Definite Molecular Weight Product, E.g., Dimer, Etc. Patents (Class 585/510)
  • Patent number: 4463211
    Abstract: A process for the oligomerization of normal C.sub.2 -C.sub.10 olefins, for example n-butenes by passing a feed containing said olefins in liquid phase through a fixed bed of acid, cation exchange resin at a temperature in the range of 40.degree. to 185.degree. C. at LHSV of 0.10 to 10 and recovering the oligomer product. In the case of n-butenes the principal component of the oligomer product is C.sub.8 dimer.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: July 31, 1984
    Assignee: Petro-Tex Chemical Corporation
    Inventor: Harold E. Manning
  • Patent number: 4454367
    Abstract: 1-Butane and isobutene are effectively separated without isomerization of 1-butene by contacting an isobutene-containing hydrocarbon mixture with a solid acid catalyst having a solid acid quantity of 0.05 to 0.25 mmol/g of solid acid catalyst, represented by the adsorption quantity of pyridine, thus low-polymerizing selectively isobutene and then separating the low polymers of isobutene from 1-butene.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: June 12, 1984
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Satoshi Sakurada, Takao Hashimoto, Nobuaki Tagaya, Tsugio Maeshima, Kayako Ueda, Masahiro Kokubo
  • Patent number: 4451685
    Abstract: A process to convert propylene to gasoline blending stock products comprises contacting C.sub.2 -C.sub.3 olefins under conversion conditions with an AMS-1B crystalline borosilicate catalyst composition.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: May 29, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: Thomas D. Nevitt, Norman F. Jerome
  • Patent number: 4451689
    Abstract: Preparation of high molecular weight, branched-chain olefins by the co-dimerization of C.sub.9 -C.sub.21 branched-chain internal olefins by a process comprising (a) contacting a propylene oligomer feedstock having from 9 to 21 carbon atoms in a reaction zone with a catalyst selected from the group consisting of hydrogen fluoride, boron trifluoride-alkanol and aluminum chloride; (b) maintaining the temperature in the reaction zone between about 0.degree. C. and 75.degree. C.; and (c) maintaining the pressure in the reaction zone between about 0 psig and 100 psig.
    Type: Grant
    Filed: July 27, 1982
    Date of Patent: May 29, 1984
    Assignee: Chevron Research Company
    Inventor: Joseph Z. Pasky
  • Patent number: 4451684
    Abstract: Preparation of C.sub.20 -C.sub.40 branched-chain olefins by the co-oligomerization of C.sub.12 -C.sub.18 branched-chain internal olefins with C.sub.5 'C.sub.6 olefins by a process comprising (a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C.sub.5 -C.sub.6 olefin feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst; (b) maintaining the temperature in the reaction zone between about 0.degree. C. and 80.degree. C.; and (c) maintaining the pressure in the reaction zone between about 0 psig and 200 psig.
    Type: Grant
    Filed: July 27, 1982
    Date of Patent: May 29, 1984
    Assignee: Chevron Research Company
    Inventor: Joseph Z. Pasky
  • Patent number: 4447668
    Abstract: Alkyl tertiary butyl ether or alkyl tertiary amyl ether is dissociated by vapor phase contact with a cation acidic exchange resin at temperatures in the range of 150.degree. to 250.degree. F. at LHSV of 0.1 to 20 to produce a stream consisting of unreacted ether, isobutene or isoamylene and an alcohol corresponding to the alkyl radical. After the alcohol is removed, the ether/isoolefin stream may be fractionated to obtain a high purity isoolefin (99+%) or the ether/isoolefin stream can be contacted in liquid phase with a cation acidic exchange resin to selectively dimerize the isoolefin in a highly exothermic reaction, followed by fractionation of the dimerization product to produce high purity diisoolefin (97+%). In the case where the alkyl is C.sub.3 to C.sub.6 and the corresponding alcohol is produced on dissociation of the ether, combined dissociation-distillation may be carried out such that isoolefin is the overhead product and alcohol the bottom.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: May 8, 1984
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Edward M. Jones, Jr., Dennis Hearn
  • Patent number: 4436947
    Abstract: Olefin oligomers suitable as lubricants are prepared with a catalyst comprising boron trifluoride and a mixture of an alcohol, a polyol and a ketone. 1-Decene is oligomerized to a liquid product having a high trimer to tetramer ratio using boron trifluoride and a mixture of n-butanol, ethylene glycol and methylethyl ketone.
    Type: Grant
    Filed: September 11, 1981
    Date of Patent: March 13, 1984
    Assignee: Gulf Research & Development Company
    Inventors: Neal E. Morganson, Adam V. Vayda
  • Patent number: 4436946
    Abstract: This invention is a process for the selective conversion of propylene and the n-butylenes to their dimers, in the presence of a heterogeneous palladium cyanide catalyst. The product dimers are predominantly of straight-chain structure.
    Type: Grant
    Filed: November 19, 1982
    Date of Patent: March 13, 1984
    Assignee: Shell Oil Company
    Inventor: Edgar J. Smutny
  • Patent number: 4429177
    Abstract: An alpha-olefin is oligomerized in the presence of a three-component catalyst comprising a particulate solid adsorbent, boron trifluoride and elemental oxygen. The process also activates the catalyst. For example, 1-decene is oligomerized to a product predominating in the trimer and tetramer using boron trifluoride, elemental oxygen and silica as the solid adsorbent.
    Type: Grant
    Filed: August 4, 1982
    Date of Patent: January 31, 1984
    Assignee: Gulf Research & Development Company
    Inventors: Neal E. Morganson, Paul G. Bercik
  • Patent number: 4423269
    Abstract: A process for oligomerizing gaseous olefins using intermediate pore size molecular sieves is disclosed.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: December 27, 1983
    Assignee: Chevron Research Company
    Inventor: Stephen J. Miller
  • Patent number: 4420646
    Abstract: Novel feedstocks for the production of synthetic lubricant base oils are described. The feedstock is a blend of internal and alpha olefins with the internal olefins comprising more than 50 but less than 99 weight percent of the blend. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. The olefins may be oligomerized over a boron trifluoride catalyst and a promoter. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco Inc.
    Inventors: Jerome W. Darden, Lewis W. Watts, Jr., Edward T. Marquis
  • Patent number: 4420647
    Abstract: A synthetic lubricating oil composition comprising a major portion of a synthetic lubricant component or a mixture of a synthetic lubricant component and a hydrocarbon mineral base oil and a minor portion of various additive components is described. The synthetic lubricant component is manufactured from internal olefins.The process for making the synthetic lubricant component utilizes boron trifluoride catalysis with a promoter to produce oligomer mixtures that have surprisingly low viscosities at low temperatures and surprisingly high viscosity indexes as compared with the oligomers found in other methods. It is important that internal olefins be used predominantly to make the oligomers. Alpha olefins make up the balance of the olefins.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: December 13, 1983
    Assignee: Texaco Inc.
    Inventors: Kenneth G. Hammond, Joseph C. Sendra, Lewis W. Watts, Jr., Edward T. Marquis, John M. Larkin
  • Patent number: 4413154
    Abstract: The present invention provides a process which is adapted for cyclodimerization of 1,3-butadiene to 4-vinylcyclohexene under Diels-Alder conditions in the presence of a large-pore carbon molecular sieve.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: November 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 4404415
    Abstract: A process is provided for the production of nonenes or of a nonenes/dodecenes mixture, wherein: propylene is introduced into a liquid reaction phase containing a soluble dimerization catalyst, the temperature is 20.degree.-60.degree. C., at least a portion of the resultant hexenes is recycled and the propylene concentration is maintained between 0.05 and 1% by weight.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: September 13, 1983
    Assignee: Institut Francais du Petrole
    Inventor: Jean Gaillard
  • Patent number: 4400565
    Abstract: A method for oligomerizing olefins in the presence of boron trifluoride and a co-catalyst comprising a heterogeneous cationic ion exchange resin catalyst is described. While the resin catalyst cannot oligomerize olefins by itself at temperatures around 75.degree.-85.degree. C., when used together with boron trifluoride an oligomer mixture may be created which has improved properties over oligomers made over only boron trifluoride. If a resin catalyst is used, a protonic promoter is not required.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: August 23, 1983
    Assignee: Texaco Inc.
    Inventors: Jerome W. Darden, Edward T. Marquis, Lewis W. Watts, Jr.
  • Patent number: 4396787
    Abstract: Formation of undesirable popcorn polymer on the walls of a reaction vessel during thermal dimerization of butadiene is prevented by coating the walls with a falling film of aqueous sodium nitrite solution.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: August 2, 1983
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventors: Karl-Heinz Gluzek, Olaf Petersen, Wilhelm Neier, Gunter Strehlke, Karl-Heinz Heinemann
  • Patent number: 4388480
    Abstract: A process for preparing 4-methyl-1-pentene comprising dimerizing propylene in the presence of a catalyst, characterized in that the catalyst is composed of sodium and/or sodium amide supported on a carrier represented by the following formula K.sub.2 O.xAl.sub.2 O.sub.3 wherein x has a value in the range of 0.5.ltoreq..times..ltoreq.11. In one embodiment, the catalyst is hydrogenated prior to the use thereof.
    Type: Grant
    Filed: January 7, 1982
    Date of Patent: June 14, 1983
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Hirosuke Imai, Mitsuo Matsuno, Michio Kudoh
  • Patent number: 4386229
    Abstract: Internal olefins such as those obtained from a disproportionation of 1-olefins like 1-decene are dimerized over a promoted boron trifluoride catalyst to yield oils useful as lubricant basestock.
    Type: Grant
    Filed: October 1, 1981
    Date of Patent: May 31, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Louis F. Heckelsberg, William T. Nelson, Sidney Schiff, Ernest A. Zuech
  • Patent number: 4384157
    Abstract: A process is disclosed for the catalytic condensation of propylene to produce C.sub.6 -plus hydrocarbons. The process consumes all of the propylene present in a mixed propane-propylene feed stream and produces a high purity propane effluent stream. The effluent of the reaction zone is flashed with the resultant vapor being recycled to the reaction zone and the remaining liquid being passed into a fractionation column. A C.sub.3 sidecut is removed from the column and stripped to remove propylene, which is returned to the column. The overhead stream of the column is also recycled to the reaction zone.
    Type: Grant
    Filed: March 31, 1982
    Date of Patent: May 17, 1983
    Assignee: UOP Inc.
    Inventor: Richard R. DeGraff
  • Patent number: 4375576
    Abstract: In the liquid phase reaction of isobutene in the presence of resin cation exchange resins with itself in a C.sub.4 hydrocarbon stream to form dimers, the formation of higher polymers, oligomers, and co-dimer by-products is suppressed by the presence of 0.0001 to 1 mole per mole of isobutene of methyl tertiary butyl ether.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: March 1, 1983
    Assignee: Chemical Research & Licensing Co.
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4365105
    Abstract: An alpha-olefin is oligomerized in the presence of a three-component catalyst comprising a particulate solid adsorbent, boron trifluoride and elemental oxygen. For example, 1-decene is oligomerized to a product predominating in the trimer and tetramer using boron trifluoride, elemental oxygen and silica as the solid adsorbent.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: December 21, 1982
    Assignee: Gulf Research & Development Company
    Inventors: Neal E. Morganson, Paul G. Bercik
  • Patent number: 4334113
    Abstract: A synthetic hydrocarbon fluid is prepared by oligomerizing an olefin reactant in the presence of a catalyst prepared by reacting tungsten hexafluoride and water at a moderate temperature. For example, 1-butene is oligomerized at a temperature of about 40.degree. C. in the presence of a catalyst obtained by reacting tungsten hexafluoride and water in a four to one mol ratio. The liquid oligomer product is then hydrogenated to remove residual unsaturation.
    Type: Grant
    Filed: September 29, 1980
    Date of Patent: June 8, 1982
    Assignee: Gulf Research & Development Company
    Inventors: John P. Pellegrini, Jr., David L. Beach, Thaddeus P. Kobylinski
  • Patent number: 4319064
    Abstract: Internal olefins such as those obtained from a disproportionation of 1-olefins like 1-decene are dimerized over a promoted boron trifluoride catalyst to yield oils useful as lubricant basestock.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: March 9, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Louis F. Heckelsberg, William T. Nelson, Sidney Schiff, Ernest A. Zuech
  • Patent number: 4317948
    Abstract: A mixed olefin feedstock obtained from disproportionating C.sub.8 to C.sub.18 1-olefins can be used as such for a dimerization process to produce branched hydrocarbons that are useful as lubricating oils or greases.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: March 2, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Louis F. Heckelsberg
  • Patent number: 4313016
    Abstract: The isobutene in C.sub.4 hydrocarbon streams containing from 0.5 to 5% isobutene and n-butenes is reduced preferably to a level of 0.2 mole % or less by passing the feed stream at LHSV 2.5 to 12 in liquid phase through a fixed-bed cation exchange resin catalyst in a tubular reactor with a water heat exchange medium maintained at a temperature of 50.degree. to 80.degree. C., whereby the isobutene is oligomerized and easily separated from the remaining C.sub.4 's by fractionation.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: January 26, 1982
    Assignee: Petro-Tex Chemical Corporation
    Inventor: Harold E. Manning
  • Patent number: 4301315
    Abstract: A stream comprising isobutylene and n-butenes is processed to effect dimerization of the isobutylene, and the resulting isobutylene dimer is fed to an alkylation step.
    Type: Grant
    Filed: September 22, 1977
    Date of Patent: November 17, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Donald M. Haskell, Floyd Farha, Jr.
  • Patent number: 4300006
    Abstract: A mixed olefin feedstock obtained from disproportionating C.sub.8 -C.sub.10 1-olefins can be used as such, i.e. without removal of 1-olefins in a boron trifluoride catalyzed dimerization step to produce synthetic lubricating oils. The results achieved are as good as those achieved using a feedstock from which the undisproportionated 1-olefins have been removed so that this feedstock contains only internal olefins for the dimerization.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: November 10, 1981
    Assignee: Philips Petroleum Company
    Inventor: William T. Nelson
  • Patent number: 4282392
    Abstract: An alpha-olefin oligomer synthetic lubricant having an improved viscosity-volatility relationship is prepared from an alpha-olefin such as 1-decene.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: August 4, 1981
    Assignee: Gulf Research & Development Company
    Inventors: Barrett L. Cupples, William J. Heilman
  • Patent number: 4263465
    Abstract: A low viscosity synthetic lubricant is prepared by polymerizing 1-butene to an oligomer containing a number average of about 8 to 18 carbon atoms and copolymerizing the oligomer with an alpha-monoolefin having 8 to 18 carbon atoms to produce a copolymer having an average of about 20 to 40 carbon atoms. Both polymerization reactions are catalyzed by a combination of boron trifluoride and a proton donor promoter. The synthetic lubricant is preferably stripped to remove lower boiling components, such as oligomers having 20 carbon atoms or less, and optionally hydrogenated for improved stability.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: April 21, 1981
    Assignee: Atlantic Richfield Company
    Inventors: Ming N. Sheng, Mary T. Arnold
  • Patent number: 4254295
    Abstract: A process for the selective oligomerization of linear and branched chain C.sub.2 to C.sub.12 olefins is provided. The process comprises contacting of the said olefin in the liquid phase with ZSM-12 at temperatures of 80.degree. F. to 400.degree. F.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: March 3, 1981
    Assignee: Mobil Oil Corporation
    Inventor: Samuel A. Tabak
  • Patent number: 4242531
    Abstract: Olefins are dimerized in a loop reactor with flashing of the reactor effluent in a flashing zone within the loop. A subsequent flash in a second flashing zone can also be used for the removal of product as flash vapor. In another embodiment, separated product dimers or product heavies are used as absorbents for unreacted ethylene. The use of a vapor-liquid contacting device incorporated in the loop reactor is especially helpful in the dimerization of an olefin when the olefin is available in low-concentration gas streams. A thermosiphon loop reactor can also be used for low-concentration olefin streams to minimize the power requirements as the energy of the feed gas is used to induce the reactor circulation.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: December 30, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Cecil O. Carter
  • Patent number: 4242530
    Abstract: A method for the separation of isobutene from a mixture comprising n-butene and isobutene comprising feeding a C.sub.4 stream containing n-butene and isobutene to a distillation column reactor into a feed zone contacting the stream with fixed bed acidic cation exchange resin to form diisobutene which passes to the bottom of the column, said n-butene being removed overhead. The reaction and distillation occur concurrently.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: December 30, 1980
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4213001
    Abstract: A method of homopolymerizing a 1-olefin to a product including the trimer and tetramer by utilizing boron trifluoride under pressure in the presence of a suspended particulate adsorbent material. For example, 1-decene is homopolymerized at a temperature of about 25.degree. C. in the presence of a suspension of about two weight percent silica and boron trifluoride at a pressure of 125 psi.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: July 15, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Ajay M. Madgavkar, Harold E. Swift, Barrett L. Cupples
  • Patent number: 4205195
    Abstract: C.sub.8 -C.sub.20 olefins are dimerized in the presence of hydrofluoric acid, by (1) contacting for about 1 to 30 minutes, at least one C.sub.8 -C.sub.20 olefin with liquid hydrofluoric acid at a temperature of between about -20.degree. C. and +60.degree. C., in a molar ratio of hydrofluoric acid to olefin of between about 1:1 and 50:1; (2) immediately after the contacting, the hydrofluoric acid present is removed almost instantaneously from the dimerization medium; (3) a defluorination of the said medium is effected; and (4) the resultant oledimers are recovered.
    Type: Grant
    Filed: March 23, 1979
    Date of Patent: May 27, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Michel Desbois
  • Patent number: 4198534
    Abstract: A cosmetic base material which consists of a synthetic saturated aliphatic hydrocarbon having 24 to 36 carbon atoms, wherein the proton ratio of methyl group to methylene group, that is, CH.sub.3 /CH.sub.2, within the hydrocarbon chain is in the range of from 0.25 to 0.6 and the pour point is in the range of from -55.degree. C. to 10.degree. C.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: April 15, 1980
    Assignee: The Lion Fat & Oil Co., Ltd.
    Inventors: Hiroshi Mandai, Anri Tominaga, Yoshikazu Yoshimura, Hiroshi Isa
  • Patent number: 4192961
    Abstract: A method and catalyst for preparing styrene which comprises dehydrodimerization of toluene, followed by conversion of the resulting dehydrodimerization products to styrene. The conversion is conducted in the presence of ethylene using a catalyst consisting of chromium oxide, tungsten oxide and an alkali metal oxide supported by a carrier. The method according to the present invention makes it possible to increase the yield of styrene and simplify the process technology.
    Type: Grant
    Filed: October 4, 1977
    Date of Patent: March 11, 1980
    Inventors: Sergei A. Polyakov, Aron L. Shapiro, Viktor J. Gankin
  • Patent number: 4172855
    Abstract: A process for making a low viscosity, low volatility .alpha.-olefin oligomer suitable for use as a functional fluid or lubricating oil comprising dimerizing a C.sub.6-12 .alpha.-olefin, reacting the resultant dimer with a C.sub.6-18 .alpha.-olefin in the presence of a Friedel-Crafts catalyst, distilling out volatile components and hydrogenating the residual product.
    Type: Grant
    Filed: April 10, 1978
    Date of Patent: October 30, 1979
    Assignee: Ethyl Corporation
    Inventors: Ronald L. Shubkin, Ellis B. Rifkin, Martin E. Gluckstein