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HUNTSMAN Ethylene Carbonate Propylene Carbonate Butylene Carbonate UltraPureTM Ethylene Carbonate UltraPureTM Propylene Carbonate Carbonate Blends JEFFSOL® Alkylene Carbonates HUNTSMAN THE HUNTSMAN MISSION We will operate safe, clean, We have an aggressive growth efficient facilities in an philosophy which reflects the environmentally and socially spirit of free enterprise and responsible manner. maximization of long term profits, the best motives for creating We provide a work environment mutual benefits for customers, that fosters teamwork, employees, suppliers and the innovation, accountability and communities in which we are open communication. located. We will place into society assistance for those who suffer, hope for those who may need inspiration, and education for those who may feel the challenge but do not have the means. TABLE OF CONTENTS HUNTSMAN Glossary of Abbreviations ii Introduction 1 Description 2 Physical Properties 3 Applications 4 Solvents 5 Cleaners / Degreasers 7 Paint Strippers / Removers 11 Chemical Intermediates 15 Handling, Storage and Shipping Information 22 Health and Safety 25 JEFFSOL® Carbonate Literature List 28 Huntsman Sales Offices 29 HUNTSMAN GLOSSARY of ABBREVIATIONS BA Benzyl Alcohol BC 1, 2-Butylene Carbonate DB Diethylene Glycol Butyl Ether DBA Diethylene Glycol Butyl Ether Acetate DBE Dibasic Ester Mixture DMSO Dimethyl Sulfoxide DPM Dipropylene Glycol Methyl Ether EB Ethylene Glycol Butyl Ether EC Ethylene Carbonate EC-25 EC/PC (25/75 by weight) EC-50 EC/PC (50/50 by weight) EC-75 EC/PC (75/25 by weight) EEP 3-Ethoxy Ethyl Propionate EGDA Ethylene Glycol Diacetate FA Furfuryl Alcohol GBL g - Butyrolactone MEK Methyl Ethyl Ketone MIAK Methyl Isoamyl Ketone NAAC N-Amyl Acetate NMP N-Methyl-2-Pyrrolidone PB Propylene Glycol Butyl Ether PC Propylene Carbonate PM Propylene Glycol Methyl Ether PMA Propylene Glycol Methyl Ether Acetate TEG Triethylene Glycol ii INTRODUCTION HUNTSMAN Huntsman Corporation is the The JEFFSOL® Carbonates can be world's largest producer of used as "safe" and alkylene carbonates. At a environmentally friendly solvents production capacity of 65 million replacing harsh products such as pounds per year, Huntsman can methylene chloride, acetone, produce about 50% of the world's aromatic solvents, and other carbonates. highly volatile and hazardous solvents. The roots of Huntsman's carbonates experience date back Carbonates can also be used as to the 1950's; however, in 1996, reactive intermediates replacing the company brought on stream ethylene and propylene oxides the first "large" scale plant in the and ethylene and propylene world. glycols in many reactions. Huntsman produces its Where substitution occurs, use of carbonates in three separate the carbonates may allow for a manufacturing facilities on two more selective reaction and continents and maintains bulk minimizes side reactions and storage of these materials in contaminants. various sites around the world. In many cases, our technical staff In addition to JEFFSOL® Ethylene will assist our customers in Carbonate (EC), JEFFSOL® formulations, carbonate Propylene Carbonate (PC) and reactions, and development of JEFFSOL® Butylene Carbonate specialized products. (BC), the group produces a series of UltraPure™ Carbonates and is continuing to invest in specialty carbonates and carbamates. Huntsman is dedicated to developing the latest production technology and specialized derivatives for use in a variety of markets. 1 HUNTSMAN JEFFSOL® CARBONATES The JEFFSOL® Carbonates are cyclic All JEFFSOL® Carbonate products organic esters made from the are clear in appearance. reaction of ethylene oxide, ® propylene or butylene oxide with The JEFFSOL Carbonates have carbon dioxide. found use in numerous applications that require Our core products are JEFFSOL® outstanding solvency combined Ethylene Carbonate, Propylene with high flash points, low Carbonate, and Butylene evaporation rates, low VOCs, and Carbonate (see structures below). low toxicity. In addition, these molecules can be used as reactive ® Blends of JEFFSOL Ethylene intermediates. Carbonate and Propylene Carbonate are also available. They produce a variety of commercially important chemicals These blends may be used where and derivatives through liquid products are required. chemistries such as ® (Note JEFFSOL Ethylene hydroxyalkylation, Carbonate is solid at room transesterification, and carbamate temperature.) formation. JEFFSOL® EC-75, EC-50 and EC-25 are blends of JEFFSOL® Ethylene Carbonate and Propylene Carbonate in the ratios of 75/25, 50/50 and 25/75 by weight, respectively. H H H2CCH2 H2C C CH3 H2C C CH2CH3 OO OO OO C C C O O O Ethylene Propylene Butylene Carbonate Carbonate Carbonate (EC) (PC) (BC) Table1—Typical Analyses of JEFFSOL® Carbonates EC PC BC EC-75 EC-50 EC-25 Carbonate (wt.%, GLC) 99.8-99.95 99.8-99.95 99.8-99.95 99.8-99.95 99.8-99.95 99.8-99.95 Glycol Content (wt. %, GLC) 0.005-0.02 0.02-0.10 0.02-0.1 0.03-0.10 0.03-0.10 0.03-0.10 Water (wt. %, Karl Fisher 0.01-0.05 0.01-0.05 0.01-0.10 0.01-0.10 0.01-0.10 0.01-0.10 Ash (wt. %) 0-0.0002 0-0.0002 0.0002 0.0002 0.0002 0.0002 pH (10% aq. solution) 6.7-7.0 6.7-7.0 6.7-7.0 6.7-7.0 6.7-7.0 6.7-7.0 Pt-Cobalt Color 5.0-20.0 5.0-20.0 10-50 5.0-20.0 5.0-20.0 5.0-20.0 2 PHYSICAL PROPERTIES HUNTSMAN Table2—Physical Properties of JEFFSOL® Carbonates Property EC PC BC EC-75 EC-50 EC-25 Molecular Wt. (g/mole) 88.06 102.09 116.12 91.19 94.55 98.18 Boiling Point (C°) 248 242 251 246 - 247 244 - 245 243-244 Freezing Point (C°) — -49 <-45 17 -10 <-51 Melting Point (C°) 36.4 — — — — — Flash Point (°F, PMCC) 320 275 275 305 - 310 295 - 300 285 - 290 Evaporation Rate < .005 < .005 < .005 < .005 < .005 < .005 (25°C, n-BuAc = 1.00) Density (g/ml, 25°C) 1.338* 1.200 1.141 1.302 1.266 1.232 Density (g/ml, 40°C) 1.321 1.183 1.127 1.259 1.251 1.217 Molar Volume 65.8 85.1 101.8 70.6 74.6 80.3 (ml/g mole, 25°C) Viscosity (cp, 25°C) 2.56* 2.50 3.15 2.55 2.52 2.52 Viscosity (cp, 40°C) 1.95 1.86 2.24 1.92 1.90 1.88 CAS 96-49-1 108-32-7 4437-85-8 96-49-1 96-49-1 96-49-1 registry number 108-32-7 108-32-7 108-32-7 * Supercooled The vapor pressure graph below clearly illustrates the low volatility advantage of JEFFSOL® EC, PC, and BC compared to traditional solvents. Vapor Pressure Comparison 900 800 D-Limonene 700 600 e, mm Hg 500 NMP 400 essur BA 300 DBE 200 Vapor Pr EC/PC/BC 100 0 0 20 40 60 80 100 120 140 160 180 Temperature Degree C 3 HUNTSMAN APPLICATIONS JEFFSOL® Carbonates are used in a wide spectrum of applications. The matrix below illustrates some of the more common ones. Huntsman has a Technical Service staff dedicated to developing new markets, new applications, and improved formulations with JEFFSOL® Carbonates. Table 3 — JEFFSOL® CARBONATES Applications Matrix TM Application Ethylene Propylene Butylene Carbonate UltraPure Literature Carbonate Carbonate Carbonate Blends Carbonates Available "Safe" Solvents H H H k • Electrochemical H H H H H k • Ag H H H k • Cosmetics & Personal Care H H H H k Cleaners / Degreasers H H H k • Industrial & Consumer H H H k Paint Strippers / Removers H H H k Chemical Intermediates H H H H k Woodbinder Resins H H H H k Urethane (Reactive Diluent) H H H H k Foundry Sand Binders H H H H k Lubricants / Greases H H H k Photochromic H H H k Plasticizer H H H H k Gas Treating H H H k Epoxy Resins (Reactive Diluent) H H H H k Water Scavenger H H H H k Antipilling H H H H k Textile Dyeing H H H H k Superabsorbent Polymers H H k Tail Solvent (Bake Enamels) H H H k k Contact your Huntsman sales representative for more information 4 SOLVENTS HUNTSMAN The JEFFSOL® Carbonates are perchloroethylene, excellent polar solvents for many trichloroethylene, NMP, acetone, organic and inorganic materials. MEK, and toluene among others. Their excellent solvency The JEFFSOL® Carbonates offer properties combined with high outstanding properties and flash points, high boiling points, advantages as substitutes for low evaporation rates, low VOC, these targeted solvents as low toxicity, and low odor make illustrated in Tables 4 and 5. them particularly attractive choices for many solvent applications today. Some of the traditional solvents targeted for replacement in the United States include: methylene chloride, 1,1,1-trichloroethane, Table4—Volatile Organic Content (ASTM D-2369) Products %VOC(110°C) JEFFSOL® BC 18 JEFFSOL® PC 28 JEFFSOL® EC-50 31 JEFFSOL® EC 34 PM 100 DPM 100 DBE 100 BA 100 NMP 100 D-Limonene 100 Limonene 145 100 5 HUNTSMAN SOLVENTS (continued) These advantages make the Other diversified applications for JEFFSOL® Carbonates extremely JEFFSOL® Carbonates include, but beneficial in numerous solvent are not limited to: applications. l Circuit Board Cleaners Two primary uses are in l Polyurethane Cleanup Solvents cleaners/degreasers and paint l Carburetor Cleaners strippers. l Polymer/resin Cleanup In addition, the UltraPure ™ l Solvents for Inks and Ink grades are used in electronic Cleaners applications because of their high l Solvent for Dye used in purity and low glycol and water Carbonless Paper content. l Solvents for Cosmetics (wetting agent for clays) l Unsaturated Polyester Cleanup Solvent l All-Purpose Cleaners l Structural Adhesives Cleanup Solvent l Polymer Solvent for Reaction Processing l Solvent for Polyurethane Elastomer Pellets l Cleaning stereolithography parts (remove resins) Table5—AdvantagesinUsing JEFFSOL® Carbonates Products Flash Pt., Boiling Pt., Evap.
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  • United States Patent (19 11) 4,192,810 W 45) Mar

    United States Patent (19 11) 4,192,810 W 45) Mar

    United States Patent (19 11) 4,192,810 W 45) Mar. 11, 1980 54 PREPARATION OF VICINAL EPOXIDES OTHER PUBLICATIONS A. L. Shapiro et al., Jour. Org. Chem., USSR, vol. 5 75 Inventor: Yulin Wu, Bartlesville, Okla. (1969) pp. 200-203. 73) Assignee: Phillips Petroleum Company, Primary Examiner-Norma S. Milestone Bartlesville, Okla. 57 ABSTRACT Vicinal epoxides having 2 to 30 carbon atoms per mole 21) Appl. No.: 934,667 cule are prepared by heating the corresponding carbon ate esters having the general formula 22 Filed: Aug. 17, 1978 Related U.S. Application Data R---RO O 62) Division of Ser. No. 845,183, Oct. 25, 1977, Pat. No. V / 4,111,965, which is a division of Ser. No. 459,628, Apr. C 10, 1974, Pat. No. 4,069,234. I O 51) Int. Cl’............................................ C07D 301/02 52 U.S. Cl. ................................................ 260/348.16 in the presence of a catalytic amount of a catalyst se 58 Field of Search .................................... 260/348.16 lected from the group consisting of phosphonium ha lides, sulfonium halides, sulfoxonium halides and metal salts selected from the group consisting of the halides, 56) References Cited sulfates and carboxylates having 1 to 20 carbon atoms of FOREIGN PATENT DOCUMENTS iron, tin, manganese and zinc. 893037 5/1944 France ................................ 260/348.16 47-15951 12/1972 Japan ..................................... 260/340.2 8 Claims, No Drawings 4,192,810 2 PREPARATION OF WICNAL EPOXDES This is a divisional application of application Ser. No. R---R 845,183, filed Oct. 25, 1977, now U.S. Pat. No. OHOH 4,111,965, which is a divisional of application Ser.