Ether Oxygen Bonded Directly To A Benzene Ring Patents (Class 568/608)
  • Patent number: 4396776
    Abstract: A process for preparing a methyl-blocked ethoxylate comprises heating at 180.degree.-320.degree. C., in the presence of a catalytically effective amount of a noble metal catalyst, an unsubstituted ethoxylate of 3 or more ethoxy units, or a monoalkyl-, monoaryl-, mono- or di-alkylamino- or mono- or di-arylamino ethoxylate of 2 or more ethoxy units, or a monoalkyl- or monoaryl-N,N-bis(ethoxylate) of 2 or more ethoxy units, all of which are derived from vicinal glycols, whereby there is prepared a corresponding methyl-blocked ethoxylate product which, for an unsubstituted ethoxylate starting material is a dimethylethoxylate having two fewer ethoxy units than the starting ethoxylate, and for the other ethoxylate starting materials, is a methylethoxylate having one less ethoxy unit in each ethoxylate group of the starting material.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: August 2, 1983
    Assignee: Chemische Werke Huels, Aktiengesellschaft
    Inventors: Rudolf Brockhaus, Hans-Jurgen Franke
  • Patent number: 4391994
    Abstract: Oxyalkylene group of an alkylene oxide is inserted into a chain-type ether compound having at least one lower alkyl group by reacting the latter with the alkylene oxide in the presence of a catalyst prepared by mixing boron trifluoride and/or stannic chloride with an active-hydrogen compound exemplified by water or a lower aliphatic alcohol. The reaction results reduced formation of by-product dimer of the alkylene oxide even under an increased charging ratio of the alkylene oxide to the chain-type ether.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: July 5, 1983
    Assignee: Nisso Petrochemical Industrie Co., Ltd.
    Inventors: Kiyoshi Kogoma, Yu Ohashi, Jiro Niizeki, Norio Sone, Takashi Tobita
  • Patent number: 4385190
    Abstract: A process for the production of a mono- or poly-alkylene glycol diether which consists of reacting an ether having at least one lower alkyl group with alkylene oxide in the presence of a heteropoly acid or a heteropoly acid acidic salt. Heteropoly acids and their acidic salts whose ratio of the hetero and coordinate atom is 1:6 and 1:12 are preferably used.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: May 24, 1983
    Assignee: Nisso Petrochemical Industry Company Limited
    Inventors: Yu Ohashi, Norio Sone, Takashi Tobita
  • Patent number: 4376868
    Abstract: Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: March 15, 1983
    Assignee: Conoco Inc.
    Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
  • Patent number: 4359589
    Abstract: An improved process for making linear polyethers having a relatively narrow molecular weight distribution comprises contacting a monoepoxide with a salt selected from the group consisting of fluoborate, fluophosphate, fluoantimonate and fluoarsenate salts of a metal selected from the group consisting of alkali metals, alkaline earth metals, lead, nickel, aluminum, cadmium, cobalt, tin, zinc and copper in the presence of a hydroxyl-containing compound at a controlled temperature of about -78.degree. C. to less than +20.degree. C. and in the absence of any additional acid.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: November 16, 1982
    Assignee: Shell Oil Company
    Inventor: Thomas F. Brownscombe
  • Patent number: 4355188
    Abstract: Polyetherpolyols containing residues of catalysts of the double metal cyanide complex class are treated with a strong base and ion exchanged or neutralized and filtered to provide a stable polyol with reduced tendency to form allophanates with diisocyanates. Further, the addition of ethylene oxide to the polyol while in contact with the strong base serves to end cap the polyol to provide it with primary hydroxyl groups.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: October 19, 1982
    Assignee: The General Tire & Rubber Company
    Inventors: Robert J. Herold, Robert E. Bingham
  • Patent number: 4341905
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an alkali metal halide catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: July 27, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4318848
    Abstract: Chemical reaction products, obtained in an alkaline medium and which require the addition of a dispersing agent, are neutralized by addition of a free surface-active acid to which, after its preparation, basic agents have not been added or have only been added up to a pH value of 3.
    Type: Grant
    Filed: January 3, 1978
    Date of Patent: March 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Heinz Molls, Willy Schiwy, Reinhold Hornle, Reinhard Nebeling
  • Patent number: 4310708
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of phosphonium catalysts.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventors: Paul E. Strege, George A. Doorakian
  • Patent number: 4310707
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of Na.sub.2 SnO.sub.3 catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4310653
    Abstract: A method of producing essentially monomeric etherified formaldehyde condensates with a bisphenol having a plurality of formaldehyde-reactive sites is disclosed in which the bisphenol is reacted with at least about 2 moles of formaldehyde per mole of bisphenol in solution in etherifying alcohol in the presence of an insoluble strong acid cation exchange resin. The reaction is carried out at a reaction temperature of from about 30.degree. C. to about 100.degree. C. to simultaneously provide the desired methylolation and etherification without introducing soluble ionic contaminants.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: January 12, 1982
    Assignee: DeSoto, Inc.
    Inventors: John J. Krajewski, Edward J. Murphy
  • Patent number: 4310706
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an imidazole catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4302349
    Abstract: Compounds of the following formula are suitable for reducing the interfacial surface tension of oily phases with respect to water: ##STR1## wherein z is 1 or 2,R, for z=1, is alkyl, aralkyl, or alkylaryl of 8-22 carbon atoms in the alkyl chain, or hydroxyalkyl of 2-22 carbon atoms, and, for z=2, is (aryl)alkylene of 4-18 carbon atoms,R' and R" each independently is hydrogen or C.sub.1 -C.sub.20 -alkyl wherein R' and R" are not simultaneously hydrogen and R' and R" together have 8-20 total carbon atoms,x is 10-40 andy is 1.2-5.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: November 24, 1981
    Assignee: Chemische Werke Huls, A.G.
    Inventors: Kurt Kosswig, Ekkehard Wienhoefer
  • Patent number: 4288639
    Abstract: New liquid thickeners for aqueous liquids are obtained by capping a liquid straight chain polyoxyalkylene compound derived from ethylene oxide or ethylene oxide and at least one other lower alkylene oxide by reacting said alkylene oxides with at least one active hydrogen-containing initiator having only one active hydrogen atom. The new thickeners are prepared at a molecular weight of about 1000 to about 25,000 utilizing an alpha-olefin oxide having a carbon chain of about 12 to about 18 aliphatic carbon atoms. Both block and heteric polyoxyalkylene compounds are useful. Alternatively, the new thickeners can be made by copolymerizing ethylene oxide or mixed lower alkylene oxides in the presence of said alpha-olefin oxide. The new thickeners exhibit an unexpected increase in viscosity in aqueous systems as compared with prior art liquid polyether thickening agents.
    Type: Grant
    Filed: October 22, 1979
    Date of Patent: September 8, 1981
    Assignee: BASF Wyandotte Corporation
    Inventor: Ronald L. Camp
  • Patent number: 4282387
    Abstract: The invention describes an improved process for preparing polyols by reacting a mono-epoxy compound such as propylene oxide with a hydroxyl-containing initiator compound such as glycerine in the presence of a catalyst, the improvement being that the catalyst is added in the form of a calcium, strontium or barium salt of an organic acid such as acetic acid.Polyols prepared by this process can be employed to prepare polyurethanes without removing the catalyst.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: August 4, 1981
    Assignee: The Dow Chemical Company
    Inventors: Franciszek Olstowski, John L. Nafziger
  • Patent number: 4275244
    Abstract: Linear polypropylene ether glycols of high molecular weight are made by reacting a linear polypropylene ether glycol of lower molecular weight first with an alkaline agent such as sodium hydroxide or other suitable base to form an alcoholate, and then coupling the alcoholate with a suitable difunctional coupling agent, such as the benzene-sulfonic acid diester of ethylene glycol or with some other suitable arylsulfonic acid diester of a C.sub.2 to C.sub.6 alcohol, thereby obtaining a 100 percent linear polypropylene ether glycol of a desirably higher molecular weight. Materials so produced find use in an aqueous medium as defoaming agents, thickeners, or emulsifiers, and use as protective colloids to improve the low-temperature stability of polyurethane and other latices.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: June 23, 1981
    Assignee: BASF Wyandotte Corporation
    Inventors: Herbert Helfert, Pauls Davis
  • Patent number: 4270003
    Abstract: The novel hydroquinone derivatives of the formula (I) are useful intermediates for the preparation of coenzyme Q, vitamin K and the polyprenyltrimethylquinones: ##STR1## wherein R.sup.1 is lower alkyl, lower alkoxy lower alkyl or methoxyethoxymethyl, R.sup.2 and R.sup.3 are each methyl or methoxy, or R.sup.2 and R.sup.3, taken together with the carbon atoms from which they depend, define a benzene ring, and R.sup.4 is a substituted or unsubstituted aromatic hydrocarbon. The compounds (I) are readily prepared either by reacting a Grignard reagent of the formula (II) with a halosulfone (III) in the presence of a copper compound, or by reacting a copper derivative (II') of the Grignard reagent (II) with a halo-sulfone (III), as follows: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined as above, and X is a halogen atom or a tosyl group.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: May 26, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Takashi Ohnishi, Takashi Nishida
  • Patent number: 4260730
    Abstract: A bisphenol is reacted with formaldehyde in solution in alcohol in the presence of an alkali metal hydroxide, preferably at a pH of from 7-10, to provide a polymethylol derivative. Nitric acid is then added to precipitate the hydroxide and an excess is preferably used to provide an acid pH, preferably pH 1-3, and the acidic mixture is heat reacted to remove water of etherification. The nitric acid catalyst is then precipitated with alkali metal hydroxide to enable easy removal of both acid and alkali as an insoluble salt.
    Type: Grant
    Filed: January 3, 1980
    Date of Patent: April 7, 1981
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Thomas H. Plaisance
  • Patent number: 4249024
    Abstract: The present invention discloses an improved method for the in situ end point determination of the oxyethylation of phenols. In the present invention, the oxyethylation reactions occur in the presence of catalysts and at temperatures in excess of 100.degree. C. The reaction end point is monitored by continuous measurements of the electrical conductivity of the reaction mixture and the reaction is terminated when a preselected rate of change of conductance is attained.The method of the present invention may be used with complex phenolic systems wherein alkali metal hydroxides, quarternary ammonium salts, or alkali metal alkoxides are used as oxyethylation catalysts.
    Type: Grant
    Filed: August 22, 1979
    Date of Patent: February 3, 1981
    Assignee: Great Lakes Chemical Corp.
    Inventor: David C. Sanders
  • Patent number: 4245125
    Abstract: Compounds of the formula IA.multidot.m B (I)whereinA is a compound of the formula II or III ##STR1## m is a rational number between 0.1 and 4.0, and B is H.sub.2 O.sub.2, N.sub.2 H.sub.4 or NH.sub.2 OH, andR.sub.1 is an unsubstituted or substituted aliphatic or aromatic hydrocarbon radical which has 3-30 C atoms and which can be interrupted by oxygen or sulfur atoms,R.sub.2 is hydrogen or C.sub.1 -C.sub.30 alkyl,X is --O-- or --SO.sub.2 -- and, in the case where B is N.sub.2 H.sub.4 or NH.sub.2 OH, also --S-- or --SO--,Y is the direct bond, ##STR2## Q is --CH.sub.2, --CH(OH)--CH.sub.2 -- or --CH(CH.sub.2 --OH)--, and n is 1, 2, 3, 4, 5, 6, 7 or 8.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: January 13, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4218567
    Abstract: A process for the preparation of aromatic ethers by the bromination of a compound of the formula ##STR1## wherein R.sub.1, independently, is hydrogen, hydroxy, lower alkoxy, lower alkyl; m is an integer from 1-4, and A is --CHO, --COOR.sub.3 or lower alkyl, and subsequently treating the reaction product of the bromination step with an alkali metal alkoxide in the presence of cuprous halide or oxide, is described.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: August 19, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Percy S. Manchand, John M. Townsend
  • Patent number: 4183821
    Abstract: There are disclosed polyoxyalkylene compound demulsifying agents derived from tetrahydrofuran and C.sub.2 -C.sub.4 vicinal alkylene oxides which are heteric/block copolymers; a process for the preparation of said polyoxyalkylene compounds; a demulsified petroleum crude oil; and a batch or continuous process for the demulsification of crude petroleum oil.
    Type: Grant
    Filed: May 26, 1978
    Date of Patent: January 15, 1980
    Assignee: BASF Wyandotte Corporation
    Inventors: William K. Langdon, Ronald L. Camp
  • Patent number: 4146736
    Abstract: Oxalkylene groups of oxacycloalkanes are inserted into chain-type ethers by reacting the latter with the oxacycloalkanes in the presence of Lewis acids. The ethers or ether mixtures obtained can be used for many purposes owing to their hydrophilic-hydrophobic character, for example as absorption and extraction agents, as solvents and as additives to hydraulic fluids.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: March 27, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scheffel, Reinhold Obermeier
  • Patent number: 4143072
    Abstract: This invention relates to a process for the removal of troublesome secondary products, particularly small quantities of water, solvents, low molecular weight glycols, and pungent-smelling substances, from polyethers by means of a tubular coil evaporator.
    Type: Grant
    Filed: April 27, 1978
    Date of Patent: March 6, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Hetzel, Pramod Gupta, Hans-Joachim Sandhagen
  • Patent number: 4137398
    Abstract: An improvement in the process of alkaline catalyst removal from crude polyoxyalkylene ether polyols is achieved by treating a mixture of crude polyol, adsorbent, and water with magnesium carbonate and carbon dioxide just prior to filtration.
    Type: Grant
    Filed: June 9, 1978
    Date of Patent: January 30, 1979
    Assignee: BASF Wyandotte Corporation
    Inventor: John A. Muzzio
  • Patent number: 4137396
    Abstract: An improvement in the process for the removal of residual catalyst from polyether polyols is achieved by the use of a solvent wash and recovery system.
    Type: Grant
    Filed: August 31, 1977
    Date of Patent: January 30, 1979
    Assignee: BASF Wyandotte Corporation
    Inventors: Joseph F. Louvar, Michael A. Capraro, William M. Herring
  • Patent number: 4105580
    Abstract: A process for preparing non-ionic surface active agents comprises condensing crude glycidol, in the presence of an alkaline catalyst on an organic compound containing an active hydrogen atom. The crude glycidol is prepared by dehydrochlorinating glycerol monochlorohydrin with sodium or potassium hydroxide in the presence of a solvent, neutralizing excess sodium or potassium hydroxide with a strong acid and separating the major portion of the sodium or potassium chloride formed.
    Type: Grant
    Filed: October 20, 1976
    Date of Patent: August 8, 1978
    Assignee: L'Oreal
    Inventors: Henri Sebag, Guy Vanlerberghe