Patents Represented by Attorney Delbert E. McCaslin
  • Patent number: 4172948
    Abstract: Diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are prepared by employing a superatmospheric pressure of anhydrous hydrogen chloride to catalytically rearrange an (alkoxycarbonyl)phenylaminomethylphenyl compound having the general formula ##STR1## INCLUDING THE HIGHER HOMOLOGS OF SUCH COMPOUNDS, WHEREIN X, Y AND Z, WHICH ARE DIFFERENT ON THE RING, ARE AN ALKYL GROUP HAVING FROM 1 TO 3 CARBON ATOMS, AN --NHCOOR, --CH.sub.2 ArNHCOOR or --N(COOR)CH.sub.2 Ar group; x, y and z may also be at least one hydrogen; R is a 1 to 3 carbon atom alkyl group and Ar is phenyl which may be substituted with a 1 to 3 carbon atom alkyl group.
    Type: Grant
    Filed: January 24, 1979
    Date of Patent: October 30, 1979
    Assignee: Atlantic Richfield Company
    Inventor: Edward T. Shawl
  • Patent number: 4171450
    Abstract: A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent, and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R.sub.1 to R.sub.4 which may be the same or different is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound, a copper for 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: June 22, 1977
    Date of Patent: October 16, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4171316
    Abstract: A process for the preparation of maleic anhydride in high yield and selectivity which comprises partially oxidizing an unsaturated aliphatic hydrocarbon selected from 1-butene, 2-butene and 1,3-butadiene or mixtures thereof in the vapor phase at elevated temperatures with oxygen or an oxygen-containing gas in the presence of a single phase vanadium(IV)bis(metaphosphate) catalyst having the formula VO(PO.sub.3).sub.2. Preferably the reaction is carried out in the presence of steam to enhance the selectivity to maleic anhydride.
    Type: Grant
    Filed: March 24, 1978
    Date of Patent: October 16, 1979
    Assignee: Atlantic Richfield Company
    Inventor: S. Erik Pedersen
  • Patent number: 4166913
    Abstract: A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide, oxygen, at least a stoichiometric amount of an enol ether or alkoxycycloalkene and at least an equal molar quantity of an alcohol based on the enol ether or alkoxycycloalkene, with a diolefin having the formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different 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 may be employed as a co-catalyst.
    Type: Grant
    Filed: July 8, 1977
    Date of Patent: September 4, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Haven S. Kesling, Jr., Lee R. Zehner
  • Patent number: 4165299
    Abstract: A method for the preparation of a single phase vanadium(IV)bis(metaphosphate), VO(PO.sub.3).sub.2, catalyst having an improved surface area and useful for the vapor phase oxidation of linear C.sub.4 unsaturated olefins, such as the n-butenes, to prepare maleic anhydride.
    Type: Grant
    Filed: May 23, 1978
    Date of Patent: August 21, 1979
    Assignee: Atlantic Richfield Company
    Inventor: S. Erik Pedersen
  • Patent number: 4162362
    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 formaldehyde, para-formaldehyde or trioxane in the presence of an organic sulfonic or halogenated organic sulfonic acid which has an acid concentration of at least 75 percent, at temperatures of from ambient to about 170.degree. C. and optionally in the presence of an inert solvent.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: July 24, 1979
    Assignee: Atlantic Richfield Company
    Inventor: Edward T. Shawl
  • Patent number: 4146727
    Abstract: Diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are produced by the protonic or Lewis acid catalyzed rearrangement of an (alkoxycarbonyl)phenylaminomethylphenyl compound having the general formula ##STR1## INCLUDING THE HIGHER HOMOLOGS OF SUCH COMPOUNDS, WHEREIN X, Y AND Z, WHICH ARE DIFFERENT ON THE RING, ARE AN ALKYL GROUP HAVING FROM 1 TO 3 CARBON ATOMS, AN --NHCOOR, --CH.sub.2 ArNHCOOR or --N(COOR)CH.sub.2 Ar group; x, y and z may also be at least one hydrogen; R is a 1 to 3 carbon alkyl group and Ar is phenyl which may be substituted with a 1 to 3 carbon atom alkyl group.
    Type: Grant
    Filed: May 15, 1978
    Date of Patent: March 27, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Edward T. Shawl, John G. Zajacek
  • Patent number: 4144399
    Abstract: A process for the preparation of acrylic acid or methacrylic acid by the ruthenium and/or osmium catalyzed conversion of peroxide (peroxy) intermediate compounds, derived from the autoxidation of acrolein or methacrolein, to the corresponding .alpha.,.beta.-unsaturated carboxylic acid, particularly the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: March 23, 1977
    Date of Patent: March 13, 1979
    Assignee: Atlantic Richfield Company
    Inventors: Ming N. Sheng, Jar-lin Kao
  • Patent number: 4130633
    Abstract: A method for the removal and recovery of selenium from a urethane solution containing selenium compounds, which may be in the form of inorganic selenium and/or organoselenium compounds, which comprises contacting the selenium-containing urethane solution at a suitable temperature with an aqueous hydrogen peroxide solution and recovering the selenium from the resulting selenium compound enriched aqueous phase in a form suitable for reuse in the preparation of urethanes, the deselenized urethane remaining in the hydrocarbon and/or organic phase.
    Type: Grant
    Filed: December 27, 1977
    Date of Patent: December 19, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Edward T. Shawl, Ming N. Sheng, John G. Zajacek
  • Patent number: 4124633
    Abstract: A process for the preparation of acrylic acid or methacrylic acid which comprises catalytically decomposing or converting in the presence of tellurium the peroxide (peroxy) compounds contained in the oxidate solution derived from the autoxidation of acrolein or methacrolein, particularly, the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: August 1, 1977
    Date of Patent: November 7, 1978
    Assignee: Atlantic Richfield Company
    Inventors: John J. Leonard, Jar-lin Kao
  • Patent number: 4124635
    Abstract: A process for the liquid phase oxidation of .alpha.,.beta.-unsaturated aliphatic aldehydes, such as methacrolein and the in situ decomposition or conversion of unsaturated peroxy (peroxide) compounds formed during the oxidation to the corresponding .alpha.,.beta.-unsaturated aliphatic carboxylic acids which comprises passing oxygen or an oxygen-containing gas such as air through an inert solvent solution of the unsaturated aldehyde at a suitable temperature and pressure in the presence of an organic or inorganic zinc salt catalyst.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: November 7, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, John J. Leonard
  • Patent number: 4115440
    Abstract: A process for the preparation of acrylic acid or methacrylic acid which comprises catalytically decomposing or converting in the presence of selenium the peroxide (peroxy) compounds formed during autoxidation or contained in the oxidate solution derived from the autoxidation of the respective acrolein or methacrolein, particularly, the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.
    Type: Grant
    Filed: April 19, 1977
    Date of Patent: September 19, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Ming Nan Sheng, Jar-lin Kao
  • Patent number: 4112245
    Abstract: A process for the preparation of ethylene glycol by the vapor phase hydrogenation of oxalate esters, such as a dibutyl oxalate, at elevated temperatures and at relatively low hydrogen pressures in the presence of a suitable hydrogenation catalyst, such as a copper chromite catalyst, while minimizing the hydrogenolysis of the glycol and other side reactions and maximizing the hydrogenation catalyst activity.
    Type: Grant
    Filed: August 18, 1976
    Date of Patent: September 5, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Lee R. Zehner, R. Warren Lenton
  • Patent number: 4097523
    Abstract: A process for the liquid phase oxidation of .alpha.,.beta.-unsaturated aldehydes, and the in situ decomposition of unsaturated intermediate peroxy (peroxide) compounds formed during oxidation, to the corresponding unsaturated aliphatic acid which comprises passing oxygen or an oxygen-containing gas through an inert solvent solution of the aldehyde at a suitable temperature and pressure in the presence of a catalytic amount of a thallium salt. The solvents employed may be mixed with water forming a heterogeneous solvent system.
    Type: Grant
    Filed: January 12, 1977
    Date of Patent: June 27, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Jar-Lin Kao, John Joseph Leonard
  • Patent number: 4093649
    Abstract: A process for the preparation of .alpha.,.beta.-unsaturated aliphatic carboxylic acids by the liquid phase oxidation of the corresponding .alpha.,.beta.-unsaturated aliphatic aldehyde, such as acrolein and methacrolein, and the in situ decomposition or conversion of unsaturated peroxy (peroxide) compounds formed during oxidation, which comprises passing air or oxygen through an inert organic solvent solution of the aldehyde at a suitable temperature and pressure in the presence of a catalytic amount of an organic or inorganic bismuth salt. Heterogeneous solvent systems employing mixtures of the organic solvent and water may be used.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: June 6, 1978
    Assignee: Atlantic Richfield Company
    Inventors: Jar-lin Kao, John Joseph Leonard
  • Patent number: 4092355
    Abstract: A method for the production of .alpha.,.beta.-unsaturated aliphatic carboxylic acids by the liquid phase oxidation of the corresponding .alpha.,.beta.-unsaturated aliphatic aldehydes, particularly acrolein and methacrolein, and the in situ decomposition of unsaturated intermediate peroxy (peroxide) compounds formed during oxidation, which comprises passing oxygen or an oxygen-containing gas through an inert solvent solution of the aldehyde at a suitable temperature and pressure in the presence of a catalytic amount of an inorganic or organic antimony salt. The solvent employed may also be mixed with water forming a heterogeneous solvent system.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: May 30, 1978
    Assignee: Atlantic Richfield Company
    Inventors: John Joseph Leonard, Jar-Lin Kao
  • Patent number: 4076949
    Abstract: A process for the preparation of oxalate esters by reacting an alcohol with a mixture of carbon monoxide and oxygen in the presence of a catalytic mixture of:(a) a palladium, rhodium, platinum, copper, or cadmium metal salt compound or mixture thereof,(b) an aliphatic, cycloaliphatic, aromatic or heterocyclic amine or ammonia,(c) a copper (I), copper (II), iron (II) or iron (III) oxidant salt compound, and(d) an ammonium or substituted ammonium salt compound or acid with a counterion other than a halide.Alternatively a ligand or coordination complex compound of the metal salt compound may be employed.
    Type: Grant
    Filed: May 9, 1977
    Date of Patent: February 28, 1978
    Assignee: Atlantic Richfield Company
    Inventor: Lee R. Zehner
  • Patent number: 4069388
    Abstract: A process for the preparation of oxalate esters by the catalytic oxidative carbonylation of an alkoxycycloalkene with carbon monoxide, an alcohol and oxygen or an oxygen-containing gas in the presence of a metal salt catalyst and an amine base. In addition, a catalytic amount of particular metal oxidizing salts is employed along with a catalytic amount of an acid or an amine salt compound. Alternatively various counterions and ligands of the metal salt catalysts may be employed.
    Type: Grant
    Filed: October 22, 1976
    Date of Patent: January 17, 1978
    Assignee: Atlantic Richfield Company
    Inventor: Lee R. Zehner
  • Patent number: 4065490
    Abstract: A process for the preparation of oxalate esters by the catalytic oxidative carbonylation of an enol ether with carbon monoxide, an alcohol and oxygen-containing gas in the presence of a metal salt catalyst and an amine base. In addition, a catalytic amount of particular metal oxidizing salts is employed along with a catalytic amount of an acid or an amine salt compound. Alternatively various counterions and ligands of the metal salt catalysts may be employed.
    Type: Grant
    Filed: March 22, 1976
    Date of Patent: December 27, 1977
    Assignee: Atlantic Richfield Company
    Inventor: Lee R. Zehner
  • Patent number: 4055629
    Abstract: A process for the recovery of selenium from a urethane solution containing selenium compounds which comprises contacting the selenium-containing urethane solution at a suitable temperature with copper (I) chloride, oxygen or an oxygen-containing gas such as air, and a complexing solvent such as an amine or nitrile to form an insoluble precipitate of copper-selenium compounds or complexes. The selenium and copper may be recovered from the resulting precipitate in a form suitable for reuse in the preparation of urethanes and selenium removal respectively.
    Type: Grant
    Filed: December 13, 1976
    Date of Patent: October 25, 1977
    Assignee: Atlantic Richfield Company
    Inventors: Rudolph Rosenthal, Edward T. Shawl