Peroxy Containing Reactant Patents (Class 568/385)
  • 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: 4754073
    Abstract: Method for the preparation of ketones, by means of oxydation of the corresponding secondary alcohols, characterized in that said alcohols are catalytically oxidized by H.sub.2 O.sub.2 inside a two-phase system comprising:(a) an aqueous phase, containing hydrogen peroxide as the oxidizing agent;(b) an organic phase, containing a secondary alcohol and optionally a solvent immiscible with said aqueous phase, as well as a peroxidic catalyst having the general formula Q.sub.3 XW.sub.4 O.sub.24, wherein X represents an atom of phosphorus or of arsenic and wherein Q represents a quaternary cation, containing hydrocarbon groups having a total of from 20 to 70 C atoms.
    Type: Grant
    Filed: January 8, 1987
    Date of Patent: June 28, 1988
    Assignees: Instituto Guido Donegani S.p.A., Consiglio Nazionale Delle Ricerche
    Inventors: Carlo Venturello, Mario Gambaro, Marco Ricci
  • Patent number: 4659829
    Abstract: The invention concerns peroxide complexes of metals complying with the general formula LnMXpY, wherein M is a metal selected from groups VIII, IB and VIIB, particularly cobalt, X is an anionic group, for example carboxylate, R is an alkyl, cycloalkyl or arylalkyl group, n=1 or 2, p=0 or 1 and n+p=2.L is a tridentated ligand from the group of 1,3 bis (2-pyridylimino) isoindolines.These complexes are obtained by reaction of a hydroperoxide ROOH with a complex of formula LnMXp. They can be used in oxidizing hydrocarbons to a mixture of alcohols and ketones, either as reactants or as catalysts.They are particularly useful to prepare tert-butanol by oxidation of isobutane in liquid phase, by means of an oxygen-containing gas such as air.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: April 21, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Lucien Saussine, Alain Robine, Hubert Mimoun
  • Patent number: 4626600
    Abstract: In accordance with the invention there is a process for reducing the water content of acetone prepared from cumene which includes the steps ofa. adding cleaving effective catalytic quantities of sulfuric acid to a mixture comprising cumene hydroperoxide and cumene, the cumene hydroperoxide making up about 81 to 83 weight percent of the said mixture, thereby producing a mixture comprising phenol, acetone, cumene and sulfuric acid;b. neutralizing the said sulfuric acid with an aqueous alkali hydroxide and separating the alkali metal sulfate from the mixture comprising phenol, acetone, water and cumene, the water being from about 40 to 60 weight percent of the total weight of water and cumene, the cumene being present in sufficient quantities to cause the formation of two liquid phases upon condensing the acetone fraction distillate;c. separating by distillation the acetone fraction from the phenol fraction, said acetone fraction containing acetone, water, aldehyde, and other organics including cumene;d.
    Type: Grant
    Filed: February 21, 1985
    Date of Patent: December 2, 1986
    Assignee: General Electric Company
    Inventors: John W. Fulmer, William D. Kight
  • Patent number: 4618724
    Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 21, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hitosi Nozaki, Koichiro Oshima
  • Patent number: 4609763
    Abstract: A process for the oxidation of alkanes or alkenes is described. The process uses a hydrocarbyl hydroperoxide as an oxidizing agent in combination with a ruthenium catalyst and optionally a hydrogen bromide or hydrobromide acid promoter. The products of the oxidation are alcohols, ketones or a mixture of both.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: September 2, 1986
    Assignee: The British Petroleum Company P.L.C.
    Inventors: Colin G. Griggs, Anthony R. Middleton
  • Patent number: 4607126
    Abstract: The invention relates to a process for the preparation of glyoxal, alkylglyoxals and acetals thereof by reacting .alpha.,.beta.-unsaturated dialkylacetals with the equivalent amount of ozone and subsequently subjecting the ozonization products to catalytic hydrogenation, the peroxide-containing ozonization solution being fed continuously into a suspension of the hydrogenation catalyst, while a peroxide content of not more than 0.1 mole/liter is maintained, and cleaving the ozonization products by reduction, after which the dialkylacetals formed in the hydrogenation are, if desired, cleaved to give glyoxal or alkylglyoxals.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: August 19, 1986
    Assignee: Chemie Linz Aktiengesellschaft
    Inventor: Alexander Sajtos
  • Patent number: 4587057
    Abstract: Novel peroxide compounds and the use thereof. In particular, the present invention concerns .beta.-hydroxycyclopentylperoxide compounds of the general formula: ##STR1## wherein R.sub.1 represents hydrogen or an organic residue of 1 to 9 carbon atoms. These novel peroxide compounds are useful as an intermediate in the production of glutaraldehydes.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: May 6, 1986
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
  • Patent number: 4567304
    Abstract: Benzene, toluene and ethylbenzene is removed from the heavy residues of a phenol distillation in a phenol and acetone from cumene process.
    Type: Grant
    Filed: May 24, 1984
    Date of Patent: January 28, 1986
    Assignee: General Electric Company
    Inventor: John W. Fulmer
  • Patent number: 4551553
    Abstract: The process of decomposing a hydroperoxide by contacting the hydroperoxide with a catalytic quantity of a catalyst system comprised of chromium and ruthenium. The catalyst system is characterized by its high stability while exhibiting improved activity for hydroperoxide decomposition and selectivity to desired alcohol and ketone products.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: November 5, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Paul D. Taylor, Michael T. Mocella
  • Patent number: 4513150
    Abstract: But-2-ene-1,4-diones substituted in the 1,4-positions, of the formula ##STR1## where R.sup.1 and R.sup.2 are each an aliphatic hydrocarbon radical of 1 to 17 carbon atoms, are prepared by a process in which a 2,5-disubstituted furan of the formula ##STR2## where R.sup.1 and R.sup.2 have the above meaning, is oxidized with a percarboxylic acid in the presence of a carboxylic acid.
    Type: Grant
    Filed: March 23, 1984
    Date of Patent: April 23, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Hans-Martin Weitz, Hardo Siegel
  • Patent number: 4503259
    Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: March 5, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
  • Patent number: 4490566
    Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising an intermediate pore size zeolite such as ZSM-5.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: December 25, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Bruce P. Pelrine
  • Patent number: 4490565
    Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising zeolite beta.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: December 25, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Bruce P. Pelrine
  • Patent number: 4487970
    Abstract: Secondary-alkyl substituted benzene hydroperoxides are cleaved to form phenols and ketones by contacting the secondary-alkyl substituted benzene hydroperoxide with a catalyst consisting essentially of about 3:1 to 1:10 by weight of SbF.sub.5 and graphite in the presence of an aromatic or ketone solvent at a temperature of from about 0.degree.-100.degree. C.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: December 11, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4486606
    Abstract: Pinacolone is prepared by adding 2,3-dimethyl-2-butene and an aqueous solution of hydrogen peroxide at a temperature of 20.degree. to 90.degree. C. to a solution which contains water and one or more carboxylic acids having 1 to 8 C atoms and which can, if desired, also contain small amounts of a strong acid, increasing the temperature after substantial or complete reaction of the hydrogen peroxide, and distilling off as an azeotropic mixture with water the pinacolone formed.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gebhard Rauleder, Helmut Waldmann
  • Patent number: 4482757
    Abstract: Secondary alkyl-substituted benzene hydroperoxides are cleaved to phenols and ketones by contacting the hydroperoxide with a mixture consisting essentially of an organic phosphonium halide compound and an acid at a temperature from about 0.degree.-200.degree. C.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: November 13, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4480135
    Abstract: A process for oxidizing primary and/or secondary alcohols to the corresponding aldehyde and/or ketone derivatives, consisting of reacting said alcohols with an aqueous solution of hydrogen peroxide in the presence of synthetic zeolites containing titanium atoms, of general formula:xTiO.sub.2.(1-x)SiO.sub.2,where x lies between 0.0001 and 0.04, and possibly in the presence of one or more solvents, operating at a temperature of between 20.degree. and 100.degree. C.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: October 30, 1984
    Assignee: Anic S.p.A.
    Inventors: Antonio Esposito, Carlo Neri, Franco Buonomo
  • Patent number: 4480141
    Abstract: Secondary alkyl-substituted hydroperoxides are cleaved to phenols and ketones by contacting the secondary alkyl-substituted benzene hydroperoxide with boron phosphate, at a temperature of from about 20.degree.-200.degree. C.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: October 30, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4480134
    Abstract: Benzene is removed from the heavy residues of a phenol distillation in a phenol and acetone from cumene process.
    Type: Grant
    Filed: April 5, 1983
    Date of Patent: October 30, 1984
    Assignee: General Electric Company
    Inventor: John W. Fulmer
  • Patent number: 4459427
    Abstract: A mixture of the alcohol and ketone derivatives of alkanes is produced by reacting the alkane with a hydrocarbyl hydroperoxide, eg t-butyl hydroperoxide, at ambient or elevated temperature and pressure in the presence as catalyst of an iron or manganese square planar complex having heterocyclic nitrogen-donor ligands, e.g. a porphyrin or phthalocyanine complex, which complex has either no axial ligands, eg the lower valency or cationic complex, or an axial ligand which is non-coordinating or weakly-coordinating.
    Type: Grant
    Filed: October 26, 1982
    Date of Patent: July 10, 1984
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Anthony R. Middleton, David J. H. Smith
  • Patent number: 4434305
    Abstract: High quality hydroquinone is produced from p-diisopropylbenzene dihydroperoxide at a high yield according to the disclosed process. The p-diisopropylbenzene dihydroperoxide is decomposed in the presence of an acid catalyst and the concentration of the hydroperoxide is maintained in the range of 0.1 to 1% by weight; the remaining hydroperoxide in the decomposition step is further subjected to an acid decomposition prior to the recovery of the formed hydroquinone product.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: February 28, 1984
    Assignee: Mitsui Petrochemicals Industry, Ltd.
    Inventors: Nobuo Kurosaka, Makoto Yasuda, Tadateru Murakami
  • Patent number: 4421679
    Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: December 20, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
  • Patent number: 4420423
    Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene); then oxidizing the resulting product using formic acid and hydrogen peroxide; then reducing the resulting ketone(s) with an alkali metal borohydride; and then, optionally, reacting the resulting alcohol(s) with acetic anhydride to form one or more esters; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure ##STR1## wherein R.sub.12 represents hydroxyl:--OH]or acetoxy having the structure: ##STR2## and wherein R.sub.3, R.sub.4, R.sub.5, R.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: December 13, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
  • Patent number: 4408083
    Abstract: Disclosed is a method of treating hydroperoxide mixtures, which comprises bringing an oily hydroperoxide mixture containing (A) an aromatic hydroperoxide having a hydroperoxymethyl group directly bonded to the aromatic nucleus and (B) an aromatic hydroperoxide having a 2-hydroperoxy-2-propyl group bonded directly to the aromatic nucleus into contact with an aqueous alkali solution, separating the aqueous phase from the oil phase and decomposing at least a part of the component (A) extracted in the aqueous phase.According to this method, the starting oily hydroperoxide mixture can be converted to a mixture in which the primary hydroperoxide content is reduced without substantial loss of the tertiary hydroperoxide. Therefore, aromatic hydroperoxide mixtures suitable for production of phenols can advantageously be proceeded.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: October 4, 1983
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Masakazu Toyoura, Koichi Shomura, Hirotoshi Tsuchida, Tadateru Murakami
  • Patent number: 4379942
    Abstract: Methyl ketones are prepared in liquid phase by oxidizing terminal olefins of the formula R--CH.dbd.Ch.sub.2, where R is a hydrocarbon radical. The oxidizing agent is hydrogen peroxide or an organic hydroperoxide, and the catalyst is a palladium catalyst of the formula Pd AA' whereA is fluoborate, acetate or trifluoroacetate, andA' is OOR.sub.1 and where R.sub.1 is a hydrocarbon radical.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: April 12, 1983
    Assignee: Institut Francais du Petrole
    Inventors: Hubert Mimoun, Robert Charpentier, Michel Roussel
  • Patent number: 4358618
    Abstract: A cumene oxidation product containing cumene hydroperoxide (CHP) and dimethylphenylcarbinol (DMPC) is decomposed with acid catalyst in a first step at mild temperatures that lowers the CHP concentration to about 0.5-5% and converts most of the DMPC to dicumylperoxide (DCP). In a second step at mild temperatures the CHP concentration is lowered below 0.4%. In a third step the DCP is decomposed at a higher temperature for a short time to alpha-methylstyrene (AMS), phenol and acetone, with any remaining DMPC also converted to AMS. The DCP concentration is monitored during the third step, and the reaction is stopped by cooling when about 0.5-5% of the DCP remains undecomposed so as to maximize AMS yield.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: November 9, 1982
    Assignee: Allied Corporation
    Inventors: Stylianos Sifniades, Allen A. Tunick, Fred W. Koff
  • Patent number: 4329509
    Abstract: A process for the co-production of 2-alkanones having at least five carbon atoms and phenol or a substituted phenol. In the first step, benzene or a substituted benzene is alkylated with an alkyl moiety of at least five carbon atoms to selectively produce the 2-arylalkane isomer. Subsequent oxidation to the hydroperoxide and acid cleavage thereof yields the desired product. The alkylation step is carried out in the presence of a novel class of selective crystalline zeolite materials having pore openings with a major dimension of six to seven angstroms.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: May 11, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Lewis B. Young
  • Patent number: 4322560
    Abstract: Exothermic hydroperoxide decomposition reactions catalyzed by solid polymeric acid catalysts are controlled by contacting the reactants with a thin film of the acid catalyst supported on the surface of an impermeable heat exchanger element and contacting the opposite side of the heat exchanger element with a heat transfer fluid.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: March 30, 1982
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4310704
    Abstract: Methyl ketones are prepared in liquid phase by oxidizing terminal olefins of the formula R--CH.dbd.CH.sub.2, where R is a hydrocarbon radical. The oxidizing agent is hydrogen peroxide or an organic hydroperoxide, and the catalyst is a palladium catalyst of the formula Pd AA', (L.sub.m) whereA is fluoborate, acetate or trefrafluoroacetateA' is the same as A or is .pi.-allyl,m is 0 or 2, andL is a ligand selected from the amines, the phosphines, the arsines, the stibines and the amides.
    Type: Grant
    Filed: December 18, 1979
    Date of Patent: January 12, 1982
    Assignee: Institut Francais du Petrole
    Inventors: Hubert Mimoun, Robert Charpentier, Michel Roussel
  • Patent number: 4297518
    Abstract: Cumene hydroperoxide in a solvent comprising phenol and acetone is decomposed to phenol and acetone using a soluble rhenium compound.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: October 27, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Ching-Yong Wu, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4267380
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a Lewis acid catalyst of the group tungsten hexafluoride, silicon tetrafluoride, stannous chloride, stannic fluoride, antimony pentachloride, sulfur monochloride and sulfur tetrafluoride.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: May 12, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4267379
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using boron trifluoride or boron trifluoride complexed with an oxygen-containing polar compound as the decomposition catalyst. The boron trifluoride in the reaction product is then complexed with an amine such as trimethyl amine for recovery and reuse in the process.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: May 12, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4259527
    Abstract: A catalytic system for oxidation of organic compounds including olefins, cyclic ketones and secondary alcohols. Soluble peroxo or solid supported oxo or peroxo complexes of molybdenum or tungsten are used in the presence of hydrogen peroxide to effect the oxidation. The resulting products include lactones, hydroxy acids, ketoacids, hydroxy esters and ketoesters from cyclic ketones; ketones from secondary alcohols and polyols or derivatives thereof from allylic alcohols.
    Type: Grant
    Filed: May 18, 1979
    Date of Patent: March 31, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang
  • Patent number: 4257985
    Abstract: Compounds containing at least one keto group and at least one peroxy group, each peroxy oxygen being joined to a tertiary carbon atom.Examples: 2-Methyl-2-(t-butylperoxy)-4-pentanone. 2,6-Dimethyl-2,6-bis(t-butylperoxy)-4-heptanone. 3,5,5-Trimethyl-3-(t-butylperoxy)cyclohexanone.The compounds are prepared by the strong acid catalyzed addition of a tertiary hydroperoxide to an .alpha.,.beta.-unsaturated ketone. Illustration: Mesityl oxide and pinanyl hydroperoxide, in slight excess, were reacted at 0.degree. C. in the presence of 77% sulfuric acid; the reaction mix was stirred for 16 hours at 25.degree. C. Product 2-methyl-2-pinanylperoxy-4-pentanone was recovered.
    Type: Grant
    Filed: May 7, 1968
    Date of Patent: March 24, 1981
    Assignee: Pennwalt Corporation
    Inventor: Wilbur H. McKellin
  • Patent number: 4246203
    Abstract: The invention relates to a process in which an aromatic hydroperoxide of formula: ##STR1## wherein independently R.sub.1 is methyl or ethyl, R.sub.2 is hydrogen, methyl or ethyl, or where R.sub.1 and R.sub.2 together form an alicyclic ring of 5 or 6 carbon atoms, R.sub.3 is hydrogen or alkyl and R.sub.4 and R.sub.5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n.sup.1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: January 20, 1981
    Assignee: BP Chemicals Limited
    Inventor: Max M. Wirth
  • Patent number: 4238417
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using boron trifluoride or a boron trifluoride complex as the decomposition catalyst. The boron trifluoride in the reaction product is reacted with a phosphorus-containing salt of an alkali metal such as sodium phosphate for recovery and reuse in the process.
    Type: Grant
    Filed: August 15, 1979
    Date of Patent: December 9, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4217290
    Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: August 12, 1980
    Assignee: Brichima S.p.A.
    Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
  • Patent number: 4210606
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a halogen-substituted thiophenol as the catalyst.
    Type: Grant
    Filed: June 15, 1979
    Date of Patent: July 1, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4210607
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using an isolable nitrosonium or nitronium salt as the catalyst. Nitrosonium tetrafluoborate catalyzes the decomposition of cumene hydroperoxide to phenol and acetone.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: July 1, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4209465
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using an isolable carbonium, tropylium or oxonium salt as the catalyst. Triphenylcarbonium tetrafluoborate catalyzes the decomposition of cumene hydroperoxide to phenol and acetone.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: June 24, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4207264
    Abstract: A continuous process for cleaving aralkyl hydroperoxides in acid media to yield phenols and carbonyl compounds in a reactor arranged and operated to limit the total residence time to less than the time required to form discoloration products.
    Type: Grant
    Filed: March 27, 1973
    Date of Patent: June 10, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: John E. Anderson, Ernest G. Hildenbrand
  • Patent number: 4207265
    Abstract: A process is provided for the preparation of hydroquinone by oxidizing a phenol having in the paraposition a 1-cycloalkenyl or .alpha.-methylene-(alkyl or aralkyl) group. The oxidation is carried out using hydrogen peroxide or a hydrocarbyl peroxide in the presence of an inert solvent and a catalytic amount of a strong acid which is not oxidized by the peroxide. The other product of the reaction is the ketone derived by oxidation of the para-substituent in the starting phenol, e.g. p-isopropenylphenol gives hydroquinone and acetone. The reaction forms a particularly convenient route for conversion of phenol to hydroquinone in that phenol is condensed with acetone to bisphenol A, the latter is degraded by alkaline hydrolysis to a mixture of phenol and p-isopropenylphenol, which latter is subjected, without separation, to the above process to give a mixture of hydroquinone, phenol, and acetone.
    Type: Grant
    Filed: March 31, 1975
    Date of Patent: June 10, 1980
    Assignee: The Upjohn Company
    Inventor: Peter S. Carleton