DOCSLIB.ORG

WO 2018/136208 Al O

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
WO 2018/136208 Al O (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/136208 Al 26 July 2018 (26.07.2018) W !P O PCT (51) International Patent Classification: (72) Inventor: LEWIS, Kyle, G.; 12726 Apple Bend Circle, C07C 321/14 (2006.01) CI 0M 105/72 (2006.01) Houston, TX 77044 (US). C07C 321/28 (2006.01) (74) Agent: CHEN, Siwen et al; ExxonMobil Chemical Com (21) International Application Number: pany, Law Department, P.O. Box 2149, Baytown, TX PCT/US2017/068457 77522-2149 (US). (22) International Filing Date: (81) Designated States (unless otherwise indicated, for every 27 December 2017 (27.12.2017) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, (25) Filing Language: English CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, (26) Publication Language: English DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, (30) Priority Data: KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 62/446,943 17 January 2017 (17.01.2017) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 17159135.7 03 March 2017 (03.03.2017) OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (71) Applicant: EXXONMOBIL CHEMICAL PATENTS SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, INC. [US/US]; 5200 Bayway Drive, Baytown, TX 77520 TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (US). (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (54) Title: HIGH STABILITY LUBRICATING OIL BASE STOCKS AND PROCESSES FOR PREPARING THE SAME FIG. 1 00 o (57) Abstract: Compounds having the formula (F-I) below are provided herein: (F-I), wherein: R1 is a C1-C5000 alkyl group; R2 is (i) a C4-C30 linear alkyl group or (ii) a C4-C5000 branched alkyl having the formula (F-II) below: (F-II), wherein R5 and R6 at each occurrence are each independently a hydrogen or a C1-C30 linear alkyl group and n is a positive integer, provided however, among all of R5 and R6, at least one is a C1-C30 linear alkyl group; and R7 is a hydrogen or a C1-C30 linear alkyl group; R3 is hydrogen or a Ci- o C5000 alkyl group; and R4 is a C -C alkyl group or an aromatic group. Processes for preparing compounds of formula (F-I) as well as base stock and lubricant compositions containing compounds of formula (F-I) are also provided. [Continued on nextpage] WO 2018/136208 Al llll II II 11III II I I III II 11III I III II I II GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Declarations under Rule 4.17: — as to applicant's entitlement to applyfor and be granted a patent (Rule 4.1 7( )) — as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.17(in)) Published: HIGH STABILITY LUBRICATING OIL BASE STOCKS AND PROCESSES FOR PREPARING THE SAME PRIORITY CLAIM [0001] This application claims the benefit of Provisional Application No. 62/446,943, filed January 17, 2017, the disclosures of which is incorporated herein by its reference. FIELD OF THE INVENTION [0002] This disclosure relates to sulfur-containing compounds, processes for producing the sulfur-containing compounds, and lubricating oil base stocks and lubricating oils including the sulfur-containing compounds with increased thermal and oxidative stability. BACKGROUND OF THE INVENTION [0003] Lubricants in commercial use today are prepared from a variety of natural and synthetic base stocks admixed with various additive packages and solvents depending upon their intended application. The base stocks typically include mineral oils, polyalpha-olefins (PAO), gas-to-liquid base oils (GTL), silicone oils, phosphate esters, diesters, polyol esters, and the like. [0004] A major trend for passenger car engine oils (PCEOs) is an overall improvement in quality as higher quality base stocks become more readily available. Typically the highest quality PCEO products are formulated with base stocks such as PAOs or GTL stocks. [0005] PAOs and GTL stocks are an important class of lube base stocks with many excellent lubricating properties, including high viscosity index (VI), but may have lower thermal and oxidative stability. Thermal and oxidative stability is important because of a trend requiring smaller sump sizes that may result in more thermal and oxidative stress on the lubricants. Further, performance requirements for lubricants have become more stringent and the demand for longer drain intervals continues to grow. [0006] Sulfur may be incorporated in the base stocks due to its anti-oxidant capabilities. While sulfurized PAO (S-PAO) base stocks can provide improved oxidative stability, improved durability during exposure to high temperatures and overall may extend the life of the lubricant, synthesis of S-PAO bases tocks may introduce a tertiary C-H bond in addition to the sulfur atom. For example, as shown in known scheme A below, unhydrogenated primary sulfur containing PAO PAO oligomer thiol (S-PAO) Scheme A group or aromatic compound, the sulfur addition follows the well-known "anti- Markovnikov addition," wherein the sulfur atom bonds to the less substituted carbon atom of the double bond from the unhydrogenated PAO oligomer forming a tertiary C- H bond in the S-PAO. This hydrogen atom of the C-H bond may be particularly labile to oxidative cleavage due to low tertiary C-H bond dissociation energy. Thus, such tertiary C-H bond can be prone to oxidative degradation thereby lowering the oxidative stability of the S-PAO. [0007] Therefore, there is a need for S-PAOs with increased thermal and oxidative stability and processes for making S-PAOs, which do not introduce oxidatively labile tertiary C-H bonds. More specifically, there is a need for S-PAOs and methods of preparing the same where the sulfur atom bonds to the more highly substituted carbon atom of the double bond from the unhydrogenated PAO oligomer. SUMMARY OF THE INVENTION [0008] It has been unexpectedly found that higher stability S-PAOs may be selectively synthesized without introducing oxidatively labile tertiary C-H bonds via acid catalyzed synthesis. [0009] Thus, this disclosure relates in part to a lubricant base stock comprising a compound having the formula (F-I below: (F-I) 1 2 wherein: R is a C1-C5000 alkyl group; R is (i) a C4-C30 linear alkyl group or (ii) a C4- C5000 branched alkyl group having the formula (F-II) below: (F-II), wherein R5 and R6 at each occurrence are each independently a hydrogen or a C1-C30 linear alkyl group and n is a positive integer, provided however, among all of R5 and R6, at least one is a C1-C30 linear alkyl group; and R7 is a hydrogen or a C1-C30 linear alkyl group; R3 is hydrogen or a C1-C500 alkyl group; and R4 is a C1-C50 alkyl group or an aromatic group. [0010] This disclosure also relates in part to a process for making a compound of formula (F-I) and/or a base stock comprising a compound of formula (F-I), the process comprising reacting HS-R 4 with an olefin-containing material comprising a compound having the following formula: (F-Ia) in the presence of an acid catalyst. [0011] This disclosure further relates in part to a formulated lubricant comprising one or more of the lubricant base stocks described herein. [0012] Other embodiments, including particular aspects of the embodiments summarized above, will be evident from the detailed description that follows. BRIEF DESCRIPTION OF THE DRAWINGS [0013] FIG. 1 illustrates ¾ NMR spectra of Product I. [0014] FIG. 2 illustrates H NMR spectra of Comparative Product 1. [0015] FIG. 3 illustrates ¾ NMR structural assignment of Compound-I and Compound-II. [0016] FIG. 4 illustrates ¾ NMR spectra of Product IV. [0017] FIG. 5 NMR structural assignment of compounds VII and VIII. [0018] FIG. 6 illustrates oxidative stability of Product I, Product III, Comparative Product 1, PAO 4 and Synesstic™ 5. DETAILED DESCRIPTION OF THE INVENTION [0019] In various aspects of the invention, catalysts and methods for preparing catalysts are provided. I. Definitions [0020] For purposes of this invention and the claims hereto, the numbering scheme for the Periodic Table Groups is according to the IUPAC Periodic Table of Elements as of January 1, 2017. [0021] The term "and/or" as used in a phrase such as "A and/or B" herein is intended to include "A and B", "A or B", "A", and "B". [0022] The terms "substituent", "radical", "group", and "moiety" may be used interchangeably. [0023] As used herein, and unless otherwise specified, the term "C " means hydrocarbon(s) having n carbon atom(s) per molecule, wherein n is a positive integer. [0024] As used herein, and unless otherwise specified, the term "hydrocarbon" means a class of compounds containing hydrogen bound to carbon, and encompasses (i) saturated hydrocarbon compounds, (ii) unsaturated hydrocarbon compounds, and (iii) mixtures of hydrocarbon compounds (saturated and/or unsaturated), including mixtures of hydrocarbon compounds having different values of n.
Load more

Recommended publications
  • Download (4Mb)
    University of Warwick institutional repository: http://go.warwick.ac.uk/wrap A Thesis Submitted for the Degree of PhD at the University of Warwick http://go.warwick.ac.uk/wrap/53126 This thesis is made available online and is protected by original copyright. Please scroll down to view the document itself. Please refer to the repository record for this item for information to help you to cite it. Our policy information is available from the repository home page. Synthesis and application of thiourea-S,S-dioxide derivatives by James Frederick Shuan-Liang Apps A thesis submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry University of Warwick Department of Chemistry February 2008 To my parents ii Table of Contents Abstract .............................................................................................................................. 1 Abbreviations ...................................................................................................................... 2 Chapter 1. Introduction .................................................................................................... 5 1.1 Preface .......................................................................................................................... 5 1.2 Oxidation of sulfur compounds ..................................................................................... 7 1.3 Thiourea oxides in biological systems ........................................................................ 10 1.4 Structure,
    [Show full text]
  • Development of Chemical Tools to Evaluate Mycothiol Dependent Enzymes in Multidrug Resistance in Mycobacteria
    Stemming the tide of resistance in TB: development of chemical tools to evaluate mycothiol dependent enzymes in multidrug resistance in mycobacteria Ewelina Rybak Thesis submitted for the degree of Doctor of Philosophy Department of Pharmaceutical and Biological Chemistry School of Pharmacy University College London 2019 I, Ewelina Rybak, confirm that the work presented in this thesis is my own. Where information has been derived from other sources, I can confirm that this has been indicated in the thesis. 2 Acknowledgments First, I would like to thank Dr Jess Healy, my research supervisor, for giving me the opportunity to work on this project. I would also like to thank Dr Geoff Wells, my research supervisor, for great support and guidance during my final year. Apart from my UCL supervisors, I would like to express my gratitude to Dr David Andrews for his valuable advice and suggestions over the years. I would also like to acknowledge Dr Steve Stokes for his advice and helping me to find my way around the lab during my placement at AstraZeneca. Lastly, I would like to thank all past and current G25 lab members for creating a great atmosphere in the lab. 3 Abstract Tuberculosis (TB) is an infectious disease that kills more than a million people a year and poses a significant health threat. Because of the global spread of multi- drug resistant TB and high infection rates, there is a significant unmet clinical need for new drugs. M. tuberculosis (Mtb) produces mycothiol (MSH) in place of glutathione as the most abundant low molecular weight thiol.
    [Show full text]
  • Biological Thiols and Carbon Disulfide: the Formation and Decay Of
    This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Article http://pubs.acs.org/journal/acsodf Biological Thiols and Carbon Disulfide: The Formation and Decay of Trithiocarbonates under Physiologically Relevant Conditions Maykon Lima Souza,†,§ Anthony W. DeMartino,†,‡ and Peter C. Ford* Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, United States *S Supporting Information ABSTRACT: Carbon disulfide is an environmental toxin, but there are suggestions in the literature that it may also have regulatory and/or therapeutic roles in mammalian physiology. Thiols or thiolates would be likely biological targets for an electrophile, such as CS2, and in this context, the present study examines the dynamics of CS2 reactions with various thiols (RSH) in physiologically relevant near-neutral aqueous media to form the respective trithiocarbonate anions (TTC−,alsoknownas “thioxanthate anions”). The rates of TTC− formation are markedly pH-dependent, indicating that the reactive form of RSH is the conjugate base RS−. The rates of the reverse reaction, that is, decay − of TTC anions to release CS2, is pH-independent, with rates roughly antiparallel to the basicities of the RS− conjugate base. These observations indicate that the rate-limiting step of decay is − − simple CS2 dissociation from RS , and according to microscopic reversibility, the transition state of TTC formation would be − ° simple addition of the RS nucleophile to the CS2 electrophile. At pH 7.4 and 37 C, cysteine and glutathione react with CS2 at a similar rate but the trithiocarbonate product undergoes a slow cyclization to give 2-thiothiazolidine-4-carboxylic acid.
    [Show full text]
  • Department of Labor
    Vol. 79 Friday, No. 197 October 10, 2014 Part II Department of Labor Occupational Safety and Health Administration 29 CFR Parts 1910, 1915, 1917, et al. Chemical Management and Permissible Exposure Limits (PELs); Proposed Rule VerDate Sep<11>2014 17:41 Oct 09, 2014 Jkt 235001 PO 00000 Frm 00001 Fmt 4717 Sfmt 4717 E:\FR\FM\10OCP2.SGM 10OCP2 mstockstill on DSK4VPTVN1PROD with PROPOSALS2 61384 Federal Register / Vol. 79, No. 197 / Friday, October 10, 2014 / Proposed Rules DEPARTMENT OF LABOR faxed to the OSHA Docket Office at Docket: To read or download (202) 693–1648. submissions or other material in the Occupational Safety and Health Mail, hand delivery, express mail, or docket go to: www.regulations.gov or the Administration messenger or courier service: Copies OSHA Docket Office at the address must be submitted in triplicate (3) to the above. All documents in the docket are 29 CFR Parts 1910, 1915, 1917, 1918, OSHA Docket Office, Docket No. listed in the index; however, some and 1926 OSHA–2012–0023, U.S. Department of information (e.g. copyrighted materials) Labor, Room N–2625, 200 Constitution is not publicly available to read or [Docket No. OSHA 2012–0023] Avenue NW., Washington, DC 20210. download through the Web site. All submissions, including copyrighted RIN 1218–AC74 Deliveries (hand, express mail, messenger, and courier service) are material, are available for inspection Chemical Management and accepted during the Department of and copying at the OSHA Docket Office. Permissible Exposure Limits (PELs) Labor and Docket Office’s normal FOR FURTHER INFORMATION CONTACT: business hours, 8:15 a.m.
    [Show full text]
  • This PDF Was Created from the British Library's Microfilm Copy of The
    IMAGING SERVICES NORTH Boston Spa, Wetherby West Yorkshire, LS23 7BQ www.bl.uk This PDF was created from the British Library’s microfilm copy of the original thesis. As such the images are greyscale and no colour was captured. Due to the scanning process, an area greater than the page area is recorded and extraneous details can be captured. This is the best available copy THE BRITISH LIBRARY BRITISH THESIS SERVICE TITLE STUDIES IN THE SYNTHESIS AND FUNGICIDAL ACTIVITY OF SOME SUBSTITUTED BENZYL 2-HYDROXYETHYL OLIGOSULPHIDES AND RELATED COMPOUNDS AUTHOR Ezekiel Temidayo AYODELE Ph.D AWARDING University of North London BODY DATE 1994 THESIS DX195485 NUMBER THIS THESIS HAS BEEN MICROFILMED EXACTLY AS RECEIVED The aualitv of this reproduction is dependent upon the quality of the ••risit’** submittedfor microffiming. Every effort has been made to ensure * e highest quality of reproduction. Some pages may have indistinct prinL especially if the papers vrere poorly produced or if the awarding body sent an nd«rjo'' copy. If pages Sre m T s ^ n g ! please bontact the awarding body which granted the degree. Previously copyrighted materials (journal articles, published texts, etc.) are not filmed. This coDv of the thesis has been supplied on condition that anyone who consults Î iL uncTer^^^^ that Ite copyright rests with its a u ^o r and that no information derived from it may be published without the author's prior written consent. D^r^r/^Hiirfion nf this thesis other than as permitted under the United Kingdom agreement witl^ the copyright holder, is prohibited. The University of North London in collaboration with British Technology Group PLC and The Department of Plant Science Obafemi Awolowo University, Ile-Ife, Nigeria Studies in the Synthesis and Fungicidal Activity of some Substituted Benzyl 2-Hydroxyethyl Oligosulphides and Related Compounds by Ezekiel Temidayo Ayodele, B.Sc., M.Sc.
    [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]
  • Hazardous Chemicals Handbook
    Hazardous Chemicals Handbook Hazardous Chemicals Handbook Second edition Phillip Carson PhD MSc AMCT CChem FRSC FIOSH Head of Science Support Services, Unilever Research Laboratory, Port Sunlight, UK Clive Mumford BSc PhD DSc CEng MIChemE Consultant Chemical Engineer Oxford Amsterdam Boston London New York Paris San Diego San Francisco Singapore Sydney Tokyo Butterworth-Heinemann An imprint of Elsevier Science Linacre House, Jordan Hill, Oxford OX2 8DP 225 Wildwood Avenue, Woburn, MA 01801-2041 First published 1994 Second edition 2002 Copyright © 1994, 2002, Phillip Carson, Clive Mumford. All rights reserved The right of Phillip Carson and Clive Mumford to be identified as the authors of this work has been asserted in accordance with the Copyright, Designs and Patents Act 1988 No part of this publication may be reproduced in any material form (including photocopying or storing in any medium by electronic means and whether or not transiently or incidentally to some other use of this publication) without the written permission of the copyright holder except in accordance with the provisions of the Copyright, Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency Ltd, 90 Tottenham Court Road, London, England W1T 4LP. Applications for the copyright holder’s written permission to reproduce any part of this publication should be addressed to the publishers British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloguing
    [Show full text]
  • REACTIONS of MERCAPTANS1 by GARY WAYNE DALMAN
    REACTIONS OF MERCAPTANS1 By GARY WAYNE DALMAN Bachelor of Arts Hope College Holland, Michigan 1958 Submitted to the Faculty of the Graduate School of the Oklahoma State University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY May, 1963 REACTIONS OF MERCAPTANS Thesis Approved: Dean of the Graduate School ACKNOWLEDGMENTS The author thanks his major adviser, Dr. George Gorin, for his guidance and suggestions during the preparation of this thesis and during the experimental work on which it is based. 1be author also thanks his wife, Nance, for her patience and en­ courageme.nt du.ring the course of this work. The author also wishes to thank Mr. John McDermid and Mr. Bipin Gandhi for their assistance in some of the experimental work in Part III. Thanks are also rendered to the Petroleum Research Fund of the American Chemical Society for a Research Fellowship, administered by the Research Foundation of Oklahoma State University. iii TABLE OF CONTENTS Chapter Page INTRODUCTION. • • • • • •. 0 • • • • • • • • • • • • • • • • .• 1 PART I. IONIZATION CONSTANT OF HEXANETHIOL FROM SOLUBILITY MEASUREMENTS ••••••••• . 4 I. HISTORICAL •••• • • . 0 • • .................. 5 Ioni:tation of Cysteine. • • • • . 5 Ionization of Mercaptans •••••• . 7 II. EXPERIMENTAL. 10 Reagents • •••••••••••••.•••• . 10 Attempted Determination of Hexanethiol by the Method of Kolthoff and Harris ••••••• . 12 Determination of Hexanethiol by Ultraviolet Spectrophotometry. • • • • • • • • • • • • • • • • • 12 Solubility Measurements. • • • • • • • • • • • • • • • 13 Titration of Hexanethiol and Ethanethiol. • • • • • • • 14 III. DISCUSSION. 16 PART II. OXIDATION OF HEXANETHIOL IN ALKALINE SOLUTION BY MOLECULAR OXYGEN ••••••••••••• . 20 I. HISTORICAL. ' . 21 II. EXPERIMENTAL. .. .. 25 Reagents. •. • • • • • • • • • • . • • • . • • • • • . • . 25 Oxygen Absorption Measurements ••••••• . 26 Products of the Reaction in Concentrated Sodium Hydroxide Solution •••••••••••••• 33 n:r.
    [Show full text]
  • Nicolet TGA Vapor Phase
    Nicolet TGA Vapor Phase Library Listing – 460 spectra This library includes spectra of compounds likely to evolve during TGA/FT-IR experiments. It is an extremely valuable tool for chemists studying composition and decomposition properties of materials. The TGA Vapor Phase Library contains 460 spectra FT-IR of compounds commonly found when running TGA/FT-IR studies. The spectra in the library will help identify most low molecular weight gases. However, investigators searching for spectra of more exotic species or for more combinations of functional groups should consider the Nicolet FT-IR Vapor Phase Library. Nicolet TGA Vapor Phase Index Compound Name Index Compound Name 374 (2-Butyl)benzene 28 1-Butene 108 (E)-1,2-Dichloroethylene 123 1-Decanol; Decyl alcohol 143 (E)-2-Buten-1-ol; Crotyl alcohol 32 1-Decene 33 (E)-2-Butene 120 1-Heptanol; Heptyl alcohol 35 (E)-2-Hexene 31 1-Heptene 67 (E)-2-Methyl-1,3-pentadiene 181 1-Hexanethiol; Hexyl mercaptan 250 (E)-2-Methyl-2-butenoic acid; Tiglic 119 1-Hexanol; Hexyl alcohol acid 30 1-Hexene 252 (E)-2-Methyl-2-pentenoic acid 75 1-Methyl-1-cyclohexene 39 (E)-2-Nonene 338 1-Methyl-2-pyrrolidinone 249 (E)-2-Pentenoic acid 315 1-Monoacetin; 1-Glyceryl monoacetate 37 (E)-3-Heptene 208 1-Nitropropane 36 (E)-3-Hexene 122 1-Nonanol; Nonyl alcohol 40 (E)-3-Nonene 121 1-Octanol; Octyl alcohol 38 (E)-3-Octene 180 1-Pentanethiol; Pentyl mercaptan; Amyl 61 (E)-Piperylene; (E)-1,3-Pentadiene mercaptan 387 (E)-b-Methylstyrene; (E)-1- 118 1-Pentanol; Amyl alcohol Phenylpropene; (E)-Propenylbenzene 29 1-Pentene
    [Show full text]