Preparing From Ether Patents (Class 568/866)
  • Patent number: 4873379
    Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium in the presence of an alkali metal compound.
    Type: Grant
    Filed: May 25, 1988
    Date of Patent: October 10, 1989
    Assignee: Hoechst Celanese Corporation
    Inventor: Mark A. Murphy
  • Patent number: 4870208
    Abstract: A process of preparing chiral alcohols by the asymmetric catalytic hydrogenolysis of epoxides using rhodium or ruthenium catalysts containing chiral phosphine ligands.
    Type: Grant
    Filed: June 3, 1988
    Date of Patent: September 26, 1989
    Assignee: Monsanto Company
    Inventors: Albert S. C. Chan, James P. Coleman, Grace M. Wagner
  • Patent number: 4859801
    Abstract: Process for preparing 2-alkyl-1,4-butanediols and mixtures with 1,4-butanediol which comprises bringing together, at an initial alkaline pH, and at a temperature and pressure suitable for reaction, 2,3-dihydrofuran, hydrogen, an unsubstituted aliphatic aldehyde, especially formaldehyde, and a hydrogenation catalyst. Also processes for preparing mixtures of tetrahydrofuran and 3-alkyltetrahydrofuran from the diol mixtures, and copolymers from the tetrahydrofuran mixtures.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: August 22, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard E. Ernst
  • Patent number: 4801759
    Abstract: A method for the continuous saponification of epoxides with 3-8 carbon atoms at low pressures, preferably atmospheric pressure, and low boiling temperatures with small amounts of water. Yields and selectivities are very high.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: January 31, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
  • Patent number: 4663468
    Abstract: There is disclosed a method of hydroformylating 3-methyl-3-buten-1-ol and analogs thereof with carbon monoxide and hydrogen in the presence of a rhodium compound free from modification by a ligand containing an element belonging to the group V of the periodic table as well as a method of producing 3-methylpentane-1,5-diol and .beta.-methyl-.delta.-valerolactone using such hydroformylation product.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: May 5, 1987
    Assignee: Kuraray Company, Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4661643
    Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing ruthenium to produce at least one of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. The production rate of each of said monoethylene glycol monomethyl ether, monoethylene glycol and ethanol is at least about 10 moles/kilogram ruthenium/hour.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: April 28, 1987
    Assignee: Union Carbide Corporation
    Inventor: William J. Bartley
  • Patent number: 4649225
    Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing iridium to produce at least one of monoethylene glycol monoethyl ether, monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. Monoethylene glycol monoethyl ether can be produced in significant amounts by employing the process of this invention.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: March 10, 1987
    Assignee: Union Carbide Corporation
    Inventor: William J. Bartley
  • Patent number: 4633025
    Abstract: A method for preparing important stereospecific intermediates in the synthesis of prostaglandin analogs is disclosed. Said intermediates are (+)R-2-methyl-hexane-1,2-diol and (-)S-2-methyl-hexane-1,2-diol and are prepared via an asymmetric halolactonization reaction utilizing L-proline and D-proline, respectively as the chiral agent.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: December 30, 1986
    Assignee: Miles Laboratories, Inc.
    Inventor: Paul F. Corey
  • Patent number: 4609768
    Abstract: This invention relates to the manufacture of ethylene glycol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus 1,3-dioxolane in the presence of a homogenous liquid catalyst containing an effective amount of cobalt-containing compound, a silane or germane-containing promoter dispersed in a dioxolane solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: September 2, 1986
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, Jiang-Jen Lin, Neal J. Grice
  • Patent number: 4568780
    Abstract: This invention relates to the manufacture of ethylene glycol and more particularly to a low pressure process for making ethylene glycol comprising reacting synthesis gas, i.e. a mixture of carbon monoxide and hydrogen, plus 1,3-dioxolane in the presence of a homogenous liquid catalyst containing an effective amount of cobalt-containing compound and a silane or germane-containing promoter dispersed in a hydrocarbon solvent at a temperature of at least 50.degree. C. and a pressure of at least 500 psi, where the particular solvents used allow the desired product to be separated from the reaction mixture by phase separation.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: February 4, 1986
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4533774
    Abstract: Ethylene glycol is produced by reacting at elevated temperature methanol, a polymeric source of formaldehyde and an organic peroxide having the formula R--O--O--R.sup.1 wherein R and R.sup.1 are independently either alkyl or aralkyl groups containing from 3 to 12 carbon atoms. The polymeric source of formaldehyde is preferably paraformaldehyde.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: August 6, 1985
    Assignee: The British Petroleum Company p.l.c.
    Inventor: Colin G. Griggs
  • Patent number: 4510336
    Abstract: Transetherification is carried out in a catalytic distillation reactor, wherein the catalytic structure also serves as a distillation structure, by feeding a first ether to the catalyst bed to at least partially dissociate it into a first olefin and a first alcohol while concurrently therewith feeding either a second olefin (preferably a tertiary olefin) having a higher boiling point than said first olefin or a second alcohol having a higher boiling point than said first alcohol to the catalyst whereby either the second olefin and the first alcohol or the first olefin and the second alcohol react to form a second ether which has a higher boiling point than the first ether, which second ether is concurrently removed as a bottoms in the concurrent reaction-distillation to force that reaction to completion, while the unreacted first olefin or first alcohol is removed in the overhead.
    Type: Grant
    Filed: October 20, 1982
    Date of Patent: April 9, 1985
    Assignee: Chemical Research & Licensing Company
    Inventor: Dennis Hearn
  • Patent number: 4503275
    Abstract: Butane-1,4-diol is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each, independently of the other, represent a C.sub.1 to C.sub.4 alkyl radical, and R.sub.3 and R.sub.4 each, independently of the other, represent a hydrogen atom or a C.sub.1 to C.sub.3 alkyl radical, or wherein R.sub.1 represents a C.sub.1 to C.sub.4 alkyl radical, R.sub.2 and R.sub.3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R.sub.4 represents a hydrogen atom or a C.sub.1 to C.sub.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: March 5, 1985
    Assignee: Davy McKee (London) Limited
    Inventors: Norman Harris, Alan J. Dennis, George E. Harrison
  • Patent number: 4474973
    Abstract: A coproduct continuous dealkylation process is described in which 4-t-butoxy-n-butanol is contacted with acidic silica-alumina catalyst at temperatures in the 160.degree.-200.degree. C. range (reactor wall temperature) in the liquid hourly space velocity regime of 2:0 to 6:0 liter/liter catalyst/hr. to produce in a single reactor a mixture in which the ultimate product of conversion of the 4-t-butoxy-n-butanol is 1,4-butanediol (1,4-diol) and tetrahydrofuran (THF) present in a preselected ratio (mole %) of 1,4-diol to THF ranging from 7:3 to 3:7. The 1,4-diol produced is useful in the preparation of polyesters, e.g. polybutylene terephthalates, and THF is a useful intermediate in the manufacture of certain chemicals and plastics.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: October 2, 1984
    Assignee: General Electric Company
    Inventor: Gregory R. Chambers
  • Patent number: 4368337
    Abstract: A process is described for converting glycol dialkyl ether without substantial formation of olefin oligomers by reaction with water, comprising reacting a feed glycol di-tertiary alkyl ether represented by structural formula (A) with water using a strongly acidic cation-exchange resin as a catalyst and a reaction temperature of from 40.degree. C. to 150.degree. C. under a pressure of from 1 to 70 kg/cm.sup.2 (absolute pressure) in a molar ratio of water/feed glycol di-tertiary alkyl ether represented by the structural formula (A) of from 0.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: January 11, 1983
    Assignee: Maruzen Oil Co., Ltd.
    Inventors: Kinya Tawara, Hiroki Kamiyama, Shigenori Nakashizu, Takashi Kaneko, Tadahiro Wakui, Tadashi Matsumoto
  • Patent number: 4313008
    Abstract: The S-enantiomer of 3-chloro-1,2-propanediol is prepared by reaction of a chlorodeoxy-D-saccharide having the partial structure. ##STR1## to cleave the glycol, reduce the aldehyde so formed to an alcohol, and hydrolyse the alcohol under mild acidic conditions.
    Type: Grant
    Filed: May 17, 1979
    Date of Patent: January 26, 1982
    Assignee: Tate & Lyle Ltd.
    Inventor: Haydn F. Jones
  • Patent number: 4254290
    Abstract: A de-alkylation process which comprises contacting a t-alkylether-alkanol, e.g. 4-t-butylether-n-butan-1-ol, with an acidic solid mixed oxide, e.g. silica-alumina, catalyst which results in the formation of alkanediols, e.g. 1,4-butanediol, in the substantial absence of undesirable side reactions, e.g. the formation of tetrahydrofuran. The resulting alkanediols are useful in the preparation of polyesters, e.g. polybutylene terephthalates.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: March 3, 1981
    Assignee: General Electric Company
    Inventors: Gregory R. Chambers, William E. Smith
  • Patent number: 4096192
    Abstract: A process for the preparation of 2-methyl-1,3-propanediol (MPD) by recycling mixed diols from the process for the preparation of 1,4-butanediol from acrolein and aliphatic diols until the final product is essentially 1,4-butanediol and MPD.
    Type: Grant
    Filed: March 30, 1976
    Date of Patent: June 20, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Kamlesh Kumar Bhatia, Charles Carmen Cumbo