Patents Represented by Attorney Delbert E. McCaslin
  • Patent number: 4281173
    Abstract: A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is alkyl having 1 to 8 carbon atoms or aralkyl having 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl moiety, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are each hydrogen, halogen, alkyl having 1 to 4 carbon atoms or aryl having 6 carbon atoms in the ring, by reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as aforesaid, in the presence of a catalytic amount of a platinum group metal compound, a copper or iron oxidant salt compound, a soluble vanadium salt and a stoichiometric amount of a dehydrating agent. Optionally, an anhydrous-halogen containing acid may be included.Alternatively, a ligand or coordination complex compound of the metal salt compound, and catalytic quantities of an alcohol may be employed.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: July 28, 1981
    Assignee: Atlantic Richfield Company
    Inventor: Haven S. Kesling, Jr.
  • Patent number: 4276197
    Abstract: A method for the preparation of a titanium promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of a linear C.sub.4 unsaturated olefins to prepare maleic anhydride.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: June 30, 1981
    Assignee: Atlantic Richfield Company
    Inventors: James C. Vartuli, Lee R. Zehner
  • Patent number: 4273677
    Abstract: A method for the preparation of a thallium promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of linear C.sub.4 unsaturated olefins to prepare maleic anhydride.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: June 16, 1981
    Assignee: Atlantic Richfield Company
    Inventors: James C. Vartuli, Lee R. Zehner
  • Patent number: 4264342
    Abstract: Separating carbon monoxide from mixed gases containing the same with an adsorbent which is the product of heating a mixture of ferrous acetate and polyacrylonitrile in a ratio of ferrous acetate to polyacrylonitrile of 0.5:1.0 to 2.0:1.0 at a temperature of about 200.degree.-400.degree. C. in an oxygen-containing atmosphere for from about 2 to 10 hours.
    Type: Grant
    Filed: March 28, 1980
    Date of Patent: April 28, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Mary T. Arnold, John J. Leonard, John J. McCoy
  • Patent number: 4260814
    Abstract: A process for the preparation of bromoalkyl esters and vicinal glycol esters which comprises thermally decomposing at temperatures of from 100.degree. C. to 200.degree. C. a bis(2-bromoalkyl)tellurium dicarboxylate compound of the formula ##STR1## wherein at least one R is hydrogen or R is a methyl group and R' is hydrogen or an alkyl group having 1 to 3 carbon atoms in the presence of an aliphatic monocarboxylic acid selected from formic, acetic, propionic or butyric acid employed as solvent and to facilitate solvolysis in the reaction to give in addition to the bromoalkyl ester, the vicinal glycol ester. An inert acetonitrile solvent may be employed alone to give predominately the bromoalkyl ester or an admixture with the acid may be employed. Oxygen is preferably employed with the carboxylic acid solvent to provide an increase in the mole ratio of vicinal glycol ester to the bromoalkyl ester produced.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: April 7, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, Ming N. Sheng
  • Patent number: 4258208
    Abstract: A process for the preparation of 2-bromoalkyl esters and vicinal glycol esters which comprises thermally decomposing at temperatures of from 100.degree. C. to 200.degree. C. an organic bromoalkyl tellurium compound selected from 2-bromoalkyltellurium tribromide or bis(2-bromoalkyl)tellurium dibromide, wherein the alkyl group is ethyl, propyl or butyl, in a carboxylic acid having from 1 to 4 carbon atoms which is employed as solvent as well as to supply the ester moiety to the esters produced. The esters may be converted to the respective glycol with water or an aqueous base.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: March 24, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, Ming N. Sheng
  • Patent number: 4256912
    Abstract: A method for the removal of soluble tellurium compounds from vicinal glycol ester solutions, prepared with tellurium-halide ion catalyst systems, by diluting the tellurium-containing vicinal glycol ester solution with water and contacting said glycol-water solution with a strongly acidic sulfonated ion exchange resin leaving an essentially tellurium-free vicinal glycol ester reaction product which may then be processed to recover the desired ester product and by-products without loss of valuable tellurium. The tellurium may be recovered from the ion exchange resin and treated to recover tellurium in a form suitable for reuse.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: March 17, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Alfred A. Wolsky, Richard B. Papp, James G. Victor
  • Patent number: 4247465
    Abstract: A process for the preparation of a cyclic alkylene carbonate ester which comprises reacting in a liquid phase a cyclic or linear olefin having from 2 to 15 carbon atoms with carbon dioxide at a temperature of from 30.degree. to 160.degree. C., at a total pressure of from 100 to about 2,000 psig and a pH value of between about 4 and 8, in the presence of oxygen or an oxygen-containing gas and a catalytic amount of a mixture of (a) iodine or an iodide of a metal selected from Groups IA, IB, IIA, IIB, VB, VIIB and VIII of the Periodic Table of Elements, (b) a carbonate of a metal selected from Groups IB, IIA, IIB and VIII of the Periodic Table of Elements, (c) a catalytic iron compound and (d) a catalytic soluble cupric salt, and recovering resulting cyclic alkylene carbonate ester.
    Type: Grant
    Filed: August 23, 1979
    Date of Patent: January 27, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Jar-Lin Kao, Gregory A. Wheaton, Harold Shalit, Ming N. Sheng
  • Patent number: 4247419
    Abstract: A method for the preparation of a single phase crystalline vanadium(IV)bis(metaphosphate), VO(PO.sub.3).sub.2, catalyst having an improved intrinsic surface area of from about 5 to 15 m.sup.2 /g. and useful for the vapor phase oxidation of linear C.sub.4 unsaturated olefins, such as n-butenes, to prepare maleic anhydride.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: January 27, 1981
    Assignee: Atlantic Richfield Company
    Inventors: James C. Vartuli, Lee R. Zehner
  • Patent number: 4247524
    Abstract: A process for producing zeolite A of the formulaNa.sub.x (AlO.sub.2).sub.x (SiO.sub.2).sub.y.ZH.sub.2 Owherein x=10 to 14, y/x=0.8 to 1.2 and Z=1 to 30, which comprises heating at a temperature of 60.degree. to 150.degree. C. an aqueous slurry comprising (a) at least one gram of clinoptilolite of the formulaNa.sub.x (AlO.sub.2).sub.x (SiO.sub.2).sub.y. ZH.sub.2 Owherein x=5 to 7, y/x=4.5 to 5.5 and Z=1 to 30, per 100 cc of slurry, (b) at least a stoichiometric amount of sodium aluminate, and (c) at least 1% by weight of sodium hydroxide until zeolite A forms and recovering zeolite A. Sodalite which may have the formulaNa.sub.6 (AlO.sub.2).sub.6 (SiO.sub.2).sub.6.2NaClcan be produced by carrying out the aforesaid process in the presence of sodium chloride.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: January 27, 1981
    Assignee: Atlantic Richfield Company
    Inventor: John J. Leonard
  • Patent number: 4244936
    Abstract: A process for the recovery of tellurium compounds which have been retained on a strongly acidic sulfonated ion exchange resin employed to remove soluble tellurium compounds from tellurium-containing vicinal glycol ester solutions, by elution of the resin with dilute mineral acids, such as hydrochloric, to form a tellurium-containing acid eluate and treating the eluate by stripping or distilling to remove contained water and acid leaving a tellurium compound concentrate which may be treated in the presence of air or oxygen to convert the tellurium to a form suitable for reuse in the preparation of vicinal glycol esters.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: January 13, 1981
    Assignee: Atlantic Richfield Company
    Inventors: James G. Victor, Richard B. Papp, Alfred A. Wolsky
  • Patent number: 4236023
    Abstract: A process for the preparation of an unsaturated monoester having the formula ##STR1## wherein R is an alkyl group of from 1 to 4 carbon atoms and R' is hydrogen, a halogen or a methyl group, by reacting carbon monoxide, oxygen, and at least a stoichiometric amount of an enol ether, or a 1-alkoxycycloalkene dehydrating agent with a diolefin having the formula ##STR2## wherein R' is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound and a copper or iron oxidant salt compound.Alternatively, a ligand or coordination complex compound of the metal salt compound and catalytic quantitites of an alcohol may be employed.
    Type: Grant
    Filed: June 26, 1979
    Date of Patent: November 25, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4231937
    Abstract: A process for the preparation of alkylene carbonates having from 3 to 31 carbon atoms per molecule of the general formula ##STR1## which comprises reacting in the liquid phase the corresponding alkylene iodohydrin having from 2 to 30 carbon atoms per molecule with carbon dioxide in the presence of oxygen or an oxygen-containing gas and an effective amount of a catalytic mixture of(1) an iodide of the metals selected from groups IA, IB, IIA, IIB and VIII of the Periodic Table of Elements and(2) a carbonate of the metals selected from the groups IB, IIA, and IIB of the Periodic Table of Elements,at a temperature of from 30.degree. C. to 120.degree. C., and at a total carbon dioxide and oxygen pressure between about atmospheric and 1400 psig, at a pH value of between 3 and 10.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: November 4, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, Ming N. Sheng
  • Patent number: 4230877
    Abstract: A method for increasing the 4,4' disubstituted isomer of the diphenylmethane dicarbamates produced by the acid catalyzed condensation of an N-aryl carbamic acid ester, such as ethylphenylcarbamate, with a carbonyl compound, such as formaldehyde, which comprises carrying out the condensation in a single phase system with a dilute solution of the N-aryl carbamic acid ester in an inert solvent having a dielectric constant of at least 20 at 20.degree. C. The solvent must have good solubility for the carbamates, which carbamates are employed in the solvent at concentrations of from about 0.1 to 50 weight percent to provide a product enriched with the 4,4'-diphenylmethane dicarbamate isomer.
    Type: Grant
    Filed: March 22, 1979
    Date of Patent: October 28, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Edward T. Shawl, Gerald A. Bullano
  • Patent number: 4224301
    Abstract: A method for the removal and recovery of tellurium from a vicinal glycol ester solution containing soluble tellurium compounds by contacting the tellurium-containing glycol ester solution at a suitable temperature with granular activated carbon to adsorb the soluble tellurium compounds. The tellurium may be recovered from the activated carbon and converted to a form suitable for reuse in the preparation of the vicinal glycol esters.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: September 23, 1980
    Assignee: Atlantic Richfield Company
    Inventor: Thomas A. Washall
  • Patent number: 4224223
    Abstract: A process for the preparation of a cyclic alkylene carbonate ester which comprises reacting in a liquid phase a cyclic or linear olefin having from 2 to 15 carbon atoms with carbon dioxide at a temperature of from 50 to 160.degree. C., at a total pressure of from 200 to about 2,000 psig and a pH value of between about 4 and 8, in the presence of oxygen or an oxygen-containing gas and a catalytic amount of a mixture of (a) iodine or an iodide of a metal selected from Groups IA, IB, IIA, IIB, VB, VIIB and VIII of the Periodic Table of Elements and (b) a catalytic iron compound, copper compound of mixture thereof deposited on an inert supporting material, and recovering resulting cyclic alkylene carbonate ester.
    Type: Grant
    Filed: August 23, 1979
    Date of Patent: September 23, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Gregory A. Wheaton, Jar-lin Kao, Ming N. Sheng
  • Patent number: 4202986
    Abstract: Diphenylmethane dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are produced by the condensation of N-aryl carbamic acid esters, such as ethylphenylcarbamate, with a carbonyl compound selected from formaldehyde, para-formaldehyde or trioxane at a temperature of between about ambient and 170.degree. C. in the presence of a Lewis acid intercalated in graphite and optionally in the presence of an inert solvent.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: May 13, 1980
    Assignee: Atlantic Richfield Company
    Inventor: Edward T. Shawl
  • Patent number: 4195184
    Abstract: A process for the preparation of an unsaturated monoester having the formula ##STR1## wherein R is an alkyl group of from 1 to 4 carbon atoms and R' is hydrogen or a methyl group which comprises reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R' is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound, a copper or iron oxidant salt compound and a stoichiometric amount of a dehydrating agent.Alternatively, a ligand or coordination complex compound of the metal salt compound, and catalytic quantities of an alcohol may be employed.
    Type: Grant
    Filed: May 26, 1978
    Date of Patent: March 25, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4189599
    Abstract: A process for the preparation of dimethyl adipate by the hydrogenation of dimethyl hex-3-endioate, having the formula CH.sub.3 O.sub.2 CCH.sub.2 CH.dbd.CHCH.sub.2 CO.sub.2 CH.sub.3, derived from the oxidative carbonylation of 1,3-butadiene with a mixture of carbon monoxide and oxygen at a temperature of from 60.degree. C. to 200.degree. C. and pressures of from 15 psig to 5000 psig in the presence of a catalytic mixture of a platinum group metal compound and a copper or iron oxidant salt compound with at least a stoichiometric amount of a dehydrating agent, which comprises subjecting the dimethyl hex-3-endioate to a liquid phase hydrogenation at temperatures of from about ambient to about 150.degree. C. under hydrogen pressures of from about 10 psig to 1000 psig in the presence of an effective amount of a hydrogenation catalyst to produce dimethyl adipate, and recovering the dimethyl adipate.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: February 19, 1980
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4180681
    Abstract: A process for the recovery of methacrylic acid formed from an aqueous sodium methacrylate solution derived from the silver catalyzed oxidation reaction of methacrolein and an aqueous solution of sodium hydroxide which comprises contacting the aqueous sodium methacrylate solution at a suitable temperature, in the presence of a high gaseous carbon dioxide pressure, with a water immiscible alkane, cycloalkane, alkyl benzene, or carboxylic acid ester solvent to extract and form a methacrylic acid-containing organic solvent phase, an aqueous phase and a precipitated sodium bicarbonate solid phase and recovering the methacrylic acid from the organic solvent phase. Liquid CO.sub.2 which may be employed with the water immiscible solvent at 800 psig may also be employed alone at its equilibrium vapor pressure as the reactant and extractant medium.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: December 25, 1979
    Assignee: Atlantic Richfield Company
    Inventors: John J. Leonard, Harold Shalit