New renewably-sourced polyesters from limonene-derived monomers

被引：53
作者：
Thomsett, Megan R. [1 ]
Moore, Jonathan C. [1 ]
Buchard, Antoine [2 ]
Stockman, Robert A. [1 ]
Howdle, Steven M. [1 ]
机构：
[1] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England
[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
来源：
GREEN CHEMISTRY | 2019年 / 21卷 / 01期
基金：
英国工程与自然科学研究理事会;
关键词：
CATIONIC ISOMERIZATION POLYMERIZATION; RING-OPENING POLYMERIZATION; HIGH-MOLECULAR-WEIGHT; BETA-PINENE; ANIONIC-POLYMERIZATION; RADICAL POLYMERIZATION; POLYMERS; BLOCK; POLYAMIDES; RESOURCES;
D O I：
10.1039/c8gc02957a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive M(n)s of up to 30 kDa with T(g)s between -6 and 24 degrees C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.
引用
收藏
页码：149 / 156
页数：8
相关论文
共 55 条
  • [1] Thermodynamic Control of the Polymerizability of Five-, Six-, and Seven-Membered Lactones
    Aleman, Carlos
    Betran, Oscar
    Casanovas, Jordi
    Houk, K. N.
    Hall, H. K., Jr.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 6237 - 6244
  • [2] Ananikov V. P., 2015, SUSTAINABLE CATALYSI, V55
  • [3] Green Chemistry: Principles and Practice
    Anastas, Paul
    Eghbali, Nicolas
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) : 301 - 312
  • [4] Stereocomplexed Poly(Limonene Carbonate): A Unique Example of the Cocrystallization of Amorphous Enantiomeric Polymers
    Auriemma, Finizia
    De Rosa, Claudio
    Di Caprio, Maria Rosaria
    Di Girolamo, Rocco
    Ellis, W. Chadwick
    Coates, Geoffrey W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1215 - 1218
  • [5] Cyclic limonene dicarbonate as a new monomer for non-isocyanate oligo- and polyurethanes (NIPU) based upon terpenes
    Baehr, Moritz
    Bitto, Alexandro
    Muelhaupt, Rolf
    [J]. GREEN CHEMISTRY, 2012, 14 (05) : 1447 - 1454
  • [6] HYDROBORATION OF TERPENES .8. CYCLIC HYDROBORATION OF D-(+)-LIMONENE - STEREOSELECTIVE SYNTHESIS OF D-(-)-(1R, 2R, 4R)-LIMONENE-2,9-DIOL AND D-(-)-(1R, 2R, 4R)-CARVOMENTHOL
    BROWN, HC
    PFAFFENBERGER, CD
    [J]. TETRAHEDRON, 1975, 31 (08) : 925 - 928
  • [7] Alternating copolymerization of limonene oxide and carbon dioxide
    Byrne, CM
    Allen, SD
    Lobkovsky, EB
    Coates, GW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) : 11404 - 11405
  • [8] Polyester-graft-phosphorylcholine prepared by ring-opening polymerization and click chemistry
    Cooper, Beth M.
    Chan-Seng, Delphine
    Samanta, Debasis
    Zhang, Xiongfei
    Parelkar, Sangram
    Emrick, Todd
    [J]. CHEMICAL COMMUNICATIONS, 2009, (07) : 815 - 817
  • [9] Duda A., 2009, Handbook of Ring-Opening Polymerization, P1, DOI DOI 10.1002/9783527628407.CH1
  • [10] Renewable polyamides and polyurethanes derived from limonene
    Firdaus, Maulidan
    Meier, Michael A. R.
    [J]. GREEN CHEMISTRY, 2013, 15 (02) : 370 - 380
123456