Patents by Inventor Duane C. Hargis

Duane C. Hargis has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4950799
    Abstract: Monocarboxylic acids or esters thereof are reduced to aldehydes using hydrogen and a vanadium catalyst. For example, meta-phenoxybenzoic acid can be effectively converted to meta-phenoxybenzaldehyde in a vapor phase process using hydrogen as the carrier gas/reductant and a catalyst composed at least initially of vanadium pentoxide, either supported or unsupported.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: August 21, 1990
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4929764
    Abstract: By reacting a primary aromatic amine with a dialkyl ether in the presence of a titanium dioxide alkylation catalyst having a surface area below about 130 square meters per gram, preferably in the anatase crystallographic form, at a suitably elevated temperature above about 300.degree. C., the amount of exclusively ring-alkylated product formed exceeds the amount of exclusively N-alkylated product formed.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4798894
    Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: January 17, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4725681
    Abstract: An ethanolamine, preferably diethanolamine, is converted to triethylenediamine or 1,4-bis(2-hydroxyethyl)piperazine, or both by pyrolysis using a B-subgroup metal oxide such as titanium dioxide or zirconium dioxide, as catalyst. In addition it has also been discovered that 1,4-bis(2-hydroxyethyl)piperazine and N-(2-hydroxyethyl)piperazine can be converted in high yields and conversions into triethylenediamine by pyrolysis using the same type of catalyst. When using an ethanolamine as the feedstock and a Group IV-B metal oxide as the catalyst, the process usually results in the coproduction of triethylenediamine and 1,4-bis(2-hydroxyethyl)piperazine, and the latter can be recovered and used as a raw material for the production of additional triethylenediamine, as by recycle to the same reactor or as feedstock to an additional pyrolysis reactor.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: February 16, 1988
    Assignee: Ethyl Corporation
    Inventors: Ronald L. Shubkin, Duane C. Hargis
  • Patent number: 4721810
    Abstract: Aromatic amines are alkylated by reaction with an acyclic ether or an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide with or without a minor proportion of a Group VI-B or Group VIII metal oxide, so that alkylation of the aromatic amine occurs. Under most reaction conditions ether alkylating agents such as diethyl ether not consumed in the alkylation reaction pass through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: January 26, 1988
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4626592
    Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: December 2, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4613705
    Abstract: Aromatic amines are alkylated by reaction with an alcohol in the presence of a Group V-B metal oxide alkylation catalyst, preferably a major proportion of a Group V-B metal oxide such as V.sub.2 O.sub.5 in combination with a minor proportion of an A-subgroup metal oxide such as SnO.sub.2, so that alkylation of the aromatic amine occurs. Under most reaction conditions a considerable portion of the alcohol alkylating agent such as ethanol not consumed in the alkylation reaction passes through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: September 23, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4605766
    Abstract: Alkylation of aromatic amines with ethers in the presence of iron oxide catalysts is described. By means of the process aniline, o-toluidine, and the like can be selectively orthoalkylated with such ethers as dimethyl ether, diethyl ether, tetrahydrofuran, and 1,4-dioxane at elevated temperatures in the presence of a catalyst containing iron oxide. With ethers such as dipropyl ether, diisopropyl ether and dibenzyl ether, N-alkylation is the predominant reaction. By appropriately modifying the iron oxide catalyst the process can be rendered selective for the para-alkylation of the amine. An advantage of the process is that the unreacted ether is not extensively decomposed in the process and thus can be recovered for recycle or other use.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: August 12, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4599449
    Abstract: Aromatic amines are alkylated by reaction with an alcohol in the presence of a Group VII-B metal oxide alkylation catalyst, preferably a major proportion of a Group VII-B metal oxide such as MnO.sub.2 in combination with a minor proportion of a Group VIII metal oxide such as Fe.sub.2 O.sub.3, so that alkylation of the aromatic amine occurs. Under most reaction conditions a considerable portion of the alcohol alkylating agent such as ethanol not consumed in the alkylation reaction passes through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: July 8, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4562296
    Abstract: One or more aldehydes or ketones, or both, are produced by pyrolyzing an alcohol having at least two carbon atoms or an aldehyde having at least two carbon atoms, or both, over a Group VIII metal oxide catalyst, preferably a catalyst composed predominantly of iron oxide, notably ferric oxide. Preferably, the catalyst additionally contains a minor proportion of a Group IV-A metal oxide, most preferably germanium dioxide. The process provides a good yield of lower molecular weight aldehydes, such as formaldehyde, or higher molecular weight ketones, such as acetone, 2-pentanone and the like. Selective manufacture of products enriched either in aldehyde or in ketone can be achieved by a simple adjustment in the reaction conditions employed.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4415749
    Abstract: A process for the selective formation of ethanol and methyl acetate by contacting methanol, hydrogen and carbon monoxide with a catalyst comprising rhodium and iron in the reduced state deposited on a support of alumina containing a minor amount of an alkaline metal at reaction conditions correlated so as to favor the formation of a substantial proportion of ethanol and methyl acetate.
    Type: Grant
    Filed: September 15, 1981
    Date of Patent: November 15, 1983
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Michael Dubeck
  • Patent number: 4370507
    Abstract: A process for selectively preparing ethanol by contacting methanol, hydrogen and carbon monoxide with a solid catalyst comprising rhodium and iron in the reduced state deposited on a support of alumina impregnated with a promoter amount of a heterocyclic amine at reaction conditions correlated so as to favor the formation of a substantial proportion of ethanol.
    Type: Grant
    Filed: January 8, 1982
    Date of Patent: January 25, 1983
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Michael Dubeck
  • Patent number: 4361499
    Abstract: A process for selectively preparing ethanol by contacting methanol, hydrogen and carbon monoxide with a solid catalyst comprising rhodium and iron in the reduced state deposited on a support of alumina impregnated with a promoter amount of a heterocyclic amine at reaction conditions correlated so as to favor the formation of a substantial proportion of ethanol.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: November 30, 1982
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Michael Dubeck
  • Patent number: 4309314
    Abstract: A process for the selective formation of ethanol and methyl acetate by contacting methanol, hydrogen and carbon monoxide with a catalyst comprising rhodium and iron in the reduced state deposited on a support of alumina containing a minor amount of an alkaline metal at reaction conditions correlated so as to favor the formation of a substantial proportion of ethanol and methyl acetate.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: January 5, 1982
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Michael Dubeck
  • Patent number: 4261865
    Abstract: A process for selectively preparing alpha-olefins having from 2 to about 22 carbon atoms by contacting a gaseous mixture containing carbon monoxide and hydrogen with an iron titanate-alkali metal hydroxide catalyst at reaction conditions correlated so as to favor the formation of a substantial proportion of such alpha-olefin product.
    Type: Grant
    Filed: November 6, 1979
    Date of Patent: April 14, 1981
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4261864
    Abstract: A process for selectively preparing alpha-olefins having from 2 to about 22 carbon atoms by contacting a gaseous mixture containing carbon monoxide and hydrogen with an iron tungstate-alkali metal hydroxide catalyst at reaction conditions correlated so as to favor the formation of a substantial proportion of such alpha-olefin product.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: April 14, 1981
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4072732
    Abstract: Catalytic process for converting dimethyl ether and methanol to higher hydrocarbons, comprising contacting the dimethyl ether and/or methanol with an alumina, silica or zirconia-supported zirconium sulfate catalyst, at an elevated temperature.
    Type: Grant
    Filed: April 2, 1976
    Date of Patent: February 7, 1978
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Lawrence J. Kehoe
  • Patent number: 4072733
    Abstract: Catalytic process for converting methanol and dimethyl ether to higher hydrocarbons comprising contacting the methanol and/or dimethyl ether with an alumina, silica, or zirconia-supported aluminum sulfate catalyst, at an elevated temperature.
    Type: Grant
    Filed: April 2, 1976
    Date of Patent: February 7, 1978
    Assignee: Ethyl Corporation
    Inventors: Duane C. Hargis, Lawrence J. Kehoe
  • Patent number: RE32896
    Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: March 28, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis