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Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: synthesis of poly(ω-pentadecalactone-co-butylene-co-carbonate).
Biomacromolecules 2011; 12(5):1912-9B

Abstract

Candida antarctica lipase B (CALB) was successfully used to promote synthesis of aliphatic poly(carbonate-co-ester) copolymers from dialkyl carbonate, diol, and lactone monomers. The polymerization reactions were carried out in two stages: first-stage oligomerization under low vacuum, followed by second-stage polymerization under high vacuum. Therefore, copolymerization of ω-pentadecalactone (PDL), diethyl carbonate (DEC), and 1,4-butanediol (BD) yielded PDL-DEC-BD copolymers with a M(w) of whole product (nonfractionated) up to 33 000 and M(w)/M(n) between 1.2 and 2.3. Desirable reaction temperature for the copolymerization was found to be ∼80 °C. The copolymer compositions, in the range from 10 to 80 mol % PDL unit content versus total (PDL + carbonate) units, were effectively controlled by adjusting the monomer feed ratio. Reprecipitation in chloroform/methanol mixture allowed isolation of the purified copolymers in up to 92% yield. (1)H and (13)C NMR analyses, including statistical analysis on repeat unit sequence distribution, were used to determine the polymer microstructures. The synthesized PDL-DEC-BD copolymers possessed near random structures with all possible combinations of PDL, carbonate, and butylene units via either ester or carbonate linkages in the polymer chains and are more appropriately named as poly(PDL-co-butylene-co-carbonate).

Authors+Show Affiliations

Biomedical Engineering Department, Yale University, New Haven, Connecticut 06511, United States. zhaozhong.jiang@yale.edu

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21449602

Citation

Jiang, Zhaozhong. "Lipase-catalyzed Copolymerization of Dialkyl Carbonate With 1,4-butanediol and Ω-pentadecalactone: Synthesis of Poly(ω-pentadecalactone-co-butylene-co-carbonate)." Biomacromolecules, vol. 12, no. 5, 2011, pp. 1912-9.
Jiang Z. Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: synthesis of poly(ω-pentadecalactone-co-butylene-co-carbonate). Biomacromolecules. 2011;12(5):1912-9.
Jiang, Z. (2011). Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: synthesis of poly(ω-pentadecalactone-co-butylene-co-carbonate). Biomacromolecules, 12(5), pp. 1912-9. doi:10.1021/bm2002522.
Jiang Z. Lipase-catalyzed Copolymerization of Dialkyl Carbonate With 1,4-butanediol and Ω-pentadecalactone: Synthesis of Poly(ω-pentadecalactone-co-butylene-co-carbonate). Biomacromolecules. 2011 May 9;12(5):1912-9. PubMed PMID: 21449602.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: synthesis of poly(ω-pentadecalactone-co-butylene-co-carbonate). A1 - Jiang,Zhaozhong, Y1 - 2011/04/18/ PY - 2011/4/1/entrez PY - 2011/4/1/pubmed PY - 2011/9/10/medline SP - 1912 EP - 9 JF - Biomacromolecules JO - Biomacromolecules VL - 12 IS - 5 N2 - Candida antarctica lipase B (CALB) was successfully used to promote synthesis of aliphatic poly(carbonate-co-ester) copolymers from dialkyl carbonate, diol, and lactone monomers. The polymerization reactions were carried out in two stages: first-stage oligomerization under low vacuum, followed by second-stage polymerization under high vacuum. Therefore, copolymerization of ω-pentadecalactone (PDL), diethyl carbonate (DEC), and 1,4-butanediol (BD) yielded PDL-DEC-BD copolymers with a M(w) of whole product (nonfractionated) up to 33 000 and M(w)/M(n) between 1.2 and 2.3. Desirable reaction temperature for the copolymerization was found to be ∼80 °C. The copolymer compositions, in the range from 10 to 80 mol % PDL unit content versus total (PDL + carbonate) units, were effectively controlled by adjusting the monomer feed ratio. Reprecipitation in chloroform/methanol mixture allowed isolation of the purified copolymers in up to 92% yield. (1)H and (13)C NMR analyses, including statistical analysis on repeat unit sequence distribution, were used to determine the polymer microstructures. The synthesized PDL-DEC-BD copolymers possessed near random structures with all possible combinations of PDL, carbonate, and butylene units via either ester or carbonate linkages in the polymer chains and are more appropriately named as poly(PDL-co-butylene-co-carbonate). SN - 1526-4602 UR - https://www.unboundmedicine.com/medline/citation/21449602/Lipase_catalyzed_copolymerization_of_dialkyl_carbonate_with_14_butanediol_and_ω_pentadecalactone:_synthesis_of_poly_ω_pentadecalactone_co_butylene_co_carbonate__ L2 - https://dx.doi.org/10.1021/bm2002522 DB - PRIME DP - Unbound Medicine ER -