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Kinetic Analysis and Improvement of the Williamson Reaction for the Synthesis of Poly(ethylene glycol) Propionaldehyde
Zhao, Yong-Jiang1,2; Zhai, Yan-Qin1,2; Ma, Guang-Hui1; Su, Zhi-Guo1; Ma, GH
2009-02-05
Source PublicationJOURNAL OF APPLIED POLYMER SCIENCE
ISSN0021-8995
Volume111Issue:3Pages:1638-1643
AbstractPolyethylene glycol) (PEG) propionaldehyde is an important polymer derivative used in protein modification; it is usually synthesized by the Williamson reaction of 3-chloropropionaldehyde diethyl acetal (CPADA) with PEG alkoxide followed by hydrolysis to deprotect the aldehyde group. However, the side reaction of the Williamson reaction has been a severe drawback leading to a low-aldehyde-content product. In this study, we established a kinetic model to depict the competition of the Williamson reaction and its side reaction. Based on a kinetic analysis, experiments were performed to systemically investigate the influence of the process parameters on the yield of PEG aldehyde, including the reaction solvents, reaction temperature, and molar equivalents of CPADA. The best reaction solvent was determined to be dioxane because the conversion of methoxy pol(ethylene glycol) in dioxane was higher than that in other solvents and because dioxane has low toxicity and is easily handled. The reaction temperature was set as the refluxing point of dioxane to effectively convert PEG into its alkoxide. The equivalents of CPADA were optimized to be 15 to obtain a quantitative yield of mPEG propionaldehyde and avoid wasting the reagent. The quantitative yield of mPEG propionaldehyde was achieved under these optimum conditions. 2008 Wiley Periodicals, Inc. J Appl Polym Sci 111: 1638-1643, 2009
KeywordBiological Applications Of Polymers Functionalization Of Polymers Synthesis
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1002/app.29140
Indexed BySCI
Language英语
WOS KeywordPROTEIN PEGYLATION ; PEPTIDE
WOS Research AreaPolymer Science
WOS SubjectPolymer Science
WOS IDWOS:000261660200059
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Version出版稿
Identifierhttp://ir.ipe.ac.cn/handle/122111/6727
Collection生化工程国家重点实验室
Corresponding AuthorMa, GH
Affiliation1.Chinese Acad Sci, Inst Proc Engn, Natl Key Lab Biochem Engn, Beijing 100080, Peoples R China
2.Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhao, Yong-Jiang,Zhai, Yan-Qin,Ma, Guang-Hui,et al. Kinetic Analysis and Improvement of the Williamson Reaction for the Synthesis of Poly(ethylene glycol) Propionaldehyde[J]. JOURNAL OF APPLIED POLYMER SCIENCE,2009,111(3):1638-1643.
APA Zhao, Yong-Jiang,Zhai, Yan-Qin,Ma, Guang-Hui,Su, Zhi-Guo,&Ma, GH.(2009).Kinetic Analysis and Improvement of the Williamson Reaction for the Synthesis of Poly(ethylene glycol) Propionaldehyde.JOURNAL OF APPLIED POLYMER SCIENCE,111(3),1638-1643.
MLA Zhao, Yong-Jiang,et al."Kinetic Analysis and Improvement of the Williamson Reaction for the Synthesis of Poly(ethylene glycol) Propionaldehyde".JOURNAL OF APPLIED POLYMER SCIENCE 111.3(2009):1638-1643.
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