"Hydrocarbons," In: Ullmann's Encyclopedia of Industrial Chemistry

Total Page:16

File Type:pdf, Size:1020Kb

Article No : a13_227 Hydrocarbons KARL GRIESBAUM, Universit€at Karlsruhe (TH), Karlsruhe, Federal Republic of Germany ARNO BEHR, Henkel KGaA, Dusseldorf,€ Federal Republic of Germany DIETER BIEDENKAPP, BASF Aktiengesellschaft, Ludwigshafen, Federal Republic of Germany HEINZ-WERNER VOGES, Huls€ Aktiengesellschaft, Marl, Federal Republic of Germany DOROTHEA GARBE, Haarmann & Reimer GmbH, Holzminden, Federal Republic of Germany CHRISTIAN PAETZ, Bayer AG, Leverkusen, Federal Republic of Germany GERD COLLIN, Ruttgerswerke€ AG, Duisburg, Federal Republic of Germany DIETER MAYER, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany HARTMUT Ho€KE, Ruttgerswerke€ AG, Castrop-Rauxel, Federal Republic of Germany 1. Saturated Hydrocarbons ............ 134 3.7. Cumene ......................... 163 1.1. Physical Properties ................ 134 3.8. Diisopropylbenzenes ............... 164 1.2. Chemical Properties ............... 134 3.9. Cymenes; C4- and C5-Alkylaromatic 1.3. Production ....................... 134 Compounds ...................... 165 1.3.1. From Natural Gas and Petroleum . .... 135 3.10. Monoalkylbenzenes with Alkyl Groups 1.3.2. From Coal and Coal-Derived Products . 138 >C10 ........................... 166 1.3.3. By Synthesis and by Conversion of other 3.11. Diphenylmethane .................. 167 Hydrocarbons . .................. 139 4. Biphenyls and Polyphenyls .......... 168 1.4. Uses ............................ 140 4.1. Biphenyl......................... 168 1.5. Individual Saturated Hydrocarbons ... 142 4.2. Terphenyls....................... 171 2. Olefins .......................... 144 4.3. Polyphenyls ...................... 172 2.1. Monoolefins ...................... 144 5. Hydrocarbons from Coal Tar ........ 172 2.1.1. Properties . ...................... 145 5.1. Acenaphthene .................... 172 2.1.2. Production of Higher Olefins . ......... 145 5.2. Indene .......................... 174 2.1.2.1. Production from Paraffins . ......... 146 5.3. Fluorene......................... 175 2.1.2.2. Oligomerization of Lower Olefins . .... 149 5.4. Fluoranthene ..................... 176 2.1.3. Uses of Higher Olefins. ............. 154 5.5. Phenanthrene..................... 177 2.1.4. Economic Aspects of Higher Olefins .... 157 5.6. Pyrene .......................... 178 2.2. Dienes and Polyenes................ 157 6. Toxicology and Occupational Health ... 179 2.2.1. Low Molecular Mass 1,3-Dienes . .... 157 6.1. Alkanes ......................... 179 2.2.2. Synthesis of Dienes and Polyenes by 6.2. Alkenes ......................... 180 Oligomerization. .................. 158 6.3. Alkylbenzenes .................... 180 2.2.3. Synthesis of Dienes and Polyenes by 6.4. Biphenyls and Polyphenyls .......... 181 Metathesis. ...................... 159 6.5. Hydrocarbons from Coal Tar ........ 181 3. Alkylbenzenes .................... 160 6.5.1. Biological Effects .................. 181 3.1. Trimethylbenzenes................. 160 6.5.1.1. Carcinogenicity and Mutagenicity . .... 181 3.2. Tetramethylbenzenes ............... 161 6.5.1.2. Mammalian Toxicity and Toxicokinetics . 182 3.3. Penta- and Hexamethylbenzene ....... 162 6.5.1.3. Ecotoxicology . .................. 182 3.4. Diethylbenzenes ................... 162 6.5.2. Safety Regulations.................. 182 3.5. Triethylbenzenes and More Highly References ....................... 182 Ethylated Benzenes ................ 162 3.6. Ethylmethylbenzenes (Ethyltoluenes)... 163 Ó 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim DOI: 10.1002/14356007.a13_227 134 Hydrocarbons Vol. 18 1. Saturated Hydrocarbons oxidation, sulfoxidation, halogenation, sulfochlor- ination, and nitration. Industrial ionic reactions of The class of saturated hydrocarbons comprises a saturated hydrocarbons are restricted to acid- myriad of individual compounds. A large number catalyzed processes with strong acids. Such reac- of the theoretically possible saturated hydrocar- tions are employed mainly in the processing of bons is known [1], although only a limited num- petroleum by catalytic cracking, isomerization, and ber of individual saturated hydrocarbons are used alkylation; they yield complex mixtures of products. as raw materials in the chemical industry. Other ionic reactions of saturated hydrocarbons can becarriedoutwith superacids(e.g., FSO3H–SbF5, HF – SbF5): the alkylation of alkanes by alkanes 1.1. Physical Properties [3], alkylation of benzene by alkanes [3], and ionic chlorination [5] and bromination [6] of alkanes have Saturated hydrocarbons are colorless nonpolar been explored, but are not used industrially (see also substances, immiscible with polar solvents, but ! Acylation and Alkylation). miscible with many nonpolar organic solvents. Reactions of saturated hydrocarbons, because Some physical properties are given in Table 1. of the lack of functional groups, are nonselective, The boiling points and, starting with C3, melting with respect to both the region of attack (regios- points of n-alkanes increase with increasing mo- electivity) and the number of reaction sites (de- lecular mass. At 20 C and atmospheric pressure, gree of substitution), unless the molecule pos- C1 to C4 n-alkanes are gases, C5 to C16 are liquid, sesses specific structural features, e.g., tertiary and from C17 solid. i-Alkanes do not display a hydrogen atoms. Such reactions frequently af- definite correlation between the number of car- ford mixtures of isomeric or structurally analo- bon atoms and their boiling- and melting points. gous compounds which can only be separated The boiling points of i-alkanes all are lower than with difficulty or not at all. those of the corresponding n-alkanes; this is also On the basis of free enthalpy of formation (see true for many of the melting points. Furthermore, Table 2) most of the saturated hydrocarbons are the boiling points of isomeric alkanes decrease thermodynamically unstable with respect to the with increasing degree of branching. The boiling elements carbon and hydrogen. They are, however, points and melting points of cycloalkanes are kinetically stable at ambient temperature. Thermal generally higher than those of n-alkanes having decomposition of saturated hydrocarbons proceeds the same number of carbon atoms (Table 1). stepwise by loss of hydrogen or hydrocarbon The density of the saturated hydrocarbons in fragments with concomitant formation of industri- the liquid state at 20 Cis<1 g/cm3 ; it varies ally useful unsaturated cracking products, such as from 0.6 g/cm3 for compounds with low carbon acetylene, olefins, or aromatic hydrocarbons. numbers to 0.8 g/cm3 for compounds with high On ignition, mixtures of saturated hydrocar- carbon numbers (Table 1). Additional physical bons and oxygen or air may lead to combustion or properties are compiled in Tables 2–5. explosion, depending on the ratio of hydrocarbon and oxygen. Such reactions can be initiated either by imposed ignition or, if the ignition tempera- 1.2. Chemical Properties ture of the mixture is exceeded, by self-ignition. These reactions are the basis for the use of Alkanes and cycloalkanes are saturated, nonpolar, hydrocarbons as heating- and engine fuel. Perti- and lack functional groups; such hydrocarbons can nent fuel properties of individual saturated hy- undergo reaction only after cleavage of CÀHor drocarbons are summarized in Table 4. CÀC bonds. Consequently, the scope of primary reaction steps is essentially limited to dehydroge- nation, substitution, and chain- or ring cleavage. 1.3. Production Saturated hydrocarbons cannot undergo addition reactions, which represent a versatile synthetic tool By far the largest amount of saturated hydrocar- for unsaturated hydrocarbons (see Chap. 2). Most bons is obtained from the natural sources natural industrial reactions involving saturated hydrocar- gas and petroleum, either by isolation or by bons are radical reactions, e.g., thermal cracking, suitable conversion reactions. Additional sources Vol. 18 Hydrocarbons 135 Table 1. Physical properties of saturated hydrocarbons [2] 20 Compound Empirical CAS registry mp, C bp, C h (20 C), r (20 C), nD formula number mPa Á s g/cm3 a Methane CH4 [74-82-8] À182.5 À161.5 a Ethane C2H6 [74-84-0] À183.27 À 88.6 a b Propane C3H8 [74-98-6] À187.69 À 42.1 0.5005 Cyclopropane C3H6 [75-19-4] À127.4 À 32.8 b b n-Butane C4H10 [106-97-8] À138.4 À 0.5 0.5788 1.3326 b a Cyclobutane C4H8 [287-23-0] À 90.7 12.5 0.6943 1.365 b 2-Methylpropane C4H10 [75-28-5] À159.6 À 11.7 0.5572 n-Pentane C5H12 [109-66-0] À129.7 36.1 0.234 0.62624 1.35748 Cyclopentane C5H10 [287-92-3] À 93.9 49.3 0.438 0.74538 1.40645 2-Methylbutane C5H12 [78-78-4] À159.9 27.9 0.224 0.61967 1.35373 b b 2,2-Dimethylpropane C5H12 [463-82-1] À 16.6 9.5 0.5910 1.342 n-Hexane C6H14 [110-54-3] À 95.3 68.7 0.3117 0.65937 1.37486 2-Methylpentane C6H14 [107-83-5] À153.7 60.3 0.65315 1.37145 3-Methylpentane C6H14 [96-14-0] 63.3 0.66431 1.37652 2,2-Dimethylbutane C6H14 [75-83-2] À 99.9 49.7 0.64916 1.36876 2,3-Dimethylbutane C6H14 [79-29-8] À128.5 58.0 0.66164 1.37495 n-Heptane C7H16 [142-82-5] À 90.6 98.4 0.4169 0.68376 1.38764 2-Methylhexane C7H16 [591-76-4] À118.3 90.1 0.67859 1.38485 3-Methylhexane C7H16 [589-34-4] 91.9 0.68713 1.38864 3-Ethylpentane C7H16 [617-78-7] À118.6 93.5 0.69816 1.39339 2,2-Dimethylpentane C7H16 [590-35-2] À123.8 79.2 0.67385 1.38215 2,3-Dimethylpentane C7H16 [565-59-3] 89.8 0.69508 1.39196 2,4-Dimethylpentane C7H16 [108-08-7] À119.2 80.5 0.67270 1.38145 d 3,3-Dimethylpentane C7H16 [562-49-2] À134.46 86.1 0.69327 1.39092 2,2,3-Trimethylbutane C7H16
Recommended publications
  • Download Flyer
    NexantThinkingTM Special Reports C5 Chemicals: Unlocking Hidden Opportunities in Steam Crackers? Brochure January 2017 NexantThinkingTM Special Reports C5 Chemicals: Unlocking Hidden Opportunities in Steam Crackers? Brochure January 2017 A50801. Special Reports This Report was prepared by Nexant, Inc. (“Nexant”) and is part of the NexantThinking™ suite. Except where specifically stated otherwise in this Report, the information contained herein is prepared on the basis of information that is publicly available, and contains no confidential third party technical information to the best knowledge of Nexant. Aforesaid information has not been independently verified or otherwise examined to determine its accuracy, completeness or financial feasibility. Neither Nexant, Subscriber nor any person acting on behalf of either assumes any liabilities with respect to the use of or for damages resulting from the use of any information contained in this Report. Nexant does not represent or warrant that any assumed conditions will come to pass. The Report is submitted on the understanding that the Subscriber will maintain the contents confidential except for the Subscriber’s internal use. The Report should not be reproduced, distributed or used without first obtaining prior written consent by Nexant. Each Subscriber agrees to use reasonable effort to protect the confidential nature of the Report. Copyright © by Nexant Inc. 2017. All rights reserved. Contents Section Page 1 Introduction and Report Objectives .......................................................................................
    [Show full text]
  • Measuring and Predicting Sooting Tendencies of Oxygenates, Alkanes, Alkenes, Cycloalkanes, and Aromatics on a Unified Scale
    Measuring and Predicting Sooting Tendencies of Oxygenates, Alkanes, Alkenes, Cycloalkanes, and Aromatics on a Unified Scale Dhrubajyoti D. Dasa,1, Peter St. Johnb,1, Charles S. McEnallya,∗, Seonah Kimb, Lisa D. Pfefferlea aYale University, Department of Chemical and Environmental Engineering, New Haven CT 06520 bNational Renewable Energy Laboratory, Golden CO 80401 Abstract Soot from internal combustion engines negatively affects health and climate. Soot emissions might be reduced through the expanded usage of appropriate biomass-derived fuels. Databases of sooting indices, based on measuring some aspect of sooting behavior in a standardized combustion environment, are useful in providing information on the comparative sooting tendencies of different fuels or pure compounds. However, newer biofuels have varied chemical structures including both aromatic and oxygenated functional groups, making an accurate measurement or prediction of their sooting tendency difficult. In this work, we propose a unified sooting tendency database for pure compounds, including both regular and oxygenated hydrocarbons, which is based on combining two disparate databases of yield-based sooting tendency measurements in the literature. Unification of the different databases was made possible by leveraging the greater dynamic range of the color ratio pyrometry soot diagnostic. This unified database contains a substantial number of pure compounds (≥ 400 total) from multiple categories of hydrocarbons important in modern fuels and establishes the sooting tendencies of aromatic and oxygenated hydrocarbons on the same numeric scale for the first time. Using this unified sooting tendency database, we have developed a predictive model for sooting behavior applicable to a broad range of hydrocarbons and oxygenated hydrocarbons. The model decomposes each compound into single-carbon fragments and assigns a sooting tendency contribution to each fragment based on regression against the unified database.
    [Show full text]
  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
    [Show full text]
  • Petroleum Refinery Process Stream Additions
    American Petroleum Institute Petroleum Refinery Process Stream Additions CasNo Substance Definition Caveat 129813-66-7 Alkanes, C10-13 68551-17-7 Alkanes, C10-13-iso- 93924-07-3 Alkanes, C10-14 68551-18-8 Alkanes, C10-14-iso- 329909-27-5 Alkanes, C10-15-iso-, cyclic and linear 73138-29-1 Alkanes, C10-18 289711-49-5 Alkanes, C10-24 289711-48-4 Alkanes, C10-24-branched 129813-67-8 Alkanes, C12-14 68551-19-9 Alkanes, C12-14-iso- 68551-20-2 Alkanes, C13-16-iso- 90622-46-1 Alkanes, C14-16 74664-93-0 Alkanes, C14-30 70024-92-9 Alkanes, C7-8-iso- 68551-15-5 Alkanes, C8-10-iso- 68551-16-6 Alkanes, C9-11-iso- 68990-23-8 Alkenes, C12-26 .alpha.-, sulfated 93762-80-2 Alkenes, C15-18 68603-35-0 Alkenes, C18-24 .alpha.-, bisulfited 72162-34-6 Alkenes, C18-24 .alpha.-, sulfurized 93924-10-8 Alkenes, C20-24 .alpha.- 93924-11-9 Alkenes, C24-28 .alpha.- 131459-42-2 Alkenes, C24-54-branched and linear .alpha.- 68409-73-4 Aromatic hydrocarbons, biphenyl-rich A complex combination of hydrocarbons produced by the Substance found at hydrodealkylation and distillation of toluene. It consists refineries, but also may be predominantly of aromatic hydrocarbons having a carbon number produced in separate C6 or greater, primarily biphenyl, and boiling in the range of petrochemical approximately 79.degree.C to 398.degree.C (175.degree.F to manufacturing facilities. 750.degree.F). 68989-41-3 Aromatic hydrocarbons, biphenyl-rich, The complex combination of hydrocarbons obtained from a Substance found at thermal hydrodealkylation residues thermal hydrodealkylation process.
    [Show full text]
  • United States Patent (19) (11) 3,855,105 Diveley (45) Dec
    United States Patent (19) (11) 3,855,105 Diveley (45) Dec. 17, 1974 54 THOPHOSPHORYLATING ASATURATED 3,284,540 1 1/1966 D'Alelio.............................. 260/869 HYDROCARBON GROUP 75 Inventor: William R. Diveley, Oakwood Hills, Primary Examiner-Benjamin R. Padgett Del. Attorney, Agent, or Firm-George H. Hopkins 73 Assignee: Hercules incorporated, Wilmington, (57) ABSTRACT Del. Disclosed is a process for making certain organo thio 22) Filed: June 16, 1969 phosphates and dithiophosphates, a number of which 21 ) Appl. No.: 833,741 have utility as insecticides. The process comprises ef fecting by free radical catalysis at about 0-150°C. re Related U.S. Application Data action of an organic compound characterized by a sat (63) Continuation-in-part of Ser. No. 514,652, Dec. 17, urated carbon with at least one hydrogen replaceable 1965, abandoned. under free radical conditions, and halo-thiophosphate of the formula: 52 U.S. C. ..... 204/162 R, 204/158 R, 260/329 R, 260/329 P, 260/340.6, 260/347.2, 260/958, 7, OR . 1 / 260/963, 260/971 X-S-P (51) Int. Cl................................................ B01j 1/10 N 58 Field of Search ............ 204/162, 158; 260/329, OR 260/340.6, 347.2,958, 963,971 wherein X is a halo radical, Z is selected from the (56) References Cited group consisting of the oxo and thioxo radicals, and R UNITED STATES PATENTS and R' are organic radicals. 3,256,370 6/1966 Fitch et al........................... 260/972 24 Claims, No Drawings 3,855, 105 2 THIOPHOSPHORYLATING ASATURATED rated carbons, each of which has one or more hydrogen HYDROCARBON GROUP radicals replaceable under free radical conditions.
    [Show full text]
  • Transport of Dangerous Goods
    ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions.
    [Show full text]
  • 1 Transformer Oil 2 Residual Fuel Oil 3 Diesel Oil Heavy 4
    1 TRANSFORMER OIL 2 RESIDUAL FUEL OIL 3 DIESEL OIL HEAVY 4 SPINDLE OIL MIXTURES CONTAINING 5 CRUDE OIL 6 MOTOR OIL 7 ROAD OIL 8 FUEL OIL NO.4 9 FUEL OIL NO.5 10 FUEL OIL NO.6 LUBRICATING OILS AND 11 BLENDING STOCKS 12 PENETRATING OIL 13 TURBINE OIL 3 14 ROOFERS FLUX 15 CRUDE OIL 16 STRAIGHT RUN RESIDUE OCTAMETHYLCYCLOTETRA 17 SILOXANE BENZENEPROPANOIC ACID, 3,5- 1,1- 3,5-BIS(1,1-DIMETHYLETHYL 18 4- ), -C7-C9 4-HYDROXY-C7-C9ALCOHOL S BRANCHED AND LINEAR 19 1- -1- 1-PHENYL-1-XYLYL ETHANE BENZENETRICARBOXYLIC 20 ACID, TRIOCTYL ESTER 21 CASTOR OIL IMIDAZOLIUM COMPOUNDS, 1- -4,5- -1- 1-BENZYL-4,5-DIHYDRO-1-(H 22 -2- YDROXYETHYL)-2-NORCOC O ALKYL, CHLORIDES 4 2-PROPENOIC ACID 2- POLYMER WITH 4- 1,1- 4-(1,1-DIMETHYLETHYL)PHE 2,5- NOL,FORMALDEHYDE, 23 2- 2,5-FURANDIONE, 65% / 2-METHYLOXIRANE AND OXIRANE (65% IN NAPHTHA/XYLENE) 24 n-PENTYL PROPIONATE 25 -2- 2-ETHYLHEXYL ACRYLATE 26 DECYL ACRYLATE 27 RAPESEED OIL RAPESEED OIL (low erucic acid 4% 28 containing less than 4% free fatty acids) RAPE SEED OIL FATTY ACID 29 METHYL ESTERS ALCOHOLS (C12-C13), C12-C13 30 PRIMARY, LINEAR AND ESSENTIALLY LINEAR 31 C13+ ALCOHOLS (C13+) 5 ALCOHOLS (C14-C18), C14-C18 32 PRIMARY, LINEAR AND ESSENTIALLY LINEAR ALCOHOLS (C8-C11), C8-C11 33 PRIMARY, LINEAR AND ESSENTIALLY LINEAR ACID OIL MIXTURE FROM SOYABEAN, CORN (maize) 34 AND SUNFLOWER OIL REFINING NAPHTHALENE CRUDE 35 (MOLTEN) 36 SOYABEAN OIL SOYBEAN OIL FATTY ACID 37 METHYL ESTER 38 BUTYLBENZENE (all isomers) 39 TALLOW 40 TALLOW FATTY ACID (2- BIS(2-ETHYLHEXYL) 41 ) TEREPHTHALATE 42 -(2- ) DI-(2-ETHYLHEXYL)
    [Show full text]
  • SUMMARY of an INVESTIGATION of the COMPOSITION of a MIDCONTINENT PETROLEUM DISTILLATE, BOILING BETWEEN 100° and 130° C.L
    U. S. DEPARTMENT OF COMMERCE NATIONAL BUREAU OF STANDARDS RESEARCH PAPER RP1174 Part of Journal of Research of the National Bureau of Standards, Volume 22, February 1939 SUMMARY OF AN INVESTIGATION OF THE COMPOSITION OF A MIDCONTINENT PETROLEUM DISTILLATE, BOILING BETWEEN 100° AND 130° C.l By Robert T. Leslie 2 ABSTRACT The results of 7 years of investigation of the composition of the naphtha fraction of petroleum boiling between 1000 and 1300 C are summarized. Of the 130 liters found to boil in this range after the first laboratory distillation, the constitu­ ents of about one-sixth of the volume were identified or characterized by physical properties, isolated or concentrated, and their concentration in the petroleum roughly estimated. About one-fourth of the volume remains as unidentified distillate. This is composed in part of material of which the constitution is only predicted (about one-twelfth of the volume) and of additional quantities of the constituents which were isolated previously (about one-sixth of the volume). The remainder was lost during the investigation or distilled out of the range on subsequent distillations. Photomicrographic studies were made of those con­ centrations of distillate which could be crystallized. There is given a bibliography of the physical constant s of hydrocarbons reported to boil within this range. CONTENTS Page I. Introduction __ __ ________ __ ____ ______ ________________________ ____ 153 II. Study of the composition of the distillate ___ ___________ __ ___ ________ 164 1. Distillate between 98 0 and 102 0 C ___ _________ ________________ 164 2. Distillate between 1030 and 106 0 C _ _ _ _ __ __ __ __ __ _ __ _ _ _ __ __ _ __ 164 3.
    [Show full text]
  • Aldrich Vapor
    Aldrich Vapor Library Listing – 6,611 spectra This library is an ideal tool for investigator using FT-IR to analyze gas phase materials. It contains gas phase spectra collected by Aldrich using a GC-IR interface to ensure chromatographically pure samples. The Aldrich FT-IR Vapor Phase Library contains 6,611 gas phase FT-IR spectra collected by Aldrich Chemical Company using a GC interface. The library includes compound name, molecular formula, CAS (Chemical Abstract Service) registry number, Aldrich catalog number, and page number in the Aldrich Library of FT-IR Spectra, Edition 1, Volume 3, Vapor-Phase. Aldrich Vapor Index Compound Name Index Compound Name 6417 ((1- 3495 (1,2-Dibromoethyl)benzene; Styrene Ethoxycyclopropyl)oxy)trimethylsilane dibromide 2081 (+)-3-(Heptafluorobutyryl)camphor 3494 (1-Bromoethyl)benzene; 1-Phenylethyl 2080 (+)-3-(Trifluoroacetyl)camphor bromide 262 (+)-Camphene; 2,2-Dimethyl-3- 6410 (1-Hydroxyallyl)trimethylsilane methylenebicyclo[2.2.1]heptane 6605 (1-Methyl-2,4-cyclopentadien-1- 2828 (+)-Diisopropyl L-tartrate yl)manganese tricarbonyl 947 (+)-Isomenthol; [1S-(1a,2b,5b)]-2- 6250 (1-Propynyl)benzene; 1-Phenylpropyne Isopropyl-5-methylcyclohexano 2079 (1R)-(+)-3-Bromocamphor, endo- 1230 (+)-Limonene oxide, cis + trans; (+)-1,2- 2077 (1R)-(+)-Camphor; (1R)-(+)-1,7,7- Epoxy-4-isopropenyl-1- Trimethylbicyclo[2.2.1]heptan- 317 (+)-Longifolene; (1S)-8-Methylene- 976 (1R)-(+)-Fenchyl alcohol, endo- 3,3,7-trimethyltricyclo[5.4.0 2074 (1R)-(+)-Nopinone; (1R)-(+)-6,6- 949 (+)-Menthol; [1S-(1a,2b,5a)]-(+)-2- Dimethylbicyclo[3.1.1]heptan-2-
    [Show full text]
  • Directive Effects in Abstraction Reactions of the Phenyl Radical Robert Frederick Bridger Iowa State University
    Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1963 Directive effects in abstraction reactions of the phenyl radical Robert Frederick Bridger Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Bridger, Robert Frederick, "Directive effects in abstraction reactions of the phenyl radical " (1963). Retrospective Theses and Dissertations. 2336. https://lib.dr.iastate.edu/rtd/2336 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. This dissertation has been 63-5170 microfilmed exactly as received BRIDGER, Robert Frederick, 1934- DIRECTIVE EFFECTS IN ABSTRACTION RE­ ACTIONS OF THE PHENYL RADICAL. Iowa State University of Science and Technology Ph.D., 1963 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan DIRECTIVE EFFECTS IN ABSTRACTION REACTIONS OF THE PHENYL RADICAL by Robert Frederick Bridger A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Subject: Organic Chemistry Approved: Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. Head of Major Depart me6jb Signature was redacted for privacy. Iowa State University Of Science and Technology Ames, Iowa 1963 ii TABLE OF CONTENTS Page INTRODUCTION 1 LITERATURE REVIEW 3 RESULTS 6 DISCUSSION 36 EXPERIMENTAL 100 SUMMARY 149 REFERENCES CITED 151 ACKNOWLEDGEMENTS 158 iii LIST OF FIGURES Page Figure 1.
    [Show full text]
  • SAFETY DATA SHEET Classified in Accordance with Health Canada Hazardous Products Regulations (SOR/2015-17)
    Version: 8.0 Revision Date: 01/02/2020 SAFETY DATA SHEET Classified in accordance with Health Canada Hazardous Products Regulations (SOR/2015-17) 1. Identification Product identifier: Hydrocarbons C5 Rich Other means of identification Common name(s), Crude Isoprene; Isoprene/Piperylene Concentrate; C5 Mixture; Isoprene synonym(s): Product SDS number: NOVA-0007 Recommended use and restriction on use Recommended use: Petrochemical feedstock. Restrictions on use: All uses other than the identified. Manufacturer/Importer/Supplier/Distributor Information Manufacturer Company Name: NOVA Chemicals Address: P.O. Box 2518, Station M Calgary, Alberta, Canada T2P 5C6 Telephone: Product Information: 1-412-490-4063 SDS Information Email: [email protected] Emergency telephone number: 1-800-561-6682, 1-403-314-8767 (NOVA Chemicals) (24 hours) 2. Hazard(s) identification Hazard Classification According to Hazardous Products Regulations Physical Hazards Flammable liquids Category 1 Static-accumulating flammable liquid Category 1 Health Hazards Acute toxicity (Oral) Category 4 Skin Corrosion/Irritation Category 2 Serious Eye Damage/Eye Irritation Category 2A Germ Cell Mutagenicity Category 2 Carcinogenicity Category 1B Specific Target Organ Toxicity - Category 3 Single Exposure Aspiration Hazard Category 1 Environmental Hazards Acute hazards to the aquatic Category 3 environment Chronic hazards to the aquatic Category 3 environment Label Elements Hazard Symbol: SDS_CA 1/14 Version: 8.0 Revision Date: 01/02/2020 Signal Word: Danger Hazard Statement: Extremely flammable liquid and vapour. Static accumulating flammable liquid can become electrostatically charged even in bonded and grounded equipment. Sparks may ignite liquid and vapour. May cause flash fire or explosion. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation.
    [Show full text]
  • Material Safety Data Sheet Hexamethylbenzene MSDS
    Material Safety Data Sheet Hexamethylbenzene MSDS# 96291 Section 1 - Chemical Product and Company Identification MSDS Name: Hexamethylbenzene Catalog Numbers: AC120570000, AC120570050, AC120570100, AC120570250 Synonyms: None known. Acros Organics BVBA Company Identification: Janssen Pharmaceuticalaan 3a 2440 Geel, Belgium Acros Organics Company Identification: (USA) One Reagent Lane Fair Lawn, NJ 07410 For information in the US, call: 800-ACROS-01 For information in Europe, call: +32 14 57 52 11 Emergency Number, Europe: +32 14 57 52 99 Emergency Number US: 201-796-7100 CHEMTREC Phone Number, US: 800-424-9300 CHEMTREC Phone Number, Europe: 703-527-3887 Section 2 - Composition, Information on Ingredients ---------------------------------------- CAS#: 87-85-4 Chemical Name: Hexamethylbenzene %: 99+ EINECS#: 201-777-0 ---------------------------------------- Hazard Symbols: None listed Risk Phrases: None listed Section 3 - Hazards Identification EMERGENCY OVERVIEW Caution! The toxicological properties of this material have not been fully investigated. May cause eye, skin, and respiratory tract irritation. Target Organs: None known. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. May be harmful if absorbed through the skin. Ingestion: May cause irritation of the digestive tract. May be harmful if swallowed. Inhalation: May cause respiratory tract irritation. May be harmful if inhaled. Chronic: No information found. Section 4 - First Aid Measures Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower Eyes: eyelids. If irritation develops, get medical aid. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and Skin: shoes. Get medical aid if irritation develops or persists. Ingestion: Do not induce vomiting.
    [Show full text]