Efficient synthesis of polyethers from isosorbide by microwave-assisted phase transfer catalysis

Chatti, Saber; Bortolussi, M.; Loupy, André; Blais, Jean‐Claude; Bogdał, Dariusz; Majdoub, Mustapha

doi:10.1016/s0014-3057(02)00071-x

Cited by 74 publications

(39 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A monomodal Synthwave 402 reactor, manufactured by Societè Prolabo, allowed to regulate temperature by modulating the emitted field and to monitor the reaction temperature on the surface of the vials by an infrared detector; toluene (1 mL for 5 mg of reagents) was used as a solvent to enhance temperature control and lower the mixture viscosity. Several advantages using microwave heating were reported: similar yields were obtained in 30 min instead of 1 day of reaction in an oil bath; products showed higher molecular weights and better homogeneities; a different termination mechanism generates ethylenic instead of hydroxylated chain ends (Chatti et al, 2002). Few years later the same group described the synthesis of novel poly(ether-ester)s from adipoyl chloride and aliphatic diols derived from isosorbide: polycondensations under microwave conditions proceeded five times faster (95% yield after 5 min at 150 °C) and the polymer showed higher molecular weights (M w = 4,200 g/mol vs 4,050 g/mol obtained by thermal heating).…”

Section: Other Step Growth Polymerizationsmentioning

confidence: 99%

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Frediani¹,

Giachi²,

Rosi³

et al. 2011

Microwave Heating

View full text Add to dashboard Cite

Section: Other Step Growth Polymerizationsmentioning

confidence: 99%

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Frediani¹,

Giachi²,

Rosi³

et al. 2011

Microwave Heating

View full text Add to dashboard Cite

“…[71] Loupy and co-workers observed shifts in selectivity (as a consequence of microwave irradiation) for the polyetherification of isosorbide (1,4:3,6-dianhydro-D-sorbitol) or isoidide (1,4:3,6-dianhydro-L-iditol) with 1,8-dibromo and 1,8-dimesyloctane (Scheme 7). [72,73] A solution of equimolar amounts of the corresponding educts in toluene was subjected to phase-transfer catalyzed polymerization in the presence of tetrabutylammonium bromide and aqueous potassium hydroxide under microwave irradiation (Synthewave 402, Prolabo) as well as conventional heating. For the isosorbide-containing polymers, it was found that the reaction rates increased under microwave irradiation, providing polymers in yields of around 70% within 30 min.…”

Section: Phase-transfer Catalysismentioning

confidence: 99%

Microwave‐Assisted Polymer Synthesis: State‐of‐the‐Art and Future Perspectives

Wiesbrock

Hoogenboom

Schubert

2004

Macromol. Rapid Commun.

464

256

View full text Add to dashboard Cite

Summary: Monomodal microwaves have overcome the safety uncertainties associated with the precedent domestic microwave ovens. After fast acceptance in inorganic and organic syntheses, polymer chemists have also recently discovered this new kind of microwave reactor. An almost exponential increase of the number of publications in this field reflects the steadily growing interest in the use of microwave irradiation for polymerizations. This review introduces the microwave systems and their applications in polymer syntheses, covering step‐growth and ring‐opening, as well as radical polymerization processes, in order to summarize the hitherto realized polymerizations. Special attention is paid to the differences between microwave‐assisted and conventional heating as well as the “microwave effects”.Results of search on number of publications on microwave‐assisted polymerizations, sorted by year.imageResults of search on number of publications on microwave‐assisted polymerizations, sorted by year.

show abstract

“…Anhydrous sugar alcohols, such as isosorbide, are known for their uses in therapeutics, food additives, surfactants and more recently in polyesters [1][2][3] and polyethers [4]. Incorporation of isosorbide into known polymers may be of interest for three reasons [2].…”

Section: Introductionmentioning

confidence: 99%

H3PW12O40/SiO2 for sorbitol dehydration to isosorbide: High efficient and reusable solid acid catalyst

Sun

et al. 2010

Korean J. Chem. Eng.

View full text Add to dashboard Cite

Tungstophosphoric acids (PW) supported on various metal oxides (SiO 2 , γ-Al 2 O 3 , TiO 2 , ZrO 2 and CeO 2 ) were synthesized and used as catalysts for sorbitol dehydration to isosorbide for the first time. 30% PW/SiO 2 exhibited the best catalytic performance for sorbitol dehydration, over which 56% isosorbide selectivity could be gained at a 95% sorbitol conversion at 250 o C. The catalytic performance of regenerated 30% PW/SiO 2 catalysts by dichloromethane elution showed no loss after recycling five runs. Characterizations with UV-Vis, XRD, NH 3 -TPD and thermal analysis techniques revealed that PW had a good dispersion, and the primary Keggin structure was preserved after supporting PW on different supports. The interaction between PW and oxides resulted in different acidity of catalysts, which affected conversion of sorbitol and selectivity for isosorbide. The final acidity order of supported PW catalysts was the following: SiO 2 >γ-Al 2 O 3 >TiO 2 ≈ZrO 2 >CeO 2 .

show abstract

Efficient synthesis of polyethers from isosorbide by microwave-assisted phase transfer catalysis

Cited by 74 publications

References 30 publications

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Microwave‐Assisted Polymer Synthesis: State‐of‐the‐Art and Future Perspectives

H3PW12O40/SiO2 for sorbitol dehydration to isosorbide: High efficient and reusable solid acid catalyst

Contact Info

Product

Resources

About