Polymerisation of Beta-alanine through catalytic ester-amide exchange

P. Steunenberg; P.M. Könst; E.L. Scott; M.C.R. Franssen; H. Zuilhof; J.P.M. Sanders

doi:10.1016/j.eurpolymj.2013.03.032

Polymerisation of Beta-alanine through catalytic ester-amide exchange

P. Steunenberg, P.M. Könst, E.L. Scott, M.C.R. Franssen, H. Zuilhof, J.P.M. Sanders

Research output: Contribution to journal › Article › Academic › peer-review

24 Citations (Scopus)

Abstract

Herein we present the use of group (IV) metal alkoxides as catalysts for the polymerisation of esters of p-alanine and its derivatives. The influence of different group (IV) metal alkoxides, different esters, temperature and solvents on the polymerisation are investigated. The order in which the group (IV) metal alkoxides catalyse the polymerisation is: Hf(Ot-Bu)(4) - >= Zr(Ot-Bu)(4) > Ti(Oi-Pr) 4 > Ti(On-Bu)(4). Polymers with the highest degree of polymerisation are obtained performing a neat polymerisation of p-alanine methyl ester in the presence of Hf(Ot-Bu)(4) as a catalyst at 50 degrees C. The polymerisation can also be carried out efficiently in solution, in different solvents and at higher reaction temperatures. This method could also be applied for the formation of other polypeptides. (c) 2013 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1773-1781
Journal	European Polymer Journal
Volume	49
Issue number	7
DOIs	https://doi.org/10.1016/j.eurpolymj.2013.03.032
Publication status	Published - 2013

Keywords

nitrogen-containing chemicals
ring-opening polymerization
amino-acids
biobased production
cyanophycin
peptides
esterification
acrylamide
polymers
mild

Access to Document

10.1016/j.eurpolymj.2013.03.032

Cite this

@article{0cceddced1914d12b0e32ad22b75b6c7,

title = "Polymerisation of Beta-alanine through catalytic ester-amide exchange",

abstract = "Herein we present the use of group (IV) metal alkoxides as catalysts for the polymerisation of esters of p-alanine and its derivatives. The influence of different group (IV) metal alkoxides, different esters, temperature and solvents on the polymerisation are investigated. The order in which the group (IV) metal alkoxides catalyse the polymerisation is: Hf(Ot-Bu)(4) - >= Zr(Ot-Bu)(4) > Ti(Oi-Pr) 4 > Ti(On-Bu)(4). Polymers with the highest degree of polymerisation are obtained performing a neat polymerisation of p-alanine methyl ester in the presence of Hf(Ot-Bu)(4) as a catalyst at 50 degrees C. The polymerisation can also be carried out efficiently in solution, in different solvents and at higher reaction temperatures. This method could also be applied for the formation of other polypeptides. (c) 2013 Elsevier Ltd. All rights reserved.",

keywords = "nitrogen-containing chemicals, ring-opening polymerization, amino-acids, biobased production, cyanophycin, peptides, esterification, acrylamide, polymers, mild",

author = "P. Steunenberg and P.M. K{\"o}nst and E.L. Scott and M.C.R. Franssen and H. Zuilhof and J.P.M. Sanders",

year = "2013",

doi = "10.1016/j.eurpolymj.2013.03.032",

language = "English",

volume = "49",

pages = "1773--1781",

journal = "European Polymer Journal",

issn = "0014-3057",

publisher = "Elsevier",

number = "7",

}

TY - JOUR

T1 - Polymerisation of Beta-alanine through catalytic ester-amide exchange

AU - Steunenberg, P.

AU - Könst, P.M.

AU - Scott, E.L.

AU - Franssen, M.C.R.

AU - Zuilhof, H.

AU - Sanders, J.P.M.

PY - 2013

Y1 - 2013

N2 - Herein we present the use of group (IV) metal alkoxides as catalysts for the polymerisation of esters of p-alanine and its derivatives. The influence of different group (IV) metal alkoxides, different esters, temperature and solvents on the polymerisation are investigated. The order in which the group (IV) metal alkoxides catalyse the polymerisation is: Hf(Ot-Bu)(4) - >= Zr(Ot-Bu)(4) > Ti(Oi-Pr) 4 > Ti(On-Bu)(4). Polymers with the highest degree of polymerisation are obtained performing a neat polymerisation of p-alanine methyl ester in the presence of Hf(Ot-Bu)(4) as a catalyst at 50 degrees C. The polymerisation can also be carried out efficiently in solution, in different solvents and at higher reaction temperatures. This method could also be applied for the formation of other polypeptides. (c) 2013 Elsevier Ltd. All rights reserved.

AB - Herein we present the use of group (IV) metal alkoxides as catalysts for the polymerisation of esters of p-alanine and its derivatives. The influence of different group (IV) metal alkoxides, different esters, temperature and solvents on the polymerisation are investigated. The order in which the group (IV) metal alkoxides catalyse the polymerisation is: Hf(Ot-Bu)(4) - >= Zr(Ot-Bu)(4) > Ti(Oi-Pr) 4 > Ti(On-Bu)(4). Polymers with the highest degree of polymerisation are obtained performing a neat polymerisation of p-alanine methyl ester in the presence of Hf(Ot-Bu)(4) as a catalyst at 50 degrees C. The polymerisation can also be carried out efficiently in solution, in different solvents and at higher reaction temperatures. This method could also be applied for the formation of other polypeptides. (c) 2013 Elsevier Ltd. All rights reserved.

KW - nitrogen-containing chemicals

KW - ring-opening polymerization

KW - amino-acids

KW - biobased production

KW - cyanophycin

KW - peptides

KW - esterification

KW - acrylamide

KW - polymers

KW - mild

U2 - 10.1016/j.eurpolymj.2013.03.032

DO - 10.1016/j.eurpolymj.2013.03.032

M3 - Article

SN - 0014-3057

VL - 49

SP - 1773

EP - 1781

JO - European Polymer Journal

JF - European Polymer Journal

IS - 7

ER -

Polymerisation of Beta-alanine through catalytic ester-amide exchange

Abstract

Keywords

Access to Document

Fingerprint

Cite this