Halogen Containing Reactant Patents (Class 568/437)
  • Patent number: 5059716
    Abstract: Aromatic and aliphatic aldehydes can be prepared from the corresponding aromatic or aliphatic carboxylic acids or the esters, anhydrides or halides thereof at elevated temperature by catalytic gas phase hydrogenation using hydrogen if use is made of a catalyst system composed of oxides of titanium and/or vanadium and of one or more co-metals, the co-metals being selected from the group consisting of chromium, molybdenum, cobalt, nickel, zinc, cadmium and copper.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Winfried Joentgen, Helmut Fiege
  • Patent number: 5041683
    Abstract: Process for the preparation of nuclear-fluorinated trifluoromethylbenzaldehydes from nuclear-chlorinated trifluoromethylbenzaldehydes, and new nuclear-fluorinated trifluoromethylbenzaldehydes.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Rudolf Braden
  • Patent number: 4983776
    Abstract: The invention relates to the synthesis of functional fluoro derivatives and more particularly that of perfluorinated aldehydes of the type R.sub.F -CHO where R.sub.F denotes a linear or branched perfluoroalkyl radical.A perfluoroalkyl iodide R.sub.F I is reacted over the zinc-copper metal couple, in the presence of a radical initiator, with an amide RCONR.sub.1 R.sub.2, R denoting a hydrogen atom or a methyl or ethyl radical, and each of R.sub.1 and R.sub.2 denoting a C.sub.1 -C.sub.4 alkyl radical.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: January 8, 1991
    Assignee: Societe Atochem
    Inventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
  • Patent number: 4978802
    Abstract: 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: Grant
    Filed: December 20, 1988
    Date of Patent: December 18, 1990
    Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
    Inventors: Philippe Campo, Panayotis Cocolios, Paul Dognin, Henry Ledon
  • Patent number: 4845304
    Abstract: 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: Grant
    Filed: May 4, 1988
    Date of Patent: July 4, 1989
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Yoshikazu Kimura
  • Patent number: 4824956
    Abstract: 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: Grant
    Filed: March 10, 1986
    Date of Patent: April 25, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Herbert Krug, Heinz Nohe
  • Patent number: 4782187
    Abstract: The preparation of 4,4'-stilbenedialdehydes from the corresponding acid chlorides in the presence of a noble metal catalyst.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: November 1, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Heinz Steiner
  • Patent number: 4733012
    Abstract: 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: Grant
    Filed: March 17, 1987
    Date of Patent: March 22, 1988
    Assignee: Wacker-Chemie GmbH
    Inventors: Hermann Braunling, Dieter Kippe
  • Patent number: 4670443
    Abstract: 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: Grant
    Filed: July 2, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventors: George D. Hartman, Brian T. Phillips
  • Patent number: 4645852
    Abstract: 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: Grant
    Filed: September 16, 1985
    Date of Patent: February 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Richard C. Krauss
  • Patent number: 4613702
    Abstract: Aldehydes are facilely prepared in high yields by catalytically hydrocarbonylating an organic halide with gaseous admixture of hydrogen and carbon monoxide in the presence of a neutralizing agent for the hydrogen acid produced thereby, said hydrocarbonylation being carried out in an inert, liquid carboxylic acid reaction medium, i.e., a liquid carboxylic acid which is inert under the reaction conditions of temperature and pressure.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: September 23, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Philippe Leconte
  • Patent number: 4590281
    Abstract: 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: Grant
    Filed: March 7, 1984
    Date of Patent: May 20, 1986
    Assignee: Nippon Petrochemicals Company
    Inventors: Yasuo Yamazaki, Takehiko Suzuki
  • Patent number: 4584410
    Abstract: 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: Grant
    Filed: November 13, 1984
    Date of Patent: April 22, 1986
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Kazuhiko Hamada, Gohfu Suzukamo, Fujio Masuko, Makoto Nakamura
  • Patent number: 4571438
    Abstract: 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: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4540826
    Abstract: 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: Grant
    Filed: August 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Jim D. Byers
  • Patent number: 4533754
    Abstract: 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: Grant
    Filed: July 23, 1984
    Date of Patent: August 6, 1985
    Assignee: Atlantic Richfield Company
    Inventor: Roger A. Grey
  • Patent number: 4476056
    Abstract: 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: Grant
    Filed: November 5, 1982
    Date of Patent: October 9, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Beverly A. Pawson
  • Patent number: 4474993
    Abstract: 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: Grant
    Filed: April 28, 1982
    Date of Patent: October 2, 1984
    Inventors: Goran L. F. Hag, Risto K. Rantala
  • Patent number: 4469894
    Abstract: 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: Grant
    Filed: June 16, 1982
    Date of Patent: September 4, 1984
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Kazuhiko Hamada, Gohfu Suzukamo
  • Patent number: 4450298
    Abstract: 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: Grant
    Filed: July 20, 1982
    Date of Patent: May 22, 1984
    Assignee: Central Glass Company, Limited
    Inventors: Takeshi Kondow, Koshi Okazaki, Yutaka Katsuhara, Kimiaki Matsuoka
  • Patent number: 4439620
    Abstract: 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: Grant
    Filed: July 14, 1982
    Date of Patent: March 27, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Klaus Grohe
  • Patent number: 4426534
    Abstract: 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: Grant
    Filed: July 26, 1982
    Date of Patent: January 17, 1984
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4421675
    Abstract: 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: Grant
    Filed: January 8, 1982
    Date of Patent: December 20, 1983
    Assignee: Texaco Inc.
    Inventor: Robert A. Sawicki
  • Patent number: 4399311
    Abstract: 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: Grant
    Filed: July 13, 1981
    Date of Patent: August 16, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shigeo Yoshinaka, Tsukasa Toki, Misuzu Wakatsuki, Seiji Uchiyama
  • Patent number: 4367348
    Abstract: 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: Grant
    Filed: October 10, 1980
    Date of Patent: January 4, 1983
    Assignee: Occidental Chemical Corporation
    Inventors: R. Simon-Bierenbaum, David Y. Tang
  • Patent number: 4335263
    Abstract: 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: Grant
    Filed: December 19, 1980
    Date of Patent: June 15, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Masayoshi Minai
  • Patent number: 4328374
    Abstract: 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: Grant
    Filed: July 7, 1980
    Date of Patent: May 4, 1982
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Shigeo Yoshinaka, Masaharu Doya
  • Patent number: 4324922
    Abstract: 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: Grant
    Filed: June 9, 1980
    Date of Patent: April 13, 1982
    Assignee: The Dow Chemical Company
    Inventor: William E. Smith
  • Patent number: 4318848
    Abstract: 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: Grant
    Filed: January 3, 1978
    Date of Patent: March 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Heinz Molls, Willy Schiwy, Reinhold Hornle, Reinhard Nebeling
  • Patent number: 4317934
    Abstract: 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: Grant
    Filed: August 15, 1980
    Date of Patent: March 2, 1982
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4277421
    Abstract: 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: Grant
    Filed: November 14, 1979
    Date of Patent: July 7, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Franz Landauer, Georg Schaeffer
  • Patent number: 4229379
    Abstract: 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: Grant
    Filed: November 6, 1978
    Date of Patent: October 21, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Friedrich Bruhne, Karl-August Lipper
  • Patent number: 4225527
    Abstract: Novel 9-(halo-substituted phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful in treating dermatological conditions.
    Type: Grant
    Filed: December 15, 1977
    Date of Patent: September 30, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4225694
    Abstract: 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: Grant
    Filed: September 6, 1977
    Date of Patent: September 30, 1980
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Augustine I. Dalton, Jr., Henry J. Doran, Robert D. H. Murray
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4211727
    Abstract: Carboxylic acid halides are reduced to the corresponding aldehydes using zinc borohydride or cadmium borohydride as the reducing agent.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: July 8, 1980
    Assignee: Shell Oil Company
    Inventors: Ian D. Entwistle, Robert A. W. Johnstone
  • Patent number: 4206139
    Abstract: 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: Grant
    Filed: September 27, 1978
    Date of Patent: June 3, 1980
    Assignee: Polaroid Corporation
    Inventors: Elbert M. Idelson, Charles E. Jandrue