Hydroperoxy Containing Patents (Class 568/568)
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Patent number: 6225510Abstract: A process for production of a t-alkyl peroxide compound includes the steps of: a) reacting an n-alkyl t-alkyl ether with a reactant mixture comprising an acid catalyst and a compound of the formula RO2H (I) where R is H or t-alkyl, provided that if R is t-alkyl the t-alkyl peroxide compound product is a di-t-alkyl peroxide, and b) isolating a reaction product comprising said t-alkyl peroxide compound from the mixture resulting from step a). The process can be used to prepare t-butyl hydroperoxide or di-t-butyl peroxide from methyl t-butyl ether. Sulfuric acid may be used as the acid catalyst.Type: GrantFiled: December 10, 1999Date of Patent: May 1, 2001Assignee: Crompton CorporationInventors: Peter Frenkel, Ted M. Pettijohn, Lawrence R. Brecker
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Patent number: 6054625Abstract: The process of preparing geminal dihydroperoxy alkyl peroxides and 1,1-dihydroperoxydialkyl peroxides, which comprises reacting an aqueous composition comprising a ketone with hydrogen peroxide in the presence of a heteropolyacid.Type: GrantFiled: May 27, 1999Date of Patent: April 25, 2000Assignee: Witco CorporationInventors: Peter Frenkel, Delphine Nwoko, Ted M. Pettijohn
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Patent number: 6034263Abstract: A process for the production of lower molecular weight polymers by free radical polymerization, characterized in that there is added to the polymerization system a compound of the general formula I ##STR1## wherein R.sup.1 is hydrogen, chlorine, an alkyl group, or a group capable of activating the vinylic carbon towards free radical addition;R.sup.2 is hydrogen or an optionally substituted alkyl, alkenyl, aryl, cycloalkenyl or cycloalkyl group or the group --COZ, where Z is R.sup.3 or OR.sup.3, where R.sup.3 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group.X is a hydrogen atom, an alkyl or aryl group, or a halogen, and the two X groups may be the same or different.The invention also includes polymers or oligomers made by the process and novel compounds of the generated formula I as defined above.Type: GrantFiled: June 6, 1995Date of Patent: March 7, 2000Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Ezio Rizzardo, Gordon Francis Meijs, San Hoa Thang
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Patent number: 6028193Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.Type: GrantFiled: April 15, 1999Date of Patent: February 22, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
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Patent number: 6023001Abstract: Peroxides are prepared from organic compounds and oxygen in a reaction vessel by introducing organic compound and oxygen to the reaction vessel and by simultaneously withdrawing a first liquid product stream from adjacent the top of the reactor and a second liquid product stream from adjacent the bottom of the reaction vessel. Suitable organic compounds include, but are not limited to, alkanes and all aryl compounds.Type: GrantFiled: March 18, 1998Date of Patent: February 8, 2000Assignee: Huntsman ICI Chemicals LLCInventors: William K. Culbreth, III, Mark E. Taylor, Kyle L. Preston, Mark A. Mueller
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Patent number: 6011183Abstract: The invention relates to a process for preparing organic hydroperoxides by oxidation of a hydrocarbon feed with molecular oxygen at supercritical conditions, which process is carried out in the presence of a separate liquid water phase that is present in an amount of 0.5 to 20% weight on the weight of the feed as a water film on the inner walls of the reactor vessel.Type: GrantFiled: November 13, 1998Date of Patent: January 4, 2000Assignee: Shell Oil CompanyInventors: Stephen William Bourne, Pieter Oldenhove
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Patent number: 5959155Abstract: A process for extraction of hydroperoxides wherein 1,3-di-(2-hydroperoxy-2-propyl)benzene and 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene are extracted from a raw solution comprising 1,3-di-(2-hydroperoxy-2-propyl)benzene, 3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene and an aqueous sodium hydroxide solution, said process using methyl isobutyl ketone containing not more than 10 ppm by weight of a phenol or phenols as a solvent for extraction.Type: GrantFiled: December 10, 1997Date of Patent: September 28, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Toshikazu Ohmae, Shigefumi Tokumasu, Hideo Ohki
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Patent number: 5939589Abstract: Catalytic reactions are carried out in a reactor which contains a liquid phase in which at least one catalyst is suspended, and which may additionally contain a gas phase, by a process in which the liquid phase and, if present, also the gas phase are fed, at least partly, through an apparatus having orifices or channels in the reactor, the hydraulic diameter of which orifices or channels is from 0.5 to 20 mm, preferably from 1 to 10 mm, particularly preferably from 1 to 3 mm.Type: GrantFiled: March 18, 1997Date of Patent: August 17, 1999Assignee: BASF AktiengesellschaftInventors: Gerd Kaibel, Franz Josef Brocker, Manfred Stroezel
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Patent number: 5705708Abstract: Discoloration of cumene hydroperoxide is reduced or inhibited by adding to the cumene hydroperoxide an effective amount on the order of 30 to 1000 ppm of a stabilizer of the formula R'C(O)OM wherein R' is alkyl, alkenyl, cycloalkyl or aryl containing 1-40 carbon atoms, or the formula R.sub.4 NOH wherein each R is independently alkyl or cycloalkyl containing 1-40 carbon atoms.Type: GrantFiled: September 23, 1996Date of Patent: January 6, 1998Assignee: Witco CorporationInventor: Peter Frenkel
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Patent number: 5475147Abstract: Isobutane containing a significant amount of isobutylene is treated at conditions effective to oligomerize a predominance of the isobutylene, isobutane substantially free of isobutylene is separated from the oligomer products, and the isobutane substantially free of isobutylene is oxidized to tertiary butyl hydroperoxide.Type: GrantFiled: October 19, 1994Date of Patent: December 12, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Thomas S. Zak
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Patent number: 5436375Abstract: Tertiary butyl hydroperoxide and tertiary butyl alcohol are prepared from isobutane and oxygen in a vertical reactor by sparging a mixture of isobutane with oxygen to the bottom of the reactor, by charging a reaction mixture recycle stream to the reactor above the sparge point, by centrally charging a downwardly flowing stream of cooled fresh isobutane to the top of the reactor to induce central downflow of the fresh isobutane annular and upflow of the sparged mixture and the recycle stream, by withdrawing a liquid product stream adjacent the top of the reactor, by withdrawing a vapor product stream from the top of the reactor, by condensing entrained liquids in the vapor product, by recycling the condensed liquids and by recovering the liquid product stream.Type: GrantFiled: August 26, 1994Date of Patent: July 25, 1995Assignee: Texaco Chemical Inc.Inventors: Karen A. Thomas, Kyle L. Preston
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Patent number: 5422417Abstract: Substituted phenyl compounds endowed with chain extension activity for formulations such as polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 1-1000 and m is 1-100; and R.sub.1 and R.sub.2 are each independently selected from the group --C.sub.2 H.sub.4 -- and --C.sub.3 H.sub.6 --; and R.sub.3 is from the group consisting of: ##STR2## and the diasteromeric salts thereof.Type: GrantFiled: March 31, 1994Date of Patent: June 6, 1995Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, William W. Wilkison, III
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Patent number: 5399777Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % tertiary butyl hydroperoxide.Type: GrantFiled: March 21, 1994Date of Patent: March 21, 1995Assignee: Texaco Chemical Inc.Inventor: Mark A. Mueller
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Patent number: 5395980Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % ditertiary butyl peroxide.Type: GrantFiled: March 21, 1994Date of Patent: March 7, 1995Assignee: Texaco Chemical Inc.Inventors: Mark A. Mueller, John R. Sanderson
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Patent number: 5346983Abstract: Substituted phenyl compounds endowed with chain extension activity for formulations such as polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 1-1000; R.sub.1 .dbd.R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2, --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 is from the group consisting of: ##STR2## and the diasteromeric salts thereof.Type: GrantFiled: May 28, 1993Date of Patent: September 13, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
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Patent number: 5338887Abstract: A process for the preparation of dihydroxy polyphenyl compounds is disclosed which comprises the simultaneous steps of (a) contacting the corresponding diisoalkyl polyphenyl compound or an oxidation intermediate thereof with oxygen under reaction conditions sufficient to form a corresponding dihydroperoxyalkyl polyphenyl compound and (b) contacting the dihydroperoxyalkyl polyphenyl compound with an acid under reaction conditions sufficient to form the corresponding dihydroxy polyphenyl compound. In addition, the intermediate dihydroperoxyalkyl polyphenyl compound is a novel compound.Type: GrantFiled: November 6, 1991Date of Patent: August 16, 1994Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Kenneth A. Burdett
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Patent number: 5288761Abstract: Open chain enediyne dihydroperoxides having eight carbons between the hydroperoxide groups that cleave DNA are disclosed, as are methods of making and using the same.Type: GrantFiled: January 28, 1993Date of Patent: February 22, 1994Assignee: The Scripps Research InstituteInventors: Kyriacos C. Nicolaou, Erik Sorensen, Chan-Kou Hwang, Robert Discordia, Robert G. Bergman, Robert E. Minto
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Patent number: 5233078Abstract: The invention relates to a process for preparing dialkyl malonates by ozonolysis of diketene, subsequent catalytic hydrogenation and esterification of the reaction products, the by-products being alkyl formates and dialkyl acetals.Type: GrantFiled: June 4, 1992Date of Patent: August 3, 1993Assignee: BASF AktiengesellschaftInventors: Ludwig Schuster, Klaus Halbritter
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Patent number: 5220075Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is oxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The oxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited.Type: GrantFiled: July 17, 1992Date of Patent: June 15, 1993Assignee: ABB Lummus Crest Inc.Inventor: George Ember
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Patent number: 5154912Abstract: The peroxides which include the O.sup.17 isotope, especially the hydrogen peroxides and peroxides and hydroperoxides prepared therefrom, are well adapted as nonradioactive labeled compounds for use in the medicinal and biological arts.Type: GrantFiled: September 20, 1990Date of Patent: October 13, 1992Assignee: AtochemInventors: Jean-Pierre Schirmann, Jean-Jacques Barieux
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Patent number: 5149883Abstract: This invention relates to an improved process for preparing dihydroperoxyalkanes and, particularly, dimethyldihydroperoxyhexane. The improvement resides in utilizing a tetrahydrofuran derivative which is a liquid as a feedstock. This feedstock then is reacted with hydrogen peroxide in the presence of sulfuric acid to form the dihydroperoxide.Type: GrantFiled: May 13, 1991Date of Patent: September 22, 1992Assignee: Air Products and Chemicals, Inc.Inventors: John A. Marsella, Reinaldo M. Machado
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Patent number: 5068455Abstract: There is provided a novel organic hydroperoxide, 3-(2-hydroperoxy-2-propyl)phenol. The hydroperoxide is produced by oxidizing 3-(2-hydroxy-2-propyl)phenol or m-isopropenylphenol with hydrogen peroxide in the presence of an acid catalyst.There is further provided a method of producing resorcinol which comprises decomposing the 3-(2-hydroperoxy-2-propyl)phenol in the presence of an acid catalyst.Type: GrantFiled: September 6, 1990Date of Patent: November 26, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kiyotaka Yorozu, Hiroyasu Ohno
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Patent number: 5032688Abstract: A process for the preparation of aralkyl hydroperoxides having the formula (I) is described ##STR1## in which n=1, 2 or 3, Ar means a phenyl group which can be substituted with halogen or one or more branched or straight chain alkyl groups with 1 to 5 C-atoms, or a naphthyl group, and each radical R.sup.1 and R.sup.2 means a low alkyl radical, the alkyl radicals R.sup.1 and R.sup.2 together having 2 to 4 carbon atoms, by reaction of aralkyl carbinols having the formula (II) ##STR2## in which Ar, R.sup.1, R.sup.2 and n have the meaning given for formula (I), with hydrogen peroxide under acid conditions, the reaction being carried out in the presence of an acid-combining agent. An alkali sulphate, ammonium sulphate, alkali hydrogen sulphate and/or ammonium hydrogen sulphate is used in preference as the acid-combining agent. Tert.aralkyl hydroperoxides can be prepared in high yield with a high purity in a simple and safe manner with this process.Type: GrantFiled: November 7, 1989Date of Patent: July 16, 1991Assignee: Peroxid-Chemie GmbHInventors: Maximilian Dorn, Eberhard Hagel, Werner Zeiss
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Patent number: 5030767Abstract: There is provided a novel organic hydroperoxide, 3-(2-hydroperoxy-2-propyl)phenol. The hydroperoxide is produced by oxidizing 3-(2-hydroxy-2-propyl)phenol or m-isopropenylphenol with hydrogen peroxide in the presence of an acid catalyst.There is further provided a method of producing resorcinol which comprises decomposing the 3-(2-hydroperoxy-2-propyl)phenol in the presence of an acid catalyst.Type: GrantFiled: February 2, 1989Date of Patent: July 9, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kiyotaka Yorozu, Hiroyasu Ohno
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Patent number: 5004780Abstract: A novel cyclic monoperoxyketal represented by the following general formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 represent hydrogen atoms, or same or different alkyl groups having 1-3 carbon atoms, R.sup.4 represents an alkyl group having 1-5 carbon atoms, R.sup.5 represents an alkyl group having 1-3 carbon atoms, and R.sup.6 and R.sup.7 may be separate groups, in which R.sup.6 represents an alkyl group having 1-3 carbon atoms and R.sup.7 represents an alkyl group having 2-10 carbon atoms, a cycloalkyl group or an aryl group, or may be combined into a cylcoalkylene group having 3-12 carbon atoms, has high stability and excellent decomposition property, and is useful as a polymerization initiator of unsaturated monomers and as a curing agent of unsaturated polyester resin.Type: GrantFiled: March 8, 1989Date of Patent: April 2, 1991Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Kazuo Matsuyama, Takashi Sugiura, Takeshi Komai
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Patent number: 4983777Abstract: Disclosed is a process for the oxidation of 4,4'-diisopropylbiphenyl which gives an excellent ratio of dihydroperoxide to monohydroperoxide and a low amount of other oxygenated compounds. The dihydroperoxide can be converted, by known procedures, to 4,4'-biphenyldiol or a diester thereof which are valuable monomers used in the manufacture of high performance polyesters. Certain of the disclosed compounds such as the dihydroperoxide, monohydroperoxides and diesters are new compositions of matter.Type: GrantFiled: November 6, 1989Date of Patent: January 8, 1991Assignee: Eastman Kodak CompanyInventor: Dale E. Van Sickle
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Patent number: 4962040Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.Type: GrantFiled: August 10, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Herbert Hugl, Aloysius Engel, Klaus Wehling
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Patent number: 4947004Abstract: High-purity 1,1,3,3-tetramethylbutyl hydroperoxide can be easily and safely produced without the formation of dangerous acetone peroxide, by the reaction of neopentyldimethylcarbinol with hydrogen peroxide in the presence of sulfuric acid.Type: GrantFiled: April 4, 1989Date of Patent: August 7, 1990Assignee: Nippon Oil and Fats Company, Ltd.Inventors: Shuji Suyama, Mitsukuni Kato, Jun Takada, Hiroshi Okada
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Patent number: 4634551Abstract: This invention relates to bleaching compounds and compositions that provide effective and efficient surface bleaching of textiles over a wide range of bleach solution temperatures. The bleaching compounds of the invention yield a peroxyacid with a polar amide link in the hydrophobic chain when used in the bleaching composition. In a preferred embodiment, the bleaching compositions of the invention are also detergent compositions.Type: GrantFiled: June 3, 1985Date of Patent: January 6, 1987Assignee: Procter & Gamble CompanyInventors: Michael E. Burns, Frederick E. Hardy
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Patent number: 4513109Abstract: The invention relates to phenols which contain a number of aromatic nuclei and in which the bridge formation of these nuclei is in the meta-position to the OH groups. These phenols have the formula I, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1.The novel phenols are most suitable for use as stabilizers for organic polymers and lubricants and have particularly good color properties.Type: GrantFiled: January 27, 1984Date of Patent: April 23, 1985Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
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Patent number: 4464304Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.Type: GrantFiled: June 30, 1982Date of Patent: August 7, 1984Assignee: Duke UniversityInventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
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Patent number: 4396526Abstract: A peroxide system or composition for use in resin polymerization consists of 1,4-diisopropylbenzene monohydroperoxide dissolved in an organic solvent which is a solvent for hydrogen peroxide and 1,4-diisopropylbenzene dihydroperoxide. The peroxide composition is characterized by its storage stability, resistance to detonation, low flammability, ease of handling and improved catalytic properties in the polymerization of certain resins. The preferred peroxide, based on economic considerations, is a crude diisopropylbenzene hydroperoxide mixture comprising a major amount of 1,4-diisopropylbenzene monohydroperoxide and a minor amount of 1,4-diisopropylbenzene dihydroperoxide, together with solvents and unreacted materials obtained as a byproduct in the commercial manufacture of p-diisopropylbenzene dihydroperoxide.Type: GrantFiled: November 5, 1980Date of Patent: August 2, 1983Assignee: CL Industries, Inc.Inventors: Wayne D. Woodson, Patrick H. Stewart
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Patent number: 4350834Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.Type: GrantFiled: August 27, 1980Date of Patent: September 21, 1982Assignee: Duke UniversityInventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
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Patent number: 4283553Abstract: Disclosed are novel hydroperoxide derivatives of hydroxyethylated compounds of the general formula: ##STR1## a-whole number 10 to 30, b, c are absent, R=n-alkyl from C.sub.8 to C.sub.20, secondary alkyl of C.sub.14, C.sub.15 and ##STR2## where R.sub.2 =n-alkyl from C.sub.8 to C.sub.12 ##STR3## where R.sub.3 and R.sub.4 =R.sub.8 --C.dbd.O, where R.sub.8 =--CH.sub.3 or H, if R.sub.6,7,9 =H R.sub.5 is absent or ##STR4## where R.sub.9 =--CH.sub.3 or H, if R.sub.6,7,8 =H, R.sub.5 is absent; R.sub.10 =n-alkyl of C.sub.1 to C.sub.9 of R.sub.3 .noteq.R.sub.4 R.sub.5 =--CH.sub.2 if R.sub.6,7,8,9 =H; if R.sub.5 is absent, R.sub.1 is acyclic and is ##STR5## R.sub.6 =--CH.sub.3 or H, if R.sub.7,8,9 =H, R.sub.5 is absent, R.sub.7 =--CH.sub.3 or H, if R.sub.6,8,9 =H, R.sub.5 is absent, with x=--O--, b-whole number of 8 to 24, (a+c)-whole number of 6 to 30R=R.sub.Type: GrantFiled: September 24, 1979Date of Patent: August 11, 1981Inventors: Sergei S. Ivanchev, Anatoly A. Syrov, Valery N. Pavljuchenko, Ninel N. Lesnikova, Diana A. Rozhkova
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Patent number: 4271321Abstract: Process for the preparation of araliphatic dihydroperoxides which comprises oxidizing a hydrocarbon of the formula: ##STR1## with oxygen or an oxygen-containing gas, (2) extracting the resulting dihydroperoxide with an alkali metal hydroxide solution of a concentration of 1-12% thereby producing an aqueous extract and an organic raffinate, (3) neutralizing any alkali metal hydroxide remaining in the organic raffinate with carbon dioxide, thereby producing alkali metal carbonate or bicarbonate in the raffinate, (4) washing the alkali metal carbonate or bicarbonate remaining in the raffinate with wash-water, (5) extracting from the wash-water used in step (4) any dissolved hydroperoxides remaining therein with a hydrocarbon solvent, and (6) optionally recycling the hydroperoxide-containing hydrocarbon solvent into the process. The resulting wash-water effluent is free of polluting and contaminating materials.Type: GrantFiled: October 9, 1979Date of Patent: June 2, 1981Assignee: Chemische Werke Huls AktiengesellschaftInventor: Heinz W. Voges
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Patent number: 4267387Abstract: An improved process for the preparation of an aromatic hydroperoxide by oxidizing a hydroxyalkyl-substituted aromatic compound having at least one hydroxyalkyl group directly bonded to an aromatic ring carbon of the aromatic compound and being represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 each are a lower alkyl group, with hydrogen peroxide in the presence of an acid catalyst in a heterogeneous system of a water-immiscible inert aromatic hydrocarbon solvent at a reaction temperature of up to about 70.degree. C. while removing by-product water as an azeotrope with the aromatic hydrocarbon solvent in the oxidation system; characterized in that said oxidation is carried out while feeding a vapor of a water-immiscible inert aromatic hydrocarbon solvent having a temperature higher than the reaction temperature but not exceeding about 90.degree. C. into a liquid phase of the oxidation system.Type: GrantFiled: October 17, 1979Date of Patent: May 12, 1981Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Ichiro Imai, Isao Hashimoto, Keiji Suzuki, Hiroaki Nakagawa
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Patent number: 4252985Abstract: The process relates to the preparation of o-methallyloxyphenol by the action of methallyl chloride on pyrocatechol in the presence of a basic agent.It consists in carrying out the reaction in a two-phase liquid reaction medium comprising water and a water-immiscible organic solvent, at a temperature between 50.degree. and 140.degree. C., in the presence of a catalyst chosen from amongst quaternary ammonium derivatives and phosphonium derivatives, using, as the basic agent, an alkali metal or alkaline earth metal hydroxide or an alkali metal carbonate or bicarbonate.It makes it possible to obtain the monoether selectively by minimizing the formation of diether and of alkylation products of the benzene nucleus of the pyrocatechol.Type: GrantFiled: June 18, 1979Date of Patent: February 24, 1981Assignee: PhilagroInventor: Michel Rakoutz
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Patent number: 4154768Abstract: Increase in yields of alkyl hydroperoxides from corresponding olefins by reacting the olefin with an inorganic peroxide in the presence of an acid catalyst, the acid concentration being adjusted to an optimum range which is generally about 15-30% by total weight of the reactive ingredients. Where the olefin contains over 7 carbon atoms, peroxide-compatible surfactants are included in the reaction mixture and the yield of hydroperoxide is further improved.Type: GrantFiled: August 27, 1973Date of Patent: May 15, 1979Assignee: Argus Chemical CorporationInventor: Newton G. Leveskis
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Patent number: 4152358Abstract: In autoxidation of tertiary, aryl or cycloalkanes the selectivity for organic hydroperoxides can be substantially increased by using a phosphate compound of Li, Na, Mg, Ca, Sr, Fe, Cu, U or B. For example an autoxidation of isopentane with 0.05 wt. % boron phosphate at 9.9 mole % conversion gave selectivities of t-amyl hydroperoxides -- 75.0 mole %, acetone -- 18.3 mole % and t-amyl alcohol -- 1.5 mole %. The same reaction without the phosphate at 10.0 mole % conversion gave selectivities of t-amyl hydroperoxide -- 56.8 mole %, acetone -- 31.2 mole % and t-amyl alcohol -- 4.8 mole %.Type: GrantFiled: October 9, 1973Date of Patent: May 1, 1979Assignee: Petro-Tex Chemical CorporationInventor: Bruno J. Barone
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Patent number: 4133835Abstract: An aliphatic or cycloaliphatic hydroperoxide, an olefin such as a 1-aromatic-1-substituted ethylene and a halide corresponding to the ethylene are reacted under essentially anhydrous conditions, in the absence of a free acid, at a temperature below the decomposition temperature of the halide to obtain a peroxide corresponding to the hydroperoxide and the ethylene.Preferably the product peroxide is recovered by treating the reaction product mixture with aqueous alkali metal hydroxide to destroy the halide and hydroperoxide therein; then distilling the treated mixture in the presence of a substantial amount of liquid water at sub-atmospheric pressure to remove overhead impurities.Example: Dicumyl peroxide is prepared by reacting at about 30.degree. C for about 5 hours cumene hydroperoxide, .alpha.-methylstyrene and cumyl chloride, which compounds has been charged to the reaction zone in a mole ratio of 1.25: 0.86: 0.Type: GrantFiled: October 28, 1968Date of Patent: January 9, 1979Assignee: Pennwalt CorporationInventors: Richard A. Bafford, Orville L. Mageli