United States Patent Office Patented Aug

Total Page:16

File Type:pdf, Size:1020Kb

United States Patent Office Patented Aug y 2,847,481 United States Patent Office Patented Aug. 12, 1958 2 invention produces a mixture of these isomers from which the desired CsCl isomer may be separately re 2,847,481 covered in substantially pure form. Apparently, the PRODUCTION OF OCTACHELOROMETHYLENE preparation of octachloromethylenecyclopentene has CYCLOPENTENE been of only academic interest as no attempt has been made to obtain the material by an economic process Aylmer H. Maude and David S. Rosenberg, Niagara suitable for commercial manufacture. Falls, N.Y., assignors to Hooker Electrochemical Com Octachloromethylenecyclopentene is a valuable chem pany, Niagara Falls, N.Y., a corporation of New York ical intermediate, useful in the synthesis of various other No Drawing. Application August 9, 1954 0 chemicals having diverse uses in the commercial arts. Serial No. 448,736 For example, it may be used as the starting material for making perchlorofulvene by reacting it with aluminum 5 Claims. (CI. 260-648) shavings in the presence of freshly sublimed aluminum chloride in ether solution for a period of about 12 hours This invention is concerned with the production of 5 (see Roedig, Ann. 569, 161-183, (1950)). Also, various unsaturated cyclic chlorocarbons having the empirical ketones may be made from octachloromethylenecyclo formula CsCl and more particularly to the production pentene by reaction with sulfuric acid. of octachloromethylenecyclopentene. The process of It is the object of this invention to provide a method the present invention involves introducing a mixture for the production of octachloromethylenecyclopentene of a C chlorohydrocarbon containing at least three 20 by an economic process which has a direct and simple chlorine atoms and chlorine into a reaction Zone con procedure and which is readily adaptable to commercial taining a porous surface active catalyst maintained at operation. It is a further object to provide a method an elevated temperature to produce the CsCls chloro for the production of octachloromethylenecyclopentene carbon in the desired yield. from inexpensive starting materials. Other objects will One isomer of CsCl was first produced by H. J. Prins 25 become apparent to those skilled in the art on considera (J. Prakt. Chem. (2) 89, 421 (1914)). This isomer tion of our complete specifications and claims. melting at 183 degrees centigrade has the following We have now found that these and related objects theoretical structural formula: are accomplished by reacting chlorine with a C6 chloro Cl-C C-Cl hydrocarbon having at least three chlorine atoms in the C-C-Cl 30 presence of a porous surface active catalyst at tem peratures between about 250 and 460 degrees centigrade. Cl-C C-Cl The starting C6 chlorohydrocarbon must have at least and is designated as octachloromethylenecyclopentene. three chlorine atoms; however, the exact ratio of hydro Prins prepared it from hexachloropropylene using cop gen to chlorine atoms is not critical. Any Cs chloro per-bronze in methanol solution (see also Rec. Trav. hydrocarbon containing more than three, and preferably Chem. 51, 1065 (1932) and 72, 253-261 (1953)). A about eight to nine chlorine atoms may be employed in Roedig (Experimentia 4, 305-307 (1948)) prepared the practicing our invention. Various Ca hydrocarbons may compound from hexachloropropylene using aluminum be used as starting materials for preparing the chloro shavings in ethereal solution. Further (Ann. 569, 161 hydrocarbon; for example, n-hexane, iso-hexane, meth 183 (1950)), Roedig again prepared the compound by 40 ylcyclopentane, as well as the corresponding olefins and dechlorinating either octachloropropane or hexachloro diolefins, and mixtures thereof. propene with aluminum powder. Prins also prepared When carrying out the reaction, the proportion of free the compound from these same two starting materials chlorine to employ is slightly (about 10 percent) more and in addition from heptachloropentene-1 (Rec. Trav. than the theoretical amount required to make octachloro Chem. 65, 435 (1946)). Prins later made the isomer methylenecyclopentene from the chosen starting mate of CsCl of melting point 183 degrees centigrade by two rials. While a slight excess of chlorine (about 10 per different methods (a) action of copper powder upon cent) is desired, a higher percentage will not prove detri hexachloropropene in alcoholic solution, and (b) reac mental to the reaction, but the amount of chlorine will tion of chloroform and trichloroethylene in the presence be governed by economics of the process. The following of aluminum chloride (Rec. Trav. Chem. 68, 419-425 50 equations are illustrative of this point. (1949)). The prior art refers to isolation of three of the four possible structural isomers of CsCls having melting points of 45, 94, and 183 degrees centigrade. These structural Materials selected from the group consisting of silica isomers of empirical formula CsCls may have any of 55 gel, bauxite, active carbon, kieselguhr brick, fuller's the following theoretical configurations: earth, floridin, attapulgite, diatomaceous earth and mix Cl-C C-Cl2 . Cl-C C-Cl2 tures thereof are suitable porous surface active solids for use in this invention. These solids all have exten =C-Cl CeC-Cl sive active surface areas and are substantially unaffected C-C C-Cl Cl-C -Cl 60 chemically during their life in the reaction zone. They II tend to become ineffective in use, probably due to re duction in porosity, and must be periodically replaced Cl-C C-Cl Cl-C C-Cl by fresh material. In general, the low cost of such C-C-Cls C Cl-C-Cla solids renders it uneconomic to regenerate them when 65 spent, but this can be done if desired. Cl- -Cla C-C TC-Cl The porous inorganic solid employed in the reaction III IV Zone can be pretreated by various techniques, such as, These isomers are believed to be interconvertible. Al extrusion under pressure, acid extraction, impregnation though the present invention relates primarily to the with various salts, etc., whereby enhanced results are production of octachloromethylenecyclopentene which 70 obtained in this invention. is believed to have the structural formula correspond The porous solids may be impregnated with the chlo ing to configuration I above, the process of the present ride salts of various metals to enhance their activity; for 2,847,481 3. example, iron, cobalt, or nickel, which are metals of from such preferred stock as n-hexane, iso-hexane, various group V of the periodic table. mixed hexanes, or methylcyclopentane. The exit from The reaction temperature should be maintained be the catalyst tube was connected to a condenser consist tween 250 and 460 degrees centigrade to obtain a high ing of a section of 2-inch nickel pipe holding a glass yield of octachloromethylenecyclopentene. The pre cooling thimble with water cooling. ferred range of temperature wherein we have obtained the A nominal retention time of about three to fifteen best results is between about 275 and 350 degrees centi seconds was used. The time was calculated as indicated grade. The most desirable temperature for any particu in the examples. lar starting material is that low enough for a minimum The organic product from the reactor was distilled in yield of hexachlorobenzene and high enough to reduce 0. a column (20 mm. bore and 4 feet high) packed with to a minimum hydrogen-containing, organic products. protruded nickel packing. Fractionation was carried out The porous solid in the fore portion of the reaction at an absolute pressure of about 10 mm. of mercury. zone is advantageously graded with lower activity mate Essentially pure octachloromethylenecyclopentene was ob rial where the reactant vapors first contact it to avoid an tained by crystallization from suitable solvents. excessively rapid exothermic reaction with a resulting 5 The following examples illustrate our invention but are temperature above the range indicated whereby chlo not to be construed as limiting the same to these ex rinolysis would result. The temperature should be main amples. tained fairly uniform and in order to accomplish this Example I condition it may be necessary to heat or cool the various About 1160 grams of n-hexane were photochemically reaction zones depending upon catalyst activity and the 20 chlorinated as above described to a specific gravity of exothermic or endothermic character of the reaction about 1.6 which corresponds to a product having an taking place in that Zone. For example, if chlorine con average molecular formula of C6H54Cls.6. tent of C chlorohydrocarbon feed were high, it may be A feed of 386 grams per hour (1.01 moles per hour) necessary to heat the entire reaction Zone; if low, cooling of such polychlorohexane and 348 grams per hour (4.9 may be required in the initial zone and heat in the final moles per hour) of chlorine was fed to a reactor tube, ZOC holding 720 cubic centimeters of catalyst of fine granular The undesirable effects of localized overheating in the fore portion of the reaction zone containing the porous particle size. The first quarter of the tube was charged solid, whereby chlorinolysis is effected, may be minimized with a mixture of 1 part pressure activated floridin and 30 6 parts pumice. The pumice used was inert in this re by diluting the gaseous reactants with an inert diluent. action and serves to reduce the activity per unit catalyst Hydrogen chloride concomitantly produced with the Cs volume. The second quarter of the tube was charged chiorohydrocarbons may be conveniently and advan with 1 part pressure activated floridin and 3 parts pumice. tageously used as an effective diluent for this purpose; The third and fourth quarters were packed with pressure however, other diluents such as nitrogen or carbon di 35 activated floridin alone. The retention time was about oxide can be used. seven seconds, calculated on a reaction temperature of The reactants are introduced into the reaction Zone in 300 degrees centigrade, on the molal feed rates and the the vapor state at substantially atmospheric pressure and free space in the catalytic bed.
Recommended publications
  • 1 Abietic Acid R Abrasive Silica for Polishing DR Acenaphthene M (LC
    1 abietic acid R abrasive silica for polishing DR acenaphthene M (LC) acenaphthene quinone R acenaphthylene R acetal (see 1,1-diethoxyethane) acetaldehyde M (FC) acetaldehyde-d (CH3CDO) R acetaldehyde dimethyl acetal CH acetaldoxime R acetamide M (LC) acetamidinium chloride R acetamidoacrylic acid 2- NB acetamidobenzaldehyde p- R acetamidobenzenesulfonyl chloride 4- R acetamidodeoxythioglucopyranose triacetate 2- -2- -1- -β-D- 3,4,6- AB acetamidomethylthiazole 2- -4- PB acetanilide M (LC) acetazolamide R acetdimethylamide see dimethylacetamide, N,N- acethydrazide R acetic acid M (solv) acetic anhydride M (FC) acetmethylamide see methylacetamide, N- acetoacetamide R acetoacetanilide R acetoacetic acid, lithium salt R acetobromoglucose -α-D- NB acetohydroxamic acid R acetoin R acetol (hydroxyacetone) R acetonaphthalide (α)R acetone M (solv) acetone ,A.R. M (solv) acetone-d6 RM acetone cyanohydrin R acetonedicarboxylic acid ,dimethyl ester R acetonedicarboxylic acid -1,3- R acetone dimethyl acetal see dimethoxypropane 2,2- acetonitrile M (solv) acetonitrile-d3 RM acetonylacetone see hexanedione 2,5- acetonylbenzylhydroxycoumarin (3-(α- -4- R acetophenone M (LC) acetophenone oxime R acetophenone trimethylsilyl enol ether see phenyltrimethylsilyl... acetoxyacetone (oxopropyl acetate 2-) R acetoxybenzoic acid 4- DS acetoxynaphthoic acid 6- -2- R 2 acetylacetaldehyde dimethylacetal R acetylacetone (pentanedione -2,4-) M (C) acetylbenzonitrile p- R acetylbiphenyl 4- see phenylacetophenone, p- acetyl bromide M (FC) acetylbromothiophene 2- -5-
    [Show full text]
  • Experimental Deformation of Polyphase Rock Analogues
    GEOLOGICA ULTRAJECTINA Mededelingen van de Faculteit Aardwetenschappen der Universiteit Utrecht No. 110 Experimental deformation of polyphase rock analogues PAUL DIRK BONS Experinlelltal defornlation of polyphase rock analogues Experimentele deformatie van polyfase gesteente-analogen (met een samenvatting in het Nederlands) PROEFSCHRIFT TER VERKRllGING VAN DE GRAAD VAN DOCTOR AAN DE UNIVERSITEIT UTRECHT OP GEZAG VAN DE RECTOR MAGNIFICUS, PROF. DR l.A. VAN GINKEL, INGEVOLGE HET BESLUIT VAN HET COLLEGE VAN DECANEN IN HET OPENBAAR TE VERDEDIGEN OP WOENSDAG 22 SEPTEMBER 1993 DES OCHTENDS TE 10.30 UUR DOOR PAUL DIRK BONS GEBOREN OP 20 FEBRUARI 1964 TE SYDNEY, AUSTRALIE PROMOTOREN: PROF. DR S.H. WHITE (FACULTEIT AARDWETENSCHAPPEN, UNIVERSITEIT UTRECHT) PROF. DR C.W. PASSCHIER (lNSTITUT FUR GEOWISSENSCHAFTEN, JOHANNES GUTENBERG-UNIVERSITAT, MAINZ, BONDSREPUBLIEK DUITSLAND) CO-PROMOTOREN: DR J.L. URAl (SHELL RESEARCH B.V., RIJSWIJK) DR M.W. JESSELL (DEPARTMENT OF EARTH SCIENCES, MONASH UNIVERSITY, CLAYTON, AUSTRALIE) Dit proefschrift werd mogelijk gemaakt met financiele steun van de Nederlandse Organisatie voor Wetenschappelijk Onderzoek (N.W.O.), c.q. de Stichting Aardwetenschappelijk Onderzoek Nederland (A.W.O.N.), projectnummer 751-353­ 021 CIP-GEGEVENS KONINKLIJKE BIBLIOTHEEK, DEN HAAG Bons, Paul Dirk Experimental deformation of polyphase rock analogues / Paul Dirk Bons. - Utrecht: Faculteit Aardwetenschappen der Universiteit Utrecht. ­ (Geologica Ultraiectina, ISSN 0072-1026; no. 110) Proefschrift Universiteit Utrecht. - Met lit. opg. - Met samenvatting in het Nederlands. ISBN 90-71577-64-3. Trefw.: deformatie / polyfase materialen / gesteente-analogen. Some questions on polyphase materials: How many strawberries, how large in the "charlotte auxfraises"? How to characterise their distribution? How should one put the pears (aspect ratio, distribution ..
    [Show full text]
  • Crystallinity Changes and Phase Transitions of Selected Pharmaceutical Solids with Processing
    CRYSTALLINITY CHANGES AND PHASE TRANSITIONS OF SELECTED PHARMACEUTICAL SOLIDS WITH PROCESSING by MARION W.Y. WONG B.Sc. (Pharm), The University of British Columbia, 1988 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF’ PHILOSOPHY in THE FACULTY OF GRADUATE STUDIES Faàulty of Pharmaceutical Sciences Division of Pharmaceutics and Biopharmaceutics We accept this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA November 1993 © Marion W.Y. Wong, 1993 _______________________ In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the head of my department or by his or her representatives, It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. (Signature) Department of The University of British Columbia Vancouver, Canada Date jt7’ / DE-6 (2/88) 11 ABSTRACT The solid state properties of drugs and pharmaceutical excipients can be significantly affected by processing (e.g. grinding, tabletting, heating and additive incorporation) and reflect structural changes within a solid. Such changes may involve alterations in both the chemical and physical nature of the crystal structure (e.g. hydrates), complete rearrangements of the same chemical components in three-dimensional space (e.g. polymorphs), or more subtle changes which involve neither the chemical composition nor the space lattice. These more subtle changes do not involve phase changes and are referred to as changes in the degree of crystallinity, X.
    [Show full text]
  • United States Patent 0 1C6 Patented Nov
    r: 3,287,425 United States Patent 0 1C6 Patented Nov. 22, 1966 1 2 propanes; acyclic compounds containing one or more car 3,287,425 bon-to-oarbon double bonds such as hexachloropropene, FLUORINATED COMPOUNDS AND THEIR PREPARATION 3-hydropentachloropene, octachlorobutenes, heptachloro John T. Maynard, Brandywine Hundred, Del., assignor to butenes, hexachlorobutenes, hexachloro-1,3-butadiene, and E. I. du Pont de Nemours and Company, Wilmington, perchloro-l,5-hexadiene; saturated carbocyclic compounds Del., a corporation of Delaware such as perchlorocyclopentane and perchlorocyclohexane; No Drawing. Filed Mar. 7, 1961, Ser. No. 93,860 and carbocyclic compounds containing one or two car 14 Claims. (Cl. 260-6533) bon-to-carbon double bond-s in the ring such as octachloro cyclopen-tene. This application is a continuation-in-part of my co 10 As indicated above, the polychlorohyd-rocarbon com pending application Serial No. 12,973, ?led March 7, pounds are added to an agitated suspension of an alkali 1960, now abandoned. metal ?uoride which is either potassium ?uoride, cesium This invention relates to a novel process for preparing ?uoride, or rubidium fluoride. If desired, mixtures of ?uorinated compounds. In addition, this invention re these alkali metal ?uorides may be used. The alkali metal lates to novel 2-hydrohepta?uorobutenes. 15 ?uoride should be ?nely divided and anhydrous. The Fluorine-containing compounds are of great potential amount of alkali metal ?uoride to be used depends upon value for a wide variety of purposes. However, use of the number of chlorine atoms to be replaced in the poly many of these compounds is severely limited because of chlorohydrocarb-on starting material.
    [Show full text]
  • Selective Solvent Extraction of Tantalum and Niobium Fluorides Using N-Benzoyl-N-Phenylhydroxylamine
    SELECTIVE SOLVENT EXTRACTION OF TANTALUM AND NIOBIUM FLUORIDES USING N-BENZOYL- N-PHENYLHYDROXYLAMINE By JAMES SPENCER ERSKINE Bachelor of Science Northwestern State College Alva, Oklahoma 1963 Submitted to the faculty of the Graduate College of the Oklahoma State University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE May, 1966 OKLAHOMA STATE UN!VERSlft LIBRARY NOV 8 196~ '"' ••• _••• , ...... ,,,. ·~ ''"1 ••• SELECTIVE SOLVENT EXTRACTION OF TANTALUM AND NIOBIUM FLUORIDES USING N-BENZOYL- N-PHENYLHYDROXYLAMINE Thesis Approved: Thesis Advise:tt'.7 621523 ii ACKNOWLEDGMENTS In.works of this nature the author becomes indebted to many people. I wish to express my sincere gratitude to Dr. L. P. Varga, my adviser, for his patience, encouragement and helpful criticism during this work. Thanks are extended to Mike Sink, who helped in the preparation of the many solutions necessary in this work and to the National Science Foundation for the sponsorship of Mike Sink as a summer re­ search assistant. I am indebted, in addition, to the Department of Chemistry at Oklahoma St.ate University for the use of their labora·ory facilities and for financial aid in the form of a teaching assistantship, and to the Dow Chemical Company for their generous research scholarship dur­ ing the summer of 1965. I also wish to express my appreciation to the many persons, mentioned or not, who have provided influence, guidance or inspiration during my graduate work. iii TABLE OF CONTENTS Chapter Page I. INTRODUCTION 1 II. HISTORICAL . 3 III. THEORY .•• • • • • 14 Extraction Model. • • • • • . ..••• 14 Least Squares Curve-Fit ting . • • • • • • . • • 17 IV.
    [Show full text]
  • Ep 0968157 B1
    Europäisches Patentamt *EP000968157B1* (19) European Patent Office Office européen des brevets (11) EP 0 968 157 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C06D 3/00 of the grant of the patent: 13.11.2002 Bulletin 2002/46 (86) International application number: PCT/NL98/00149 (21) Application number: 98911262.8 (87) International publication number: (22) Date of filing: 13.03.1998 WO 98/040330 (17.09.1998 Gazette 1998/37) (54) COMPOSITION FOR GENERATING SMOKE RAUCH ERZEUGENDE ZUSAMMENSETZUNG COMPOSITION FUMIGENE (84) Designated Contracting States: • SCHONEWILLE, Elisabeth CH DE ES FI FR GB IE IT LI NL SE NL-2063 KJ Haarlem (NL) (30) Priority: 13.03.1997 NL 1005529 (74) Representative: Prins, Adrianus Willem et al Vereenigde, (43) Date of publication of application: Nieuwe Parklaan 97 05.01.2000 Bulletin 2000/01 2587 BN Den Haag (NL) (73) Proprietor: NEDERLANDSE ORGANISATIE VOOR (56) References cited: TOEGEPAST-NATUURWETENSCHAPPELIJK DE-A- 2 451 701 DE-B- 1 180 657 ONDERZOEK TNO DE-B- 2 819 850 FR-A- 2 249 590 2628 VK Delft (NL) GB-A- 2 056 632 US-A- 1 886 394 US-A- 3 329 624 US-A- 3 625 855 (72) Inventors: • VAN DRIEL, Christoffel, Adrianus • CHEMICAL ABSTRACTS, vol. 119, no. 10, 6 NL-2622 BJ Delft (NL) September 1993 Columbus, Ohio, US; abstract • LEENDERS, Adriana, Petronella, Martina no. 99248x, J. DOLINEK ET AL.: "Metal chloride NL-2635 KA Den Hoorn (NL) smoke-generating composition with increased • LEEUWENBURGH, Arnold, Barend infrared screening properties" page 226; NL-2716 XE Zoetermeer (NL) XP000431169 & CZ 274 925 A (J.
    [Show full text]
  • Proquest Dissertations
    Estimating the entropy of melting from structure Item Type text; Dissertation-Reproduction (electronic) Authors Dannenfelser, Rose-Marie, 1959- Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 26/09/2021 04:06:30 Link to Item http://hdl.handle.net/10150/288729 INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI fihns the text dvectfy from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter &ce, whfle others may be from any type of computer printer. The quality of this reproductioii is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, b^inning at the upper left-hand comer and continuing from left to right in equal sections with small overiaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. Photographs included in the original manuscript have been reproduced xerographicalfy in this copy.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,304,589 B2 Fukuju Et Al
    USOO83 04589B2 (12) United States Patent (10) Patent No.: US 8,304,589 B2 Fukuju et al. (45) Date of Patent: *Nov. 6, 2012 (54) PROCESS OF MAKING ACHLORINATED (52) U.S. Cl. ......................... 570/247; 570/246; 570/257 HYDROCARBON (58) Field of Classification Search ........................ None See application file for complete search history. (75) Inventors: Tadahiro Fukuju, Shunan (JP); Kikuo Yamamoto, Shunan (JP); Masayuki (56) References Cited Moriwaki, Shunan (JP); Yasutaka Komatsu, Shunan (JP); Akihiro Saito, U.S. PATENT DOCUMENTS Shunan (JP); Shunsuke Hosaka, Shunan 3,823, 195 A 7, 1974 Smith (JP); Dai Tsunoda, Shunan (JP); Jun 3,926,758 A 12, 1975 Smith Kawakami, Shunan (JP) 4,650,914 A * 3/1987 Woodard ...................... 570,236 (73) Assignee: Tokuyama Corporation, Shunan-Shi 5,446,217 A 8/1995 Van Der Puy et al. (JP) FOREIGN PATENT DOCUMENTS JP 50-4006 A 1, 1975 (*) Notice: Subject to any disclaimer, the term of this JP 60-36429 A 2, 1985 patent is extended or adjusted under 35 JP 2-47969 B2 10, 1990 U.S.C. 154(b) by 0 days. JP 2007-23050 A 2, 2007 This patent is Subject to a terminal dis OTHER PUBLICATIONS claimer. International Search Report for International Patent Application No. PCT/JP2010/060695, mailed on Aug. 31, 2010. (21) Appl. No.: 13/406,238 * cited by examiner (22) Filed: Feb. 27, 2012 Primary Examiner — Sudhakar Katakam (65) Prior Publication Data (74) Attorney, Agent, or Firm — Birch, Stewart, Kolasch & US 2012/O157723 A1 Jun. 21, 2012 Birch, LLP Related U.S. Application Data (57) ABSTRACT A process of making a chlorinated hydrocarbon through a (62) Division of application No.
    [Show full text]
  • Process for Producing Ethylene-Propylene Copolymer Rubber
    Europaisches Patentamt J European Patent Office Publication number: 0 264 169 Office europeen des brevets A1 © EUROPEAN PATENT APPLICATION © Application number: 87305349.0 © int. CM: C08F 210/16 © Date of filing: 16.06.87 ® Priority: 16.06.86 JP 138252/86 © Applicant: TOA NENRYO KOGYO KABUSHIKI 16.06.86 JP 138253/86 KAISHA 16.06.86 JP 138254/86 1-1 Hitotsubashi, 1-Chome Chiyoda-Ku Tokyo 100(JP) © Date of publication of application: 20.04.88 Bulletin 88/16 @ Inventor: Ueki, Satoshi '@_•@« 4-7-301 Tate 2-chome © Designated Contracting States: Shiki-shi Saitama-ken(JP) BE DE FR GB IT NL SE inventor: Furuhashi, Hiroyuki 4-6 Nishitsurugaoka 1-chome Ooi-maci Iruma-gun Saitama-ken(JP) Inventor: Kusano, Yoshihisa 1734-3 Ooaza Takahagi Hidaka-machi Iruma-gun Saitama-ken(JP) Inventor: Fukazawa, Nobuyuki 4-4-436 Nishitsurugaoka 1-chome Ooi-machi Iruma-gun Saitama-ken(JP) Inventor: Maruyama, Kouji 13-8 Chou 2-chome Kamifukuoka-shi Saitama-ken(JP) Inventor: Ueno, Hiroshi 398-1 Ooaza Haneo Namegawa-machi Hiki-gun Saitama-ken(JP) Inventor: Mizukami, Haruo 71 Higashifukai Nagareyama-shi Chiba-ken(JP) © Representative: Dew, Melvyn John et al Exxon Chemical Limited Exxon Chemical Technology Centre P.O. Box 1 Abingdon Oxfordshire, OX13 6BB(GB) ^© Process for producing ethylene-propylene copolymer rubber. C5 The rmm® present invention provides a process for producing an ethylene-propylene copolymer rubber containing 15-90 mol% of ethylene, wherein ethylene and propylene are copolymerized in the presence of a polymerization g catalyst composed of a catalyst component and an organoaiuminum compound, said catalyst component being by ^obtained contacting (A) a metal oxide, (B) a dihydrocarbyl magnesium, and (C) a hydrocarbyloxy group- containing compound with one another, contacting the thus obtained contact product with (D) O a halogen- containing alcohol, and finally contacting the thus obtained contact product with (E) a titanium compound, and Q.
    [Show full text]
  • Kinetics of the Radiolysis of Chloroform: Combined Effects of Dose Rate and Temperature
    This dissertation has been microfilmed exactly as received 66—1751 ABRAMSON, Fred Paul, 1941- KINETICS OF THE RADIOLYSIS OF CHLOROFORM: COMBINED EFFECTS OF DOSE RATE AND TEMPERATURE. The Ohio State University, Ph.D., 1965 Chemistry, physical University Microfilms, Inc., Ann Arbor, Michigan Copyright by Fred Paul Abramson 1966 KINETICS OF THE RADIOLYSIS OF CHLOROFORM: COMBINED EFFECTS OF DOSE RATE AND TEMPERATURE DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University Fred Paul Abramson> A. B* ****** The Ohio State University 1965 Approved by Adviser Department of Chemistry ACKNOWLEDGMENTS I wish primarily to thank Dr. Richard F. Firestone for his guidance and instruction throughout the past years. It is hoped that this work» as well as future work» will partially repay him for the time and effort which he has put forth on my behalf. The other members of the Radiation Chemistry section are also owed a great debt of gratitude for it has been their assistance and enthusiasm which has made my graduate program more complete and re­ warding. I also gratefully acknowledge the support of the Department of Healthy Education and Welfare for its award of a National Defense Education Act Title IV Fellowship from 1962 to the present time. This work was also supported by the United States Atomic Energy Com­ mission (Contract AT(ll-l)-ll6 ) which sponsored my Research Assistant- ship during the summer months. A special acknowledgment is made to Dr. Clinton Foulk and the Numerical Computation Laboratories of The Ohio State University for their support and assistance with the digital computer programs and the award of computer time.
    [Show full text]
  • United States Patent Office Patented Sept
    3,274,035 United States Patent Office Patented Sept. 20, 1966 2 Example I 3,274,035 METALEC COMPOSTON FOR PRODUCTION OF Ingredients: Percent by weight HYGROSCOPEC SMOKE Lithium carbonate ---------------------- 19.34 Lohr A. Barkardt and William G. Finnegan, China Lake, Hexachloroethane ----------------------- 20.66 Calif., assignors to the United States of America as Aluminum ----------------------------- 20.50 represented by the Secretary of the Navy Potassium perchlorate ------------------- 39.50 No Drawing. Fied June 5, 1964, Ser. No. 375,402 This composition burns completely and leaves no resi 4 (Caims. (C. 49-40) due, i.e., all the reaction products are volatilized. The The invention herein described may be manufactured 0. percentages of lithium carbonate and hexachloroethane and used by or for the Government of the United States may vary from the values stated so long as their mutual of America for governmental purposes without the pay proportions remain the same. ment of any royalties thereon or therefor. The ingredients are blended and compression molded This invention relates to new compositions for pyro into appropriate containers. technic production of hygroscopic Smokes. Example II Many compositions and methods are known to the art for producing smokes for concealment purposes as well Ingredients: Percent by weight as cloud seeding. A variety of haloid compositions have Lithium carbonate ----------------------- 16.9 been made which are said to produce hygroscopic Smoke. Hexachloroethane ------------------------ 18.1 They consist essentially of an admixture of an oxidant, 20 Aluminum ------------------------------ 22.3 a fuel, a halogen donor and a halogen receptor. Other Potassium perchlorate -------------------- 42.7 substances, which dispersed, have cloud nucleating char The above composition was mixed and pressed into acteristics include the well-known iodides, silver, lead, a cylinder one-inch diameter, one-half inch long with a and copper, cupro-oxide, copper sulphide, copper selenide, one-fourth inch hole.
    [Show full text]
  • Estimation of Radiative Efficiency of Chemicals with Potentially Significant Global Warming Potential Don Betowski,*† Charles Bevington,‡ and Thomas C
    Supporting Information Estimation of Radiative Efficiency of Chemicals with Potentially Significant Global Warming Potential Don Betowski,*† Charles Bevington,‡ and Thomas C. Allison§ †U.S. Environmental Protection Agency, National Exposure Research Laboratory, Environmental Sciences Division, P.O. Box 93478, Las Vegas, Nevada 89193-3478 ‡U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxics, Risk Assessment Division, 1200 Pennsylvania Avenue, N. W., Mail Code: 7408M, Washington, D.C. 20460 §Material Measurement Laboratory, National Institute of Standards and Technology, 100 Bureau Drive, Stop 8320, Gaithersburg, Maryland, 20899-8320 Contents: Data sources for Radiative Efficiency values. Computational Radiative Efficiency values for 1300 compounds. Table S1-Referenced Radiative Efficiency Values References Table S-2. Calculated RF values for 1300 chemicals. S1 S2 For chemicals, which already had a measured radiative efficiency value reported through IPCC,WMO, EPA, or the open literature, these values were compiled in the Supporting Information, Table S1. In cases, where multiple values were reported they are compiled together in Table S1. Hodnebrog 2013 constant profile, not lifetime adjusted, radiative efficiency values were chosen when available as the most appropriate value to compare to ab initio estimates. When these were not available, IPPC5 or values from other sources were chosen as indicated by bold in the table below. Two new data sources, IPPC5 and Hodnebrog were compared to previous IPCC, WMO, EPA
    [Show full text]