2-Hydroxymethyl-1,3-propanediol nitrate ester
AssigneeThiokol Corporation
InventorMichael W. Barnes
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Abstract
2-hydroxymethyl-1,3-propanediol trinitrate, processes for its preparation, and compounds related thereto are disclosed. The final product is useful as a platicizer of relatively low volatility in double based propellant compositions and as a liquid explosive.
Claims4
A compound 2-hydroxymethyl-1,3-propanediol trinitrate, said compound being a water white liquid at room temperature.
A process for the preparation of 2-hydroxymethyl-1,3-propanediol trinitrate which comprises:
- (a) preparing 2-hydroxymethyl-1,3-propanediol by treating bis-(hydroxymethyl)acetaldehyde with an aldehyde carbonyl group reducing agent selected from hydrogen adsorbed on a platinum, rhodium or palladium hydrogenation catalyst, or an alkali metal dissolving in a lower alkanol;
- and
- (b) treating the product of step a with nitric acid in a substantially non-aqueous medium in the presence of a water absorber.
A process for the preparation of 2-hydroxymethyl-1,3-propanediol trinitrate which comprises:
- (a) preparing 2-hydroxymethyl-1,3-propanediol by treating a compound of the formula:
- ##STR7## wherein the R moieties are the same or different and are lower alkyl, with a hydroxyl group protecting reagent to produce a compound of the formula:
- ##STR8## wherein X represents the protected hydroxyl groups and R is as defined hereinabove;
- (b) treating the product of step a with an ester group hydrolysis reagent so as to produce a compound of the formula:
- ##STR9## wherein X and R are as defined hereinabove;
- (c) treating the product of step b with an ester group reducing agent selected from hydrogen adsorbed on a catalyst, aluminum hydrides, borohydrides, borane-dimethyl sulfoxide, or an alkali metal dissolving in a lower alkanol to give a product of the formula:
- ##STR10## wherein X is as defined hereinabove;
- and (d) removing the hydroxyl protecting group from the product of step c;
- and
- (e) treating the product of step (d) with nitric acid in a substantially anhydrous medium in the presence of a water absorber.
A process for the preparation of 2-hydroxymethyl-1,3-propanediol trinitrate which comprises:
- (a) preparing 2-hydroxymethyl-1,3-propanediol by treating a compound of the formula:
- ##STR11## wherein the R moities are the same or different and are lower alkyl, with an adduct of borane and dimethyl sulfide;
- and
- (b) treating the product of step a with nitric acid in a substantially non-aqueous medium in the presence of a water absorber.
Dependencies are inferred from the claim text.