Enzymatic Synthesis of Polyesters in Ionic Liquids

Uyama, Hiroshi; Takamoto, Tetsufumi; Kobayashi, Shiro

doi:10.1295/polymj.34.94

Cited by 91 publications

(76 citation statements)

References 26 publications

(28 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The lipase-catalyzed ROP of e-CL was carried out for the first time in ionic solvents, such as 1-butyl-3-methylimidazolium salts, to give poly(e-CL) with M n 4 200 (M w =M n ¼ 2.7) at 97% yield at 60 8C. [67] Ionic liquids are nonvolatile, thermally stable, and highly polar liquids, which allows them to dissolve many organic, inorganic, metallo-oraganic compounds, and also polymeric materials. Thus, ionic liquids have become popular for the synthesis and modification of polymers from the standpoint of ''green solvents''.…”

Section: Reaction Solventsmentioning

confidence: 99%

“…The polycondensation of diethyl adipate and butane-1,4-diol using lipase CA as catalyst efficiently proceeded in 1-butyl-3-methylimidazolinium tetrafluoroborate or hexafluorophosphate under reduced pressure at 60 8C to produce the polyester with M n up to 1 500 after 72 h at 91% yield. [67] Polycondensation of diethyl sebacate and butane-1,4-diol in 1-butyl-3-methylimidazolinium hexafluorophosphate took place, even at room temperature, in the presence of lipase PC. [116] Transesterifications using lipase catalyst are often very slow owing to the reversible nature of the reactions.…”

Section: Transesterification Polycondensationmentioning

confidence: 99%

“…The reaction was carried out under reduced pressure to remove ethanol, since the ionic liquid is nonvolatile. [67] Lipase catalyst induced the polycodensation to produce aromatic polyesters efficiently from aromatic diacid divinyl esters. The divinyl esters of isophthalic acid, terephthalic acid, and p-phenylene diacetic acid were polymerized with various glycols to give polyesters containing aromatic moiety in the main chain with the highest M n of 7 200 by lipase CA catalyst in heptane at 60 8C for 48 h. [126] Enzymatic polymerization of divinyl esters and aromatic diols also afforded aromatic polyesters.…”

Section: S Kobayashimentioning

confidence: 99%

See 2 more Smart Citations

Recent Developments in Lipase‐Catalyzed Synthesis of Polyesters

Kobayashi

2009

Macromol. Rapid Commun.

Self Cite

254

205

View full text Add to dashboard Cite

Polyester synthesis by lipase catalyst involves two major polymerization modes: i) ring-opening polymerization of lactones, and, ii) polycondensation. Ring-opening polymerization includes the finding of lipase catalyst; scope of reactions; polymerization mechanism; ring-opening polymerization reactivity of lactones; enantio-, chemo- and regio-selective polymerizations; and, chemoenzymatic polymerizations. Polycondensation includes polymerizations involving condensation reactions between carboxylic acid and alcohol functional groups to form an ester bond. In most cases, a carboxylic acid group is activated as an ester form, such as a vinyl ester. Many recently developed polymerizations demonstrate lipase catalysis specific to enzymatic polymerization and appear very useful. Also, since lipase-catalyzed polyester synthesis provides a good opportunity for conducting "green polymer chemistry", the importance of this is described.

show abstract

Section: Reaction Solventsmentioning

confidence: 99%

Section: Transesterification Polycondensationmentioning

confidence: 99%

Section: S Kobayashimentioning

confidence: 99%

See 1 more Smart Citation

Recent Developments in Lipase‐Catalyzed Synthesis of Polyesters

Kobayashi

2009

Macromol. Rapid Commun.

Self Cite

254

205

View full text Add to dashboard Cite

show abstract

“…They have recently been described as new green reaction media of the future [12][13]. A number of organic reactions [14][15][16][17][18][19][20] have been investigated in these new solvents, as well as polymerizations, mainly free-radical [21][22][23][24][25][26], electrochemical [27][28], cationic [29] and enzyme-catalyzed [30] polymerizations. However, only a few articles deal with polycondensation reactions in ionic liquids [31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

High temperature reaction between poly(glycolic acid) and ε-caprolactone in ionic liquids

et al. 2007

View full text Add to dashboard Cite

ε-Caprolactone (CL) was reacted with PGA oligomers in ionic liquids in the presence of Ti(OBu) 4 , both ring-opening polymerization initiator and polyesterification catalyst. C NMR studies showed that the fast polymerization of CL was followed by simultaneous slow polyesterification and ester-interchange reactions leading to random PGA/CL copolyesters after 6 h reaction. The nature of the catalyst and the ionic liquid did not influence much reaction rate. Hydroxyacetyl end-groups appeared to be much less reactive than the corresponding hydroxycaproyl end-groups, which were consumed at the beginning of reaction. The 50/50 and 60/40 oxyacetyl (G)/oxycaproyl (L) (mass-%) copolyesters were amorphous, while copolyesters containing larger amounts of G units were semi-crystalline. The variations of the T g of all copolyesters versus composition follow the Flory-Fox law.

show abstract

“…Candida Antarctica lipase (lipase CA) catalyzed formation of biodegradable polyesters in [BMIM]PF 6 and [BMIM]BF 4 has been reported (89). Ring-opening polymerization of ε-caprolactone and polycondensation of dicarboxylic acid diesters with 1,4-butanediol were examined.…”

Section: Enzyme-catalyzed Polymerizationmentioning

confidence: 99%

Polymerization in Ionic Liquids

Zhang

Behera

Hong

et al. 2015

Encyclopedia of Polymer Science and Technology

View full text Add to dashboard Cite

Room temperature ionic liquids (RTILs) have proved over recent years to be useful and unique reaction media for a variety of chemical reactions. Faster reaction rates and better selectivities are often observed in RTILs as compared to those in common organic solvents. In addition to these advantages, the low volatility, nonflammability, and recycling potential also help RTILs become a preferred alternative reaction medium to meet environmental and other requirements. This is evidenced by the ever increasing number of papers published in this area every year and interesting and important discoveries. When conventional free radical polymerizations are carried out in RTILs, there is an increase in the propagation rate due to the high polarity of the RTIL and a decrease in the termination rate because of the high viscosity of the RTILs, and thus the overall reaction rate is greatly increased along with an increase in molecular weight. For living/controlled polymerization such as atom transfer radical polymerization and radical addition‐fragmentation and transfer, the reactions in RTILs are still controllable with faster reaction rates and easy separation of catalysts and/or ligands from the resulting polymers. Nearly all types of polymerization processes have now been successfully conducted in RTILs, often with advantageous effects.

show abstract

Enzymatic Synthesis of Polyesters in Ionic Liquids

Cited by 91 publications

References 26 publications

Recent Developments in Lipase‐Catalyzed Synthesis of Polyesters

Recent Developments in Lipase‐Catalyzed Synthesis of Polyesters

High temperature reaction between poly(glycolic acid) and ε-caprolactone in ionic liquids

Polymerization in Ionic Liquids

Contact Info

Product

Resources

About