Heterogeneous-phase reaction of glycidyl methacrylate and chondroitin sulfate: Mechanism of ring-opening-transesterification competition

Qiang Li; Dong-An Wang; Jennifer H. Elisseeff

doi:10.1021/ma021190w

Heterogeneous-phase reaction of glycidyl methacrylate and chondroitin sulfate: Mechanism of ring-opening-transesterification competition

Qiang Li
, Dong-An Wang
, Jennifer H. Elisseeff

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

84 Citations (Scopus)

Abstract

Addressing the different solubility/miscibility of the water-soluble CS and the water-insoluble GMA, a slow heterogeneous-phase reaction of CS with GMA was designed and performed in aqueous medium regardless of GMAs potential side-reaction with water. By monitoring the methacrylate-conjunction with NMR, a different reaction mechanism was discovered. Two reactions, including a rapid reversible transesterification and a slow irreversible ring-opening conjugation, took place simultaneously. As the reaction proceeded, there was a decline in the amount of transesterification products, while the concentration of ring-opening products gradually increased with time.

Original language	English
Pages (from-to)	2556-2562
Journal	Macromolecules
Volume	36
Issue number	7
DOIs	https://doi.org/10.1021/ma021190w
Publication status	Published - 8 Apr 2003
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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title = "Heterogeneous-phase reaction of glycidyl methacrylate and chondroitin sulfate: Mechanism of ring-opening-transesterification competition",

abstract = "Addressing the different solubility/miscibility of the water-soluble CS and the water-insoluble GMA, a slow heterogeneous-phase reaction of CS with GMA was designed and performed in aqueous medium regardless of GMAs potential side-reaction with water. By monitoring the methacrylate-conjunction with NMR, a different reaction mechanism was discovered. Two reactions, including a rapid reversible transesterification and a slow irreversible ring-opening conjugation, took place simultaneously. As the reaction proceeded, there was a decline in the amount of transesterification products, while the concentration of ring-opening products gradually increased with time.",

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T2 - Mechanism of ring-opening-transesterification competition

AU - Li, Qiang

AU - Wang, Dong-An

AU - Elisseeff, Jennifer H.

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

PY - 2003/4/8

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N2 - Addressing the different solubility/miscibility of the water-soluble CS and the water-insoluble GMA, a slow heterogeneous-phase reaction of CS with GMA was designed and performed in aqueous medium regardless of GMAs potential side-reaction with water. By monitoring the methacrylate-conjunction with NMR, a different reaction mechanism was discovered. Two reactions, including a rapid reversible transesterification and a slow irreversible ring-opening conjugation, took place simultaneously. As the reaction proceeded, there was a decline in the amount of transesterification products, while the concentration of ring-opening products gradually increased with time.

AB - Addressing the different solubility/miscibility of the water-soluble CS and the water-insoluble GMA, a slow heterogeneous-phase reaction of CS with GMA was designed and performed in aqueous medium regardless of GMAs potential side-reaction with water. By monitoring the methacrylate-conjunction with NMR, a different reaction mechanism was discovered. Two reactions, including a rapid reversible transesterification and a slow irreversible ring-opening conjugation, took place simultaneously. As the reaction proceeded, there was a decline in the amount of transesterification products, while the concentration of ring-opening products gradually increased with time.

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U2 - 10.1021/ma021190w

DO - 10.1021/ma021190w

M3 - RGC 21 - Publication in refereed journal

SN - 0024-9297

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JO - Macromolecules

JF - Macromolecules

IS - 7

ER -

Heterogeneous-phase reaction of glycidyl methacrylate and chondroitin sulfate: Mechanism of ring-opening-transesterification competition

Abstract

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