Preparing Polyoxy Alcohol Esters From Olefins Patents (Class 560/246)
  • Patent number: 9371267
    Abstract: A method for preparation of secondary alcohols with a high proportion of hydroxyl group at the C2 position is disclosed. Alkyl carboxylates, high in alpha-methylcarboxylate content, are produced via reaction of an alpha-olefin and a carboxylic acid in the presence of a cerium catalyst. The resultant alkyl carboxylate is hydrolyzed to yield a secondary alcohol with a high 2-hydroxyl content. The secondary alcohol may be used to prepare esters, especially phthalate esters or cyclohexanoate diesters, which are useful as plasticizers. These esters are more effective as plasticizers than esters derived from other secondary alcohols due to their high C2 point of attachment.
    Type: Grant
    Filed: November 16, 2010
    Date of Patent: June 21, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Karla S. Colle, Allen D. Godwin
  • Patent number: 9290426
    Abstract: A system and a method for forming oxygenates from a non-catalytic reaction. A hydrocarbon gas and an oxygen-containing gas are fed into a mixer and then heated to form a reactant gas stream. The reactant gas stream is fed into a fluidized bed reactor where the reaction of the gases occurs by oxidization to produce oxygenates. The oxygenate products are then removed from the reactor.
    Type: Grant
    Filed: May 9, 2013
    Date of Patent: March 22, 2016
    Assignee: Stranded Solutions, LLC
    Inventor: Nathan Pawlak
  • Patent number: 8729295
    Abstract: The present invention provides methods of using a novel sulfonated resin catalyst, showing improved performance. The catalyst has reduced or partial functionalization, throughout the sulfonated region of the polymer, leading to reduced by-product formation and other desirable features. This catalyst has particular usefulness in reactions or processes sensitive to high acidity, e.g., esterification-transesterification.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: May 20, 2014
    Assignee: The Purolite Company
    Inventors: James A. Dale, Luc Froment, Satish Bapat
  • Patent number: 8664423
    Abstract: A process for the preparation of acylated secondary alcohol alkoxylates and a process for making secondary alcohol alkoxy sulfates comprising the steps of:— preparing secondary alcohol alkoxylates by the afore-mentioned process; and sulfating the secondary alcohol alkoxylates is described.
    Type: Grant
    Filed: October 28, 2009
    Date of Patent: March 4, 2014
    Assignee: Shell Oil Company
    Inventors: Harry Van Der Heijden, Renata Helena Van Der Made, Jan Hermen Hendrik Meurs, Quoc An On, Arie Van Zon
  • Publication number: 20110237817
    Abstract: A process for the preparation of acylated secondary alcohol alkoxylates and a process for making secondary alcohol alkoxy sulfates comprising the steps of: preparing secondary alcohol alkoxylates by the afore-mentioned process; and sulfating the secondary alcohol alkoxylates is described.
    Type: Application
    Filed: October 28, 2009
    Publication date: September 29, 2011
    Inventors: Harry Van Der Heijden, Renata Helena Van Der Made, Jan Hermen Hendrik Meurs, Quoc An On, Arie Van Zon
  • Publication number: 20090112016
    Abstract: The present invention provides methods of using a novel sulfonated resin catalyst, showing improved performance. The catalyst has reduced or partial functionalization, throughout the sulfonated region of the polymer, leading to reduced by-product formation and other desirable features. This catalyst has particular usefulness in reactions or processes sensitive to high acidity, e.g., esterification-transesterification.
    Type: Application
    Filed: October 24, 2008
    Publication date: April 30, 2009
    Applicant: THE PUROLITE COMPANY
    Inventors: James A. Dale, Luc Froment, Satish Bapat
  • Patent number: 6300515
    Abstract: The invention provides a process that includes isomerizing at least one allylic substrate having an acyloxyl group or a hydroxyl group at the allyl position thereof, to produce a corresponding allylic isomer, wherein the isomerizing is conducted in the presence of a catalyst that includes a Group VIII-X metal compound and a phosphite compound.
    Type: Grant
    Filed: April 17, 2000
    Date of Patent: October 9, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mikael Retboll, Yoshinori Hara, Hisao Urata, Hironobu Ohno
  • Patent number: 5874610
    Abstract: A process for the recovery of a carbonylation product from a liquid reaction composition of an iridium-catalysed carbonylation reaction of a carbonylatable reactant comprises subjecting the composition to a vaporization with or without the addition of heat to produce a vapor-fraction and a liquid fraction, the vapor fraction comprises carbonylation product and the liquid fraction has a water concentration of at least 0.5% by weight to stabilize the iridium catalyst.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: February 23, 1999
    Assignee: BP Chemicals Limited
    Inventors: Kirsten Everald Clode, Derrick John Watson, Carl Jozef Elsa Vercauteren
  • Patent number: 5777155
    Abstract: A process for producing an unsaturated glycol diester disclosed, which process comprises reacting a conjugated diene with a carboxylic acid and molecular oxygen in the presence of a solid catalyst comprising (1) palladium and (2) tellurium as active components supported on a carrier, wherein a said carrier is a solid carrier in which a proportion of the volume of pores having a pore radius in the range of from 5 to 50 nm is 80% or more relative to the total volume of pores having a pore radius in the range of from 1.8 to 10,000 nm.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: July 7, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masato Sato, Hironobu Ohno, Nobuyuki Murai, Hiroshi Iwasaka
  • Patent number: 4593135
    Abstract: A method for promoting the activity and/or extending the life of a cation-exchangeable layered clay catalyst in reactions susceptible to catalysis by protons which method comprises the addition to the catalyst of water as the sole additive. The quantity of water employed is suitably up to 40%, preferably up to 10% based on weight of reactants. The layered clay catalyst can be for example montmorillonite, bentonite or vermiculite. Suitable proton catalyzed reactions include formation of esters, (e.g. by reaction of olefin and carboxylic acid), ethers, aldehydes, thioethers and alkylation and cracking reactions.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: June 3, 1986
    Assignee: The British Petroleum Company P.L.C.
    Inventor: Reginald Gregory
  • Patent number: 4556730
    Abstract: Novel compounds made from the reaction of 5-vinyl-2-norbornene with carboxylic acid anhydrides in the presence of oxygen are described. The process to make these novel esters is preferably conducted at a temperature in the range from about 50.degree. to 150.degree. C. and in the presence of a catalyst. A transition metal borate catalyst is preferred. Such ester compounds are potentially useful plasticizers, lubricants, solvents and fuel additives.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: December 3, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward C. Y. Nieh, Lewis W. Watts, Jr.
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4517374
    Abstract: A process for the production of cycloalkane epoxides from cycloalkenes in the presence of an oxide catalyst, oxygen and a carboxylate ion source via air oxidation is described. The oxide catalyst may have as a cation boron, chromium, iron, nickel, copper, zinc or terbium or mixtures thereof. Combination catalysts such as ferric oxide/zinc oxide and nickel oxide/copper oxide/chromium oxide/boric oxide complexes are also found to be useful. The reaction is conducted at a temperature in the range of 50.degree. to 150.degree. C. and a pressure of one atmosphere or greater. Cycloalkane epoxides are useful in the preparation of resins, plasticizers, etc.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: May 14, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Terry L. Renken
  • Patent number: 4451668
    Abstract: A process for the production of alkane acetates from olefins in the presence of transition metal borate catalysts, oxygen and acetic anhydride or acetic acid and acetic anhydride via oxidative esterification is described. The reaction is conducted at a temperature in the range of 80.degree. to 280.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: May 29, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr.
  • Patent number: 4450290
    Abstract: A process for the production of alkane acetates from olefins in the presence of a transition metal borate catalyst, oxygen and acetic acid alone via oxidative esterification is described. The reaction is conducted at a temperature in the range of 120.degree. to 220.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: May 22, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Walter H. Brader, Jr.
  • Patent number: 4436931
    Abstract: A process for the production of alkane acetates from olefins in the presence of an oxide catalyst selected from the group of oxides consisting of niobium oxide, iron oxide and bismuth oxide, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 100.degree. to 250.degree. C. and a pressure of 1 atmosphere or greater. Iron oxide catalysts are preferred. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr., Terry L. Renken
  • Patent number: 4436926
    Abstract: A process for the production of alkane acetates from olefins in the presence of a catalyst containing a rare earth oxide, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 100.degree. to 250.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Terry L. Renken, Lewis W. Watts, Jr.
  • Patent number: 4436929
    Abstract: A process for the production of alkane acetates from olefins in the presence of an alkali earth metal borate catalyst, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 50.degree. to 280.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr.
  • Patent number: 4436927
    Abstract: A process for the production of alkane acetates from olefins in the presence of a thallium borate catalyst, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 120.degree. to 220.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr.
  • Patent number: 4436928
    Abstract: A process for the production of alkane acetates from olefins in the presence of an oxide/borate catalyst system, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 100.degree. to 250.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Terry L. Renken, Lewis W. Watts, Jr.
  • Patent number: 4436932
    Abstract: A process for the production of alkane acetates from olefins in the presence of an ammonium borate catalyst, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 80.degree. to 280.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Steven H. Vanderpool, Lewis W. Watts, Jr.
  • Patent number: 4436930
    Abstract: A process for the production of alkane acetates from olefins in the presence of an alkali metal borate catalyst, oxygen and a carboxylate ion source via oxidative esterification is described. The reaction is conducted at a temperature in the range of 50.degree. to 280.degree. C. and a pressure of 1 atmosphere or greater. Alkane diacetates and hydroxy acetates are produced which may be used as precursors to alkylene oxides, alkylene glycols and other useful compounds.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: March 13, 1984
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Lewis W. Watts, Jr.
  • Patent number: 4420634
    Abstract: The invention relates to a process for the oxidation of unsaturated hydrocarbons, particularly butenes and isobutylene, for the production of acetic acid, propionic acid and acetone. Specifically the invention comprises the highly selective oxidation of an unsaturated hydrocarbon or of a mixture of unsaturated hydrocarbons in the presence of a catalyst consisting of a complex of trivalent cobalt and of a carbonyl compound, of the aldehydic or ketonic type.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: December 13, 1983
    Inventors: Franco Codignola, Paolo Gronchi, Renato del Rosso, Paolo Centola
  • Patent number: 4389389
    Abstract: This invention is generally directed to an improved process for the preparation of tellurium in high purity which comprises reacting tellurium dioxides, with a diol, and subjecting the resulting tellurium ester, subsequent to purification, to a reduction reaction.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: June 21, 1983
    Assignee: Xerox Corporation
    Inventor: Santokh S. Badesha
  • Patent number: 4324909
    Abstract: In the process for catalytically reacting olefin and oxygen to provide glycol or a mixture of glycol and glycol ester, higher rates of reaction and/or higher selectivities for the desired product(s) are obtained employing as catalyst, a composition comprising a mixture of molecular iodine and hydrobromic acid; hydriodic acid and hydrobromic acid; or, at least one oxide of antimony, bismuth or tellurium in admixture with at least one member of the group consisting of hydriodic acid; molecular iodine; hydriodic acid and molecular iodine; molecular iodine and hydrobromic acid; and, hydriodic acid and hydrobromic acid in a water or water-carboxylic acid reaction medium.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: April 13, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventors: David Horvitz, Thomas S. Brima
  • Patent number: 4297506
    Abstract: An organic ester is produced by conversion of an organic halide employing excess alkali metal carboxylate. A resultant reaction mass including solids comprised of alkali metal halide is obtained containing occluded in the solids portion an amount of otherwise difficult-to-recover desired ester product. At least a portion of said solids is recycled to the conversion whereby to prevent further occlusion of desired product. In an embodiment of the invention, potassium acetate salt is recycled for reuse.
    Type: Grant
    Filed: January 8, 1980
    Date of Patent: October 27, 1981
    Assignee: Phillips Petroleum Co.
    Inventor: Kiplin D. Cowan
  • Patent number: 4263448
    Abstract: An oxidizable hydrocarbon is oxidized in a reaction zone at elevated temperature in the presence of a liquid reaction medium by introducing the hydrocarbon and a feed stream containing molecular oxygen to the reaction zone under conditions sufficient to oxidize at least a portion of the hydrocarbon; withdrawing at least a portion of the liquid reaction medium from the reaction zone; passing at least a portion of the withdrawn liquid reaction medium to an oxygen injection zone located external to the reaction zone; contacting the liquid in said oxygen-injection zone with a gas stream containing molecular oxygen under conditions sufficient to form a two-phase gas/liquid mixture; and passing said two-phase gas/liquid mixture to the reaction zone as the feed of molecular oxygen thereto.
    Type: Grant
    Filed: March 30, 1979
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: James Leacock
  • Patent number: 4256912
    Abstract: A method for the removal of soluble tellurium compounds from vicinal glycol ester solutions, prepared with tellurium-halide ion catalyst systems, by diluting the tellurium-containing vicinal glycol ester solution with water and contacting said glycol-water solution with a strongly acidic sulfonated ion exchange resin leaving an essentially tellurium-free vicinal glycol ester reaction product which may then be processed to recover the desired ester product and by-products without loss of valuable tellurium. The tellurium may be recovered from the ion exchange resin and treated to recover tellurium in a form suitable for reuse.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: March 17, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Alfred A. Wolsky, Richard B. Papp, James G. Victor
  • Patent number: 4244936
    Abstract: A process for the recovery of tellurium compounds which have been retained on a strongly acidic sulfonated ion exchange resin employed to remove soluble tellurium compounds from tellurium-containing vicinal glycol ester solutions, by elution of the resin with dilute mineral acids, such as hydrochloric, to form a tellurium-containing acid eluate and treating the eluate by stripping or distilling to remove contained water and acid leaving a tellurium compound concentrate which may be treated in the presence of air or oxygen to convert the tellurium to a form suitable for reuse in the preparation of vicinal glycol esters.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: January 13, 1981
    Assignee: Atlantic Richfield Company
    Inventors: James G. Victor, Richard B. Papp, Alfred A. Wolsky
  • Patent number: 4245114
    Abstract: In the preparation of glycol esters by the liquid phase reaction of an olefin, molecular oxygen, and a carboxylic acid in the presence of a catalyst system comprising a variable valent cation in association with bromine, chlorine, a bromine-containing compound or a chlorine-containing compound, improved reaction rate and product selectively are achieved by carrying out the reaction in a vertical reaction zone communicating with at least one zone for movement of liquid from the top of the vertical reaction zone to the bottom of said reaction zone, and providing gaseous and liquid feeds in predetermined relationships and providing predetermined vertical superficial liquid velocities.
    Type: Grant
    Filed: December 19, 1978
    Date of Patent: January 13, 1981
    Assignee: Halcon Research and Development Corporation
    Inventor: Alan Peltzman
  • Patent number: 4239911
    Abstract: Alkylene glycol dicarboxylates are obtained by reacting carboxylic acid esters of monohydric or polyhydric aliphatic short-chain alcohols with an olefin and oxygen in the presence of a catalyst, a hydrolyzing agent and water.
    Type: Grant
    Filed: May 24, 1977
    Date of Patent: December 16, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Juergen Hartig
  • Patent number: 4238624
    Abstract: Ethylene glycol mono- and dialkanoates are produced by the vapor phase reaction of ethylene, molecular oxygen, and a lower alkanoic acid at about 150.degree. C.-225.degree. C. in the presence of an iodine source and a catalyst consisting essentially of bismuth-stabilized TeO.sub.2 on a carbon support.
    Type: Grant
    Filed: November 2, 1979
    Date of Patent: December 9, 1980
    Assignee: The Dow Chemical Company
    Inventors: Nancy J. Morris, George D. Shier
  • Patent number: 4237312
    Abstract: In the oxidation of acyclic conjugated dienes, recovery and recycle of the oxidation catalyst is accomplished by distilling off the oxidation solvent, extraction of the oxidation product with a suitable solvent, and removal of the extraction solvent residue from the catalyst, and recycle of the catalyst to the oxidation step.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: December 2, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4228301
    Abstract: In a process for preparing diacetoxybutene by subjecting butadiene, acetic acid and oxygen to reaction, the discharge gas from the reaction system or purification system, containing butadiene and/or acetic acid, is treated by contacting with diacetoxybutene and/or diacetoxybutane (absorbent) to allow butadiene and/or acetic acid to be absorbed by said absorbent. A part of the diacetoxybutene separated in a distillation tower from the reaction product solution containing diacetoxybutene produced by said three-component reaction can be used as said absorbent. In this case, butadiene and/or acetic acid can be recovered from said discharge gas by supplying the absorption solution into said distillation tower. Also usable as said absorbent is diacetoxybutane obtained by hydrogenation of diacetoxybutene.
    Type: Grant
    Filed: October 11, 1978
    Date of Patent: October 14, 1980
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yoshinori Yoshida, Hironobu Shinohara
  • Patent number: 4224301
    Abstract: A method for the removal and recovery of tellurium from a vicinal glycol ester solution containing soluble tellurium compounds by contacting the tellurium-containing glycol ester solution at a suitable temperature with granular activated carbon to adsorb the soluble tellurium compounds. The tellurium may be recovered from the activated carbon and converted to a form suitable for reuse in the preparation of the vicinal glycol esters.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: September 23, 1980
    Assignee: Atlantic Richfield Company
    Inventor: Thomas A. Washall
  • Patent number: 4221916
    Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.
    Type: Grant
    Filed: August 25, 1978
    Date of Patent: September 9, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4221917
    Abstract: Monoolefins and diolefins are converted to corresponding esters in a process by contacting together at least one monoolefin, diolefin or mixture thereof, oxygen, at least one iodosoaryl dicarboxylate and at least one carboxylic acid, carboxylic acid anhydride or mixture thereof.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: September 9, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4220800
    Abstract: Saturated vicinal esters are produced by reacting olefins with carboxylic acids and oxygen in the presence of a boron-containing catalyst component.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: September 2, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4219666
    Abstract: Carboxylic acid esters of vicinal glycols are prepared by oxidizing olefins with oxygen in the presence of carboxylic acids and of halogen and tellurium salts as catalysts, the reaction being carried out in vessels and apparatus consisting of, or lined with, zirconium or alloys of not less than 80% by weight of zirconium, the remainder being tin and/or hafnium.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: August 26, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Platz, Hans-Martin Weitz, Juergen Hartig
  • Patent number: 4208534
    Abstract: Ethylene glycol esters are obtained from the oxyacylation reaction of ethylene, oxygen and a carboxylic acid in the vapor phase at an elevated temperature and at a controlled pressure in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxides.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: June 17, 1980
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib
  • Patent number: 4205181
    Abstract: A process for preparing unsaturated esters by oxyacylation which comprises contacting a C.sub.3 or higher olefin, oxygen and a carboxylic acid in the vapor phase at an elevated temperature and at a controlled pressure in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxides.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 27, 1980
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib
  • Patent number: 4189600
    Abstract: Diacetates of 1,2-glycols are manufactured by reacting acetic acid with an olefin and oxygen, using oxygen dissolved in the liquid phase of the reaction mixture and avoiding the presence of gaseous oxygen in the reaction space.
    Type: Grant
    Filed: July 18, 1977
    Date of Patent: February 19, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Juergen Hartig, Ludwig Vogel, Helmuth Grube
  • Patent number: 4180676
    Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: December 25, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4164615
    Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: August 14, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4162363
    Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.
    Type: Grant
    Filed: August 25, 1977
    Date of Patent: July 24, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4154957
    Abstract: A method is disclosed for preparing esters by reacting an olefin with an acid in the presence of oxygen and a catalyst system, the improvement consisting in that the catalyst system is a compound of tin or cerium, used in the presence of iodine or of a iodine-yielding compound. High productivities are achieved and no pollution problems are to be solved.
    Type: Grant
    Filed: January 4, 1977
    Date of Patent: May 15, 1979
    Assignee: Anic S.p.A.
    Inventors: Carlo Neri, Antonio Esposito
  • Patent number: 4153806
    Abstract: Ethylene glycol esters or propylene glycol esters are recovered from their mixtures with high- and low-boiling organo-halogens by (1) distilling the mixture in a first distillation zone to form a first bottoms stream comprising the high-boiling organo-halogen impurities and a first overhead stream comprising the ethylene glycol esters or propylene glycol esters together with the low-boiling organo-halogen impurities, and (2) distilling at least a portion of the first overhead stream in a second distillation zone to form a second overhead stream containing the low-boiling organo-halogen impurities and a second bottoms stream comprising the desired ethylene glycol esters or propylene glycol esters having a substantially reduced concentration of the organo-halogen impurities.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: May 8, 1979
    Assignee: Halcon Research and Development Corp.
    Inventor: Alan Peltzman
  • Patent number: 4152295
    Abstract: A conjugated diolefin is reacted with at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride in the presence of oxygen and a catalyst comprising a rare earth metal compound, an alkali metal compound and a halide compound.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: May 1, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Paul R. Stapp
  • Patent number: 4144396
    Abstract: Alkylene glycol esters are produced by the reaction of an olefin, a carboxylic acid and molecular oxygen employing a bromine-containing substance and a nitrogen oxide as a catalyst.
    Type: Grant
    Filed: June 27, 1977
    Date of Patent: March 13, 1979
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takeshi Okano, Naoto Wada, Yoshimitsu Kobayashi