation catalyst which allows for the separation of the aldehyde product by selective volatilization. Alternatively, the carbonylation catalyst can be selected from perfluoroalkyl sulfonic acids having 2 to 18 carbon atoms, perfluoroether sulfonic acids having 2 to 18 carbon atoms, BF3(ROH)x wherein R represents CH3 or H and X is a number within the range of from 0.2 to 2, GaBr3, GaCl3, TaF5, NbF5, and NbBr5, with the proviso that when the catalyst is TaF5, NbF5, or NbBr5, then the reaction takes place in the absence of added HF. Preferably, all of the carbonylation reactions take place in the absence of added HF. The alkyl aromatic aldehydes can be oxidized to form an aromatic acid.Type: GrantFiled: September 10, 1999Date of Patent: October 16, 2001Assignee: ExxonMobil Chemicals Patents Inc.Inventors: Ramzi Yanni Saleh, Christopher L. Becker, Robert C. Michaelson, Richard H. Schlosberg
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Patent number: 6300525Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields.Type: GrantFiled: September 1, 2000Date of Patent: October 9, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter A. Scrivens
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Patent number: 6297405Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields. The particular novel multi-substituted benzaldehydes are also encompassed within this invention.Type: GrantFiled: September 1, 2000Date of Patent: October 2, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter Scrivens
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Patent number: 6087537Abstract: This invention relates to a process for preparing specific substituted benzaldehydes through the reaction of substituted benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, at a low temperature, and in the presence of at most a catalytic amount of an acid (preferably aqueous HCl). The resultant substituted benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, nucleating agents, polymer additives, and the like. The inventive method provides a very cost-effective and safe procedure for producing such substituted benzaldehydes at very high yields.Type: GrantFiled: March 16, 1999Date of Patent: July 11, 2000Assignee: Milliken & CompanyInventors: Walter A. Scrivens, John G. Lever
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Patent number: 6080892Abstract: This invention relates to a process for preparing specific substituted benzaldehydes through the reaction of substituted benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, at a low temperature, and in the presence of at most a catalytic amount of acid (preferably aqueous HCl) and a solvent. The resultant substituted benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, nucleating agents, polymer additives, and the like. The inventive method provides a very cost-effective and safe procedure for producing such substituted benzaldehydes at very high yields.Type: GrantFiled: March 16, 1999Date of Patent: June 27, 2000Assignee: Milliken & CompanyInventors: Walter A. Scrivens, John G. Lever
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Patent number: 5910613Abstract: A process for producing aromatic aldehydes by carbonylation of an arene in the presence of triflic acid catalyst is described by reacting an arene, such as toluene, with carbon monoxide in the presence of triflic acid (as a catalyst), for a reaction time less than 90 minutes, at a carbon monoxide partial pressure of about 700-2000 psig, at a temperature of from about 0-50.degree. C. to produce an aromatic aldehyde such as tolualdehyde and by-products, the by-products being less than 5% by weight based on the total reaction products.The mole ratio of triflic acid to arene is between about 0.8 to 20, with the reaction having an isomer selectivity greater than 95% by weight for the para isomer aldehyde, and showing substantially no meta isomer.Type: GrantFiled: May 6, 1998Date of Patent: June 8, 1999Assignee: HNA Holdings, Inc.Inventors: David Anthony Schiraldi, Jeffrey Charles Kenvin
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Patent number: 5679867Abstract: The present invention is directed to a process for the carbonylation of an arylene to an arylaldehyde (e.g., toluene to tolualdehyde) in the presence of a solid acid catalyst. The process for making tolualdehyde comprises carbonylating toluene in the presence of either carbon monoxide or a source of carbon monoxide and in contact with a solid acid catalyst. The reaction is carried out at a temperature ranging from -40.degree. to 200.degree. C., and at a pressure ranging from 20-4000 psig.Type: GrantFiled: March 1, 1996Date of Patent: October 21, 1997Assignee: Hoechst Celanese CorporationInventors: David Alan Bruce, Mario L. Occelli, David Anthony Schiraldi, Dhiraj Sudesh Sood, Cindy Elyse Sullivan, Mark Gilmore White
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Patent number: 5436374Abstract: A process for producing a 4-formyl-4'-methylbiphenyl from a biphenyl which comprises conducting the carbonylation of the biphenyl with carbon monoxide in the presence of a HF-BF.sub.3 catalyst in a carbonylation reactor to obtain the resulting reaction product solution containing a 4-formylbiphenyl, separating the 4-formylbiphenyl from the reaction product solution, hydrogenating the separated 4-formylbiphenyl to obtain a 4-methylbiphenyl, recycling the 4-methylbiphenyl to the carbonylation reactor, and then conducting both the carbonylation of the biphenyl with carbon monoxide to obtain a formylbiphenyl and the carbonylation of the 4-methylbiphenyl with carbon monoxide to obtain a 4-formyl-4'-methylbiphenyl simultaneously in the presence of the HF-BF.sub.3 catalyst in the carbonylation reactor.Type: GrantFiled: July 28, 1994Date of Patent: July 25, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Komatsu, Susumu Fujiyama, Koichi Kida, Mitsuharu Kitamura
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Patent number: 5395978Abstract: Process for preparing hydroxybenzaldehydes of the formula (1) ##STR1## in which R.sup.1 -R.sup.4 are hydrogen, fluorine, chlorine, bromine, alkyl, alkoxy, phenyl, naphthyl, phenylalkyl, naphthylalkyl, phenoxy or saturated or unsaturated cyclopentane or cyclohexane radicals, and R.sup.1 -R.sup.4 may with the hydroxybenzene ring carbon atoms on which they are located form 1 or 2 saturated or unsaturated isocyclic or heterocyclic rings, by admixing 1 mol of a phenol of the formula (2) ##STR2## in which R.sup.1 -R.sup.4 have the stated meanings, in a pressure vessel with from 5 to 100 mol of hydrogen fluoride and from 0.5+x to 1.5+x mol of boron trifluoride, where x is the number of oxygen atoms contained in the starting compound (formula (2)), setting the mixture to from -10.sup..degree. to 100.degree. C. and then passing carbon monoxide into this mixture until a pressure of from 10 to 150 bar is reached and allowing the mixture to react at the desired pressure reached.Type: GrantFiled: November 18, 1993Date of Patent: March 7, 1995Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Robert Neunteufel, Heinz Strutz
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Patent number: 5260477Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step (I) of dehydrogenating p-isobutylethylbenzene in a gaseous phase in the presence of a dehydrogenating metal catalyst to form p-isobutylstyrene and at least one unsaturated hydrocarbon compound selected from a group A defined in Claim 1; a step (II) of reacting p-isobutylstyrene obtained in the step (I) with carbon monoxide and hydrogen or with carbon monoxide and water or a lower alcohol in the presence of a transition metal complex carbonylating catalyst to form .alpha.-(4-isobutylphenyl)propionic acid or its precursor; and a step (III) of hydrogenating at least one unsaturated hydrocarbon compound selected from the group A obtained in the dehydrogenation step (I) to form p-isobutylethylbenzene, and recycling the thus formed p-isobutylethylbenzene through the step (I) as the raw material of the step (I).Type: GrantFiled: December 18, 1989Date of Patent: November 9, 1993Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
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Patent number: 5166419Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises the following steps (I), (II) and (III):step (I): subjecting isobutylbenzene and a polyalkylbenzene to disproportionation reaction in order to form p-isobutylethylbenzenestep (II): dehydrogenating p-isobutylethylbenzene obtained in the step (I) to form p-isobutylstyrene, andstep (III): the following step (IIIa) or (IIIb):step (IIIa): reacting p-isobutylstyrene obtained in the step (II) with carbon monoxide and hydrogen to prepare .alpha.-(4-isobutylphenyl)propionaldehyde, orstep (IIIb): reacting p-isobutylstyrene obtained in the preceding step (II) with carbon monoxide and water or a lower alcohol to prepare .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester.Type: GrantFiled: August 22, 1990Date of Patent: November 24, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Yuuichi Tokumoto, Isoo Shimizu, Satoru Inoue
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Patent number: 5126492Abstract: Aromatic aldehydes are produced by catalytic formylation of aryl chlorides in the presence of a palladium chelating phosphine ligand complex of the formula (R.sub.2 R.sub.2 P(CH.sub.2).sub.n PR.sub.3 R.sub.4).sub.2 Pd, wherein n is 3 or 4 and R.sub.1 to r.sub.4 are H, alkyl, cycloalkyl or aryl, at least one of them being alkyl or cycloalkyl.Type: GrantFiled: July 2, 1990Date of Patent: June 30, 1992Assignee: Yeda Research and Development Co. Ltd.Inventors: David Milstein, Yehoshua Ben-David
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Patent number: 5103053Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with a dialkylacetal.Type: GrantFiled: March 18, 1991Date of Patent: April 7, 1992Assignee: Ethyl CorporationInventors: Joe D. Sauer, Kim R. Smith, James E. Borland
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Patent number: 4982007Abstract: A process for selectively hydroformylating a diolefin, which comprises reacting a (1-arylethyl)vinylbenzene with carbon monoxide and hydrogen under the conditions of 40.degree. to 200.degree. C. in reaction temperature and 5 kg/cm.sup.2 or above in reaction pressure in the presence of a transition metal carbonylation catalyst to thereby selectively hydroformylating only the vinyl group and produce .alpha.-((1-arylethenyl)phenyl)propionaldehyde. The starting material to be hydroformylated may be a mixture of the (1-arylethenyl)vinylbenzene with a 1,1-di(substituted aryl)ethylene not substituted by a vinyl group.Type: GrantFiled: March 2, 1990Date of Patent: January 1, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4978801Abstract: Aromatic aldehydes are more efficiently produced by reacting carbon monoxide/hydrogen admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous based and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the CO/H.sub.2 ratio is less than 1.Type: GrantFiled: April 28, 1987Date of Patent: December 18, 1990Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4973741Abstract: A process for producing a .beta.-hydroxyester product or a .beta.-hydroxyaldehyde product from ethylene oxide, carbon monoxide, and, optionally, hydrogen, is disclosed. This process uses, as a catalyst, a catalyst comprising rhodium, ruthenium, and a Group Va promoter.Type: GrantFiled: June 29, 1989Date of Patent: November 27, 1990Assignee: Eastman Kodak CompanyInventor: William A. Beavers
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Patent number: 4942240Abstract: Aromatic aldehydes are more rapidly produced by reacting hydrogen/carbon monoxide admixture with an aromatic halide in the presence of a noble metal-based catalyst, a tertiary nitrogenous base and, if necessary, a noble metal complexing agent, e.g., a phosphine or phosphite, wherein the concentration of said tertiary nitrogenous base, expressed in moles per liter of reaction mixture, is maintained at a value of at least two moles/liter over the course of the reaction.Type: GrantFiled: April 28, 1987Date of Patent: July 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Norbert Bluthe, Robert Perron
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Patent number: 4933497Abstract: Hydroxybenzaldehydes, e.g., vanillin, are prepared by hydrocarbonylating a corresponding halophenol, e.g., 4-bromo-2-methoxyphenol, in the presence of (a) a tertiary amine, (b) a catalyst based on a noble metal, and (c) a phosphine.Type: GrantFiled: July 13, 1989Date of Patent: June 12, 1990Assignee: Rhone-Poulenc ChimieInventors: Patricia Fompeyrine, Francois Metz
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Patent number: 4788325Abstract: A process for making a carbonyl-containing compound is disclosed. In this process an allylic ether is contacted with water in the presence of a cobalt-containing material under an atmosphere of carbon monoxide gas.Type: GrantFiled: May 29, 1987Date of Patent: November 29, 1988Assignee: National Distillers and Chemical CorporationInventor: Biau-Hung Chang
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Patent number: 4720594Abstract: Process for the preparation of aromatic aldehydes by hydrocarbonylation of chloro- or bromoaromatic compounds. In the presence of an acceptor for an oxygen-free acid, a palladium/phosphine complex and, if appropriate, a phosphine, a mixture of carbon monoxide and hydrogen is reacted with chloro- or bromoarenetricarbonylchromiums.Type: GrantFiled: June 13, 1986Date of Patent: January 19, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Jean-Marie Basset, Robert Mutin
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Patent number: 4691048Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.Type: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4622429Abstract: Substituted benzaldehydes are prepared by reaction of the substituted benzenes from which they are derived with carbon monoxide and hydrogen chloride in the presence of metal halides, the process being performed in the presence of 0.5 to 10 mols of hydrogen chloride per mol of metal halide at a partial pressure of carbon monoxide from 1 to 100 bars and a temperature from -20.degree. C. to +100.degree. C. and, if desired, in the presence of an inert diluent. The substituted benzaldehyde which contains, as a substituent, alkyl with at least 2 carbon atoms, cycloalkyl or optionally substituted benzyl, is prepared by reacting the appropriately substituted benzene with the additional presence of a benzene which does not contain the substituents mentioned, but which is identical in respect of further substituents which are optionally present with the benzene from which it is derived.Type: GrantFiled: August 13, 1984Date of Patent: November 11, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters, Otto Neuner
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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