Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization

被引：7
作者：
Wolf, William J. [1 ]
Li, Jiaming [1 ]
Jones, Simon C. [2 ]
Stoltz, Brian M. [3 ]
Grubbs, Robert H. [1 ]
机构：
[1] CALTECH, Arnold & Mabel Beckman Lab Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA
[2] CALTECH, Electrochem Technol Grp, Jet Prop Lab, Pasadena, CA 91109 USA
[3] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
MACROMOLECULES | 2020年 / 53卷 / 18期
关键词：
TERTIARY; DIMETHYLATION; ETHYLENE; KETONES; COPOLYMERIZATION; ISOBUTYLENE; METHYLATION; CATALYSTS; CARBONYL; HALIDES;
D O I：
10.1021/acs.macromol.0c01606
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
A robust synthesis of gem-dialkyl acyclic diene monomers has been developed. This route is scalable, flexible, and bio-renewable, allowing for the production of a wide range of diene monomers of different lengths and different gem-dialkyl substitutions starting from unsaturated esters derived from seed oils. The metathesis polymerization of these monomers and the hydrogenation of the resulting polyolefins lead to telechelic gem-dialkyl polyethylenes, which can be used as elastomers in the synthesis of polyurethanes and other block polymers.
引用
收藏
页码：7803 / 7809
页数：7
相关论文
共 31 条
  • [1] Homologous Poly(isobutylene)s: Poly(isobutylene)/High-Density Poly(ethylene) Hybrid Polymers
    Binder, Wolfgang H.
    Kurzhals, Steffen
    Pulamagatta, Bhanuprathap
    Decker, Ulrich
    Pawar, Gjanan Manohar
    Wang, Dongren
    Kuehnel, Christa
    Buchmeiser, Michael R.
    [J]. MACROMOLECULES, 2008, 41 (22) : 8405 - 8412
  • [2] The acetoacetic ester condensation V The condensation of higher esters
    Briese, RR
    McElvain, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 1697 - 1700
  • [3] Chemical routes for the transformation of biomass into chemicals
    Corma, Avelino
    Iborra, Sara
    Velty, Alexandra
    [J]. CHEMICAL REVIEWS, 2007, 107 (06) : 2411 - 2502
  • [4] Acyclic diene metathesis polymerization: History, methods and applications
    da Silva, Lucas Caire
    Rojas, Giovanni
    Schulz, Michael D.
    Wagener, Kenneth B.
    [J]. PROGRESS IN POLYMER SCIENCE, 2017, 69 : 79 - 107
  • [5] SOLVENT-FREE CYCLIZATION OF LINEAR DIENES USING OLEFIN METATHESIS AND THE THORPE INGOLD EFFECT
    FORBES, MDE
    PATTON, JT
    MYERS, TL
    MAYNARD, HD
    SMITH, DW
    SCHULZ, GR
    WAGENER, KB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) : 10978 - 10980
  • [6] Access to "Friedel Crafts-Restricted" tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
    Hartsel, Joshua A.
    Craft, Derek T.
    Chen, Qiao-Hong
    Ma, Ming
    Carlier, Paul R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) : 3127 - 3133
  • [7] Polyisobutylene-Based Polyurethanes with Unprecedented Properties and How They Came About
    Kang, Jungmee
    Erdodi, Gabor
    Kennedy, Joseph P.
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (18) : 3891 - 3904
  • [8] Processable epoxy-telechelic polyalkenamers and polyolefins for photocurable elastomers
    Kassekert, Luke A.
    Dingwell, Claire E.
    De Hoe, Guithem X.
    Hillmyer, Marc A.
    [J]. POLYMER CHEMISTRY, 2020, 11 (03) : 712 - 720
  • [9] QUATERNARY CARBONS BY ALKYLATION OF TERTIARY HALIDES WITH ALUMINUM ALKYLS - A MODEL FOR INITIATION AND TERMINATION IN CATIONIC POLYMERIZATION
    KENNEDY, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (02) : 532 - &
  • [10] KIM CU, 1994, TETRAHEDRON LETT, V35, P3017
1234