Hydroxy Containing (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/675)
  • Patent number: 5198598
    Abstract: Alkadienyl ethers are prepared by the telomerization of conjugated dienes with polyols by continuous addition of the alkadiene to a reaction mixtue comprised of the polyol, secondary alcohol solvent, a portion of the alkadiene to be added, and low palladium catalyst concentration.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: March 30, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karlheinz Hill, Steven D. Axt, Kenneth J. Weese
  • Patent number: 5191123
    Abstract: A process for preparing hydroxyl-containing compounds which comprises contacting a carboxylated hydroxyl-containing compound with a metal oxide catalyst under conditions effective to produce the hydroxyl-containing compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5153179
    Abstract: A composition useful as a medicament with improved penetration of cell membranes comprising an active material and a compound of general formula: ##STR1## wherein either residue R.sub.1 or R.sub.2 is an alkyl, alkylene, alkynyl or alkoxy group of 3-7 carbon atoms, and the other residue is a hydrogen atom, together with pharmaceutical additives and dilution agents.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: October 6, 1992
    Assignee: Max-Planck-Gesellschaft zur Foerderung der Wissenschaft e.V.
    Inventor: Hansjorg Eibl
  • Patent number: 5146005
    Abstract: New, cationically curable oxyalkylene ethers and the synthesis thereof are disclosed. The oxyalkylene ethers, are of the general, average formula ##STR1## wherein R.sup.1 is an n-valent residual group derived from a compound (R.sup.1)H.sub.n from which n active hydrogen atoms have been split off and is capable of entering into an addition reaction with oxiranes, or a univalent alkyl or aryl group, and n.gtoreq.1;R.sup.2 is a hydrogen, hydrocarbon or R.sup.3 OCH.sub.2 -- group;R.sup.3 and R.sup.4 are each hydrogen, hydrocarbon or acyl groups, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may have different meanings in the molecule;R.sup.5, R.sup.6 and R.sup.7 are each hydrogen or alkyl groups with 1 to 8 carbon atoms, or R.sup.5 and R.sup.7, or R.sup.6 and R.sup.7 together are a constituent of a cyclic, non-aromatic hydrocarbon group with 5 or 6 carbon atoms;m is at least 1 and at most n;x is the average molecule=3 to 100, andy in the average molecule=0 to 100, provided that 3.ltoreq.x+y<150.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: September 8, 1992
    Assignee: TH. Goldschmidt AG
    Inventors: Christian Weitemeyer, Hardi Dohler
  • Patent number: 5126493
    Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: June 30, 1992
    Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
  • Patent number: 5053556
    Abstract: A one-step process for producing an alkenyl ether in only one step and under mild conditions by reacting an aldehyde of the formula ##STR1## with an alcohol of the formulaR.sup.3 --OHin the presence of an acidic catalyst in liquid phase, and recovering as the reaction product an alkenyl ether of the formula ##STR2## wherein R.sup.1 is a 2-8 C alkyl or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group,R.sup.2 is a 1-6 C alkyl,R.sup.3 is a linear or branched 6-12 C alkyl, a cyclohexyl, a hydroxyhexamethylenyl or ##STR3## wherein R' is H and n is 2 or 3, R.sup.4 is hydrogen or R--CH.sub.2 --CH.dbd. wherein R is a 1-8 C alkyl group, andR.sup.5 is a 2-8 C alkyl or R--CH.dbd.CH-- wherein R is a 1-8 C alkyl.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: October 1, 1991
    Assignee: Chisso Corporation
    Inventor: Noriyuki Ohnishi
  • Patent number: 5049681
    Abstract: A novel optically active allyl alcohol derivative represented by the following general formulae (I), (II), (III) and (IV): ##STR1## The novel optically active allyl alcohol can be used effectively for producing leucotrienes B.sub.4 by the process of reacting an optically active halogen substituted allyl alcohol and a novel optically active acetylene-substituted allyl alcohol.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: September 17, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 5037802
    Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 or C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: August 6, 1991
    Assignee: BASF K & F Corporation
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • Patent number: 5011943
    Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.24 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: April 30, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventor: Zhaoyin Wang
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4973765
    Abstract: Dien-1-ols of the general formula I ##STR1## where the radicals R.sup.1 to R.sup.7 are identical to or different from one another and each is hydrogen or straight-chain or branched alkyl of 1-12 carbon atoms and n is 1-14, are prepared by dehydrating a hydroxyalkenyl tert-butyl ether of the formula II ##STR2## in the presence of an acidic catalyst at elevated temperatures and essentially at the same time splitting off the tert-butyl protective group, as is 9-hydroxydodec-10-enyl 1-tert-butyl ether which is useful as an intermediate for synthesizing 8,10-dodecadienol.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: November 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Mackenroth, Wolfgang Hoelderich, Rainer Becker, Walter Seufert
  • Patent number: 4965376
    Abstract: 3,9-Dihydroxynonyne and its derivatives protected at the 9-OH function, of the general formula I ##STR1## where R is hydrogen or a conventional alcohol protective group, and processes for the preparation of the compounds I.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
  • Patent number: 4960754
    Abstract: Described are 3,7-dimethyl-6,7-dioxo-1,3-octadienes or mixtures of same defined according to the structure: ##STR1## wherein R is hydrogen or ethyl and X is one of the moieties: ##STR2## and wherein the wavy lines represent a "E" or "Z" configuration of the methyl and vinyl moiety about the 3,4-pi-bond of the molecule, as well as methods for methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of at least one of said 3,7-dimethyl-6,7-dioxo-1,3-octadienes.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: October 2, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, Michael J. Zampino, Braja D. Mookherjee, Robert W. Trenkle, Anton Van Ouwerkerk, Myrna L. Hagedorn, Michael G. Monteleone
  • Patent number: 4929769
    Abstract: A halogenated polyether is provided having a chemical structure which has been found to possess the requisite characteristics for satisfactory service as a promoter of good adhesion between a polymeric surface (e.g., a polyethylene terephthalate tire cord) and an elastomeric material (e.g., rubber). The halogenated polyether may be formed by (1) the reaction of an organic polyhydroxy compound with epihalohydrin (e.g., epichlorohydrin) to create ether linkages, (2) the epoxidation of the ends of the ether chains which extend from the residual portion of the organic polyhydroxy compound, and (3) the substantial hydrolysis of the epoxy groups (as described). The resulting halogenated polyether is substantially free of epoxy groups, contains at least one 2-halomethyloxyethylene unit, and contains 2,3-dihydroxypropyl end groups (as described). Such halogenated polyether optionally may be provided in the form of an oligomer (as described).
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: May 29, 1990
    Assignees: Hoechst Celanese Corporation, Alkaril Chemicals, Inc.
    Inventors: Norman S. Anderson, Albert L. Promislow, Randy L. Rayborn, Rastko Vukov
  • Patent number: 4843180
    Abstract: Conjugated diolefins such as 1,3-butadiene are converted to ethers by reaction with aliphatic hydroxyl-containing compounds such as ethylene glycol in the presence of a chelating phosphine adduct of zero valent nickel. A preferred chelating phosphine ligand is 1,2-bis(diphenylphosphino)ethane.
    Type: Grant
    Filed: June 21, 1988
    Date of Patent: June 27, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Mullins
  • Patent number: 4774363
    Abstract: This invention relates to compounds having the structure ##STR1## wherein M is an alkali metal and n is an integer having a value of from 0 to 12. The invention also relates to the method of preparing said metal derivatives of butenediol and to their catalytic use in vinylation reactions.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: September 27, 1988
    Assignee: GAF Corporation
    Inventor: Lowell R. Anderson
  • Patent number: 4722978
    Abstract: A cationic ring-opening polymerization of a cyclic ether ("CE") in conjunction with an unsaturated alcohol (propagator) having an allyl double bond, produces a polyether macromer having an allylic group near one end and a hydroxyl group at the other. The polymerization proceeds by polyaddition of the CE to the OH group which is the propagating species. The CE is an alkylene oxide or an aliphatic or aromatic glycidyl ether; the propagator is a primary or secondary alcohol which, if cyclic may have a single internal double bond in one ring. The catalyst is a Friedel-Crafts acid, strong protic organic or inorganic acid, oxonium salt, or the like.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: February 2, 1988
    Assignee: The B. F. Goodrich Company
    Inventor: Simon H. Yu
  • Patent number: 4721819
    Abstract: In a process for the preparation of allylic ethers which comprises contacting and reacting an allylic alcohol reactant comprising one or more C.sub.6 to C.sub.20 allylic alcohols with a glycol reactant comprises one or more C.sub.2 or C.sub.3 alkylene glycols and their polyalkylene glycols in the presence of a cuprous salt catalyst and an acidic co-catalyst, the invention is the improvement which comprises contacting the allylic alcohol and alkylene glycol reactants in an agitated reaction mixture containing a solvent for the allylic alcohol reactant and the ether product which is substantially immiscible with the alkylene glycol reactant, said solvent being present in the reaction mixture in a quantity by weight which is at least about three times the weight of the allylic alcohol reactant. The improvement of the invention substantially increases the selectivity of the process for the production of the allylic ethers.
    Type: Grant
    Filed: December 30, 1986
    Date of Patent: January 26, 1988
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 4683344
    Abstract: A process for the preparation of a pulverulent organomagnesium compound involves bringing together into intimate admixture a particulate hydroxyl functional material with an organomagnesium-containing material. The process is conducted at a temperature below the melting point of the hydroxyl functional material but at a temperature sufficient to convert at least a portion of the hydroxyl functional material to the pulverulent organomagnesium compound. The aforesaid organomagnesium compounds are useful as intermediates in generating anionic sites for anionic polymerization.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: July 28, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Robert B. Hodek, Jerome A. Seiner
  • Patent number: 4617287
    Abstract: Ruthenium carbonyl-cobalt carbonyl catalyst mixtures effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals, wherein said acetal may be prepared separately or in situ from an aldehyde and an alcohol. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium carbonyl-cobalt carbonyl catalyst to form the monomethyl ether of ethylene glycol.The invention also is directed to the ruthenium carbonyl-promoted cobalt carbonyl catalysts per se, including novel precipitated forms of these ruthenium-cobalt carbonyl catalyst mixtures.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: October 14, 1986
    Assignee: Sun Refining and Marketing Company
    Inventor: James E. Lyons
  • Patent number: 4590294
    Abstract: The invention relates to the use of hydrogen ion-exchanged layered clays in organic reactions which are catalyzed by protons. Such organic reactions include the production of ethers by the reaction of an alcohol with an olefin or an olefin oxide, the production of an ether by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of an alkyl aromatic compound by the reaction of an aromatic hydrocarbon with an olefin or a C.sub.2 or higher alcohol and the production of an alcohol by the hydration of an olefin.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 20, 1986
    Assignee: The British Petroleum Company Limited
    Inventors: James A. Ballantine, Reginald Gregory, John H. Purnell, John M. Thomas, David J. Westlake
  • Patent number: 4590300
    Abstract: Allyl methyl ethers are transetherified with alcohols by use of a catalyst of a solid acid that contains no mercury or cuprous salt catalyst.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: May 20, 1986
    Assignee: The Dow Chemical Company
    Inventors: Michael J. Mullins, Percy J. Hamlin
  • Patent number: 4576967
    Abstract: Triglycerine monoalkyl ethers of the general formula (I), which are novel polyol ether compounds, ##STR1## in which R represents a saturated or unsaturated, linear or branched fatty hydrocarbon group having from 8 to 24 carbon atoms.The ethers (I) of the present invention are prepared from firstly subjecting 1,3-bis-o-(2,3-o-isopropylideneglyceryl)glycerine (II) and an etherifying agent (IV) to Williamson's ether synthesis reaction, and the resulting 1,3-bis-o-(2,3-o-isopropylideneglyceryl)-2-o-alkylglycerine (III) is subsequently subjected to hydrolysis.The ethers according to the invention are chemically stable because no linkages susceptible to decomposition, e.g. ester bond, are contained in the molecular structure of the ethers. Moreover, the ethers give a reduced degree of stimulus to the skin and have the surface activity, so that they are useful as an emulsifier, oil (emolient), humectant, thickener and particularly as a component of cosmetics.
    Type: Grant
    Filed: July 16, 1984
    Date of Patent: March 18, 1986
    Assignee: KAO Corporation
    Inventors: Koichi Urata, Naotake Takaishi, Yuji Suzuki
  • Patent number: 4568774
    Abstract: Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF.sub.3 and metal alkyls or metal alkoxides, SiF.sub.4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: February 4, 1986
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4544775
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene; C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxo reaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: October 1, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4543258
    Abstract: Disclosed is a polyol ether compound represented by the general formula (I): ##STR1## in which R represents a saturated or unsaturated, straight-chain or branched aliphatic hydrocarbon group having 8 to 24 carbon atoms, and R' represents a saturated or unsaturated, straight-chain or branched hydrocarbon group having 1 to 24 carbon atoms.A preparation process of the compound (I) is also disclosed.Compounds according to the invention show excellent emulsification stability and are suitable to be a cosmetic composition.
    Type: Grant
    Filed: November 1, 1983
    Date of Patent: September 24, 1985
    Assignee: Kao Corporation
    Inventors: Koichi Urata, Naotake Takaishi, Yoshiaki Inamoto, Yuji Suzuki
  • Patent number: 4540828
    Abstract: Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: September 10, 1985
    Assignee: Vista Chemical Company
    Inventor: Kang Yang
  • Patent number: 4521634
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4479016
    Abstract: The invention relates to ethoxylates of diacetylene dialcohols as well as the use of these compounds as surfactants.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: October 23, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Erhard Klahr, Walter Rebafka, Axel Nissen, Wolfgang Trieselt, Albert Hettche
  • Patent number: 4465869
    Abstract: The specification describes a process for the production of a 4-alkoxymethyl-1,3-dioxolan in good yield, in high purity and in a simple manner by reacting an alkyl glycidyl ether with a carbonyl compound in the presence of an acid catalyst. The 4-alkoxymethyl-1,3-dioxolan is useful as an intermediate for the production of an .alpha.-monoalkyl glyceryl ether by hydrolysis.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: August 14, 1984
    Assignee: Kao Corporation
    Inventors: Naotake Takaishi, Kouichi Urata, Yoshiaki Inamoto
  • Patent number: 4418207
    Abstract: Unsaturated acetoacetic acid esters are suitable as comonomers in the polymerization of unsaturated compounds in an aqueous medium. Particularly suitable are acetylacetoxyalkyl-allyl ethers which may be synthesized in an easy manner and correspond to the formulae ##STR1## Said allyl ether derivatives are especially prepared by reacting an allyl alcohol with an epoxide and reacting the resulting hydroxyalkyl-allyl ether with diketene. Both reaction steps are carried out at a temperature of from 0.degree. to 100.degree. C., preferably in the presence of a catalyst. The allyl ether derivatives may be copolymerized especially with vinyl compounds, such as vinyl esters, acrylic acid esters, olefins, vinyl halides and vinyl aromatic hydrocarbons.
    Type: Grant
    Filed: July 9, 1980
    Date of Patent: November 29, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Braun, Helmut Rinno, Karl J. Rauterkus
  • Patent number: 4390734
    Abstract: Propylene glycol monoalkyl ethers are prepared in good yield by reacting acetaldehyde and an alkanol (or by reacting an acetal) with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt-containing compound and a cocatalyst comprising a member of the group consisting of rhodium-containing compounds, ruthenium-containing compounds and nickel-containing compounds, and heating the resulting mixture at moderate temperatures and pressures for sufficient time to produce the desired glycol monoalkyl ether, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: June 28, 1983
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4385185
    Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: May 24, 1983
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Walter Hafner
  • Patent number: 4360698
    Abstract: A process to form glycol ethers by reacting an organic compound (A) having at least one aliphatic hydroxyl group with an oxirane compound (B) under reaction conditions in the presence of a catalytic amount of a polymeric material that is substantially insoluble in the reaction mixture, said polymeric material having a plurality of pendant sulfonate moieties with divalent metal counterions. Preferential formation of the mono adduct of glycol ethers is noted.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: November 23, 1982
    Assignee: The Dow Chemical Company
    Inventor: James H. Sedon
  • Patent number: 4328368
    Abstract: A method if provided for continuously hydrolyzing urethane foam in a vertically oriented hydrolysis reactor. In a preferred practice, a bed of foam particles is formed in the reactor. Superheated steam is flowed continuously upward through the bed at a temperature and rate such that only the foam particles then adjacent the bottom of the reactor are hydrolyzed and the bulk of the bed is not fluidized. Unreacted steam heats the unhydrolyzed foam. Liquid hydrolysis products are drained as they are formed to prevent hydrolysis-impeding liquid saturation of unhydrolyzed particles.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: May 4, 1982
    Assignee: General Motors Corporation
    Inventors: Robert J. Salloum, Clifford C. Duff
  • Patent number: 4313004
    Abstract: A method for preparing a diaminoalkoxy compound of the formula: ##STR1## wherein m and n are both numbers from 0 to about 25 and m+n equals at least 1, R.sub.1 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms; and R.sub.2 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms; which comprises incrementally introducing a dicyanoglycol compound of the formula: ##STR2## wherein m, n, R.sub.1 and R.sub.2 have the values indicated above into a reaction medium at a rate sufficient to minimize cleavage reactions, at a temperature of from about 90.degree. C. to about 160.degree. C. in the presence of hydrogen at a pressure of from about 800 psi to about 2200 psi; ammonia in an amount of from about 10 to about 40 weight percent based on the weight of dicyanoglycol compound; and a nickel catalyst in an amount sufficient to catalyze said reaction, whereby said dicyanoglycol compound is reduced to said diaminoalkoxy compound.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: January 26, 1982
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Andre M. Goineau
  • Patent number: 4310709
    Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka
  • Patent number: 4281197
    Abstract: Porous polyurethane solids such as open cell polyurethane foams are rapidly heated and hydrolytically decomposed into separate polyol component and diamine component by contacting the porous solids with saturated steam in a heated vacuum chamber. Separation of high quality liquid polyol and diamine is achieved.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: July 28, 1981
    Assignee: Ford Motor Company
    Inventor: Fred G. Oblinger
  • Patent number: 4239907
    Abstract: This invention is concerned with the employment of a water-soluble initiator, of sucrose, sorbitiol, trimethylpropane, ammonia or amine and water to form an initiator which is mixed and reacted with alkylene oxide in the presence of water and without the use of an added catalyst to produce polyether polyols for use in the production of urethane foams.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: December 16, 1980
    Inventor: William C. Bedoit, Jr.
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4196148
    Abstract: A method for hydrolysis of polyurethane foam and recovery of diamines and polyethers (or polyesters) from the hydrolysate carried out near atmospheric pressure and temperatures above about 185.degree. C. in a reaction zone containing water vapor which comprises increasing the rate of diamine production by inclusion of a minor, but effective amount of ammonia in the reaction zone. Volitilized diamines separated from the foam are preferably removed from the reaction zone, e.g. in an overhead stream, while polyethers (or polyesters) separated from the foam are recovered as liquid bottoms from the reaction zone.
    Type: Grant
    Filed: March 16, 1979
    Date of Patent: April 1, 1980
    Assignee: Ford Motor Company
    Inventor: Lee R. Mahoney
  • Patent number: 4192953
    Abstract: Polyprenyl derivatives having the formula ##STR1## in which R.sup.1 and R.sup.2 may be the same or different and each represents hydrogen atom, hydroxyl group, an alkoxy group having 1-8 carbon atoms, an aliphatic acyloxy group having 2-18 carbon atoms, an aromatic acyloxy group or an araliphatic acyloxy group having 2-3 carbon atoms in the aliphatic acyl moiety, R.sup.3 represents hydrogen atom, an alkyl group having 1-8 carbon atoms, an aliphatic acyl group having 2-18 carbon atoms, an aromatic acyl group or an araliphatic acyl group having 2-3 carbon atoms in the aliphatic acyl moiety, n is an integer of 1-4 and, when n is an interger of 2-4, R.sup.2 's may be the same or different; provided that, when n is 1 or 2, at least one of R.sup.2 and R.sup.2 's is hydroxyl group, an alkoxy group, an aliphatic acyloxy group, an aromatic acyloxy group or an araliphatic acyloxy group. These derivatives are useful as medicines for treating peptic ulcer.
    Type: Grant
    Filed: January 4, 1979
    Date of Patent: March 11, 1980
    Assignee: Sankyo Company Limited
    Inventors: Hiroshi Mishima, Akira Ogiso, Shinsaku Kobayashi
  • Patent number: 4191842
    Abstract: A synthesis of vitamin E in racemic or optically active forms from methacryolein or beta-hydroxyisobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: March 4, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4180682
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: December 25, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4179579
    Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: December 18, 1979
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
  • Patent number: 4169209
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: September 25, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4142042
    Abstract: Disclosed is a process for preparing alkenyl ethers from high molecular weight polyols in a liquid phase system containing concentrated alkali metal hydroxide, water, water immiscible hydrocarbon solvent and high molecular weight polyol such that the addition of an alkenyl halide results in a reaction which yields an alkenyl ether product which is not readily distillable from the reaction solution at slightly elevated temperatures and atmospheric pressures.
    Type: Grant
    Filed: October 6, 1977
    Date of Patent: February 27, 1979
    Assignee: Diamond Shamrock Corporation
    Inventor: Paul H. Goble