Halogen Containing Reactant Patents (Class 568/437)
-
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
-
Patent number: 5041683Abstract: Process for the preparation of nuclear-fluorinated trifluoromethylbenzaldehydes from nuclear-chlorinated trifluoromethylbenzaldehydes, and new nuclear-fluorinated trifluoromethylbenzaldehydes.Type: GrantFiled: April 25, 1990Date of Patent: August 20, 1991Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Rudolf Braden
-
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
-
Patent number: 4978802Abstract: Aromatic aldehydes are produced by oxidation with oxygen of a para-cresol derivative in a solvent, in the presence of a base and a catalytic amount of a cobalt compound. The catalyst is a chelated complex of cobalt with a rigid structure that is slightly oxidizable selected from the group consisting of bis-(4-methylpyridine isoindolinato)cobalt(II) acetate, phthalocyaninatocobalt(II), and sulfophthalocyaninanatocobalt(II). The process is particularly suited to the production of p-hydroxy benzaldehydes.Type: GrantFiled: December 20, 1988Date of Patent: December 18, 1990Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges ClaudeInventors: Philippe Campo, Panayotis Cocolios, Paul Dognin, Henry Ledon
-
Patent number: 4845304Abstract: A process for producing a fluorobenzaldehyde of the formula: ##STR1## wherein X is a chlorine atom, a bromine atom or an iodine atom, n is an integer of from 1 to 5, and m is an integer of from 1 to 5, provided n.gtoreq.m, which comprises reacting a halogenated benzaldehyde of the formula: ##STR2## wherein X and n are as defined above, with a metal fluoride in the presence of a catalyst, wherein at least one member selected from the group consisting of quaternary phosphonium salts and quaternary ammonium salts is used as the catalyst.Type: GrantFiled: May 4, 1988Date of Patent: July 4, 1989Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yasuo Yoshida, Yoshikazu Kimura
-
Patent number: 4824956Abstract: Aliphatic, cycloaliphatic, aromatic or araliphatic halogen compounds are reductively dehalogenated by reaction with hydrocarbons in the presence of carbon in the liquid phase at from 100.degree. to 450.degree. C. with formation of hydrogen halides.Type: GrantFiled: March 10, 1986Date of Patent: April 25, 1989Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Herbert Krug, Heinz Nohe
-
Patent number: 4782187Abstract: The preparation of 4,4'-stilbenedialdehydes from the corresponding acid chlorides in the presence of a noble metal catalyst.Type: GrantFiled: December 10, 1986Date of Patent: November 1, 1988Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Heinz Steiner
-
Patent number: 4733012Abstract: A process for the preparation of 4-chloromethylbenzaldehyde, 4-bromomethylbenzaldehyde and 4-iodomethylbenzaldehyde is disclosed. The desired 4-halomethylbenzaldehyde is prepared by reacting 4-hydroxymethylbenzaldehyde with the appropriate gaseous hydrogen halide and/or with the appropriate aqueous hydrohalic acid. The 4-halomethylbenzaldehydes produced by the disclosed process are useful as raw materials for pharmaceuticals and serve as starting materials for the preparation of conductive organic compounds.Type: GrantFiled: March 17, 1987Date of Patent: March 22, 1988Assignee: Wacker-Chemie GmbHInventors: Hermann Braunling, Dieter Kippe
-
Patent number: 4670443Abstract: Benzo(f)isoquinoline compounds, particularly, penta- and tetrahydrobenzo(f)isoquinoline dicarboxylic acid compounds, their preparation and their use as calcium entry blockers are disclosed.Type: GrantFiled: July 2, 1985Date of Patent: June 2, 1987Assignee: Merck & Co., Inc.Inventors: George D. Hartman, Brian T. Phillips
-
Patent number: 4645852Abstract: In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.Type: GrantFiled: September 16, 1985Date of Patent: February 24, 1987Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Richard C. Krauss
-
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
-
Patent number: 4590281Abstract: Provided is a process for preparing an aldehyde or aldehydes represented by the following formula (III), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted with an unsaturated alcohol represented by the following formula (II) in a solvent containing a base in the presence of a transition metal catalyst at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ] X.sup..crclbar. (I)CHR.sub.1 .dbd.CR.sub.2 --CH.sub.2 OH (II)Ar.sub.3 --CHR.sub.1 --CHR.sub.2 --CHO (III)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups, X.sup..crclbar. is a counter ion which is inert to the above reaction, Ar.sub.3 is the same aryl group as Ar.sub.1 or Ar.sub.2, and R.sub.1 and R.sub.2 are each hydrogen atom or an alkyl group of C.sub.1 to C.sub.12.Type: GrantFiled: March 7, 1984Date of Patent: May 20, 1986Assignee: Nippon Petrochemicals CompanyInventors: Yasuo Yamazaki, Takehiko Suzuki
-
Patent number: 4584410Abstract: In a Reimer-Tiemann reaction for the preparation of a mixture of two hydroxybenzaldehydes (i.e., salicylaldehyde and p-hydroxybenzaldehyde) by reacting phenol with chloroform and an aqueous alkali solution in a heterogeneous system, the two hydroxybenzaldehydes can be prepared in a controlled formation ratio, yield and reaction rate depending upon the conditions used when the reaction is carried out in the presence of a phase transfer catalyst selected from the group consisting of a cationic type phase transfer catalyst, an amphoteric type phase transfer catalyst and an anionic type phase transfer catalyst.Type: GrantFiled: November 13, 1984Date of Patent: April 22, 1986Assignee: Sumitomo Chemical Co., Ltd.Inventors: Kazuhiko Hamada, Gohfu Suzukamo, Fujio Masuko, Makoto Nakamura
-
Patent number: 4571438Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: March 21, 1985Date of Patent: February 18, 1986Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Dennis S. Banasiak
-
Patent number: 4540826Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: August 12, 1983Date of Patent: September 10, 1985Assignee: Phillips Petroleum CompanyInventors: Dennis S. Banasiak, Jim D. Byers
-
Patent number: 4533754Abstract: A process for the preparation of aldehydes of the formula ##STR1## wherein R is a substituted or unsubstituted aryl group containing one or more benzenoid rings which comprises reacting an aryl acid halide with an organozinc compound in solvent in the presence of a palladium metal complex catalyst.Type: GrantFiled: July 23, 1984Date of Patent: August 6, 1985Assignee: Atlantic Richfield CompanyInventor: Roger A. Grey
-
Patent number: 4476056Abstract: Aromatic retinoids bearing a trifluoromethoxy substituent on the aromatic nucleus which are useful as antitumor agents and in the treatment of dermatological disorders as well as a method for their manufacture are disclosed.Type: GrantFiled: November 5, 1982Date of Patent: October 9, 1984Assignee: Hoffmann-La Roche Inc.Inventor: Beverly A. Pawson
-
Patent number: 4474993Abstract: The disclosure relates to a continuous method and an apparatus for the hydrolysis of .alpha.-chlorinated toluene compounds, preferably benzyl chloride. The hydrolysis, which takes place in a hydrolysis zone, is characterized by being conducted in countercurrent between the aqueous phase containing the hydrolyzing agent and the organic phase containing the .alpha.-chlorinated toluene compound and an inert organic solvent, such as toluene. After the hydrolysis, the organic phase is washed with water in a washing zone, while the aqueous phase is extracted with inert solvent in an extraction zone. The resulting product of hydrolysis, preferably benzyl alcohol, is thereafter separated from the organic phase by distillation, suitably in two stages, by means of two distillation columns connected in series.Type: GrantFiled: April 28, 1982Date of Patent: October 2, 1984Inventors: Goran L. F. Hag, Risto K. Rantala
-
Patent number: 4469894Abstract: In a Reimer-Tiemann reaction for the preparation of a mixture of salicylaldehyde and p-hydroxybenzaldehyde, improved yield of the product and high selectivity of salicylaldehyde can be obtained when an alkali metal salt of a phenol is reacted with a reaction mixture comprised of chloroform and a slurry of an alkali metal hydroxide (preferably, in a fine powder state thereof) and an inert organic solvent and optionally, a catalytic amount of a surfactant.Type: GrantFiled: June 16, 1982Date of Patent: September 4, 1984Assignee: Sumitomo Chemical Co., Ltd.Inventors: Kazuhiko Hamada, Gohfu Suzukamo
-
Patent number: 4450298Abstract: Vapor phase contact reaction between water and benzal chloride or a substitute expressed by C.sub.6 H.sub.(5-n) X.sub.n CHCl.sub.2, wherein X representing a halogen atom or a trifluoromethyl group and n being 1 or 2, to form benzaldehyde or a substitute expressed by C.sub.6 H.sub.(5-n) X.sub.n CHO can efficiently be achieved by using activated carbon treated with an acid such as sulfuric acid or impregnated with a metal chloride such as ferric chloride and/or a metal sulfate such as cupric sulfate as catalyst. The activated carbon catalyst long retains its high activity even when the starting material has trifluoromethyl group, which is liable to undergo partial decomposition with formation of hydrogen fluoride.Type: GrantFiled: July 20, 1982Date of Patent: May 22, 1984Assignee: Central Glass Company, LimitedInventors: Takeshi Kondow, Koshi Okazaki, Yutaka Katsuhara, Kimiaki Matsuoka
-
Patent number: 4439620Abstract: The invention relates to 2,4-dichloro-r-fluorobenzoyl halide (particularly the chloride) and methods for its production. Also included in the invention are intermediates useful for the production of said 2,4-dichloro-5-fluorobenzoyl halide (particularly the chloride).Type: GrantFiled: July 14, 1982Date of Patent: March 27, 1984Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Klaus Grohe
-
Method for producing aldehydes and ketones using 2,2'-bipyridinium chlorochromate as oxidizing agent
Patent number: 4426534Abstract: 2,2'-bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.Type: GrantFiled: July 26, 1982Date of Patent: January 17, 1984Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr. -
Patent number: 4421675Abstract: A novel catalyst, possessing phase transfer properties contains an alumina or silica substrate bearing at least one poly(oxyethylene) or poly(oxypropylene) residue bonded through an oxygen atom to the substrate.Type: GrantFiled: January 8, 1982Date of Patent: December 20, 1983Assignee: Texaco Inc.Inventor: Robert A. Sawicki
-
Patent number: 4399311Abstract: In a process for producing aromatic aldehydes by reacting chlorinated methylbenzenes with nitric acid, the improvement wherein a lead compound is added to the residue left after separation and recovery of the resulting aromatic aldehydes from the reaction mixture thereby to remove a chlorine ion present in the residue as a precipitate of lead chloride, and the residue left after removal of the lead chloride is recycled to the reaction of the chlorinated methylbenzenes with nitric acid.Type: GrantFiled: July 13, 1981Date of Patent: August 16, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shigeo Yoshinaka, Tsukasa Toki, Misuzu Wakatsuki, Seiji Uchiyama
-
Patent number: 4367348Abstract: Novel meta- and para-trifluoromethyl benzal chlorides and ring-halogenated derivatives are useful chemical intermediates for the preparation of meta- and para-trifluoromethyl benzaldehydes and various other useful end products. The novel compounds can be prepared from readily-available xylene starting materials in a process comprising (a) chlorinating meta- or para-xylene, or a ring -halogenated meta- or para-xylene, to form a trichloromethyl benzal chloride product and (B) reacting the trichloromethyl benzal chloride product with about 3 moles or less of anhydrous hydrogen fluoride in the presence of a halogen exchange catalyst.Type: GrantFiled: October 10, 1980Date of Patent: January 4, 1983Assignee: Occidental Chemical CorporationInventors: R. Simon-Bierenbaum, David Y. Tang
-
Patent number: 4335263Abstract: A process for preparing an aromatic aldehyde represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a lower alkyl group or R.sub.1 and R.sub.2 may jointly form an alkylene group, provided that R.sub.1 and R.sub.2 do not represent a hydrogen atom at the same time.Type: GrantFiled: December 19, 1980Date of Patent: June 15, 1982Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
-
Patent number: 4328374Abstract: A process for the production of aromatic dialdehydes which comprises reacting xylene chloride selected from the group consisting of .alpha.,.alpha.,.alpha.'-trichloroxylene alone, or a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.'-dichloroxylene, a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene and a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene, .alpha.,.alpha.'-dichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene with nitric acid.Type: GrantFiled: July 7, 1980Date of Patent: May 4, 1982Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Shigeo Yoshinaka, Masaharu Doya
-
Patent number: 4324922Abstract: Aromatic hydroxyaldehydes, such as o- and p-hydroxybenzaldehyde, are prepared by the reaction of a phenolic compound, chloroform, and an alkali metal hydroxide at a temperature from about 70.degree. to about 105.degree. C. at elevated pressure according to the Reimer-Tiemann reaction. The process improvement results in decreased reaction time.Type: GrantFiled: June 9, 1980Date of Patent: April 13, 1982Assignee: The Dow Chemical CompanyInventor: William E. Smith
-
Patent number: 4318848Abstract: Chemical reaction products, obtained in an alkaline medium and which require the addition of a dispersing agent, are neutralized by addition of a free surface-active acid to which, after its preparation, basic agents have not been added or have only been added up to a pH value of 3.Type: GrantFiled: January 3, 1978Date of Patent: March 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Heinz Molls, Willy Schiwy, Reinhold Hornle, Reinhard Nebeling
-
Patent number: 4317934Abstract: Process for preparing an aldehyde by hydrolysis of a monohalide and a dihalide, thereby obtaining a mixture of an alcohol and an aldehyde, and further reacting said mixture with manganese dioxide to convert said alcohol to said aldehyde.Type: GrantFiled: August 15, 1980Date of Patent: March 2, 1982Assignee: Ethyl CorporationInventor: Paul D. Seemuth
-
Patent number: 4277421Abstract: p-tert.Butylbenzaldehyde and the derivatives thereof which are halogen-substituted at the nucleus are prepared by bromination of p-tert.butyltoluene and the derivatives thereof which are correspondingly halogen-substituted at the nucleus under side-chain halogenation conditions until the benzal bromide is obtained which is then saponified. Practically no undesired bromination at the nucleus or the tert.butyl group takes place.The products obtained are valuable intermediates for the manufacture of pharmaceutical agents, plant protecting agents and dyestuffs.Type: GrantFiled: November 14, 1979Date of Patent: July 7, 1981Assignee: Hoechst AktiengesellschaftInventors: Franz Landauer, Georg Schaeffer
-
Patent number: 4229379Abstract: An improved process for the preparation of benzaldehyde by hydrolysis of benzal chloride wherein hydrolysis is carried out at an elevated temperature in the presence of an excess of aqueous hydrochloric acid and in the absence of another catalyst.Type: GrantFiled: November 6, 1978Date of Patent: October 21, 1980Assignee: Bayer AktiengesellschaftInventors: Friedrich Bruhne, Karl-August Lipper
-
Patent number: 4225694Abstract: Primary and secondary unsaturated alcohols are converted to their corresponding aldehydes and/or carboxylic acids and ketones respectively with alkali metal (per) halate, preferably sodium periodate, in the presence of ruthenium catalyst. The process is particularly useful in the oxidation of chrysanthemyl alcohol. Any unconverted intermediate aldehyde formed may be converted to the acid by recycling or by a separate oxidation step.Type: GrantFiled: September 6, 1977Date of Patent: September 30, 1980Assignee: Air Products and Chemicals, Inc.Inventors: Augustine I. Dalton, Jr., Henry J. Doran, Robert D. H. Murray
-
Patent number: 4225527Abstract: Novel 9-(halo-substituted phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful in treating dermatological conditions.Type: GrantFiled: December 15, 1977Date of Patent: September 30, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
-
Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
-
Patent number: 4211727Abstract: Carboxylic acid halides are reduced to the corresponding aldehydes using zinc borohydride or cadmium borohydride as the reducing agent.Type: GrantFiled: March 15, 1979Date of Patent: July 8, 1980Assignee: Shell Oil CompanyInventors: Ian D. Entwistle, Robert A. W. Johnstone
-
Patent number: 4206139Abstract: Novel benzaldehydes of the formula: ##STR1## Where n.sup.1 is the integer 1-8 and each OR.sup.1 group is hydroxy or a protective group which can be converted or removed to provide the dihydroxyphenyl moiety.The benzaldehydes are particularly useful as intermediates in the preparation of yellow azomethine dye developers.Type: GrantFiled: September 27, 1978Date of Patent: June 3, 1980Assignee: Polaroid CorporationInventors: Elbert M. Idelson, Charles E. Jandrue