Preparing Directly By Ring Alkylation Or Dealkylaton Patents (Class 564/409)
  • Patent number: 5659084
    Abstract: Processes for preparing 2-substituted benzaldehydes of general formula (I), wherein: R.sub.1 is CH.sub.2 CH.sub.2 --(L.sub.1).sub.p --(CH.sub.2).sub.q --(L.sub.2).sub.r --CH.sub.2 --(T).sub.2 --Z; L.sub.1 and L.sub.2 are independently CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C; q is 0 to 8; p, r and s are independently 0 or 1; T is O, S, CH.sub.2, CH.dbd.CH, C.tbd.C; and Z is C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl optionally mono substituted with CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylthio, or trifluoromethylthio; and R.sub.2 and A are independently H, CF.sub.3, C.sub.1-4 alkyl, F, Cl, Br or I; are useful for preparing pharmaceutically active compounds.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: August 19, 1997
    Assignees: SmithKline Beecham Corporation, SmithKline Beecham plc
    Inventors: Kerry Joseph Gombatz, Michael Anthony Forth, Jerome Francis Hayes, Michael Barry Mitchell, Stephen Alexander Smith
  • Patent number: 5633407
    Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: May 27, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5618979
    Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 8, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5599995
    Abstract: An electrophotographic photoconductor comprises an electroconductive substrate and a photoconductive layer formed thereon comprising as an effective component at least one pyrenylamine derivative of formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, W, j, k, l, m and n are specifically defined in the specification. Furthermore, a novel pyrenylamine derivative for use in the above electrophotographic photoconductor, an aldehyde compound, which is an intermediate for producing the pyrenylamine derivative, and methods of preparing the pyrenylamine derivative and the aldehyde compound are disclosed.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 4, 1997
    Assignee: Ricoh Company, Ltd.
    Inventors: Chiaki Tanaka, Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada, Hiroshi Adachi
  • Patent number: 5571453
    Abstract: A stabilizer composition useful as an additive for polyether polyols, particularly those employed in the manufacture of polyurethane foams, is provided which comprises a diphenylamine:isobutylene:diisobutylene reaction product, a sterically hindered phenol and a trihydrocarbyl phosphite.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: November 5, 1996
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Lawrence B. Barry, Mark C. Richardson
  • Patent number: 5545715
    Abstract: The present invention provides a flame-retardant resin composition comprising 100 parts by weight of a bromine-containing copolymer composition containing 1 to 40% by weight of bromine, and comprising 0 to 30 parts by weight of a flame-retarding adjuvant and 0.5 to 30 parts by weight of a polyorganosiloxane-reinforced resin component obtained by polymerizing a vinyl monomer (d) in the presence of a polyorganosiloxane polymer. The flame-retardant resin composition of the present invention has attained a remarkably higher flame retardancy by the inclusion of a polyorganosiloxane-reinforced resin. A significant improvement in the dripping phenomenon has also been achieved. Further, this composition exhibits superior impact resistance and moldability, and a superior outer appearance in the formed products.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: August 13, 1996
    Assignee: Japan Synthetic Rubber Co. Ltd.
    Inventors: Hiroyuki Itoh, Masanori Suzuki, Akira Kamiya, Takeki Furuyama
  • Patent number: 5520848
    Abstract: A mixture containing phenothiazines which is obtainable by reacting a mixture of diphenylamines comprising______________________________________ 1 to 5% by weight a) diphenylamine of 8 to 18% by b) 4-tert-butyldiphenylamine weight of 21 to 31% by c) one or more compounds selected from weight of i) 4-tert-octyldiphenylamine ii) 4,4'-di-tert-butyldiphenylamine iii) 2,4,4'-tris-tert-butyldiphenylamine 20 to 31% by d) one or more compounds selected from weight of i) 4-tert-butyl-4'-tert-octyldiphenylamine ii) 2,2'- or 2,4'-di-tert-octyldiphenylamine iii) 2,4-di-tert-butyl-4'-tert-octyldiphenylamine, and 15 to 29% by e) the compound weight of i) 4,4'-di-tert-octyldiphenylamine, or the compounds i) 4,4'-di-tert-octyldiphenylamine and ii) 2,4-di-tert-octyl-4'-tert-butyldiphenylamine, ______________________________________with 1 to 200 mol % of elemental sulfur, in the presence of 0.
    Type: Grant
    Filed: February 7, 1995
    Date of Patent: May 28, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Samuel Evans
  • Patent number: 5451702
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: September 19, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5380946
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. M. Cheng
  • Patent number: 5283363
    Abstract: The invention relates to a new process for the preparation of (hetero)arylalk(en/in)ylamines of the formula (I) ##STR1## in which A represents ethane-1,2-diyl (ethylene, dimethylene, --CH.sub.2 --CH.sub.2 --) or represents ethene-1,2-diyl (ethenylene, vinylene, --CH.dbd.CH--) or represents ethine-1,2-diyl (ethinylene, --C.ident.C--),characterized in that(a) in the event that, in formula (I), A represents ethine-1,2-diyl, halogeno(hetero)aryl compounds of the general formula (II)Ar--X (II)are reacted with aminoalkinyl compounds of the general formula (III) ##STR2## and, if appropriate, (b) in the event that, in formula (I), A represents ethane-1,2-diyl or ethene-1,2-diyl, the new (hetero)aralkinylamines which are obtained by the process step described under (a), of the general formula (Ia), ##STR3## are reacted with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, the definitions applying to Ar, R.sup.1, R.sup.
    Type: Grant
    Filed: January 16, 1992
    Date of Patent: February 1, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Kuhnt, Thomas Himmler, Heinz Ziemann
  • Patent number: 5276194
    Abstract: A process is provided for the catalytic perfluoroalkylation of aromatic compounds, wherein a perfluoroalkyl iodide or mixture of iodides is reacted with an aromatic compound in the presence of an aqueous base, such as an alkali metal hydroxide or carbonate. The use of an aqueous strong base increases the rate of reaction. Further improvements in rate and yield are secured by employing, as the catalyst, a noble metal supported on porous silica microspheres.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: January 4, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Donald D. May
  • Patent number: 5243116
    Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5214186
    Abstract: A process for the preparation of arylidene dyes comprises the reaction of an aromatic amine with an enolate salt of a formylated active methylene compound in the presence of a sulfonyl halide compound. An enol sulfonate is postulated as a reactive intermediate in the reaction. The process gives high yields of products under mild reaction conditions and allows the use of aromatic groups containing substituents such as hydroxy that lead to side reactions and low product yields with previously known methods for making arylidene dyes.
    Type: Grant
    Filed: December 3, 1991
    Date of Patent: May 25, 1993
    Assignee: Eastman Kodak Company
    Inventor: Leslie Shuttleworth
  • Patent number: 5214211
    Abstract: Rare earth pillared clays, and especially cerium and lanthanum aluminum chlorohydrite pillared clays, are quite effective catalysts in the alkylation of diaryl amines at temperatures in the range of 100.degree.-225.degree. C. The catalysts effect alkylation using olefins as the alkylating agent with high conversion and with minimal cracking of either the olefin or the alkylated product. Catalysts may be regenerated by heating in air at temperatures of at least about 550.degree.-600.degree. C. Water in small amounts also modifies the reaction to further reduce cracking although it also reduces the activity of the catalyst.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: May 25, 1993
    Assignee: UOP
    Inventors: Paul R. Kurek, Jennifer S. Holmgren
  • Patent number: 5198595
    Abstract: Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5171915
    Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5171890
    Abstract: A process is disclosed for the preparation of methyl- and ethyl-substituted anilines by contacting anilines of specified formula at about 250.degree.-525.degree. C. and about 10 kPa-10 MPa of pressure in the of presence of a nonbasic metal oxide catalyst which when it is a zeolite has pore dimensions of at least about 0.52 nm and has cages with dimensions greater than about 0.75 nm.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: December 15, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 5132475
    Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of a quaternary ammonium fluoride catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NF where R.sup.1, R.sup.2, and R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: July 21, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Yoel Sasson
  • Patent number: 5126484
    Abstract: A process is disclosed for the preparation of methyl- and ethyl-substituted anilines by contacting anilines of specified formula at about 250.degree.-525.degree. C. and about 10 kPa-10 MPa of pressure in the of presence of a nonbasic metal oxide catalyst which when it is a zeolite has pore dimensions of at least about 0.52 nm and has cages with dimensions greater than about 0.75 nm.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: June 30, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 5124483
    Abstract: Aromatic diamines, such as toluenediamine, are alkylated in the ortho position by heating the diamine in the presence of an aluminum alloy, aluminium chloride and, optionally, zinc, and then reacting with an alkene at elevated temperatures and pressures.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: June 23, 1992
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, V. Rao Durvasula, George E. Hartwell, Kirk D. Anderson, Louis N. Moreno, Nirad N. Shah
  • Patent number: 5103059
    Abstract: Production of alkyl substituted aromatic diamines by reacting triethylaluminum with an aromatic diamine and a chloride ion source in the presence of an olefin is disclosed. The alkyl substituted aromatic diamines are useful as chain extenders in polyurethane processes.
    Type: Grant
    Filed: October 23, 1990
    Date of Patent: April 7, 1992
    Assignee: Ethyl Corporation
    Inventors: Kryn G. Ihrman, Olan W. Mitchell, R. Woodrow Wilson, Jr.
  • Patent number: 5093527
    Abstract: A process is disclosed for the preparation of methyl- and ethyl-substituted anilines by contacting anilines of specified formula at about 250.degree.-525.degree. C. and about 10 kPa-10 MPa of pressure in the of presence of a nonbasic metal oxide catalyst which when it is a zeolite has pore dimensions of at least about 0.52 nm and has cages with dimensions greater than about 0.75 nm.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: March 3, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 5087754
    Abstract: N,N-dialkylanilines can be prepared by reacting the anilines on which they are based with lower alcohols or with the corresponding ethers, at an increased temperature in the gas phase in the presence of a proton-containing zeolite catalyst of the pentasil type having an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of >60, it being advantageous to carry out the alkylation process under a pressure of 2-30 bar.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: February 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Heinrich Pelster, Lothar Puppe, Peter Wimmer
  • Patent number: 5072047
    Abstract: A catalytic intermediate useful in the preparation of ortho-alkylated aromatic amines is prepared by heating an amine in the presence of aluminum metal, zinc metal and aluminum chloride. This catalytic intermediate is used to alkylate aromatic amines which may be the same as or different from the amine used in the catalytic intermediate preparation. In a preferred embodiment, toluenediamine is alkylated in the ortho positions to form diethyltoluenediamine.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: December 10, 1991
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, V. Rao Durvasula, Kirk D. Anderson, Louis N. Moreno, Nirad N. Shah
  • Patent number: 5068435
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using gamma alumina as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.The catalyst is also effective for producing unsymmetrical disubstituted alkyl aromatic amines, e.g., ethyl or propyl toluidine where one ortho position is substituted with a methyl group and the other substituted with an ethyl or propyl group.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: November 26, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 5057625
    Abstract: Mono-ar-tert-butyl toluenediamine is selectively made by heating a mixture of toluenediamine and an aluminum halide of the formula R.sub.n AlX.sub.3-n or R.sub.3 Al.sub.2 X.sub.3 wherein n is 0, 1 or 2 and R is an alkyl containing 1-10 carbon atoms to 150.degree.-225.degree. C. and reacting the mixture with isobutylene at 500-300 psig until the yield of mono-ar-tert-butyl toluene is at or near maximum. Minor amounts of di-tert-butyl toluenediamines which form and are difficult to separate can then be lowered by venting the reaction and continuing to heat at about 130.degree.-200.degree. C. until the di-tert-butyl components are decreased to the desired level forming additional mono-ar-tert-butyl toluenediamine.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Ethyl Corporation
    Inventor: Kryn G. Ihrman
  • Patent number: 5043469
    Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizable aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: August 27, 1991
    Assignee: Eastman Kodak Company
    Inventors: Philip T. S. Lau, Danny R. Thompson
  • Patent number: 5026912
    Abstract: A process for selectively producing ortho-alkylated aromatic amines in high selectivity relative to N-alkylated aromatic amines. The process comprises reacting an aromatic amine, having at least one hydrogen atom in a position ortho to the amine functionality, and an olefin under conditions sufficient to effect an alkylation reaction, in the presence of a zeolite catalyst which has been thermally pretreated by heating the catalyst to a temperature greater than about 500.degree. C. for a period ranging from 0.5 to about 10 hours while sweeping an inert gas over the heated catalyst to remove water and ammonia formed during the thermal treatment, and subsequently recovering the alkylated aromatic amine.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: June 25, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Rakesh Agrawal, Steven R. Auvil
  • Patent number: 5001263
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines where the alkyl substituent is ortho to the amino group by reacting an N-alkylated aromatic amine with a C.sub.2-10 olefin in the presence of a solid phase acidic catalyst, e.g., silica-alumina or a zeolite. High conversion and selectivity is achieved by maintaining a mole ratio of olefin to amine of from about 1-10:1 and an operating pressure of at least 50 psig.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: March 19, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 4973759
    Abstract: Alkylated aromatic amines can be isolated from crude catalyst-containing mixtures of these with olefins by a procedure in which in general equivalent amounts of an inorganic base and water are added to the alkylation mixture, the catalyst is hydrolysed, the water present in the reaction mixture after the hydrolysis is removed by distillation and the solid catalyst residue is separated off. The catalyst-free alkylation mixture which remains is then fed to customary further working up.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: November 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alfons Klein, Helmut Fiege
  • Patent number: 4967001
    Abstract: This invention relates to an improvement in a process for producing tert-butyl-derivatives of aromatic amines, e.g., para-phenylenediamine and toluenediamine by the reaction of isobutylene with the corresponding aromatic diamine in the presence of a highly acidic crystalline alumino-silicate catalyst. The improvement constitutes adding sufficient water to the catalyst to provide at least partial saturation of the catalyst during the reaction.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: October 30, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Robert L. Fowlkes
  • Patent number: 4935545
    Abstract: Alkylated aromatic primary amines undergo disproportionation and transalkylation in the presence of a catalyst comprising activated carbon or unmodified graphite and a Group VIIIA metal at a temperature between 200.degree. C. and 500.degree. C. Suitable Group VIIIA metals are selected from the group consisting of platinum, palladium, nickel, cobalt or mixtures thereof.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: June 19, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrew F. Nordquist, Ronald Pierantiozzi
  • 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: 4914237
    Abstract: This invention relates to an improvement in a fixed bed process for producing tert-butyl-derivatives of aromatic amines, e.g., para-phenylenediamine and toluenediamine by the reaction of isobutylene with the corresponding aromatic diamine in the presence of a highly acidic crystalline alumino-silicate catalyst. The improvement for regenerating the catalyst during operation constitutes adding sufficient water to the catalyst to provide sufficient saturation of the catalyst during the reaction and generally retard the reaction and then substantially decreasing the quantity of added water or reducing the amount of water added.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: April 3, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Rakesh Agrawal
  • Patent number: 4908480
    Abstract: This invention relates to a process for producing mono-ortho-ethyl- aniline in high selectivity and at high conversion using a silica-alumina catalyst. The reaction is carried out using a fixed bed reactor. Diethylaniline derivatives are avoided by maintaining preselected mole ratios of ethylene to aniline, preselected temperatures and preselected reaction times.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: March 13, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 4892974
    Abstract: This invention relates to a process for producing mono-ortho-tert-butyl-aniline in high security selectivity and at high conversion using a silica-containing catalyst. The reaction is carried out using a fixed bed reactor. Di-tert-butyl derivatives are avoided by maintaining preselected mole ratios of isobutylene to aniline, preselected temperatures and preselected reaction times.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: January 9, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 4876377
    Abstract: This invention pertains to an improved process for the alkylation of aromatic amines. The improvement resides in the use with particular aromatic amines and olefins a catalyst which is a highly acidic partially dealuminated zeolite having an increased silica to alumina molar ratio over the original zeolite and an acidity factor of at least 0.3. The partially dealuminated zeolites are preferably exchanged with hydrogen or rare earth metal and are particularly effective for producing an alkylated aromatic amine where the alkyl group is ortho to the amine. The highly acidic partially dealuminated H-mordenite and partially dealuminated HY faujasite are very effective for the alkylation of aniline with propylene.
    Type: Grant
    Filed: March 22, 1988
    Date of Patent: October 24, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Rakesh Agrawal, Steven R. Auvil, Michel Deeba
  • Patent number: 4851579
    Abstract: This present invention is a process for alkylating aromatic amines to form ortho-alkylated products in high selectivity relative to N-alkylated products. Aromatic amines are contacted with an olefin or an alcohol in the presence of an ion exchanged zeolite in which at least a portion of the exchangeable ion sites have been exchanged with Al cations.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: July 25, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ronald Pierantozzi
  • Patent number: 4843175
    Abstract: A process for the preparation of alkylaniline having from about 10 to 30 carbon atoms in the alkyl substituent which comprises reacting aniline with an olefin having from about 10 to 30 carbon atoms in the presence of a Friedel-Crafts catalyst.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: June 27, 1989
    Assignee: Chevron Research Company
    Inventor: Robert Bacskai
  • Patent number: 4824601
    Abstract: Process is described for the production of a liquid antioxidant composition by reaction of diphenylamine with diisobutylene comprising reacting diphenylamine with diisobutylene in a molar ratio of from 1:1.1 to 1:2.5 and in the presence of an acid activated earth catalyst, while ensuring that the concentration of diisobutylene remains substantially constant throughout the reaction period at a reaction temperature of at least 160.degree. C., the reaction being effected for such a period that the content of 4,4'-dioctyldiphenylamine in the reaction mass, excluding catalyst, is below 25% by weight; and removing catalyst and unreacted diisobutylene; the product of this process; and the use of this product as a stabilizer for organic material against oxidative degradation.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: April 25, 1989
    Assignee: Ciba-Geigy-Corporation
    Inventor: Janet Franklin
  • Patent number: 4804784
    Abstract: A process is disclosed for the preparation of methyl- and ethyl-substituted anilines by contacting anilines of specified formula at about 250.degree.-525.degree. C. and about 10 kPa-10 MPa of pressure in the of presence of a nonbasic metal oxide catalyst which when it is a zeolite has pore dimensions of at least about 0.52 nm and has cages with dimensions greater than about 0.75 nm.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: February 14, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4801751
    Abstract: Alkylated aromatic primary amines undergo disproportionation and transalkylation in the presence of a carbon-containing catalyst at a temperature between 200.degree. C. and 500.degree. C. The carbon-containing catalyst may have carbon as the only active component, or optionally, may also contain a Group VIIIA metal, such as platimum, palladium, nickel, cobalt or mixtures thereof.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: January 31, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrew F. Nordquist, Ronald Pierantozzi
  • Patent number: 4795833
    Abstract: A process is disclosed for preparing an isomeric mixture of methyl-substituted aniline comprising contacting at least one of said analines with a specified zeolite catalyst.
    Type: Grant
    Filed: February 4, 1987
    Date of Patent: January 3, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard S. Mitchell
  • Patent number: 4760184
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In accordance with this process an aromatic amine is reacted with an olefin, diolefin or an alcohol using a non-zeolitic molecular sieve as a catalyst. Under the conditions of the process the catalyst is extremely active, and with aromatic amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: July 26, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ronald Pierantozzi
  • Patent number: 4760185
    Abstract: m-Phenylenediamines are alkylated in the orthoposition by heating them with an Al/Zn alloy and aluminium chloride, and reacting them with lower alkenes at elevated pressures and temperatures when the evolution of hydrogen is complete.
    Type: Grant
    Filed: May 6, 1986
    Date of Patent: July 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Becker
  • Patent number: 4749813
    Abstract: 4-Alkyl-2-trifluoromethylanilines, in particular the 4-isopropyl derivative, are starting materials for preparing valuable azo dyestuffs. While the nonionic dyestuff types can preferably be used in transfer printing synthetic hydrophobic fibre materials, the sulpho-containing dyestuffs--in particular those based on "gamma acid"--are suitable for dyeing polyamides.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: June 7, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Gerhard Wolfrum
  • Patent number: 4740620
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using an acidic crystalline molecular sieve as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: April 26, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dale D. Dixon, William F. Burgoyne, Jr.
  • Patent number: 4739121
    Abstract: Ortho-para-alkylated diphenylamines are prepared utilizing an improved, one-stage process wherein the diphenylamines are ortho-alkylated by reaction with a first olefin in the presence of an aluminum complex as the catalyst, and are subsequently para-alkylated by reaction with a second olefin using a Friedel-Crafts aluminum catalyst. The para-alkylation is carried out without prior isolation or solvent washing of the ortho-alkylated diphenylamine intermediates.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: April 19, 1988
    Assignee: The B. F. Goodrich Company
    Inventor: Chong-Kuang Shaw
  • Patent number: RE33549
    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: January 9, 1987
    Date of Patent: March 5, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert