Preparing Directly By Ring Alkylation Or Dealkylaton Patents (Class 564/409)
  • 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: 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: 4604484
    Abstract: A process for monoalkylating 1-alkyl-2,4-diaminobenzene or 1-alkyl-2,6-diaminobenzene. Propylene is reacted with 2,4-diaminotoluene in the presence of aluminum anilide catalyst. Aniline is an optional ingredient.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Kryn G. Ihrman
  • 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: 4593124
    Abstract: A process is disclosed for preparing an isomeric mixture of a monomethyl-, dimethyl- or monoethyl-substituted aniline consisting essentially of contacting at least one of said anilines with a specified zeolite at about 250.degree.-500.degree. C. and about 10 kPa-10 MPa of pressure.
    Type: Grant
    Filed: September 12, 1984
    Date of Patent: June 3, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4590263
    Abstract: Novel diazonium salts which possess excellent photo speed, good thermal stability, exceptional resistance to discoloration in the D.sub.min areas, rapid development, and allow a wide range of azo dye colors are provided. The diazonium salts are of the following formula: ##STR1## wherein R.sub.1 is tertiary butyl or tertiary amyl; Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkylthio, arylthio, alkylthio, halogen, allyl, allyloxy, allylthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, or dialkyl carbonamido;R.sub.2 and R.sub.3 are the same or different, and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, beta-chloroalkyl, branched alkyl, or a structure wherein R.sub.2 and R.sub.3 may be linked together to form a heterocyclic structure; andX is an anion.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 20, 1986
    Assignee: James River Graphics, Inc.
    Inventors: Robert C. Desjarlais, Everett W. Bennett
  • Patent number: 4436936
    Abstract: Compounds having the formula I ##STR1## as well as salts or metal salt complexes thereof, in which formula I n, R.sub.1, R.sub.2 and Z have the meanings given in claim 1, can be prepared under mild reaction conditions by reacting 1.0 mole of an aromatic amine having the formula II ##STR2## with up to three moles of an alkylating agent (III) capable of introducing a residue Z into the benzene ring of an amine (II) at a position ortho or para to the NH.sub.2 group, the reaction being effected at elevated temperature in the presence of an acid catalyst in an aqueous acid medium, containing at least 30% by weight of water, based on the acid, and optionally converting compounds (I) into salts or metal salt complexes. The compounds (I) so produced are useful in the production of intermediates for dyestuffs, additives for plastics, rubbers, oils, etc., and in the production of biologically active compounds.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: March 13, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Frederick H. Howell
  • Patent number: 4436937
    Abstract: An aniline is alkylated on the ring by treating it with an alkylating agent, preferably an alkyl chloride, in the liquid phase, and in the presence of at least 1.02 mole of an aluminum halide per mole of the aniline.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: March 13, 1984
    Assignee: Shell Oil Company
    Inventors: Frank Baardman, Robert van Helden, Margaretha J. de Nie-Sarink
  • Patent number: 4405812
    Abstract: Ortho-methyl groups are preferentially removed from o-methyl substituted aromatic amines by contacting with a nickel catalyst at about 200.degree.-400.degree. C.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventors: Walter K. Dean, Bernard R. Meltsner
  • Patent number: 4359584
    Abstract: p-Substituted aromatic amines are prepared by reacting a p-substituted, aromatic carbamic acid ester with an aromatic amine in the presence of an aliphatic or cycloaliphatic alcohol. The aromatic amines obtainable by the process according to the invention are antiseptics and valuable starting materials for the preparation of dyes, resins, finishes, plastics, pesticides and drugs.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: November 16, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4351958
    Abstract: An orthoalkylated aromatic amine is produced at a high selectivity from the reaction of an aromatic amine having at least one hydrogen atom at the ortho-positions and a primary or secondary alcohol under heating in the presence of a catalyst containing, as a main constituent, iron oxides.
    Type: Grant
    Filed: August 28, 1981
    Date of Patent: September 28, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kazunori Takahata, Katsuo Taniguchi
  • Patent number: 4341903
    Abstract: Methyl groups on N-methyl aromatic amines are redistributed to ring positions by heating in contact with an aluminum anilide catalyst and a nickel, cobalt, molybdenum or titanium-containing cocatalyst. For example, N-methyl-o-toluidine forms a mixture containing substantial quantities of 2,6-dimethylaniline, 2,4-dimethylaniline, and 2,4,6-trimethylaniline.
    Type: Grant
    Filed: April 13, 1981
    Date of Patent: July 27, 1982
    Assignee: Ethyl Corporation
    Inventors: John C. Wollensak, Kryn G. Ihrman, Chester P. Jarema
  • Patent number: 4340758
    Abstract: A process for the preparation of 2,6-dialkylaniline which comprises the reaction of 1,3-dialkylbenzene with isobutene in the presence of a hydrogen fluoride catalyst to form 1,3-dialkyl-5-tertiary-butylbenzene, which is subsequently nitrated in the presence of a soluble mercuric salt catalyst to form 2-nitro-1,3-dialkyl-5-tertiary-butylbenzene, which is then catalytically hydrogenated to give 2,6-dialkyl-4-tertiary-butylaniline, followed by pyrolysis in the presence of a heterogeneous acidic catalyst.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 20, 1982
    Assignee: Chevron Research Company
    Inventors: Seymour J. Lapporte, David M. Marquis
  • Patent number: 4317931
    Abstract: Methyl groups on o-methyl aromatic amine are redistributed to ortho positions by heating in contact with an aluminum anilide catalyst and a nickel, cobalt, molybdenum or titanium-containing cocatalyst. For example, o-toluidine forms a mixture containing an aniline, o-toluidine, 2,6-dimethylaniline, and 2,4-dimethylaniline.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: March 2, 1982
    Assignee: Ethyl Corporation
    Inventors: John C. Wollensak, Kryn G. Ihrman, Chester P. Jarema