Preparing Directly By Ring Alkylation Or Dealkylaton Patents (Class 564/409)
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Patent number: 4721810Abstract: 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: GrantFiled: June 6, 1984Date of Patent: January 26, 1988Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4613705Abstract: 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: GrantFiled: June 25, 1984Date of Patent: September 23, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4605766Abstract: 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: GrantFiled: September 14, 1984Date of Patent: August 12, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4604484Abstract: 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: GrantFiled: July 30, 1982Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Kryn G. Ihrman
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Patent number: 4599449Abstract: 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: GrantFiled: June 25, 1984Date of Patent: July 8, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4593124Abstract: 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: GrantFiled: September 12, 1984Date of Patent: June 3, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 4590263Abstract: 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: GrantFiled: September 30, 1982Date of Patent: May 20, 1986Assignee: James River Graphics, Inc.Inventors: Robert C. Desjarlais, Everett W. Bennett
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Patent number: 4436936Abstract: 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: GrantFiled: June 10, 1982Date of Patent: March 13, 1984Assignee: Ciba-Geigy CorporationInventor: Frederick H. Howell
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Patent number: 4436937Abstract: 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: GrantFiled: October 25, 1982Date of Patent: March 13, 1984Assignee: Shell Oil CompanyInventors: Frank Baardman, Robert van Helden, Margaretha J. de Nie-Sarink
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Patent number: 4405812Abstract: 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: GrantFiled: February 19, 1982Date of Patent: September 20, 1983Assignee: Ethyl CorporationInventors: Walter K. Dean, Bernard R. Meltsner
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Patent number: 4359584Abstract: 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: GrantFiled: September 8, 1980Date of Patent: November 16, 1982Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4351958Abstract: 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: GrantFiled: August 28, 1981Date of Patent: September 28, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kazunori Takahata, Katsuo Taniguchi
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Patent number: 4341903Abstract: 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: GrantFiled: April 13, 1981Date of Patent: July 27, 1982Assignee: Ethyl CorporationInventors: John C. Wollensak, Kryn G. Ihrman, Chester P. Jarema
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Patent number: 4340758Abstract: 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: GrantFiled: July 6, 1981Date of Patent: July 20, 1982Assignee: Chevron Research CompanyInventors: Seymour J. Lapporte, David M. Marquis
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Patent number: 4317931Abstract: 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: GrantFiled: March 5, 1981Date of Patent: March 2, 1982Assignee: Ethyl CorporationInventors: John C. Wollensak, Kryn G. Ihrman, Chester P. Jarema