Halogen Patents (Class 562/602)
  • Patent number: 4590292
    Abstract: A modified novel process for preparing cyclopropylamine from .gamma.-butyrolactone is described. The .gamma.-butyrolactone ring is cleaved with a hydrohalide in the presence of a novel catalyst comprising an aqueous sulfuric acid solution. The 4-chlorobutyric acid, thus formed is converted into a hindered chlorobutyrate ester. The hindered ester based on secondary and tertiary alkanols of eight or less carbon atoms, is cyclized to form the hindered cyclopropanecarboxylate ester by a novel reaction medium consisting of solid caustic in a water-immiscible solvent and a phase transfer catalyst. The hindered cyclopropanecarboxylate ester is ammoniated to form cyclopropanecarboxamide by a novel catalyst comprising an alkali metal salt of a polyol having hydroxy groups on adjacent carbons. The carboxamide formed in substantially quantitative yields is converted to cyclopropylamine by a modified Hofmann reaction utilizing continuous degradation of the intermediate with simultaneous distillation.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: May 20, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph T. Blackwell, Harold L. Daughety, Henry C. Grace, Ward H. Oliver
  • Patent number: 4518813
    Abstract: (2R,6R)-1-Chloro-2,6,10-trimethyl-undecane I, (R)-(+)-.beta.-chloro-isobutyric acid II, (S)-(+)-1-bromo-3-chloro-2-methylpropane IV and (2R)-(+)-1-chloro-2,6-dimethyl-heptane V are novel optically active units for the synthesis of the side chain of (R,R,R)-.alpha.-tocopherol. In the process according to the invention, the optically active C.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 21, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Friedrich Vogel, Joachim Paust
  • Patent number: 4491547
    Abstract: Monofluoromethylthioacetic acid (FCH.sub.2 SCH.sub.2 COOH) or difluoromethylthioacetic acid (F.sub.2 CHSCH.sub.2 COOH), or its derivative at the carboxy group can be prepared e.g. by treating a thioglycolic acid ester with monolfuorohalomethane or difluorohalomethane in the presence of a base if required followed by a conventional modification of the produced ester e.g. to make an acid by hydrolysis, a salt by neutralization, a halide with a halogenating agent, and from acid halide or anhydride an ester with an alcohol, or an amide with an amine. These compounds are useful intermediates in the production of medicinal and agricultural chemicals.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: January 1, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Teruji Tsuji, Hisao Sato, Yoshio Hamashima
  • Patent number: 4461910
    Abstract: A process for the co-production of an alkylidene dicarboxylate and a carboxylic acid, which comprises hydrogenating a carboxylic acid anhydride in the presence of carbon monoxide and a homogeneous iridium- and/or rhodium-containing catalyst, together with an organo phosphorus (III), arsenic (III), or antimony (III) compound and either molecular oxygen or a phosphorus (V), arsenic (V) or antimony (V) compound containing a X=O moiety, where X is a phosphorus, arsenic or antimony atom.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 24, 1984
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4440947
    Abstract: Substituted .alpha.-halogenopropionic acids and their derivatives of the general formula ##STR1## wherein R.sup.1 to R.sup.3, Y and X have the meanings given in the description, are prepared by a process which is characterized in that substituted vinylidene chlorides of the general formula ##STR2## are reacted with chlorine or bromine chloride in the presence of compounds of the formulaR.sup.5 --SO.sub.3 R.sup.6 (III)wherein R.sup.5 and R.sup.6 have the meaning given in the description, and the products obtained are treated, if appropriate, with water or alcohol. Certain of the substituted .alpha.-halogeno-propionic acids and the substituted vinylidene chloride of the formula ##STR3## are new. The end products are useful as herbicides and intermediates for insecticides.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: April 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 4430320
    Abstract: A radioactive diagnostic agent for renal cortex, adrenal cortex, myocardium, brain stem, spinal nerve, etc., which comprises as an essential component monoiodoacetic acid wherein the iodine atom is radioactive.
    Type: Grant
    Filed: October 8, 1981
    Date of Patent: February 7, 1984
    Assignee: Kabushiki Kaisha Seitai Kagaku Kenkyusho
    Inventors: Akiyo Shigematsu, Akira Tsuya, Michiaki Aihara, Akiko Suzuki, Michiko Matsuda
  • Patent number: 4383121
    Abstract: A mixture containing monochloroacetic acid and dichloroacetic acid as the main components are admixed with 5-25% by weight of water on the basis of sum total of monochloroacetic acid, dichloroacetic acid and water, and subjected to adiabatic cooling under a pressure of 133 to 2,660 Pa, whereby monochloroacetic acid is crystallized with a high purity.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: May 10, 1983
    Assignee: Tsukishima Kaikai Co., Ltd.
    Inventors: Ryoji Sugamiya, Kazuto Nakamaru, Keizo Takegami, Koji Miwa, Minoru Morita
  • Patent number: 4334094
    Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more palladium-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4327036
    Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.
    Type: Grant
    Filed: May 8, 1980
    Date of Patent: April 27, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank D. Marsh
  • Patent number: 4314842
    Abstract: This invention concerns certain substituted 1,3,4-thiadiazol-2-yl-4-hydroxy-1-methyl-2-imidazolidinones having herbicidal activity, their preparation, and the control of weeds therewith.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: February 9, 1982
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish
  • Patent number: 4290965
    Abstract: A procedure for making .omega.-I.sup.123 labeled fatty acids in which the .omega.-bromo-fatty acid is applied in a thin film or layer to a support and is there contacted in molten state with the I.sup.123 iodide to effect halogen exchange.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 22, 1981
    Assignee: Kernforschungsanlage Julich, Gesellschaft mit beschrankter Haftung
    Inventors: Gerhard Stocklin, Peter Laufer, Jurgen Machulla
  • Patent number: 4263157
    Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 is chlorine or --CH.sub.2 --CCl.sub.3, andR.sub.2 is --N(R.sub.3)R.sub.4, --OH.N(R.sub.3)(R.sub.4)R.sub.5 or --OR.sub.6,R.sub.3 is C.sub.1 -C.sub.24 alkyl which can be interrupted once or several times by oxygen,R.sub.4 and R.sub.5 independently of one another are hydrogen or C.sub.1 -C.sub.24 alkyl, with R.sub.3 and R.sub.4 together having at least 8 C atoms,R.sub.6 is C.sub.8 -C.sub.20 alkyl, phenyl or C.sub.7 -C.sub.15 alkylphenyl, a group of the formula --(A)R.sub.7 or --CH.sub.2 CH.sub.2 --N(R.sub.10)--CH.sub.2 CH.sub.2 --O--C(O)--CH(R.sub.1)CH.sub.2 CCl.sub.3, whereinR.sub.7 is a radical of the formula --(R.sub.8)C(R.sub.9)--O--C(O)--CH(R.sub.1)--CH.sub.2 --CCl.sub.3, whereinR.sub.8 and R.sub.9 independently of one another are hydrogen, methyl or ethyl, and R.sub.1 has the meaning defined above,A is a C.sub.1 -C.sub.7 alkylene group which is unsubstituted or substituted by one or two radicals R.sub.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: April 21, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Eginhard Steiner, Andreas Schmidt
  • Patent number: 4260820
    Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: April 7, 1981
    Assignee: Texaco Development Corp.
    Inventor: John F. Knifton
  • Patent number: 4219673
    Abstract: In vivo and in vitro cellulose fermentation by cellulose-digesting microorganisms is increased by conducting the fermentation in the presence of a minor amount of a 2-(chloromethyldithio)acetic acid.
    Type: Grant
    Filed: March 31, 1978
    Date of Patent: August 26, 1980
    Assignee: Chevron Research Company
    Inventor: Malcolm S. Singer
  • Patent number: 4195033
    Abstract: 1-acetyl or 1-cyano-2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane. These compounds are useful intermediates.
    Type: Grant
    Filed: August 4, 1978
    Date of Patent: March 25, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: Nazim Punja
  • Patent number: 4177216
    Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: December 4, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4172957
    Abstract: Continuous process for the production of monochloroacetyl chloride accompanied, if the need should arise, by monochloroacetic acid, from trichloroethylene and/or 1,1,1,2-tetrachloroethane by reaction for hydration of trichloroethylene and/or 1,1,1,2-tetrachloroethane under pressure of hydrogen chloride in liquid phase, in the presence of ferric chloride in partial suspension.
    Type: Grant
    Filed: July 12, 1978
    Date of Patent: October 30, 1979
    Assignee: Rhone-Poulenc Industries
    Inventors: Yves Correia, Gerard Dumas
  • Patent number: 4148811
    Abstract: Halogenation is carried out regiospecifically in the presence of a cyanoquinone.
    Type: Grant
    Filed: July 12, 1977
    Date of Patent: April 10, 1979
    Assignee: The Procter & Gamble Company
    Inventor: Robert J. Crawford
  • Patent number: 4144397
    Abstract: Valuable 2-aryl-propionic acids are prepared by the direct coupling of aryl magnesium bromides with a mixed magnesium halide complex of alpha-bromopropionic acid.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: March 13, 1979
    Assignee: Syntex Corporation
    Inventors: Gary J. Matthews, Robert A. Arnold
  • Patent number: 4143066
    Abstract: A lower carboxylic acid such as acetic acid is separated and recovered from an aqueous medium by the steps which include contacting, in an extraction zone, the aqueous medium with an extracting agent such as trioctyl phosphine oxide dissolved in an organic solvent such as a mixture of paraffins having a boiling range of about 160.degree. C. to 175.degree. C.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: March 6, 1979
    Assignee: The Dow Chemical Company
    Inventor: Victor Kalcevic
  • Patent number: 4123443
    Abstract: New economically valuable and convenient methods for preparing bromoacetic acid and its esters from chloroacetic acid are disclosed.
    Type: Grant
    Filed: March 6, 1978
    Date of Patent: October 31, 1978
    Assignee: Katayama Chemical Works Co., Ltd.
    Inventors: Umekawa Osamu, Takemori Koji, Katayama Sakae