Chemical compounds
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorWilliam H. Gilligan
Life of this patent
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Abstract
Dichloroformals of the formula (RCH.sub.2 O).sub.2 CCl.sub.2 wherein R is --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.su), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, or --CF.sub.2 CF.sub.3. These dichloroformals are prepared by reacting the corresponding thionocarbonate of the formula (RCH.sub.2 O).sub.2 C.dbd.S, wherein R is as defined above, with sulfuryl chloride in the presence of a Friedel-Craft catalyst (e.g., AlCl.sub.3 or TiCl.sub.4). Another method is to react the thionocarbonate with chlorine gas in the presence of a polar additive such as 2,2,2-trifluoroethanol or acetonitrile. These energetic dichloroformals are useful as explosive and propellant ingredients and as intermediates in the synthesis of other energetic explosive and propellant ingredients.
Claims15
A substituted dichloroformal of the formula
- (RCH.sub.2 O).sub.2 CCl.sub.2
- wherein R is selected from the group consisting of --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.sub.2), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, and --CF.sub.2 CF.sub.3.
A method of synthesizing dichloroformals of the formula
- (RCH.sub.2 O).sub.2 CCl.sub.2
- by reacting a thionocarbonate of the formula
- (RCH.sub.2 O).sub.2 C.dbd.S
- with sulfuryl chloride in the presence of a Friedel-Crafts catalyst, wherein R is selected from the group consisting of --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.sub.2), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, and --CF.sub.2 F.sub.3.
A method of synthesizing dichloroformals of the formula
- (RCH.sub.2 O).sub.2 CCl.sub.2
- wherein R is selected from the group consisting by of --C(NO.sub.2).sub.3, --CF(NO.sub.2).sub.2, --CF.sub.2 (NO.sub.2), --CCl(NO.sub.2).sub.2, --C(NO.sub.2).sub.2 CH.sub.3, --CCl.sub.3, --CF.sub.3, and --CF.sub.2 F.sub.3, comprising:
- (1) Forming a mixture of
- (a) a chlorinated hydrocarbon,
- (b) a polar additive, and
- (c) a thionocarbonate of the formula
- (RCH.sub.2 O).sub.2 C.dbd.S
- wherein R is as defined above;
- and
- (2) passing chlorine gas through the mixture.
Dependencies are inferred from the claim text.