DOCSLIB.ORG

Production of Glycidyl Compounds

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Production of Glycidyl Compounds Office europeen des brevets (fi) Publication number : 0 491 529 A1 @ EUROPEAN PATENT APPLICATION @ Application number : 91311630.7 © Int. CI.5: C07D 301/28, C07D 303/24 (22) Date of filing : 13.12.91 (30) Priority : 18.12.90 GB 9027448 (72) Inventor : Thoseby, Michael Robert 29 De Freville Avenue Cambridge (GB) (43) Date of publication of application : Inventor : Rolfe, William Martin 24.06.92 Bulletin 92/26 42 Vetch Walk Haverhill, Suffolk (GB) (S) Designated Contracting States : CH DE ES FR GB IT LI NL (74) Representative : Sparrow, Kenneth D. et al CIBA-GEIGY PLC. Patent Department, Central Research, Hulley Road @ Applicant : CIBA-GEIGY AG Macclesfield, Cheshire SK10 2NX (GB) Klybeckstrasse 141 CH-4002 Basel (CH) (54) Production of glycidyl compounds. (57) A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to pro- duce the 1:1 adduct, in the presence, as catal- yst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IMA of the Periodic Table of Elements (according to the IUPAC 1970 convention) ; and then dehydrochlorinating the product so obtained. CM LU Jouve, 18, rue Saint-Denis, 75001 PARIS 1 EP 0 491 529 A1 2 The present invention relates to a process for the 100 parts by weight of the alcohol reactant. production of glycidyl compounds. The alcohol reactant may be a primary, secon- The addition reaction between epoxides and dary or tertiary alcohol. While monohydric alcohols alcohols, in the presence of a catalyst, to produce an may be used, e.g. a straight - or branched CrC12 prim- ether- alcohol is well known. 5 ary -, secondary - or tertiary aliphatic monohydric In U.S. Patent 4543430, there is described a pro- alcohol such as methanol, ethanol, n-propanol, isop- cess for the preparation of addition products of ropanol, tert-butanol, 2-ethyl-1-hexanol, n-hexanol, n- epoxides and hydroxylated compounds. The epoxide octanol, n-decanol or n-dodecanol, preferably the used is an alkylene oxide or epichlorohydrin and the alcohol reactant contains two or more hydroxyl groups hydroxylated compound is an alcohol, an alkyleneg- 10 per molecule. lycol monoalkylether, a phenol compound or water, Preferred polyhydroxy reactants are those having the ratio of the hydroxylated compound/epoxide being the formula; between 2 and 20 by weight. The reaction is carried Q(OH)m I out in a homogeneous liquid phase at a temperature wherein m is an integer from 2 to 10, preferably 2 to between 40° and 250°C. The catalyst is a) a tetra- 15 6 and Q is an m-valent aliphatic, cycloaliphatic or alkylammonium triflate or b) a trifluoromethanesul- araliphatic residue. When Q is a divalent residue, it phonic acid salt of an alkali metal, a metal of Group II may be, e.g., a straight chain or branched alkylene of the Periodic Table of Elements, aluminium, cobalt, residue; or a cycloalkylene residue in which the ring nickel, zirconium or tin. The catalyst concentration in may be optionally substituted, e.g. by alkyl groups or the reaction mixture is from 1 to 100 ppm. 20 interrupted by heteroatoms, e.g. O or S atoms or sev- The process described in U.S. 4543430 has cer- eral cycloalkyl residues may be bonded together, tain deficiences. Although the catalyst used is des- optionally via a bridge member. When Q is trivalent or cribed as highly active and highly selective, the a highervalency, Q may be an organic residue having asserted high selectivity is ensured not so much by aliphatic, cycloalipharic or araliphatic structual ele- the nature of the catalyst, as by the use of a large 25 ments. Q may be substituted with functional groups excess of the hydroxylated compound, relative to the provided that such groups do not inactivate the Group epoxide (see column 2, lines 51 to 53 of U.S. IMA metal perchlorate or triflate catalyst and do not 4543430), thereby guaranteeing more of the desired undergo competing reactions with epichlorohydrin. 1:1 epoxide : hydroxylated compound adduct, but Suitable functional groups are, e.g. ester groups as resulting in increased process costs. 30 contained in polycaprolactones, and unsaturated Surprisingly, we have now found that by choos- groups, e.g. those contained in hydroxyl-terminated ing, as catalyst, a specific metal salt of perchloric acid polybutadienes or polybutadiene copolymers. or trifluoromethane sulphonic acid (triflic acid) namely Specific examples of preferred aliphatic diol reac- a salt of a metal of Group IMA of the Periodic System, tants of formula I include diethylene glycol, triethylene reaction of epichlorohydrin with an alcohol, followed 35 glycol and higher polyoxyethylene glycols; propane- by dehydrochlorination produces a high degree of 1, 2-diol, propane-1, 3-diol and higher polyoxyp- selectivity for the 1:1 glycidylated alcohol product, ropylene glycols; neopentyl glycol; butane-1,4-diol, while using only substantially stoichiometric amounts and higher poly(oxytetramethylene)glycols; pentane- of the epichlorhydrin and the alcohol. The amount of 1, 5-diol; hexane-1, 6-diol; and octane-1, 8-diol; included chlorine is significantly reduced compared to 40 Examples of preferred aliphatic triols of formula I are chlorine contents of epoxy resins prepared using con- 1,1,1-trimethylol propane, glycerol and 1,1,1-trimethy- ventional catalysts. lolethane. Other triols of formula I which are commer- Accordingly, the present invention provides a pro- cially - available and are preferred for use in the cess for the production of a glycidyl ether of an present invention include adducts of simple polyols alcohol, comprising reacting an alcohol with 45 such as glycerol, hexane-1 ,2,5-triol, hexane-1, 2,6- epichlorohydrin, in substantially the stoichiometric triol, hexane-2,4,6-triol with propylene oxide and/or proportions required to produce the 1:1 adduct in the ethylene oxide. presence, as catalyst, of a salt of perchloric acid or of Tetrafu notional aliphatic alcohols which are pre- trifluoromethanesu I phonic acid with a metal of Group ferred include pentaerythritol and 3,3,7,7-tetra(hyd- IMA of the Periodic Table of Elements (according to 50 roxymethyl)-5-oxanonane. the IUPAC 1970 convention); and then dehydrochlori- Preferred higher aliphatic poly-hydroxy com- nating the product so obtained. pounds include dipentaerythritol,tripentaerythritol, Preferably, the Group MIA metal salts are those of mannitol, sorbitol, polyvinyl alcohol, partially hyd- lanthanum, cerium, ytterbium or yttrium. rolyzed polyvinyl esters of acetals, and hydroxyalkyl The amount of the Group IMA perchlorate or trif- 55 acrylate, methacrylate or itaconate polymers and late catalyst present in the alcohol/epichlorohydrin copolymers. reaction mixture generally ranges from 0.1 to 1 0 parts Preferred cycloaliphatic alcohols of formula I by weight, preferably from 0.1 to 2 parts by weight per include resorcitol, quinitol, bis(4-hydroxycyclohexyl) 2 3 EP 0 491 529 A1 4 methane, 2,2-bis (4-hydroxycyclohexyl) propane, pyrrolidone, gamma-butyrolactone, benzyl alcohol, cyclohexanedimethanol and 1,1-bis (hydroxymethyl) dibutyl phthalate, methyl ethylketone or toluene. The cyclohex-3-one. dehydrochlorinating agent is preferably added por- Alcohols of formula I having araliphatic residues tionwise, preferably in solid form, over an extended include N,N-bis(2-hydroxyethyl) aniline and p,p'- 5 period, e.g. over a period ranging from 1 0 minutes to bis(N-(2-hydroxyethyl) aminophenyl) methane. 6 hours. Alcohols of formula I containing further functional The dehydrochlorination reaction mixture may be groups which are preferred include polycaprolactone worked up in conventional manner e.g. by washing diols and polyols and derivatives of poly with water and separating and purifying, e.g. by dis- (epichlorohydrin). 10 tillation, the organic phase containing the desired Other alcohols of interest are adducts of an glycidylated alcohol product. alkylene oxide, e.g. ethylene oxide or propylene oxide The glycidylated alcohol epoxide resins obtained with mononuclear phenols such as resorcinol or according to the process of the present invention may hydroquinone, and polynuclear phenols such as be cured in conventional manner or used as diluents bis(4-hydroxyphenyl) methane, bis(4-hydroxyphenyl) 15 for other epoxy resins so cured. Curing agents which sulphone, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, may be used include aliphatic amines; dicyan- 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3,5-dib- diamide; aromatic amines such as bis (3-ami- romo-4-hydroxyphenyl) propane, and novolacs for- nophenyl)- and bis(4-aminophenyl) sulphone and med from aldehydes such as formaldehyde, bis(4-aminophenyl) methane, which are usually used acetaldehyde, chloral and furfuraldehyde, with 20 together with an accelerator such as a BF3 - amine phenols such as phenol itself, 4-chlorophenol, 2- complex; and carboxylic acids, polycarboxylic acid methylphenol and 4-tert butylphenol. Further alcohols anhydrides such as phthalic anhydride, cyclohexane- of interest are styrene-ally alcohol copolymers. 1,2-dicarboxylic acid anydride, methylbicyclo [2,2,1] The process according to the present invention is hept-5-ene-2,3-dicarboxylicacid anhydride, pyromel- conveniently conducted by firstly heating a mixture of 25 litic acid dianhydride and benzophenone tetracar- the alcohol reactant and the Group IMA perchlorate or boxylic acid dianhydride. triflate catalyst, preferably with agitation, until a liquid The present invention also provides cured pro- solution is obtained. When the temperature of the sol- ducts, e.g. castings or fibre - reinforced composites, ution reaches a temperature within the range of from comprising a material obtained by curing a glycidy- 50°C to 200°C, especially a temperature within the 30 lated alcohol epoxide resin produced by a process range of from 100°C to 150°C, the epichlorhydrin is according to the present invention. conveniently added, preferably with agitation of the reaction mixture.
Load more

Recommended publications
  • A New Approach to Prepare Polyethylene Glycol Allyl Glycidyl Ether
    E3S Web of Conferences 267, 02004 (2021) https://doi.org/10.1051/e3sconf/202126702004 ICESCE 2021 A new approach to prepare Polyethylene Glycol Allyl Glycidyl Ether Huizhen Wang1*, Ruiyang Xie1, Mingjun Chen1*, Weihao Deng1, Kaixin Zhang2, Jiaqin Liu1 1School of Science, Xihua University, Chengdu 610039, China; 2Chengdu Jingyiqiang Environmental Protection Technology Co., Ltd. Abstract. The polyethylene glycol allyl glycidyl ether (PGAGE) is an important intermediate for preparing silicone softener that can be synthesized from allyl alcohol polyoxyethylene ether and epichlorohydrin (ECH). The performance parameters including the concentration of ECH, initial boron trifluoride diethyl etherate (BFEE) as well as CaCl2 quality were investigated respectively. The optimum process parameters which can get high capping and low by-product rate are as follows: the ECH concentration is 2.0 M, the initial BFEE concentration is 1.65mM, and the CaCl2 dosage is 1.65g/L. Under these conditions, the maximal yield can be improved to 91.36%, the percent of capping rate is higher than 98.16%, the residual concentration of F- is only 0.63 mg/L. concentrated basic solution, in which the total yield was between 90%~91% by Matsuoka et al. [10] also use the 1 Introduction two-step reaction to synthesize AGE based on the reaction Polyethylene glycol allyl glycidyl ether (PGAGE) and the of allyl alcohol with ECH using BFEE as the catalyst. allyl polyoxyethylene ether (APEG), tethering with both Their results demonstrated that the yield reaches 82% alkene and epoxy groups, are widely used as fabric under the following condition: n (ECH) : n (allyl alcohol): finishing agent [1-2] , reactive diluent [3] , cross-linking (catalysis) = 1: (1~3) : (0.01~0.002).
    [Show full text]
  • A New Coupling Process for Synthesis of Epichlorohydrin from Dichloropropanols
    2nd International Conference on Machinery, Materials Engineering, Chemical Engineering and Biotechnology (MMECEB 2015) A new coupling process for synthesis of epichlorohydrin from dichloropropanols Dawei Wu, Sumin Zhou* School of Chemical Engineering, Huaiyin Institute of Technology, Huaian 223005, China [email protected] Keywords: dichloropropanol, epichlorohydrin, tubular reactor, wiped film evaporation. Abstract. As an important material used in the production of epoxy resins, epichlorohydrin is usually derived from the saponification and cyclization of dichloropropanol in a tower reacting system. In order to reduce energy consumption and wastewater discharge, a new process of tubular reactor coupled with wiped film evaporation was adopt to produce epichlorohydrin. The effects of different technological parameters on the yield of the coupling process were investigated, such as reactants' molar ratio, reaction & evaporation temperature, residence time and so on. Results indicated that the use of coupling process will significantly reduce the material consumption and shorter the reaction time. This coupling process provided a useful suggestion for the design of the industrial plants. 1. Introduction Epichlorohydyin（ECH）, also known as 1-chloro-2, 3-epoxy propane, is an important chemical material, mainly used to synthesizing epoxy resin, chlorohydrins rubber, pesticide, plasticizer and so on [1]. The main method to produce ECH is high-temperature chlorination of propylene [2]. With the fast-development of biodiesel production, the use of glycerol for producing ECH [3-4] is going to mature and has become an important industrial technological process [5]. Although the difference raw materials were used, the processes also consist of two reaction steps as well. First step is the saponification and cyclization of dichloropropanol (DCP) to produce ECH.
    [Show full text]
  • Gasket Chemical Services Guide
    Gasket Chemical Services Guide Revision: GSG-100 6490 Rev.(AA) • The information contained herein is general in nature and recommendations are valid only for Victaulic compounds. • Gasket compatibility is dependent upon a number of factors. Suitability for a particular application must be determined by a competent individual familiar with system-specific conditions. • Victaulic offers no warranties, expressed or implied, of a product in any application. Contact your Victaulic sales representative to ensure the best gasket is selected for a particular service. Failure to follow these instructions could cause system failure, resulting in serious personal injury and property damage. Rating Code Key 1 Most Applications 2 Limited Applications 3 Restricted Applications (Nitrile) (EPDM) Grade E (Silicone) GRADE L GRADE T GRADE A GRADE V GRADE O GRADE M (Neoprene) GRADE M2 --- Insufficient Data (White Nitrile) GRADE CHP-2 (Epichlorohydrin) (Fluoroelastomer) (Fluoroelastomer) (Halogenated Butyl) (Hydrogenated Nitrile) Chemical GRADE ST / H Abietic Acid --- --- --- --- --- --- --- --- --- --- Acetaldehyde 2 3 3 3 3 --- --- 2 --- 3 Acetamide 1 1 1 1 2 --- --- 2 --- 3 Acetanilide 1 3 3 3 1 --- --- 2 --- 3 Acetic Acid, 30% 1 2 2 2 1 --- 2 1 2 3 Acetic Acid, 5% 1 2 2 2 1 --- 2 1 1 3 Acetic Acid, Glacial 1 3 3 3 3 --- 3 2 3 3 Acetic Acid, Hot, High Pressure 3 3 3 3 3 --- 3 3 3 3 Acetic Anhydride 2 3 3 3 2 --- 3 3 --- 3 Acetoacetic Acid 1 3 3 3 1 --- --- 2 --- 3 Acetone 1 3 3 3 3 --- 3 3 3 3 Acetone Cyanohydrin 1 3 3 3 1 --- --- 2 --- 3 Acetonitrile 1 3 3 3 1 --- --- --- --- 3 Acetophenetidine 3 2 2 2 3 --- --- --- --- 1 Acetophenone 1 3 3 3 3 --- 3 3 --- 3 Acetotoluidide 3 2 2 2 3 --- --- --- --- 1 Acetyl Acetone 1 3 3 3 3 --- 3 3 --- 3 The data and recommendations presented are based upon the best information available resulting from a combination of Victaulic's field experience, laboratory testing and recommendations supplied by prime producers of basic copolymer materials.
    [Show full text]
  • Comparisons of Epoxy Technology for Protective Coatings and Linings In
    ComparisonsComparisons ofof EpoxyEpoxy TechnologyTechnology forfor ProtectiveProtective CoatingsCoatings andand LiningsLinings inin WastewaterWastewater FacilitiesFacilities By John D. Durig, General Polymers, Cincinnati, Ohio, USA Aeration tank at a wastewater plant. Bis F epoxy resin with an aliphatic or a cycloaliphatic amine curing agent is appropriate. Editor’s Note: This article was first presented at SSPC (Photos courtesy of the author) 99, The Industrial Protective Coatings Conference and Exhibit, November 14-18, 1999, in Houston, TX, USA, and published in The Proceedings of the Seminars, SSPC 99-14, pp. 31-37. poxy technology and methods of curing and Epoxy Resin Technology E reacting with amine-based hardeners have There are three types of epoxy resins that find application continued to evolve since the first epoxy patents were is- in wastewater treatment facilities: bisphenol A, bisphenol sued in the 1930s. The possible reactions combined with F, and novolac resins. These resins all result from reac- wide-ranging formulation additives have resulted in a myri- tions of epichlorohydrin with phenolic compounds. The ad of products that can easily confuse decision makers type and number of phenolic groups determine both when it comes to product selection. Adding to the confu- physical and performance properties of the cured resin. sion is the wide range of environmental factors that must be considered when choosing a protective coating system. Bisphenol A Resin Structure This article will identify the primary differences be- Bisphenol A is a reaction product of phenol and acetone. tween three types of epoxies and four types of amine- Bisphenol A is reacted with epichlorohydrin to form based hardeners typically used in coatings for wastewater diglycidylether bisphenol A resin or DGEBA.
    [Show full text]
  • The Production of Epichlorohydrin from Glycerol. a Bachelor Integration Project for Delfzijl’S Chempark
    The production of epichlorohydrin from glycerol. A Bachelor Integration Project for Delfzijl’s Chempark Ruurd Feikes van der Heide University of Groningen Faculty of Science and Engineering IE&M Bachelor Thesis Supervisor 1: prof. Dr. Ir. HJ (Erik) Heeres Supervisor 2: Dr. Ing. H. Kloosterman Syncom supervisor: Dr. Ir. Andre Heeres June 2018 Pelsterstraat 32 9711 KM Groningen (06) 13787270 [email protected] student number 2674122 1 Table of content Introduction (RDP) -Problem context -Stakeholder analysis -System description -Goal statement -Design goal -Scope -Research questions -Cycle choice Abstract Backgrounds -Glycerol -Epichlorohydrin Benchmark -Propylene into epichlorohydrin, via allyl chloride -Allyl chloride to epichlorohydrin -TRL Innovation - Glycerol into epichlorohydrin -Hydrochlorination -Hexanoic acid -Acetic acid -Dehydrochlorination -TRL Cost analysis -Hexanoic acid -Solid oxide Discussion and conclusions References Appendix 2 Problem context The city of Delfzijl (Netherlands) has a chemical park with multiple factories present. The companies at the chemical park have interrelationships with each other which results that if a few of them stop producing products, the other companies will find problems in their own existence. The committee Willems started an investigation how the chemical park should optimize its competitiveness among the business environment nowadays. Willems used to be a high ranked employee of Shell before leaving the company. The committee stated that if the companies on the park want to stay in business, changes within production methods have to be made. A more sustainable production method where green raw materials like biomass are converted into valuable products is the solution to stay competitive. Prof. Dr. Ir.
    [Show full text]
  • Current Chemistry Letters Synthesis of Allyl-Glycidyl Ether by The
    Current Chemistry Letters 6 (2017) 7–14 Contents lists available at GrowingScience Current Chemistry Letters homepage: www.GrowingScience.com Synthesis of allyl-glycidyl ether by the epoxidation of diallyl ether with t-butyl hydroperoxide over the Ti-MWW catalyst Agnieszka Wróblewskaa*, Marika Walaseka and Beata Michalkiewiczb aWest Pomeranian University of Technology, Szczecin, Institute of Organic Chemical Technology, Pulaskiego 10, 70-322 Szczecin, Poland bWest Pomeranian University of Technology, Szczecin, Institute of Inorganic Chemical Technology and Environment Engineering, Pulaskiego 10, 70- 322 Szczecin, Poland C H R O N I C L E A B S T R A C T Article history: In this paper, modified hydrothermal method for Ti-MWW catalyst preparation has been Received August 21, 2016 shown. Instrumental analysis of the zeolite material Ti-MWW has been performed by means Received in revised form of UV-vis spectrometry, infrared spectrometry (IR), scanning electron microscope (SEM), X- October 24, 2016 ray diffraction (XRD), and X-ray microanalysis. Moreover, the results of the epoxidation of Accepted 8 November 2016 diallyl ether (DAE) over the titanium silicate catalyst Ti-MWW and in the presence of Available online methanol have been presented. t-Butyl hydroperoxide have been applied for the first time as 9 November 2016 an oxidant for this process. The influence of temperature (20-130°C), DAE/TBHP molar ratio Keywords: (1:1-3:1), methanol concentration (10-80 wt%), amount of catalyst (1-7 wt%) and reaction Diallyl ether time (60-1440 min.) was studied. The main functions describing the process were determined Allyl-glycidyl ether on the basis of the results obtained from the gas chromatography method.
    [Show full text]
  • Identification and Quantitation Studies of Migrants from BPA Alternative
    polymers Article Identification and Quantitation Studies of Migrants from BPA Alternative Food-Contact Metal Can Coatings Nan Zhang *, Joseph B. Scarsella and Thomas G. Hartman * Department of Food Science, Rutgers, The State University of New Jersey, 65 Dudley Road, New Brunswick, NJ 08901, USA; [email protected] * Correspondence: [email protected] (N.Z.); [email protected] (T.G.H.); Tel.: +1-848-932-5543 (N.J. & T.G.H.) Received: 28 October 2020; Accepted: 26 November 2020; Published: 29 November 2020 Abstract: Bisphenol A (BPA)-based epoxy resins have wide applications as food-contact materials such as metal can coatings. However, negative consumer perceptions toward BPA have driven the food packaging industry to develop other alternatives. In this study, four different metal cans and their lids manufactured with different BPA-replacement food-contact coatings are subjected to migration testing in order to identify migratory chemical species from the coatings. Migration tests are conducted using food simulants and conditions of use corresponding to the intended applications and regulatory guidance from the U.S. Food and Drug Administration. Extracts are analyzed by gas chromatography mass spectrometry (GC-MS) and high resolution GC-MS. The migratory compounds identified include short chain cyclic polyester migrants from polyester-based coatings and bisphenol-type migrants including tetramethyl bisphenol F (TMBPF), tetramethyl bisphenol F diglycidyl ether (TMBPF DGE), bisphenol F (BPF), bisphenol C (BPC), and other related monomers or oligomers. The concentration of the migrants is estimated using an internal standard, and validated trimethylsilyl (TMS) derivatization GC-MS methods are developed to specifically quantify TMBPF, BPF, BPC, and BPA in the coatings.
    [Show full text]
  • Section 2. Hazards Identification OSHA/HCS Status : This Material Is Considered Hazardous by the OSHA Hazard Communication Standard (29 CFR 1910.1200)
    SAFETY DATA SHEET Nonflammable Gas Mixture: 1,2-Dichloropropane / 1,2,3-Trichloropropane / 2, 3-Dichloropropene / Allyl Chloride / Butylene Oxide / Cis-1,3-Dichloropropene / Epichlorohydrin / Helium / Trans-1,3-Dichloropropene Section 1. Identification GHS product identifier : Nonflammable Gas Mixture: 1,2-Dichloropropane / 1,2,3-Trichloropropane / 2, 3-Dichloropropene / Allyl Chloride / Butylene Oxide / Cis-1,3-Dichloropropene / Epichlorohydrin / Helium / Trans-1,3-Dichloropropene Other means of : Not available. identification Product use : Synthetic/Analytical chemistry. SDS # : 013053 Supplier's details : Airgas USA, LLC and its affiliates 259 North Radnor-Chester Road Suite 100 Radnor, PA 19087-5283 1-610-687-5253 Emergency telephone : 1-866-734-3438 number (with hours of operation) Section 2. Hazards identification OSHA/HCS status : This material is considered hazardous by the OSHA Hazard Communication Standard (29 CFR 1910.1200). Classification of the : GASES UNDER PRESSURE - Compressed gas substance or mixture GHS label elements Hazard pictograms : Signal word : Warning Hazard statements : Contains gas under pressure; may explode if heated. May displace oxygen and cause rapid suffocation. Precautionary statements General : Read and follow all Safety Data Sheets (SDS’S) before use. Read label before use. Keep out of reach of children. If medical advice is needed, have product container or label at hand. Close valve after each use and when empty. Use equipment rated for cylinder pressure. Do not open valve until connected to equipment prepared for use. Use a back flow preventative device in the piping. Use only equipment of compatible materials of construction. Prevention : Use and store only outdoors or in a well ventilated place. Response : Not applicable.
    [Show full text]
  • United States Patent (19) (11) 4,284,573 Arnett Et Al
    United States Patent (19) (11) 4,284,573 Arnett et al. 45) Aug. 18, 1981 54 PREPARATION OF GLYCIDYL ETHERS OTHER PUBLICATIONS 75 Inventors: John F. Arnett, Newton; George A. Chemical Abstracts, vol. 87 (1977) 22359X. Doorakian, Bedford, both of Mass. Primary Examiner-Norma S. Milestone 73) Assignee: The Dow Chemical Company, Attorney, Agent, or Firm-Michael L. Glenn Midland, Mich. 57 ABSTRACT 21 Appl. No.: 80,769 A process for producing glycidyl ethers of phenols is described which comprises the steps of: (22 Filed: Oct. 1, 1979 (1) reacting by contacting, in liquid phase, a phenol with excess epichlorohydrin in the presence of a catalytic 5ll Int. Cl............................................. CO7D 301/28 amount of tetrahydrocarbyl phosphonium bicarbon 52 U.S. Cl. ........................... 260/348.15; 260/348.19 ate salt, to thereby produce a coupled reaction prod 58) Field of Search ...................... 260/348.15, 348.18, uct comprising the corresponding propylene 260/348.19 chlorohydrin ether of said phenol; (2) devolatilizing said coupled reaction product to re 56) References Cited move excess epichlorohydrin and volatile by-pro U.S. PATENT DOCUMENTS ducts; and (3) contacting the devolatilized reaction product from 3,948,855 4/1976 Perry ............................... 260/47 EP Step (2) with aqueous base, thereby converting the 3,992,432 11/1976 Napier et al. ... 260/348.31 . propylenechlorohydrin groups of the coupled reac 3,996,259 12/1976. Lee et al. ..... ... 260/348.18 tion product to glycidyl ether groups. FOREIGN PATENT DOCUMENTS This process is particularly useful in preparing low 893.191 7/1970 Canada . molecular weight liquid epoxy resins by the reaction of 2335199 1/1975 Fed.
    [Show full text]
  • Controlled Synthesis of Polyepichlorohydrin with Pendant
    Controlled synthesis of polyepichlorohydrin with pendant cyclic carbonate functions for isocyanate-free polyurethane networks Anne-Laure Brocas, Gabriel Cendejas, Sylvain Caillol, Alain Deffieux, Stéphane Carlotti To cite this version: Anne-Laure Brocas, Gabriel Cendejas, Sylvain Caillol, Alain Deffieux, Stéphane Carlotti. Con- trolled synthesis of polyepichlorohydrin with pendant cyclic carbonate functions for isocyanate-free polyurethane networks. Journal of Polymer Science Part A: Polymer Chemistry, Wiley, 2011, 49 (12), pp.2677-2684. 10.1002/pola.24699. hal-00591301 HAL Id: hal-00591301 https://hal.archives-ouvertes.fr/hal-00591301 Submitted on 9 May 2011 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Controlled Synthesis of Polyepichlorohydrin with Pendant Cyclic Carbonate Functions for Isocyanate-Free Polyurethane Networks ANNE-LAURE BROCAS,1 GABRIEL CENDEJAS,1 SYLVAIN CAILLOL,2 ALAIN DEFFIEUX,1 STEPHANE CARLOTTI1 1Universite´ de Bordeaux, Laboratoire de Chimie des Polyme` res Organiques, CNRS, ENSCBP, 16 avenue Pey Berland, 33607 Pessac Cedex, France 2Institut Charles Gerhardt, UMR5253 CNRS/UM2/ENSCM/UM1, Ecole Nationale Supe´ rieure de Chimie de Montpellier, 8 rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France Received 2 February 2011; accepted 1 April 2011 DOI: 10.1002/pola.24699 Published online 27 April 2011 in Wiley Online Library (wileyonlinelibrary.com).
    [Show full text]
  • Chemical Compatibility Guide
    20887Cvr:Layout 1 5/13/08 7:39 AM Page 2 Chemical Compatibility Guide Aro is pleased to present this selection guide to provide a convenient and informative reference point for pump selection. This information was compiled from information provided by material suppliers and manufacturers. The compatibility listings are intended as a guide only. We assume no liability for their accuracy on their use. The user should test under their own operating conditions to determine the suitability of any compound and material in a particular application. 20887Txt:43077 5/12/08 8:36 AM Page 1 20887Txt:43077 5/12/08 8:36 AM Page 1 THERMOPLASTIC ELASTOMERS (TPE’s) verses THERMOSETTING RUBBER DIAPHRAGMS Aro’s direction has been to move toward replacement of traditional thermoset rubber diaphragms with thermoplastic elastomers (TPE). Examples of TPE’s include: Santoprene, Nitrile (TPE) and Hytrel. TPE’s are manufactured using a plastic injection molding process where the resin, or diaphragm material, is melted and injected into a mold to produce the diaphragm. The advantages of this process includes: Features Benefits Diaphragm is molded to optimum shape Excellent flex life Homogenous part No delamination failures High performance resins Chemical, abrasion and flex life Injection molded/tight process control Low cost/consistent performance Laboratory testing has shown: Injection Mold Process Santoprene outperformed all rubber diaphragms except Buna in the mild abrasive fluids. Molded Diaphragm The Geolast diaphragm had equivalent life to the Buna diaphragms and was superior to the other rubbers compounds. 1 Teflon with the Santoprene backer exhibited the best flex life of all diaphragms during the test series.
    [Show full text]
  • WO 2017/079437 Al 11 May 2017 (11.05.2017) P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/079437 Al 11 May 2017 (11.05.2017) P O P C T (51) International Patent Classification: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, C08G 59/18 (2006.01) C08L 63/00 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, C08G 59/62 (2006.01) KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/US2016/060332 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 3 November 20 16 (03 .11.20 16) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (30) Priority Data: TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 62/250,217 3 November 2015 (03. 11.2015) US TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (71) Applicant: VALSPAR SOURCING, INC. [US/US]; PO LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Box 1461, Minneapolis, MN 55440 (US).
    [Show full text]