DOCSLIB.ORG

Process for Producing Vinyl Acetate

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Process for Producing Vinyl Acetate Europâisches Patentamt ® European Patent Office @ Publication number: 0 068 795 Office européen des brevets B1 ® EUROPEAN PATENT SPECIFICATION ® Date of publication of patent spécification: 13.03.85 © Int. ci.4: C 07 C 69/15, C 07 C 67/297 @) Application number: 82303245.3 (22) Date offiling: 22.06.82 (54) Process for producing vinyl acetate. (§) Priority: 22.06.81 JP 96296/81 ® Proprietor: MITSUBISHI GAS CHEMICAL COMPANY, INC. 5- 2, Marunouchi 2-chome Chiyoda-Ku (§) Date of publication of application: Tokyo (JP) 05.01.83 Bulletin 83/01 (72) Inventor: Isshiki, Tomiya (45) Publication of the grant of the patent: 14-11 Umegaoka 2-chome 13.03.85 Bulletin 85/1 1 Setagaya-ku Tokyo (JP) Inventor: Nawata, Takanari 19-3 Kanamachi 5-chome (84) Designated Contracting States: Katsushika-ku Tokyo (JP) DEFRGBIT Inventor: Kijima, Yasuhiko 641 Kode Matsudo-shi Chiba-ken (JP) (5$) References cited: Inventor: Ito, Akira FR-A-2 413 354 15-6 Nishikubo-cho Tokiwadaira US-A-2 425 389 Matsudo-shi Chiba-ken (JP) Inventor: Watanabe, Takayuki 6- 1 Kanamachi 1-chome 0Û Katsushika-ku Tokyo (JP) m (74) Representative: Ritter, Stephen David et al N Mathys & Squire 10 Fleet Street London EC4Y 1AY (GB) oo o o Note: Within nme months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall Û. be filed in a written reasoned statement. It shall not be deemed to hâve been filed until the opposition fee has been (Art. UJ paid. 99(1 ) European patent convention). Courier Press, Leamington Spa, England. (4) ammonium halides represented by NH4X wherein X is as defined above. This invention relates to a process for The mechanism of the decomposition of producing vinyl acetate which comprises ethylidene diacetate for forming vinyl acetate is decomposing ethylidine diacetate, and par- not perfectly clear. However, it is believed that ticularly relates to a process for producing vinyl the decomposition reaction is expressed by the acetate which comprises carrying out decom- following equation: position of ethylidene diacetate in the presence of a catalyst comprising at least one compound selected from the group consisting of fluorides, chlorides, bromides, iodides, halogens and The above reaction proceeds in a good state mixtures thereof. when a catalyst comprising a halide referred to Vinyl acetate has been produced from above is used. acetylene in the past. Recently vinyl acetate has As indicated, the halides which are usable as also been produced from ethylene. the catalyst in the practice of this invention are In addition, a process for producing vinyl bromides, iodides and mixtures thereof, iodides acetate which comprises producing ethylidene being most preferable. diacetate (1,1-diacetoxy ethane) from acetalde- Examples of the halides which are used as hyde and acetic anhydride, or dimethyl ether or the catalyst of this invention include the follow- methyl acetate and synthesis gas and causing ing. However, compounds which are not listed decomposition of the ethylidene diacetate to in the following paragraphs may also be used as form vinyl acetate (refer to Hydrocarbon the catalyst. Process, 44, (11) 287 (1965), British Patent (1) Lithium halides, including LiBr, No. 1,538,782 and U.S. Patent Nos. 2,021,698; LiBr2 . 2H2O, Lil and Lil · 3H2O. 2,425,389 and 2,860,159). However, known (2) Magnesium halides, including MgBr2, processes for decomposing ethylidene MgBr2 · 6H2O, Mgl2 and Mgl2 . 8H2O. diacetate were unsatisfactory. (3) Calcium halides, including CaCl2, CaBr2, In the prior art, protonic acids, such as Cal2, CaBr2. 6H2O and Cal2 · 6H2O. sulfuric acid, organic sulfonic acids, etc. have (4) Strontium halides, including SrBr2, Srl2, been known as catalysts for decomposing and SrBr2 . 6H2O. ethylidene diacetate. Decomposition of ethyli- (5) Barium halides, including BaBr2, Bal2 and dene diacetate by using such catalysts is BaBr2. 2H2O. unsatisfactory in respect of decomposition rate (6) Zinc halides, including ZnBr2 and Znl2. and selectivity to product. (7) Tin halides, including SnBr2, SnBr4, The present inventors carried out research to SnBr212, Snl2 and Snl4. find a process for efficiently producing vinyl (8) Antimony halides, including SbBr3, Sbl3, acetate from ethylidene diacetate. As a result, Sbl5 found novel catalysts for decomposing we The metal halides be in the state of a ethylidene diacetate to form vinyl acetate. This may hydrate, a double salt or a coordination invention is based this discovery. on compound. Mixtures of two or more metal is An object of this invention to provide a halides may be used. The metal halides may be process for producing vinyl acetate in a high in the form of solid material, powder or finely decomposition rate and in a high selectivity. divided powder. The metal halides may be sup- According to the present invention there is ported on a carrier. Metal halides supported on provided a process for producing vinyl acetate a carrier can easily be separated from the which comprises decomposing ethylidene reaction system. diacetate in the presence of at least one halide (9) Organic halides represented by R1Xp. selected from: wherein p is integer of 1-3 and X is as (1) metal halides selected from metal defined above including: bromides and iodides, and mixtures (a) Compounds wherein R1 is thereof, said metal being selected from saturated alkyl having 1 to 10 Li, Mg, Ca, Sr, Ba, Zn, Sn and Sb; carbon atoms or cycloalkyl having (2) organic halides represented by R1Xp 3-10 carbon atoms, for example wherein R1 is selected from alkyl having CH3Br, CH2BR2, CHBr3, CH31, 1-10 carbon atoms, cycloalkyl having CH2l2, CHl3, CH3CH2Br, CH3CH2l, 3-10 carbon atoms and aromatic ICH2CH2l and C6H11l. hydrocarbon having 6-10 carbon (10) Organic halides represented by R2COX atoms, X is selected from I and Br, and p wherein R2 is saturated alkyl having 1- is 1, 2 or 3; 10 carbon atoms, cycloalkyl having 3- (3) organic halides represented by R2COX 10 atoms or aryl and X is as defined wherein R2 is selected from alkyl having above including CH3COBr, CH3COl, 1-10 carbon atoms, cycloalkyl having CH3CH2COl, C6H11COl and C6H5COl. 3-10 carbon atoms and aryl, and X is as defined above; and Of the metal halides, halides of metals selected from Li, Mg, Ca, Sr, Ba, Zn, Sn and Sb another solvent is not necessary. However, the following, namely Li, Mg, Ca, Sr, Ba and Sb other organic solvents compatible with ethyli- are most preferred. dene diacetate and products under the reaction The amount of catalyst employed depends conditions may be used. Compounds which on whether the catalyst is soluble, insoluble or participate as solvent in the reaction as a partially soluble in the reaction system, or starting material, an object product or a by- whether the reaction is carried out in a fluidized product are preferable. For example, ethylidene or fixed bed when using an insoluble catalyst. In diacetate and acetic anhydride are preferable. general the amount of the catalyst employed Solvents which are usable in this invention may be in the range of 1 x 10-4-90 wt%, pre- include, for example, organic acid esters, such ferably 5xlo-1-85 wt %, most preferably as ethylene glycol diacetate, propylene glycol 1 x 10-2-80 wt % and most preferably 0.1- diacetate, methyl acetate, dimethyl adipate, 75 wt % on the basis of weight of the reaction methyl benzoate, ethyl benzoate, dimethyl solution. phthalate, diethyl phthalate, dioctyl phthalate, In practicing this invention, the reaction phenyt acetate and tolyl acetate; hydrocarbons, temperature is not critical. In general, the such as dodecane, hexadecane, benzene, reaction temperature may be within the range naphthalene, and biphenyl; inorganic acid of 20°C-500°C, preferably 60°C-350°C, esters, such as triphenyl phosphate, tricresyl more preferably 89°C-250°C and most phosphate, dibutylphenyl phosphate, tetra- preferably 80°C-200°C. methyl ortho silicate, and tetrabutyl silicate; Ethylidene diacetate which is used as a raw aromatic ethers, such as diphenyl ether; and material in this invention may be prepared by ketones, such as acetone, methyl ethyl ketone, reacting acetaldehyde with acetic anhydride, or dibutyl ketone, methyl isobutyl ketone, aceto- by reduction reaction of acetic anhydride with phenone and benzophenone. hydrogen. Alternatively, ethylidene diacetate It is desirable in the present invention that the may be prepared by reacting dimethyl ether or concentration of vinyl acetate, which tends to methyl acetate with synthesis gas as disclosed cause polymerization, be maintained at a low in Japanese Patent Publication (Kokai) Nos. level by separating the vinyl acetate from the 62045/1980, 110647/1981. and 45884/1980 reaction system. For example, it is suitable to and British Patent No. 1,538,782. Acetalde- maintain the concentration of vinyl acetate in hyde, acetic anhydride, dimethyl ether, methyl the reaction system at less than 25 wt % by acetate, methyl iodide, etc. may be incor- continuously withdrawing (for example distill- porated in ethylidene diacetate prepared by ing) the resulting vinyl acetate from the reaction such methods. However, the ethylidene system and it is preferable to maintain the diacetate containing the components in such an concentration at less than 15 wt %. amount that the components are usually incor- Retention of large amount of the acetic acid, porated in ethylidene diacetate, that is the which is formed as a by-product in the reaction ethylidene diacetate containing small amount of system, should be avoided. The reason is that the components can be used as a raw material acetic acid tends to prevent formation of the in this invention. object product. So, in general, the concen- In general, water may be incorporated in the tration of acetic acid in the reaction system may reaction system.
Load more

Recommended publications
  • The Pyrolysis of Organic Esters Dissertation
    THE PYROLYSIS OF ORGANIC ESTERS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University RICHARD JUI-FU LEE, B.S y l f .■) ®rV'«\ a.i @@ :&f a■ ' Adviser * Department of Chemistry -i- ACKMOWLEDGMEMT My sincere and profound thanks to Dr. Christo­ pher L. Wilson for the suggestion of the problem and his inspiring guidance throughout the research. My gratitude to the B. F. Goodrich Company, whose Research Fellowship I held for the entire span of this work. Finally, but not least, my deepest appreciation to Mr. Daniel Loughran for his ever cooperative assistance in making the infra-red analyses. -ii- TABLE OF CONTENTS Page I. INTRODUCTION AND STATEMENT OF PROBLEM 1 II. HISTORICAL INTRODUCTION........ ........... 5 1. Pyrolysis of Organic Compounds........ 5 A. Berthelot's Theory......... 5 B . Haber' s Rule ........................ 6 C. Rule of Least Molecular Deformation........................ 7 D. Bredt's Rule........................ 8 E. Blanc’s Rule................ 8 F. Nef's Theory......................... 9 2. Theory of Pyrolysis of Esters....... 10 A. Bilger and Hibbert's Mechanism.... 11 B. Hurd's "Hydrogen Bridge" Cyclic Mechanism....................... 13 C. Ritchie's Dual Reactions........... 16 D. Htickel's Concept (Tsugaev Reaction) 19 E. Alexander's Cis-Elimination Studies 20 F. Kinetics on the Pyrolysis of Esters 22 G. Some Contributions from the Kinetic Study of Dehydrochlorination of Chloroparaffins ...... 24 3. The Cyclic Transition State in Other Processes........... 32 A. General Considerations.............. 32 B. The Concept of O'Connor and Nace... 34 C. The Pyrolysis of Sulfites.......... 37 iii £a^e III.
    [Show full text]
  • Acetaldehyde 16.05.2020.Pdf
    Acetaldehyde Acetaldehyde (systematic name ethanal) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body. An aldehyde used as a starting material in the synthesis of 1-butanol (n-butyl alcohol), ethyl acetate, perfumes, flavourings, aniline dyes, plastics, synthetic rubber, and other chemical compounds. It has been manufactured by the hydration of acetylene and by the oxidation of ethanol (ethyl alcohol). Formula: C2H4O IUPAC ID: ethanal Boiling point: 20.2 °C Molar mass: 44.05 g/mol Density: 788 kg/m³ Melting point: -123.5 °C Preparation:- The main method of production is the oxidation of ethylene by the Wacker process, which involves oxidation of ethylene using a homogeneous palladium/copper system: 2 CH2=CH2 + O2 → 2 CH3CHO Smaller quantities can be prepared by the partial oxidation of ethanol in an exothermic reaction. This process typically is conducted over a silver catalyst at about 500–650 °C. 1 CH3CH2OH + ⁄2 O2 → CH3CHO + H2O This method is one of the oldest routes for the industrial preparation of acetaldehyde.
    [Show full text]
  • Working Fluid Selection for Space-Based Two-Phase Heat Transport Systems
    NBSIR 88-3812 Working Fluid Selection for Space-Based Two-Phase Heat Transport Systems Mark O. McLinden U.S. DEPARTMENT OF COMMERCE National Bureau of Standards Gaithersburg, MD 20899 May 1988 Issued August 1988 75 Years Stimulating America's Progress 1913-1988 Prepared for: National Aeronautics and Space Administration Goddard Space Flight Center NBSIR 88-3812 WORKING FLUID SELECTION FOR SPACE-BASED TWO-PHASE HEAT TRANSPORT SYSTEMS Mark O. McLinden U.S. DEPARTMENT OF COMMERCE National Bureau of Standards Gaithersburg, MD 20899 May 1988 Issued August 1988 Prepared for: National Aeronautics and Space Administration Goddard Space Flight Center U.S. DEPARTMENT OF COMMERCE, C. William Verity, Secretary NATIONAL BUREAU OF STANDARDS, Ernest Ambler, Director , ABSTRACT The working fluid for externally-mounted, space-based two-phase heat transport systems is considered. A sequence of screening criteria involving freezing and critical point temperatures and latent heat of vaporization and vapor density are applied to a data base of 860 fluids. The thermal performance of the 52 fluids which pass this preliminary screening are then ranked according to their impact on the weight of a reference system. Upon considering other non-thermal criteria ( f lagimability toxicity and chemical stability) a final set of 10 preferred fluids is obtained. The effects of variations in system parameters is investigated for these 10 fluids by means of a factorial design. i * . I . INTRODUCTION In order to remove the heat generated by electronics and other payloads on spacecraft some type of heat transport system is required. The heat generating equipment is typically attached to a 'cold plate'.
    [Show full text]
  • Ligand 960 Accessible Molecular Surfa
    1699 Index a acrylate 199, 1612 abiraterone 426 – derivatives 1115, 1117 abnormal lactone (AL) 1495, 1496 – esters, synthesis of 1610 π-acceptors 828 acrylic acid 126, 1612 – π*-acceptor 810 – based on CO2 1610 – ligand 960 – thermodynamic situation 1611 accessible molecular surface (AMS) 834 acrylonitrile-butadiene-polystyrene acenaphthene imine derivative ligands 257 microencapsulated Os 1514 acetaldehyde 508 actinides 1071 – from ethylene 500 activated carbon 1343 – oxidation 95 activation energy 963 acetamide, transamidation of activation reaction 233 – amino acid catalyzed 1436 active catalyst system 283 acetic acid 93, 709, 1526 active noble metal complexes, reoxidation – nickel-based catalysts 105 1264 acetic anhydride 110, 111 acyclic diene metathesis polymerization 2´-acetonaphthone 735 (ADMET) 824 acetonitrile 708, 1547 acyclic ketones, BV oxidation of 1502 acetophenones 726, 730, 732, 734, 738, 1047 acyclic precursors 1343 – derivatives 726 N-acyl-α-amino acid derivatives acetylcholinesterase (AChE) inhibitor 1496 – synthesis 1197 acetylide ligand acylamidines 1469 – on photocatalytic H2 production 1668 N-acyl amino acids 1535 N-acetylmannosamine (ManNAc) 920 acylases 913 (+)-achalensolide, asymmetric synthesis 1300 N-acyl cyclic amines 1535 acid–amine coupling 1429 acyl hydrazones, with Rh/duphos 633 – boron derivative 1429 acyl ligand 103 acid–base interactions 860 acyl palladium complex 169 acid halides 525 acylphosphite 838 acidic hydrogen ion 492 1-adamantanol 1533 π-acidic ligands 1404 adapalene 429 acidic phosphate electrolyte, electrochemical adenine-thymine (A-T) 858 properties 1142 adiabatic flash 100 acids, promotor effect 1268 adipic acid Acinetobacter calcoaceticus 908 – fermentation of 1617 – NCIMB 9871 909 – production from LA 1629 acridine-based bisphosphine ligand 1629 aerobic oxidation 1057 acrolein acetal, Heck arylation of 974 Ag/Al2O3 catalyst 1445 acrolein, arylation 974 alcohol dehydrogenase (ADH) 901, 903 Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Four Volumes, Third Edition.
    [Show full text]
  • 87 4. Production, Import, Use, and Disposal 4.1 Production
    87 4. PRODUCTION, IMPORT, USE, AND DISPOSAL 4.1 PRODUCTION It is not known whether vinyl acetate occurs naturally (IARC 1986). Vinyl acetate is a man-made compound that was first produced in 1912 as a by product in the synthesis of ethylidene diacetate (Matthews 1974). This reaction involved bubbling acetylene through a mixture of mercurous sulfate and anhydrous acetic acid (Leonard 1970). During the 1920s, the Germans converted this liquid-phase process to a vapor phase process that allowed Germany to achieve a production volume of 12 million kg per year by the 1940s and which accounted for most of the world's production of vinyl acetate until about 1970 (Leonard 1970; Rhum 1970). The vapor phase process involved passing a 4:l acetylene-to-acetic acid mixture over a catalyst bed made of zinc acetate-saturated activated carbon at 180°-200°C. (Daniels 1983; Llewellyn and Williams 1972). Mercury salts can also be used as a catalyst in this reaction when it is conducted at 40°-50°C (International Labour Office 1985). Originally, acetylene was generated from calcium carbide (Leonard 1970). More recently, acetylene has been produced by cracking petroleum (Llewellyn and Williams 1972). Currently, the manufacturing process most widely used to produce vinyl acetate is the vapor phase ethylene process, an oxidative reaction in which ethylene is bubbled through acetic acid at 120°C in the presence of palladium chloride catalyst (Daniels 1983; IAKC 1986). Impurities found in the reaction have been reported at less than 1% (for one manufacturer) and have included the following: acetaldehyde, ethyl acetate, and methyl acetate.
    [Show full text]
  • Synthesis of Vinyl Acetate Monomer from Synthesis Gas
    SYNTHESIS OF VINYL ACETATE MONOMER FROM SYNTHESIS GAS GERALD C. TUSTIN, RICHARD D. COLBERG AND JOSEPH R. ZOELLER EASTMAN CHEMICAL COMPANY RESEARCH LABORATORIES, P.O. BOX 1972 KINGSPORT, TN 37662-5150 1. Introduction The overall objective of this project is to develop a commercially viable process for the generation of vinyl acetate monomer (VAM) based entirely upon coal-generated syngas. Previous attempts at this objective have generally involved the combination of acetic anhydride (generated by carbonylation of either methyl acetate or dimethyl ether) with acetaldehyde (generated by either hydrogenation of acetic anhydride or hydrocarbonylation of either methanol or a methyl ester) to generate ethylidene diacetate (EDA) which is subsequently cracked to form VAM in a separate step. An exemplary process is shown below. 2CO + 4H2à 2MeOH 2MeOH + 2AcOH à 2AcOMe + 2H2O AcOMe + CO + H2 à AcH + AcOH AcOMe + CO à Ac2O Ac2O + AcH à EDA EDA à VAM + AcOH MeOH = methanol AcOH = acetic acid Ac2O = acetic anhydride AcH = acetaldehyde AcOMe = methyl acetate These efforts have failed to generate a commercially viable process to date. One of the key reasons for this failure is the very large quantities of recycled acetic acid (and consequently large commercial facilities) inherent in the earlier proposed processes. A specific objective of our work is to develop a syngas based process for the production of VAM that avoids the costly recycle of acetic acid to a carbonylation reactor. Although a number of approaches are possible, many of these have been eliminated on thermodynamic grounds or upon the basis of the number of steps involved. We believed that a very important reaction required for the production of VAM was the hydrogenation of acetic acid to acetaldehyde, and, if this could be accomplished, the problem of recycle of acetic acid to the carbonlyation reactor could be solved: HOAc + H2 à HAc + H2O.
    [Show full text]
  • Process for Producing Vinyl Acetate, Acetic Acid and Ethanol from Methanol, Carbon Monoxide and Hydrogen Which Is Characterised by the Following Five Steps
    Europâisches Patentamt European Patent Office (jj) Publication number 0 028 474 Office européen des brevets Bl EUROPEAN PATENT SPECIFICATION @ Date of publication of patent spécification: 05.10.83 © Int. Cl.3: C 07 C 69/1 5, C 07 C 67/36, @ Application number: 80303669.8 C 07 C 53/08, C 07 C 31/08 @ Date offiling: 17.10.80 (54) Process for producing vinyl acetate, acetic acid and ethanoi. (30) Priority: 18.10.79 JP 134358/79 (73) "Proprietor: MITSUBISHI GAS CHEMICAL COMPANY, INC. 5-2, Marunouchi 2-chome Chiyoda-Ku @ Date of publication of application: Tokyo (JP) 13.05.81 Bulletin 81/19 (72) Inventor: Tomiya, Isshiki (45) Publication of the grant of the patent: 14-11, Umegaoka 2-Chome 05.1 0.83 Bulletin 83/40 Setagaya-ku Tokyo ( JP) Inventor: Yasuhiko, Kijima 641, Koda (84) Designated Contracting States: Matsudo-shi Chiba-ken (JP) DE FR GB IT Inventor: Akira, Ito 15-6, Nishikubo-cho Tokiwadaira Matsudo-shi Chiba-ken (JP) (56) References cited: Inventor: Kenji, Ishii DE- A-2 856 791 11-16, Kanamachi 5-chome Katsushika-ku Tokyo (JP) (74) Representative: Shipton, Gordon Owen et al, W.P. THOMPSON & CO. Coopers Building Church Street Liverpool L1 3AB (GB) Note: Within nine months from the publication of the mention«of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid.
    [Show full text]
  • Related Properties from Molecular Structures
    Electronic Supplementary Material (ESI) for Green Chemistry. This journal is © The Royal Society of Chemistry 2021 1 SUPPORTING INFORMATION 2 A multi-task deep learning neural network for predicting flammability- 3 related properties from molecular structures 4 Ao Yang‡a,b, Yang Su‡c,a, Zihao Wanga, Saimeng Jina, Jingzheng Renb, Xiangping Zhangd, 5 Weifeng Shen*a and James H. Clarke 6 aSchool of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China 7 bDepartment of Industrial and Systems Engineering, The Hong Kong Polytechnic University, Hong 8 Kong SAR, China 9 cSchool of Intelligent Technology and Engineering, Chongqing University of Science and Technology, 10 Chongqing 401331, China 11 dBeijing Key Laboratory of Ionic Liquids Clean Process, CAS Key Laboratory of Green Process and 12 Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, China 13 eGreen Chemistry Centre of Excellence, University of York, York YO105D, UK 14 *Correspondence should be addressed to: Weifeng Shen ([email protected]) 15 ‡These authors contributed equally to this work. 16 S1. Signature descriptors 17 The signature descriptor1 is an effective tool for encoding molecular structures with all 18 atomic neighborhood into strings. This descriptor involving two forms: the first one is the 19 atomic signatures generated at a specified root atom in a molecule, the other one is the molecular 20 signatures combined from all atom signatures linearly. The size of each atomic signature is 21 determined by a parameter named “height”, h. An atomic Signature is a tree subgraph including 22 all atoms/bonds extending out to the predefined distance h without backtracking.
    [Show full text]
  • (Ug/M3) Long-Term ESL (Ppb) Date Derived Status Short
    Long-term Short-term ESL Short-term ESL Long-term ESL ESL Substance CASNo. (ug/m3) (ppb) (ug/m3) (ppb) Date Derived Status Short-term ESL Basis Long-term ESL Basis ((2-(Dimethylamino)ethyl)methylamino)-ethanol, 2- 2212-32-0 50 -- 5 -- 8/19/2010 Interim Health Health ([dimethylamino] methyl) phenol 25338-55-0 190 -- 19 -- 4/19/2004 Interim Health Health (2-nitrobutyl) morpholine, 4- 2224-44-4 200 -- 20 -- 4/14/2004 Interim Health Health (3-dimethylamino) propylhexahydro-s-triazine, 1,3,5-tris 15875-13-5 50 (PM10) -- 5 (PM10) -- 3/25/2004 Interim Health Health (4-Methylphenylimino)diethanol, 2,2'- 3077-12-1 50 (PM10) -- 5 (PM10) -- 10/28/2010 Interim Health Health (dimethylamino)-3,5-xylyl methylcarbamate, 4- 315-18-4 5 -- 0.5 -- 10/1/2003 Interim Health Health (dimethylbutyl, 1,3-) -n'-phenylenediamine, n- 793-24-8 10 -- 1 -- 3/30/2001 Interim Health Health (ethyl-2-nitrotrimethylene, 2-) dimorpholine, 4,4- 1854-23-5 200 -- 20 -- 11/10/2000 Interim Health Health (hydroxyethyl, 2-)-3-methoxy propanamide, n- (MHPA) 35544-45-7 700 -- 70 -- 2/16/2001 Interim Health Health (imidazole, 1H-) -1-ethanamine, 4,5-dihydro-, 2- nornaphthenyl derives 68478-61-5 50 -- 5 -- 5/10/2004 Interim Health Health (imidazolium, 1H), 1-ethyl-4,5-dihydro-3-(2- hydroxyethyl)-2-(8-heptadecnyl)-ethyl sulfate Not assigned 150 -- 15 -- 6/16/1998 Interim Health Health (mercaptopropyl, 3-) triethoxysilane, gamma- (also called EMS) 14814-09-6 50 -- 5 -- 2/17/2004 Interim Health Health (mercaptopropyl, 3-) trimethoxysilane, gamma- (also called MMS) 4420-74-0 50 -- 5 --
    [Show full text]
  • "Acetaldehyde," In: Ullmann's Encyclopedia of Industrial Chemistry
    Article No : a01_031 Acetaldehyde MARC ECKERT, Wacker Chemie AG, Werk Burghausen, Germany GERALD FLEISCHMANN, Wacker Chemie AG, Werk Burghausen, Germany REINHARD JIRA, Wacker Chemie AG, Werk Burghausen, Germany HERMANN M. BOLT, Institut fur€ Arbeitsphysiologie an der Universit€at Dortmund, Dortmund, Germany KLAUS GOLKA, Institut fur€ Arbeitsphysiologie an der Universit€at Dortmund, Dortmund, Germany 1. Introduction........................ 191 4.3.3. Isomerization of Ethylene Oxide . ...... 200 2. Physical Properties .................. 192 4.4. Production from C1 Sources ........... 200 3. Chemical Properties and Uses .......... 193 4.5. Production from Hydrocarbons......... 201 3.1. Addition Reactions................... 193 5. Quality and Analysis ................. 201 3.2. Derivatives of Aldol Addition .......... 193 6. Storage and Transportation............ 201 3.3. Reaction with Nitrogen Compounds ..... 193 6.1. Storage............................ 201 3.4. Oxidation.......................... 194 6.2. Transportation...................... 201 3.5. Reduction.......................... 194 6.3. Other Regulations ................... 202 3.6. Miscellaneous Reactions .............. 194 7. Economic Aspects ................... 202 3.7. Consumption ....................... 194 8. Polymers of Acetaldehyde ............. 203 4. Production ......................... 194 8.1. Paraldehyde........................ 203 4.1. Production from Ethanol.............. 195 8.2. Metaldehyde ....................... 203 4.2. Production from Acetylene ............ 196
    [Show full text]
  • Vinyl Acetate
    VINYL ACETATE This substance was considered by previous Working Groups, in February 1978, in June 1985 and in March 1987 (IARC, 1979, 1986, 1987a). Since that time, new data have become available and these have been incorporated into the monograph and taken into consideration in the present evaluation. 1. Exposure Data 1.1 Chemical and physical data 1.1.1 Nomenclature Chem. Abstr. Serv. Reg. No.: 108-05-4 Deleted CAS Reg. Nos.: 61891-42-7; 82041-23-4 Chem. Abstr. Name: Acetic acid, ethenyl ester IUPAC Systematic Name: Vinyl acetate Synonyms: Acetoxyethene; acetoxyethylene; l-acetoxyethylene; ethenyl acetate; ethenyl ethanoate; V A; V AC; V AM; vinyl A mono mer 1.1.2 Structural and molecular formulae and relative molecular mass H 0 H 1 Il 1 /H H-C-C-O-C=C1 ..H H C4H602 Relative molecular mass: 86.09 1.1.3 Chemical and physical properties of the pure substance (a) Description: Colourless liquid with an ether-like odour (Union Carbide Corp., i 981; Hoechst Celanese Corp., 1993) (b) Boiling-point: 72.2 (lC (Lide, 1993) (c) Melting-point: -93.2 (lC (Lide, 1993) (d) Density: 0.9317 at 20 (lC/4 (lC (Lide, 1993) (e) Spectroscopy data: Infrared (prism (982); grating (81 12l), ultraviolet (1-29), nuclear magnetic resonance (proton (10245); C-13 (1841)) and mass spectral data (136) have been reported (Sadtler Research Laboratories, 1980; Weast & Astle, 1985). (f Solubility: Slightly soluble in water (20 g/L at 20 (lC); soluble in acetone, benzene, diethyl ether, ethanol, chloroform and most organic solveÌits (Budavari, 1989; Lewis, 1993; Lide, 1993)
    [Show full text]
  • Patent Office
    ¯Öê™ëü™ü úÖµÖÖÔ»ÖµÖ úÖ ¿ÖÖÃÖúßµÖ •Ö−ÖÔ»Ö OFFICIAL JOURNAL OF THE PATENT OFFICE ×−ÖÖÔ´Ö−Ö ÃÖÓ. 02/2012 ¿ÖãÎú¾ÖÖ¸ü פü−ÖÖÓú: 13/01/2012 ISSUE NO. 02/2012 FRIDAY DATE: 13/01/2012 ¯Öê™ëü™ü úÖµÖÖÔ»ÖµÖ úÖ ‹ú ¯ÖÏúÖ¿Ö−Ö PUBLICATION OF THE PATENT OFFICE The Patent Office Journal 13/01/2012 418 INTRODUCTION In view of the recent amendment made in the Patents Act, 1970 by the Patents (Amendment) Act, 2005 effective from 01st January 2005, the Official Journal of The Patent Office is required to be published under the Statute. This Journal is being published on weekly basis on every Friday covering the various proceedings on Patents as required according to the provision of Section 145 of the Patents Act 1970. All the enquiries on this Official Journal and other information as required by the public should be addressed to the Controller General of Patents, Designs & Trade Marks. Suggestions and comments are requested from all quarters so that the content can be enriched. (P H Kurian) CONTROLLER GENERAL OF PATENTS, DESIGNS & TRADE MARKS 13th JANUARY, 2012 The Patent Office Journal 13/01/2012 419 CONTENTS SUBJECT PAGE NUMBER : 421 – 422 JURISDICTION SPECIAL NOTICE : 423 – 424 CORRIGENDUM (DELHI) 425 : EARLY PUBLICATION (DELHI) : 426 – 434 EARLY PUBLICATION (MUMBAI) : 435 – 437 EARLY PUBLICATION (CHENNAI) 438 – 445 : PUBLICATION AFTER 18 MONTHS (DELHI) : 446 – 544 PUBLICATION AFTER 18 MONTHS (MUMBAI) : 545 – 644 PUBLICATION AFTER 18 MONTHS (CHENNAI) : 645 – 743 PUBLICATION AFTER 18 MONTHS (KOLKATA) : 744 – 833 AMENDMENT UNDER SEC.57. (KOLKATA) : 834
    [Show full text]