Processes Patents (Class 568/309)
  • Patent number: 5041616
    Abstract: Disclosed is a process for the preparation of alkyl aryl ketones, cycloalkyl aryl ketones and diaryl ketones by contacting an aromatic compound with an aliphatic, cycloaliphatic or aromatic carboxylic acid in the presence of a catalytic amount of an organic sulfonic acid while removing the water of reaction as an azeotrope from the reaction mixture.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles E. Sumner, Jr.
  • Patent number: 4967009
    Abstract: This invention relates to a method for manufacturing aromatic compounds having the following formula (II) comprising the step of reacting an unsaturated aromatic compound having the following formula (I) with an aryl compound containing an iodosyl group or the salt thereof within a temperature range of from -50.degree. to 200.degree. C.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: October 30, 1990
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Kouichi Iwamoto
  • Patent number: 4960945
    Abstract: The present invention relates to a process for the production of halobenzophenone derivatives represented by the following formula (II): ##STR1## wherein X and Y are the same or different and are independently F, Cl, Br or I, m stands for an integer of from 1 to 4 and n stands for an integer of from 0 to 4. The process comprises oxidizing a compound with an aqueous nitric acid solution having a specific gravity of from 1.32 to 1.47 at 20.degree. C., said compound being represented by the following formula (I): ##STR2## wherein X, Y, m and n have the same meanings as defined above and Z is Cl or H.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: October 2, 1990
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Takashi Terauchi, Kazuo Yoshida, Yoshihisa Machida, Nobuyuki Okubo, Yutaka Konai
  • Patent number: 4945183
    Abstract: Preparation of 4-phenylquinol by oxidation of biphenyl using an aqueous mixture of cerium methanesulfonic acid in which the ratio of cerous to ceric methanesulfonic acid is in the rate of 0.2 to 50 mole percent.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: July 31, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Edward F. Moran, Jr.
  • Patent number: 4933495
    Abstract: The present invention relates to a process for the production of 3-mono or 3,5-disubstituted-4-acetoxystyrene wherein the 3- or 3,5-substitution is independently C.sub.1 to C.sub.10 alkyl, chlorine, bromine, iodine, --NO.sub.2, --NH.sub.2, or --SO.sub.3 H, a process for its polymerization, hydrolysis, and use in a variety of compositions.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: June 12, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Richard Vicari, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4874899
    Abstract: Unsaturated ketones of the formula ##STR1## and saturated ketones of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl of 1 to 12 carbon atoms or a cycloalkyl, aryl, aralkyl or alkylaryl radical which inturn may be substituted, or R.sup.1 and R.sup.3 or R.sup.2 and R.sup.3, together with the carbon atoms to which they are bonded, may form a cycloalkane, are prepared by a process in which a 5-methylene-1,3-dioxolanone which is substituted in the 4-position and is of the forumla ##STR3## where R.sup.1, R.sup.2 and R.sup.3 have the above meanings, (a) for the preparation of an unsaturated ketone, is converted in the presence of a zeolite, of a phosphate having a zeolite structure and/or of B, Ce, Fe, Zr or Sr phosphate as catalysts and (b) for the preparation of a saturated ketone, is converted in the presence of the same catalysts which additionally carry one or more hydrogenation components.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: October 17, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Leopold Hupfer, Kurt Schneider
  • Patent number: 4814508
    Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and a Lewis base, for example, N,N-dimethylformamide, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: March 21, 1989
    Assignee: Raychem Corporation
    Inventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
  • Patent number: 4772714
    Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: September 20, 1988
    Assignee: Agency of Industrial Science & Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4769464
    Abstract: The invention relates to a process for the preparation of monocarbonyl or biscarbonyl compounds by reacting organic carbon compounds having one or more olefinic or aromatic double bonds in the molecule with the equivalent amount of ozone and by subsequently catalytically hydrogenating the ozonization products, wherein the peroxide-containing ozonization solution is fed continuously into a suspension of the hydrogenation catalyst in a lower aliphatic alcohol, while a peroxide content of not more than 0.1 mole/l is maintained, and the ozonization products are continuously cleaved reductively to give the corresponding carbonyl compounds.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: September 6, 1988
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventor: Alexander Sajtos
  • Patent number: 4749804
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: June 7, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: George C. Schloemer
  • Patent number: 4734528
    Abstract: The present invention provides a method for preparing 3-ethylbenzophenone in a high purity which comprises the steps of alkylating benzene with ethylene in the presence of an alkylating catalyst to obtain an alkylated product composed mainly of unreacted benzene, ethylbenzene, polyethylbenzenes and heavier substances; subjecting the alkylated product to rectification in order to recover therefrom a fraction which has a temperature range of boiling points within the range of 275.degree. to 310.degree. C.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: March 29, 1988
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Atsushi Sato
  • Patent number: 4670108
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic or alkyl aromatic compound with ceric methanesulfonate in an aqueous, weakly acidic solution containing an organic cosolvent which has at least 2 percent solubility in water under reaction conditions and is substantially inert with respect to the acidic, oxidizing conditions.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: June 2, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4647349
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic and alkyl aromatic compound with an aqueous solution of ceric trifluoromethanesulfonate having from at least 0.75 to 7 molar concentration of free acid of trifluoromethanesulfonic acid and at least 0.2 molar cerium ion concentration. The present process provides a highly effective means of forming the desired carbonyl containing product in good yields and high selectivity.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: March 3, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4639298
    Abstract: A process for oxidizing aromatic and alkyl substituted aromatic compounds to carbonyl containing compounds by contacting an aromatic and alkyl aromatic compound with an aqueous solution of ceric methanesulfonate having from at least 1.5 to 9 molar concentration of free acid of methanesulfonic acid and at least 0.2 molar cerium ion concentration. The present process provides a highly effective means of forming the desired carbonyl containing product in good yields and high selectivity.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: January 27, 1987
    Assignee: W. R. Grace & Co.
    Inventors: Robert P. Kreh, Robert M. Spotnitz
  • Patent number: 4638094
    Abstract: A phenylacetone or its derivative having the general formula (I): ##STR1## wherein X, Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): ##STR2## wherein X, Y, and Z are as defined above, with an alkyl nitrite having the general formula (III):RONO (III)wherein R is an aliphatic, aromatic, or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned
    Type: Grant
    Filed: July 29, 1983
    Date of Patent: January 20, 1987
    Assignee: Ube Industries, Ltd.
    Inventors: Mamoru Nakai, Takuji Enomiya
  • Patent number: 4612402
    Abstract: A process for the oxidation of olefinically unsaturated substrates of the formula R--CH.dbd.CH-R' wherein R and R' are independently selected from members of the group consisting of H, alkyl, alkenyl, cycloalkyl, aryl and halo-, cyano- and ether-substituted alkyl, alkenyl, cycloalkyl and aryl which comprises reacting in the liquid phase said substrate with a rhodium nitro complex of the formula L.sub.n RhNO.sub.2, wherein n is 4 or 5 and wherein L.sub.n represents any combination of monodentate, bidentate, tridentate and tetradentate ligands such as to provide four or five bonding sites, for a time sufficient to produce an oxidized product of the formula RCH.sub.2 C(O)R' and a reduced product of the formula L.sub.n RhNO is disclosed. A preferred embodiment of the process wherein the rhodium nitro complex contains at least one ligand replaceable by olefin to be oxidized and operates to produce the oxidized product RCH.sub.2 C(O)R' in the absence of other Group VIII metals as co-catalyst is also disclosed.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: September 16, 1986
    Assignee: Allied Corporation
    Inventors: Deborah A. Muccigrosso, Frank Mares, Steven E. Diamond, Jeffrey P. Solar
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4603221
    Abstract: 6-Alkoxytetralones are prepared by gradually adding a persulfate to a heated mixture of a 6-alkoxytetralin, a salt of a divalent metal, and a tertiary amine and maintaining the 6-alkoxytetralin in intimate admixture with the persulfate until it has been oxidized to the corresponding 6-alkoxytetralone. The reaction is preferably conducted in solution or dispersion. Preferred reaction ingredients are 6-methoxytetralin, cupric sulfate, an alkylpyridine, and sodium persulfate.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: July 29, 1986
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 4602097
    Abstract: Photoinitiators of the formulaG--O--(CH.sub.2 CH.sub.2 O).sub.n --CH.sub.2 --CH.sub.2 --O--Qwherein G is a photoinitiator moiety, R is hydrogen or lower alkyl, n has a value of at least 10, and Q is G or a lower alkyl are soluble in water and common organic solvents and are useful in polymerization systems employed in coatings used in screen printing.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: July 22, 1986
    Assignee: Ulano Corporation
    Inventor: John R. Curtis
  • Patent number: 4568768
    Abstract: A method for producing m-hydroxy-acetophenone which comprises allowing m-(2-hydroxy-2-propyl)cumene hydroperoxide to react at 30.degree. to 100.degree. C. in the presence of an aqueous solution containing 0.001 to 1 mole of iron salt per mole of said compound, 0.01 to 4 moles of copper salt per mole of said iron salt, and mineral acid to give m-(2-hydroxy-2-propyl)acetophenone, then allowing the resulting compound to react at 30.degree. to 95.degree. C. in the presence of 1 to 20 moles of 5 to 90% by weight aqueous hydrogen peroxide solution per mole of said compound and acid catalyst to form m-(2-hydroperoxy-2-propyl)acetophenone, and further subjecting the product formed to acid decomposition. m-Hydroxyacetophenone is an important intermediate in the fields of pharmaceuticals, agricultural chemicals, dyestuffs and the like.
    Type: Grant
    Filed: December 13, 1984
    Date of Patent: February 4, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Nakamura, Seiichi Kai, Nobuharu Kono
  • Patent number: 4560804
    Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4560805
    Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4410705
    Abstract: A process for preparing substituted or unsubstituted benzoxazoline compound by reacting ammonia, a cycloalkanone and oxygen in the presence of metal cations.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: October 18, 1983
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • Patent number: 4402862
    Abstract: The invention relates to the stabilization against water uptake of hygroscopic salts useful as catalysts by formation of anhydrous adducts with particulate support materials in order to facilitate manipulation and storage. The adducts comprise a particulate support material and a hygroscopic salt of a species of formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 N, R.sup.1 R.sup.2 R.sup.3 R.sup.4 P, R.sup.1 R.sup.2 R.sup.3 R.sup.4 As, wherein R.sup.1 R.sup.4 which may be identical or different represent hydrogen or alkyl or aryl groups, or of Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Cu.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: September 6, 1983
    Assignee: National Research Development Corporation
    Inventor: James H. Clark
  • Patent number: 4370497
    Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.
    Type: Grant
    Filed: August 7, 1980
    Date of Patent: January 25, 1983
    Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
  • Patent number: 4297514
    Abstract: Compounds having activated methylene radicals are oxidized to various oxidation products by an improved process comprising contacting the compound with an oxidizing agent and a base of sufficient strength to deprotonate at least one hydrogen from the activated methylene radical in the presence of a catalytic amount of a synergistic combination of elemental carbon and a phase-transfer catalyst. For example, flourene is oxidized to flourenone by contacting the flourene with elemental oxygen and sodium hydroxide in the presence of a catalytic amount of the synergistic combination of charcoal and benzyltriethyl-ammonium chloride.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: October 27, 1981
    Assignee: The Dow Chemical Company
    Inventor: King W. Ma
  • Patent number: 4263458
    Abstract: 4,4'-difluoro-benzophenone is prepared from 4,4'-diamino-diphenylmethane by diazotization in anhydrous or concentrated aqueous hydrogen fluoride and decomposition of the diazonium fluoride thus produced in the presence of nitrous acid or nitrite as oxidizing agent.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: April 21, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventors: Roy D. Bowden, Leslie Burgess, Raymond J. Clark