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• Crucho, CC.
• Petrova, KT.
• Pinto, RC.
• Barros, MT.
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• Crucho, CC.
• Petrova, KT.
• Pinto, RC.
• Barros, MT.
• [+] on PubMed
• Crucho, CC.
• Petrova, KT.
• Pinto, RC.
• Barros, MT.

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Molecules 2008, 13(4), 762-770; doi:10.3390/molecules13040762

Communication

Novel Unsaturated Sucrose Ethers and Their Application as Monomers

Carina C. Crucho, Krasimira T. Petrova* , Rui C. Pinto and Maria T. Barros*

REQUIMTE, Departamento de Química - FCT, Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal

* Authors to whom correspondence should be addressed.

Received: 5 March 2008; in revised form: 26 March 2008 / Accepted: 26 March 2008 / Published: 28 March 2008

Download PDF Full-Text [141 KB, uploaded 1 October 2008 09:18 CEST]

Abstract: Novel unsaturated ethers were synthesised in good yields starting from sucrose,using a two-step mild and efficient procedure based on the Gassman method, whichconsists in forming a vinyl group by the elimination of ethanol from mixed acetals withtrimethylsilyl trifluoromethanesulfonate in the presence of alkyl amines. Mixed acetals arereadily obtained from the corresponding alcohols and ethyl vinyl ether, using an acidiccatalyst. Conventional etherification involving a primary halide was also examined. Themonomers thus obtained were successfully polymerised by a free radical mechanism,yielding unbranched linear and soluble polymers with pending sucrose moieties, and someof their physical properties were determined.

Keywords: Sustainable chemistry; vinyl sucrose ether monomers; biodegradable copolymers; natural products copolymers; free radical copolymerisation

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