Synthesis and characterization of a novel rac-PHB derivative containing α-malate units

S. Hiki, Ikuo Taniguchi, M. Miyamoto, Y. Kimura

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The ring-opening copolymerization of [RS]-β-butyrolactone (βBL) and 3-(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (BMD) was conducted in the bulk at relatively low BMD/ BL ratios with a distannoxane as the catalyst. The resulting copolymer was a terpolymer consisting of 3-hydroxybutyrate (3HB), glycolate (G), and benzyl-L-α-malate (M) repeating units, with a copolymer composition being almost identical to the monomer feed ratio. It was then subjected to hydrogenolysis at atmospheric pressure in the presence of a palladium on charcoal catalyst to remove the pendant benzyl group of the M unit quantitatively. The deprotected copolymer, having carboxyl functionalities as pendants, was reacted with 1,4-dibromobutane for its crosslinking through the pendant carboxyl group of the malate units. These results revealed that this malate-containing [RS]-PHB has high potential for use as biodegradable elastomer that can be crosslinkable.

Original languageEnglish
Pages (from-to)191-197
Number of pages7
JournalJournal of Fiber Science and Technology
Volume57
Issue number6
DOIs
Publication statusPublished - Jan 1 2001
Externally publishedYes

Fingerprint

glycolic acid
Copolymers
Derivatives
Elastomers
Hydrogenolysis
Catalysts
Terpolymers
Charcoal
3-Hydroxybutyric Acid
Palladium
Crosslinking
Copolymerization
Atmospheric pressure
Monomers
Chemical analysis
malic acid
1,4-dioxane
1,4-dibromobutane

All Science Journal Classification (ASJC) codes

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Polymers and Plastics
  • Industrial and Manufacturing Engineering

Cite this

Synthesis and characterization of a novel rac-PHB derivative containing α-malate units. / Hiki, S.; Taniguchi, Ikuo; Miyamoto, M.; Kimura, Y.

In: Journal of Fiber Science and Technology, Vol. 57, No. 6, 01.01.2001, p. 191-197.

Research output: Contribution to journalArticle

@article{41039c4d19364f8f814e32304cd22f4d,
title = "Synthesis and characterization of a novel rac-PHB derivative containing α-malate units",
abstract = "The ring-opening copolymerization of [RS]-β-butyrolactone (βBL) and 3-(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (BMD) was conducted in the bulk at relatively low BMD/ BL ratios with a distannoxane as the catalyst. The resulting copolymer was a terpolymer consisting of 3-hydroxybutyrate (3HB), glycolate (G), and benzyl-L-α-malate (M) repeating units, with a copolymer composition being almost identical to the monomer feed ratio. It was then subjected to hydrogenolysis at atmospheric pressure in the presence of a palladium on charcoal catalyst to remove the pendant benzyl group of the M unit quantitatively. The deprotected copolymer, having carboxyl functionalities as pendants, was reacted with 1,4-dibromobutane for its crosslinking through the pendant carboxyl group of the malate units. These results revealed that this malate-containing [RS]-PHB has high potential for use as biodegradable elastomer that can be crosslinkable.",
author = "S. Hiki and Ikuo Taniguchi and M. Miyamoto and Y. Kimura",
year = "2001",
month = "1",
day = "1",
doi = "10.2115/fiber.57.191",
language = "English",
volume = "57",
pages = "191--197",
journal = "Sen'i Gakkaishi",
issn = "0037-9875",
publisher = "The Society of Fiber Science and Technology, Japan",
number = "6",

}

TY - JOUR

T1 - Synthesis and characterization of a novel rac-PHB derivative containing α-malate units

AU - Hiki, S.

AU - Taniguchi, Ikuo

AU - Miyamoto, M.

AU - Kimura, Y.

PY - 2001/1/1

Y1 - 2001/1/1

N2 - The ring-opening copolymerization of [RS]-β-butyrolactone (βBL) and 3-(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (BMD) was conducted in the bulk at relatively low BMD/ BL ratios with a distannoxane as the catalyst. The resulting copolymer was a terpolymer consisting of 3-hydroxybutyrate (3HB), glycolate (G), and benzyl-L-α-malate (M) repeating units, with a copolymer composition being almost identical to the monomer feed ratio. It was then subjected to hydrogenolysis at atmospheric pressure in the presence of a palladium on charcoal catalyst to remove the pendant benzyl group of the M unit quantitatively. The deprotected copolymer, having carboxyl functionalities as pendants, was reacted with 1,4-dibromobutane for its crosslinking through the pendant carboxyl group of the malate units. These results revealed that this malate-containing [RS]-PHB has high potential for use as biodegradable elastomer that can be crosslinkable.

AB - The ring-opening copolymerization of [RS]-β-butyrolactone (βBL) and 3-(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (BMD) was conducted in the bulk at relatively low BMD/ BL ratios with a distannoxane as the catalyst. The resulting copolymer was a terpolymer consisting of 3-hydroxybutyrate (3HB), glycolate (G), and benzyl-L-α-malate (M) repeating units, with a copolymer composition being almost identical to the monomer feed ratio. It was then subjected to hydrogenolysis at atmospheric pressure in the presence of a palladium on charcoal catalyst to remove the pendant benzyl group of the M unit quantitatively. The deprotected copolymer, having carboxyl functionalities as pendants, was reacted with 1,4-dibromobutane for its crosslinking through the pendant carboxyl group of the malate units. These results revealed that this malate-containing [RS]-PHB has high potential for use as biodegradable elastomer that can be crosslinkable.

UR - http://www.scopus.com/inward/record.url?scp=0034915195&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034915195&partnerID=8YFLogxK

U2 - 10.2115/fiber.57.191

DO - 10.2115/fiber.57.191

M3 - Article

VL - 57

SP - 191

EP - 197

JO - Sen'i Gakkaishi

JF - Sen'i Gakkaishi

SN - 0037-9875

IS - 6

ER -