Acetylenically Unsaturated Patents (Class 568/855)
  • Patent number: 4584418
    Abstract: Agglomerates of spheroidal masses of malachite crystals are prepared so that they contain silicic acid. These agglomerates can be used to prepare a copper-acetylide complex, which in turn can be used as a catalyst for the preparation of 1,4-butynediol from acetylene and formaldehyde.
    Type: Grant
    Filed: March 15, 1985
    Date of Patent: April 22, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph M. Fremont
  • Patent number: 4536491
    Abstract: Agglomerates of spheroidal masses of malachite crystals are prepared so that they contain silicic acid. These agglomerates can be used to prepare a copper-acetylide complex, which in turn can be used as a catalyst for the preparation of 1,4-butynediol from acetylene and formaldehyde.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: August 20, 1985
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Joseph M. Fremont
  • Patent number: 4388216
    Abstract: A process for regenerating suspended heavy metal catalysts used in the synthesis of butynediol from acetylene and formaldehyde. The aqueous catalytic slurry removed from the reaction mixture is raised to a temperature of about 200.degree. to 500.degree. C., where appropriate with air supplied, and is left at this temperature with air being supplied, until the carbon content of the catalytic substance is about 0.5 to 3%.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: June 14, 1983
    Assignee: GAF Huls Chemie GmbH
    Inventors: Helmut Westernacher, Franz Schamann, deceased
  • Patent number: 4317905
    Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
  • Patent number: 4294997
    Abstract: In the ethynylation of formaldehyde in the presence of a copper acetylide catalyst to produce butynediol, pH is controlled by the incremental or continuous addition of an alkali metal hydroxide and an alkali metal carbonate at an equivalent ratio of hydroxide ion to carbonate ion of 1:1-4:1.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: October 13, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert M. Stock, James D. Verbsky
  • Patent number: 4288641
    Abstract: The process for the preparation of 1,4-butynediol through the reaction of acetylene with formaldehyde in the presence of a catalytic metal, preferably copper, is improved by using, as the support of the catalytic metal, a molecular sieve or synthetic zeolite to which the catalytic metal is chemically bonded through an ion exchange reaction.There are obtained increased production rates and selectivity and the polymer of acetylene, namely cuprene, is essentially prevented from being formed.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: September 8, 1981
    Assignee: Societa Italiana Serie Acetica Sintetica S.p.A.
    Inventors: Franco Codignola, Giorgio Vergini, Paolo Gronchi, Paolo Centola
  • Patent number: 4288640
    Abstract: Process for carrying out exothermic reactions between a gas and a liquid in the presence of a solid catalyst by passing the gas and the liquid cocurrently through a packed reaction vessel, preferably of elongated shape, wherein the gas and liquid pass through the packed reaction vessel in transition flow.
    Type: Grant
    Filed: July 22, 1976
    Date of Patent: September 8, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Paul Raff, Herwig Hoffmann, Rolf Schneider, Erich Flickinger
  • Patent number: 4180687
    Abstract: Formaldehyde in crude BYD, can be reacted to a polymeric substance in the presence of NaOH or Na.sub.2 CO.sub.3 at high temperatures.
    Type: Grant
    Filed: April 24, 1978
    Date of Patent: December 25, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Harry O. Burrus, Donald I. Garnett
  • Patent number: 4165330
    Abstract: An asymmetric synthesis process which involves addition of optically active chelated organometal compounds of lithium, sodium, beryllium, magnesium, zinc, copper and cadmium to prochiral unsaturated substrates. The optically active chelating agent is not consumed and can be recycled.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: August 21, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Thomas A. Whitney, Arthur W. Langer, Jr.
  • Patent number: 4149004
    Abstract: When acetylene flow to the continuous, aqueous ethynylation reaction of formaldehyde and acetylene, using a copper acetylide complex as the catalyst, is interrupted, resulting cuprene formation can be inhibited by maintaining the reaction mass at a pH of 3.5-5 until normal acetylene flow is resumed.
    Type: Grant
    Filed: July 31, 1978
    Date of Patent: April 10, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Albert M. Stock
  • Patent number: 4143231
    Abstract: Synthetic malachite of desirable particle size and distribution is coprecipitated with small amounts of uniformly dispersed bismuth. After nucleation, the crystals are grown at elevated temperatures. The malachite can be converted into a cuprous acetylide complex useful as an ethynylation catalyst.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: March 6, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph M. Fremont
  • Patent number: 4127734
    Abstract: Spheroidal agglomerates of malachite crystals are prepared by bringing together solutions of a cupric salt, a bismuth salt and an alkali metal carbonate or bicarbonate to form a mixture containing amorphous hydrated copper carbonate, and then holding the mixture, without agitation, at a temperature of less than about 55.degree. C.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: November 28, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph M. Fremont
  • Patent number: 4119790
    Abstract: In accordance with the present invention, there is provided herein an improved low pressure, stirred, catalytic process by which butynediol can be produced continuously at a high rate of production, under safe conditions, and without simultaneously forming an excessive amount of undesirable by-products. The process of this invention can be carried out by heating acetylene and formaldehyde, at relatively low temperatures as compared to other processes using supported catalysts, in the presence of a stirred aqueous slurry of a finely-divided complex cuprous acetylide catalyst prepared from a precursor containing greater than 20% and less than 35% by weight of copper, and 0-3%, preferably 2-3%, by weight of bismuth, as the oxides, on a magnesium silicate carrier.
    Type: Grant
    Filed: April 6, 1977
    Date of Patent: October 10, 1978
    Assignee: GAF Corporation
    Inventor: Eugene V. Hort
  • Patent number: 4117249
    Abstract: The invention relates to acetylenic glycols having the formula : ##STR1## wherein R is hydrogen or an alkenyl group, and to their derivatives obtained through hydrogenation or ethoxylation reactions, these compounds showing outstanding surface active properties. The invention relates also to the process for the preparation of the subject compounds starting from 6-methyl-5-hepten-2-one.
    Type: Grant
    Filed: June 23, 1976
    Date of Patent: September 26, 1978
    Assignee: Anic, S.p.A.
    Inventors: Renato De Simone, Edoardo Platone, Morello Morelli
  • Patent number: 4117248
    Abstract: There is provided herein an improved, more continuous, low pressure ethynylation process for the production of butynediol which comprises first continuously reacting formaldehyde and acetylene in a reaction zone at low pressures, in a stirred aqueous medium, in the presence of a finely-divided ethynylation catalyst, to form a reaction product mixture containing butynediol and catalyst slurry. Then the reaction product mixture is withdrawn and continuously and simultaneously filtered and concentrated to form two streams, a catalyst-free filtrate stream and a flowable, concentrated catalyst slurry stream, the latter being capable of immediate recycling to the reaction zone without further treatment. The filtrate stream containing the butynediol is available for purification and further operations.
    Type: Grant
    Filed: April 29, 1977
    Date of Patent: September 26, 1978
    Assignee: GAF Corporation
    Inventors: J. Lewis Prater, Robert L. Hedworth
  • Patent number: 4113967
    Abstract: This disclosure describes novel erythro 15,16-dioxy prostenoic acids and esters useful as bronchodilators, hypotensives and gastric acid secretion inhibitors.
    Type: Grant
    Filed: February 11, 1977
    Date of Patent: September 12, 1978
    Assignee: American Cyanamid Company
    Inventor: Martin Joseph Weiss
  • Patent number: 4111959
    Abstract: This disclosure describes novel 15,16-dioxy prostenoic acids and esters useful as bronchodilators, anti-inflammatory agents, hypotensives and gastric acid secretion inhibitors.
    Type: Grant
    Filed: February 11, 1977
    Date of Patent: September 5, 1978
    Assignee: American Cyanamid Company
    Inventor: Martin Joseph Weiss
  • Patent number: 4112001
    Abstract: The corrosion of ferrous metals by corrosive acids at elevated temperatures is inhibited by adding to environments containing the acids an effective amount of a novel .alpha., .OMEGA. (hereinafter "alpha", "omega", respectively) diacetylenic diol (e.g., with two acetylenic functionalities) having the structural formula: ##STR1## where R is an aliphatic, alicyclic or aromatic residue containing from 1 to about 12 carbon atoms and may include one or more functional groups such as halogen atoms, carbonyl, carboxyl, carbamyl, amino, formyl or nitroso radicals or other functional groups without impaired performance. The diacetylenic diols may be employed in combination with other corrosion inhibitors.
    Type: Grant
    Filed: March 25, 1977
    Date of Patent: September 5, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventors: Daniel S. Sullivan, 3rd, Charles E. Strubelt, Kenneth W. Becker
  • Patent number: 4110249
    Abstract: Spheroidal agglomerates of malachite crystals are prepared by bringing together solutions of a cupric salt, a bismuth salt and an alkali metal carbonate or bicarbonate to form a mixture containing amorphous hydrated copper carbonate, and then holding the mixture, without agitation, at a temperature of less than about 55.degree. C.
    Type: Grant
    Filed: June 6, 1977
    Date of Patent: August 29, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph M. Fremont
  • Patent number: 4107082
    Abstract: Synthetic malachite of desirable particle size and distritution is coprecipitated with small amounts of uniformly dispersed bismuth. After nucleation, the crystals are grown at elevated temperatures. The malachite can be converted into a cuprous acetylide complex useful as an ethynylation catalyst.
    Type: Grant
    Filed: May 6, 1977
    Date of Patent: August 15, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph Melvin Fremont
  • Patent number: 4093668
    Abstract: Butynediol is prepared by reacting acetylene and formaldehyde in contact with a heavy metal acetylide as catalyst, in the liquid phase by the Reppe method. Acetylene is fed upwardly through a suspension of the catalyst in formaldehyde at such a rate that it is virtually completely consumed and a liquid zone containing no catalyst is formed above the suspension.
    Type: Grant
    Filed: March 19, 1974
    Date of Patent: June 6, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reiss, Hans-Ingo Joschek, Rudolf Schnur, Siegfried Winderl, Juergen Dehler, Herwig Hoffmann