Isotactic poly(glycidyl nitrate) and synthesis thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549510, 549512, 549513, 558483, 5253332, 528408, 528409, 528417, 528403, C07D30336, C07D30100, C08G 6510

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052645967

ABSTRACT:
Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.

REFERENCES:
patent: 4885584 (1991-01-01), Millar et al.
patent: 5136062 (1992-08-01), Millar et al.
Kirk-Othmer Ency. of Chem. Tech. 3rd Ed, vol. 15, pp. 841-853.

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