Processes Patents (Class 564/298)
  • Patent number: 5578744
    Abstract: A catalytically active gel is described consisting of a silica matrix with uniform porosity, monomodal pore distribution and high surface area, within which one or metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: November 26, 1996
    Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.
    Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
  • Patent number: 5498791
    Abstract: A synergistic mixture of a carbonate and/or bicarbonate with a phosphonate, especially an organoamino methylene phosphonate or an N-oxide thereof, inhibits or reduces nitrosamine contamination during preparation, storage and/or heating of products which are susceptible to contamination with nitrosamine.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: March 12, 1996
    Assignee: Albright & Wilson, Limited
    Inventors: Michael Blezard, Glyn R. Jones, Moharam Ghadimi
  • Patent number: 5498373
    Abstract: Amine oxide surfactants contaminated with nitrite are treated under acidic conditions with materials such as maleic acid and diethylenetriaminepentaacetate (DTPA) to reduce nitrite levels below 1 ppm. Thus, C.sub.12-13 dimethyl amine is oxidized with hydrogen peroxide in the presence of maleic acid and DTPA to reduce nitrite levels. The resulting nitrite-free amine oxide is employed in various detergent compositions.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 12, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Larry E. Miller, Gene P. Hawkins, Bernard G. Durham
  • Patent number: 5466870
    Abstract: Amine oxide surfactants contaminated with nitrite are treated under acidic conditions with materials such as maleic acid and diethylenetriaminepentaacetate (DTPA) to reduce nitrite levels below 1 ppm. Thus, C.sub.12-13 dimethyl amine is oxidized with hydrogen peroxide in the presence of maleic acid and DTPA to reduce nitrite levels. The resulting nitrite-free amine oxide is employed in various detergent compositions.
    Type: Grant
    Filed: August 5, 1994
    Date of Patent: November 14, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Larry E. Miller, Gene P. Hawkins, Bernard G. Durham
  • Patent number: 5442113
    Abstract: A synergistic mixture of a carbonate and/or bicarbonate with a phosphonate, especially an organoamino methylene phosphonate or an N-oxide thereof, inhibits or reduces nitrosamine contamination during preparation, storage and/or heating of products which are susceptible to contamination with nitrosamine.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: August 15, 1995
    Assignee: Albright & Wilson Limited
    Inventors: Michael Blezard, Glyn R. Jones, Moharam Ghadimi
  • Patent number: 5399296
    Abstract: Disclosed are solid, concentrated, amine oxide surfactant compositions containing amine oxide- maleic acid salts. The molar ratio of maleic acid to amine oxide in such salts is about a 1:1. The salts are soluble in water at 25.degree. C. at a pH of above the pKa of the amine oxide. Also disclosed is a process for preparing such solid amine oxide surfactant compositions, which process comprises admixing maleic acid and amine oxide surfactants in at least about a 1:1 molar ratio, at a pH of at least about 1 units less than the pKa of the amine oxide, to thereby form a visible precipitate therein. The precipitate is separated from the mixture, preferably by mechanical means, and dried. The dried precipitate is a maleic acid-amine oxide salt which can be incorporated into cleaning products, especially solid or granular cleaning products, as a solid, concentrated source of amine oxide surfactant.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: March 21, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Thomas J. Wierenga, Raymond D. Young
  • Patent number: 5389306
    Abstract: Disclosed is a process for making solid formulations containing amine oxide surfactants. Maleic acid, or a water soluble salt thereof, is admixed with an aqueous liquid amine oxide formulation, which formulation preferably contains from about 20% to about 40% by weight of an amine oxide surfactant. The molar ratio of maleic acid to amine oxide surfactant is at least about 1:1. Admixture pH is maintained at or below, or reduced to at least, about 1 unit below the pKa of the amine oxide to form a visible precipitate therein. The precipitate is separated from the mixture, preferably by mechanical means, and dried. The dried precipitate is a maleic acid-amine oxide salt which can be incorporated into cleaning products, especially solid or granular cleaning products, as a source of amine oxide surfactant.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: February 14, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Thomas J. Wierenga, Raymond D. Young
  • Patent number: 5359139
    Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with ascorbic acid.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: October 25, 1994
    Assignee: Albemarle Corporation
    Inventors: Kim R. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5324857
    Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: June 28, 1994
    Assignee: Solvay Interox
    Inventor: Noel S. Shehad
  • Patent number: 5292955
    Abstract: Novel perhydrates having utility as surfactants and bleaching agents are obtained by reacting an anhydrous amine oxide or an amine oxide monohydrate with hydrogen peroxide in such proportions as to provide a compound corresponding to the formula RR'R"NO.multidot.xH.sub.2 O.multidot.yH.sub.2 O.sub.2 in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons; x is 0 or 1; y is 1 or 2; and x+y is .ltoreq.2.
    Type: Grant
    Filed: June 22, 1992
    Date of Patent: March 8, 1994
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5292954
    Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being an alkylphenol ethoxylate or other compound corresponding to the formula Z[OC(Z')HCH.sub.2 ].sub.m OH in which Z is an alkylphenyl group wherein the alkyl group contains 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and m is an integer of 1-100. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: March 8, 1994
    Assignee: Ethyl Corporation
    Inventors: James E. Borland, Joe D. Sauer, Kim R. Smith
  • Patent number: 5254735
    Abstract: A solid amine oxide is prepared by reacting a tert-amine with at least a stoichiometric amount of an aqueous hydrogen peroxide having a concentration of at least 50% by weight in the presence as the reaction medium of a normally gaseous material which (a) has a critical temperature <160.degree. C. and a critical pressure <12 MPa, (b) is in a liquefied, densified, or supercritical state in which it has a density of at least 0.1 g/cc, and (c) is present in an amount sufficient to maintain the reaction mixture stirrable throughout the reaction.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, Y.-D. Mark Chen, Rebecca F. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5223644
    Abstract: Bicarbonates and/or carbonates are used in greater than catalytic amounts to inhibit the formation of nitrosamines during the preparation, storage and/or use of amine oxides.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: June 29, 1993
    Assignee: Albright & Wilson Limited
    Inventors: Michael Blezard, Glyn R. Jones
  • Patent number: 5208374
    Abstract: A non-aromatic tert-amine is oxidized with hydrogen peroxide at about 20.degree.-100.degree. C. by a carbon dioxide-accelerated high solids process in which discoloration of the amine oxide product is minimized by diluting the carbon dioxide before allowing it to contact the reaction mixture so that the entire reaction is conducted in an atmosphere composed of carbon dioxide and an amount of inert gas, such as nitrogen or air, which is at least equal in volume to the amount of carbon dioxide.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: May 4, 1993
    Assignee: Ethyl Corporation
    Inventors: James E. Borland, Fred J. Impastato, Kim R. Smith
  • Patent number: 5164121
    Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a normally liquid polyethylene glycol as the sole organic solvent. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: November 17, 1992
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5130488
    Abstract: Discrete tert-amine oxides, including non-hygroscopic tert-amine oxide dihydrates, are prepared by (A) reacting a concentrated aqueous hydrogen peroxide with a tert-amine corresponding to the formula RR'R"N in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; and R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons in a reaction mixture which is maintained stirrable throughout the reaction by the use, at least during the latter part of the reaction, of an organic solvent which solubilizes the reaction mixture at the reaction temperature but permits precipitation of the tert-amine oxide at a lower temperature and (B) adjusting the water content of the product, if necessary, to achieve a water/tert-amine oxide mol ratio not higher than about 2.1/1 before recovering the tert-amine oxide.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: July 14, 1992
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland
  • Patent number: 5120469
    Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being a fatty alcohol ethoxylate or other compound corresponding to the formula Z[OC(Z')HCH.sub.2 ].sub.m OH in which Z is an alkyl group containing 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and m is an integer of 1-100. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: June 9, 1992
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland, Joe D. Sauer
  • Patent number: 5087752
    Abstract: The subject invention relates to a method of synthesizing nitroxides from secondary amines. This method uses a suitable dioxirane compound such as dimethyldioxirane (DMD), which is relatively stable and simple to synthesize, as the oxidizing agent. A quantity of a secondary amine having no hydrogen atoms directly attached to the alpha carbon atoms is mixed with a 2x molar ratio of the dioxirane. In a first reaction, the secondary amine is oxidized to form a hydroxylamine; in a second reaction, the hydroxylamine is further oxidized to form a nitroxide. When the dioxirane loses an oxygen atom it converts into a ketone; for example, dimethyldioxirane is converted into acetone. This is very convenient, since the ketone byproduct is a solvent that can be easily removed after the reaction without causing interfering reactions. This method provides a simple, highly selective, rapid reaction with very high yields.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: February 11, 1992
    Assignee: Curators of the University of Missouri
    Inventors: Robert W. Murray, Megh Singh
  • Patent number: 5082940
    Abstract: Aromatic tertiary amines are oxidized by means of hydrogen peroxide in an inert solvent medium in the presence of a catalyst selected from metal selenium and compounds of selenium.The process is applied to the preparation of oxides of heterocyclic aromatic tertiary amines and oxides of non-heterocyclic tertiary amines, in which the nitrogen atom is substituted by at least 1 aromatic nucleus.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: January 21, 1992
    Assignee: Interox (Societe Anonyme)
    Inventors: Franz Legrand, Andre Lecloux, Paul Deschrijver
  • Patent number: 5075501
    Abstract: Novel compounds which have particular utility in the preparation of dry formulations, such as laundry powders, are mixed tert-amine oxides wherein the molecules correspond to the formula RR'R"NO.multidot.nH.sub.2 O in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons; and n is 0, 1, or 2; at least some of the molecules being dihydrate molecules. The pure dihydrates are non-hygroscopic solids.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: December 24, 1991
    Assignee: Ethyl Corporation
    Inventors: James E. Borland, Kim R. Smith
  • Patent number: 5071594
    Abstract: A free-flowing granular heavy duty laundry detergent is made by blending with a detergent builder (e.g. Zeolite A) and optional other ingredients a discrete tert-amine oxide wherein the molecules correspond to the formual RR'R"NO.2H.sub.2 O in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; and R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: December 10, 1991
    Assignee: Ethyl Corporation
    Inventors: James E. Borland, Kim R. Smith
  • Patent number: 5068430
    Abstract: Amine oxides, such as amine oxide dihydrates, which have become discolored by being prepared from tert-amines and hydrogen peroxide in a liquid medium constituting not more than 50% of the weight of the reaction mixture and in the presence of carbon dioxide are bleached by exposing them to visible light, preferably incandescent light having a luminosity of at least about 1750 lumens.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: November 26, 1991
    Assignee: Ethyl Corporation
    Inventors: James E. Borland, Y.-D. Mark Chen, Joe D. Sauer, Kim R. Smith, Rebecca F. Smith
  • Patent number: 5055614
    Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being a fatty alkanolamide corresponding to the formula ZC(O)NZ'Z" in which Z is an alkyl group containing 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and Z" is a hydroxyalkyl group containing 1-3 carbons. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: October 8, 1991
    Assignee: Ethyl Corporation
    Inventors: Joe D. Sauer, Kim R. Smith, James E. Borland
  • Patent number: 5055232
    Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained be reacting a tertamine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being a fatty alkanolamide corresponding to the formula ZC(O)NZ'Z" in which Z is an alkyl group containing 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and Z" is a hydroxyalkyl group containing 1-3 carbons. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: October 8, 1991
    Assignee: Ethyl Corporation
    Inventors: Joe D. Sauer, Kim R. Smith, James E. Borland
  • Patent number: 5023376
    Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from the problems of in situ generation of nitrosamines, which are allegedly carcinogens, as impurities and impaired product formation, especially in the presence of transition metals.The problems can be ameliorated by employing a selected range of alkyleneaminopoly(methylenephosphonic acid) compounds such as cyclohexane-1,2-diaminotetra(methylenephosphonic acid).
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: June 11, 1991
    Assignee: Interox America
    Inventors: Noel S. Shehad, Laurie L. Dussack, Dirk van Hemelrijk
  • Patent number: 4970341
    Abstract: A process for accelerating the oxidation of tert-amines by hydrogen peroxide by conducting the reaction in the presence of an ascorbic acid promoter.
    Type: Grant
    Filed: February 24, 1987
    Date of Patent: November 13, 1990
    Assignee: Ethyl Corporation
    Inventor: Teresa K. Summerford
  • Patent number: 4970340
    Abstract: A highly concentrated aqueous solution of a di-C.sub.6-20 alkyl methylamine oxide containing at least 50 weight percent of the amine oxide can be made without gel formation by reacting at least 40 weight percent aqueous hydrogen peroxide with a di-C.sub.6-20 alkyl methyl or ethylamine. These concentrated solutions offer large freight savings in shipping the amine oxides to remote locations.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: November 13, 1990
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4960934
    Abstract: The reaction of aqueous hydrogen peroxide with tert-amines to yield tert-amine oxides is catalyzed by the addition of a promoter amount of ammonium carbonate, ammonium bicarbonate or ammonium carbamate or mixtures thereof.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: October 2, 1990
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, Joe D. Sauer
  • Patent number: 4942260
    Abstract: Amine oxides which have low levels of nitrosamines or are substantially-free of nitrosamines are made by reacting tert-amines with hydrogen peroxide in the presence of carbon dioxide and aluminum metal.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: July 17, 1990
    Assignee: Ethyl Corporation
    Inventors: Kathleen S. Laurenzo, Joe D. Sauer
  • Patent number: 4889954
    Abstract: Tertiary amines are converted to amine oxides in high conversion and at a faster rate by including dialkylcarbonate in the reaction of the tert-amine with aqueous hydrogen peroxide. Ascorbic acid can be used as a co-catalyst.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: December 26, 1989
    Assignee: Ethyl Corporation
    Inventors: Kathleen S. Laurenzo, Dennis P. Bauer
  • Patent number: 4748275
    Abstract: A solid non-hygroscopic flakeable di-C.sub.14-30 alkyl C.sub.1-2 alkylamine oxide is made by reacting di-C.sub.14-30 alkyl C.sub.1-2 alkylamine with aqueous hydrogen peroxide containing at least 40 weight percent H.sub.2 O.sub.2 in the absence of a solvent.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: May 31, 1988
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, James E. Borland
  • Patent number: 4661433
    Abstract: Aryl nitrones, of the type used in contrast enhancement photolithography techniques, are stabilized by adding thereto a drying agent such as molecular sieve, silica gel or an alkylalkoxysilane. The resulting compositions are substantially storage stable.
    Type: Grant
    Filed: December 31, 1984
    Date of Patent: April 28, 1987
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 4659565
    Abstract: Shampoo containing a di-C.sub.6-18 primary alkyl methylamine oxide hair conditioning agent, e.g. didecylmethylamine oxide, is very effective in improving hair body and flyaway control.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: April 21, 1987
    Assignee: Ethyl Corporation
    Inventors: Kim R. Smith, Raymond O. Johannessen, James E. Borland
  • Patent number: 4650904
    Abstract: A process for producing an aqueous solution of a straight-chain alkyl tertiary amine oxide and a branched-chain alkyl tertiary amine oxide by reacting aliphatic tertiary amines with an aqueous solution of hydrogen peroxide is disclosed. In this process, a tertiary amine which mainly consists of a branched-chain tertiary amine is first reacted with excess hydrogen peroxide, and then, a straight-chain alkyl tertiary amine which is substantially free of a branched-chain alkyl group is added to the reaction mixture for permitting further reaction with hydrogen peroxide. The process achieves a high overall conversion of the starting amines, and the final product has an extremely low level of residual hydrogen peroxide.
    Type: Grant
    Filed: November 30, 1984
    Date of Patent: March 17, 1987
    Assignee: Mitsubishi Petrochemical Company, Limited
    Inventor: Koichi Fujita
  • Patent number: 4588522
    Abstract: Betaine-amine oxides of the formula ##STR1## in which R denotes alkyl, alkenyl or hydroxyalkyl, each of which has 8-22 carbon atoms, R.sup.1 denotes hydrogen or methyl, R.sup.2 denotes ethylene, propylene or 2-hydroxypropylene, R.sup.3, R.sup.4 and R.sup.5 can be identical or different and denote C.sub.1 -C.sub.3 -alkyl or a group of the formula ##STR2## or R.sup.3 denotes a group of the formula --R.sup.2 --BR.sup.4 R.sup.5, X denotes a direct bond or a group of the formula--CO--,A and B denote a group of the formulae ##STR3## it being necessary for at least one amine oxide group and at least one betaine group to be present, a denotes 0 or 1, b denotes 1, 2 or 3, n denotes a number from 0 to 10 and m denotes 1, 2 or 3. These compounds are obtained by partially quaternizing the parent polyamines with the alkali metal salt of an .omega.-halogenocarboxylic acid and then oxidizing the non-quaternized nitrogen atoms. These betaine-amine oxides are suitable for use as surfactants in cleansing agents.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: May 13, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
  • Patent number: 4565891
    Abstract: A process for the catalytic oxidation of nonaromatic tertiary amines to the respective amine oxides is disclosed. An aqueous solvent system containing the tertiary amine is formed with an initial pH about equal to or greater than the pKa of the tertiary amine. This aqueous system is contacted with gaseous molecular oxygen at an oxygen partial pressure of at least about 50 psi and a temperature of at least about 80.degree. C. in the presence of certain octacyanomolybdate or iron (III) salts. The resulting oxidation converts the tertiary amine to the respective amine oxide in good yield.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: January 21, 1986
    Assignee: The Procter & Gamble Company
    Inventors: Paul E. Correa, Dennis P. Riley
  • Patent number: 4504666
    Abstract: Disclosed is an improvement in process for oxidizing an aromatic amine to form an aromatic amine oxide wherein a reaction mixture of the aromatic amine and a peracid is formed and maintained under non-aqueous conditions at a temperature and for a time adequate until substantially all of the aromatic amine is formed into said aromatic amine oxide. The provision for eliminating water from the reaction mixture leads to near quantitative yields of aromatic amine oxide.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: March 12, 1985
    Assignee: Sherex Chemical Company, Inc.
    Inventors: Gary W. Earl, Howard M. Hickman
  • Patent number: 4492642
    Abstract: Lubricant and liquid fuel compositions containing a product made by reacting a borating agent with an ammoninated hydrocarbyl epoxide are provided. The invention also provides the product per se and a method of reducing fuel consumption in an internal combustion engine using fuel and lubricant compositions containing same.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: January 8, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky
  • Patent number: 4425243
    Abstract: Foaming agents for use in oil and gas production comprising n-octyl dimethylamine oxide, n-decyl dimethylamine oxide, branched decyl dimethylamine oxide, and mixtures thereof, all of which generate copious quantities of stable foam even in the presence of brine and hydrocarbons.
    Type: Grant
    Filed: October 21, 1982
    Date of Patent: January 10, 1984
    Assignee: Millmaster Onyx Group, Inc.
    Inventors: Harold A. Green, Morris Weinstein, Kenneth W. Prodo
  • Patent number: 4416808
    Abstract: Bis-betaine-amine oxides of the formula ##STR1## in which R is a saturated or an olefinically unsaturated hydrocarbon radical having 1 to 3 double bonds and 8 to 22 carbon atoms,n.sup.1 and n.sup.2 each is an integer of from 2 to 3, n.sup.1 and n.sup.2 optionally being identical or different,m.sup.1 and m.sup.2 each is an integer of from 1 to 4, m.sup.1 and m.sup.2 optionally being identical or different, anda, b, c and d, being identical or different, each is a number of from 1 to 5, with the proviso that the sum (a+b+c+d) is at most 10.The compounds are prepared from primary amines of the formula RNH.sub.2, by dicyanoalkylation, hydrogenation, ethoxylation, reaction with alkali metal salts of .omega.-halocarboxylic acids, and subsequent oxidation with hydrogen peroxide. They are surfactants of mild action and suitable for formulating cosmetic and industrial cleaning agents.
    Type: Grant
    Filed: November 8, 1982
    Date of Patent: November 22, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
  • Patent number: 4415488
    Abstract: Triamine-trioxides of the formula ##STR1## in which R denotes a saturated or an olefinically unsaturated hydrocarbon radical which has 1 to 3 double bonds and 8 to 22 carbon atoms, n.sup.1 and n.sup.2 represent an integer from 2 to 3, and n.sup.1 and n.sup.2 can be identical or different, and a, b, c and d, which are identical or different, each is a number from 1 to 5, with the proviso that the sum (a+b+c+d) should be at most 10.The compounds are prepared from primary amines of the formula RNH.sub.2 by dicyanoalkylation, hydrogenation, ethoxylation and oxidation with hydrogen peroxide. They are suitable for formulating industrial and also cosmetic cleaning agents.
    Type: Grant
    Filed: November 8, 1982
    Date of Patent: November 15, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Blaschke, Alwin Reng, Jochen M. Quack
  • Patent number: 4275236
    Abstract: Disclosed are tertiary amine oxides which comprise an amine oxide nucleus substituted with an organic group and with two hydroxy groups which have carbon atoms in at least the .alpha., .beta. and .gamma. positions, a hydroxyl group on the .beta.-carbon atom, and have an effective chain length of at least 4 carbon atoms, said amine oxide being capable of being provided in ostensibly anhydrous form and being capable of being made at a concentration by weight of at least about 80% by oxidizing the corresponding tertiary amine with an oxidizing agent without solvent and without gelling during said oxidation.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: June 23, 1981
    Assignee: Sherex Chemical Company, Inc.
    Inventors: Gary W. Earl, Howard M. Hickman
  • Patent number: 4264776
    Abstract: Tertiary amines such as alkyl or benzyl amines are catalytically oxidized by oxygen over an activated carbon catalyst to selectively produce secondary amines.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: April 28, 1981
    Assignee: Monsanto Company
    Inventors: Arnold Hershman, Donald J. Bauer
  • Patent number: 4247480
    Abstract: An amine oxide is produced by oxidizing a tertiary amine having the formula ##STR1## wherein R.sub.1 and R.sub.2 respectively represent methyl or ethyl group; and R.sub.3 represent a C.sub.8 -C.sub.14 alkyl or alkenyl group in the presence of carbon dioxide and in the presence or absence of an improver selected from the group consisting of ethylenediaminetetraacetic acid, its salts, stanates, polyphosphates, salts of hydroxycaboxylic acid and salts of polycarboxylic acid.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: January 27, 1981
    Assignee: Nissan Chemical Industries Limited
    Inventors: Atsuo Murata, Syuji Tsuchiya, Akihiro Konno, Fumiyoshi Arima, Hisao Ikeda