US2381406A - Aliphatic dinitro tetranitrates - Google Patents

Description

Patented Aug. 7, 1945 UNITED STATES PATENT OFFICE ALIPHATIC DINITRO TETRANITRATES Henry B. Hass, West La Fayette, Ind., and Wilbur R. McElroy, Beacon, N. Y., assignors to Purdue Research Foundation, La Fayette, Ind., a corporation of Indiana No Drawing. Application July 29, 1944, Serial No. 547,285

4 Claims.

copending application, U. S. Serial No. 547,284, filed July 29, 1944. By the procedure there described, the desired dinitroalkane is reacted with formaldehyde in a ratio of four moles of the latter to one of dinitroalkane. The reaction is effected N02 No. 5 1n the presence of an alkallne catalyst such as 4 (CH2)n-CCH2ONO2 calcium hydroxide and a suitable solvent such as CHzONO, CEONO, ethanol. The temperature of the reaction mixture should preferably be held at about 20 C. 1n which n represents an integer less than 5. 10 In the table app g below some of the vari- As examples of compounds contemplated by the ous physical properties of certain aliphatic dinitro present invention, there may be mentioned 2,4- tetranitrates covered by the present invention are bis-(hydroxymethyl) -2,4-dinitro-1.5-pentanedio1 listed.

Table Melting Percent nitrogen gg g Percent carbon Percent hydrogen Compound pngiit,

Oalcd. Found Calcd. Found Oalcd. Found Calcd. Found 2, 5-bis (hydroxymethyD-2, 5-dinitro-l, 6-

hexancdiol tetranitrate 132-134 18.75 16.80 12.5 12.2 21.44 23.5 2.69 3.8 2, 6-b1s (hydroxymethyD-2, fi-dinitro-l, 7- heptanedioltetranitrate .1 84-85 18.18 16.86 12.1 11.9 23.38 24.4 3.05 a.

2, 7-bis (hydroxymethyD-2, 7-dinitro-l, 8- octanediol tetranitrate 128 129 tetranitrate, 2,5-bis (hydroxymethyl) 2,5-dinitro-1,

6-hexanediol tetranitrate, 2,6-bis (hydroxymethyl) 2,6-dinitro-1,7-heptanediol tetranitrate, 2,7-bisdinitro tetrol to nitration in the liquid phase, utilizing as the nitrating agent a mixture of sulphuric and nitric acids. Generally the acid mixture employed usually consists of about five parts of sulphuric acid and three parts of nitric acid by weight. A quantity of the mixed acids, eight" times the weight of tetrol to be nitrated, is placed in a suitable reaction vessel which is immersed in ice. The tetrol is slowly added in portions to the acid mixture while agitating. After the entire amount of tetrol has been added in this manner, agitation is continued for a short time and there after the contents of the reaction vessel are poured into a large volume of ice water. The tetranitrate then separates as an insoluble product. Further purification of the material thus obtained may be effected by recrystallization from methanol or other suitable solvents.

The tetrols employed in preparing the compounds of the present invention are prepared in accordance with the procedure described in our tanediol tetranitrate.

While the above data may be of value'in the of these compounds will be apparent to those skilled in the art.

Our invention now having been described, what We claim is: 1 1. Aliphatic dinitro tetranitrates of the formu- 1T0: lTTOg O NOH2CC-(CHz)n-CCH2ONOz CHaONOz CHzONOz in which n represents an integer less than 5.

2. 2,5-bis(hydroxymethyl) 2,5-dinitro-l,6-hexanediol tetranitrate.

3. 2,6-lois (hydroxymethyl) 2,6-dinitro-L'7-heptanediol tetranitrate.

4. 2,7 bis(hydroxymethyl) 2,7 dinitro-1,8-oc- HENRY B. HASS. WILBUR R. MCELROY.

CERTIFICATE OF CORRECTION. Patent No; 2,581,u06 August 7, 19L

HENRY B. HASS, ET AL.

It is hereby certified that error appears in the printed specification of the above numberedpatent requiring correction as follows: Page 1, in the table under the heading "Percent hynil.rog=;en' for "5 read +5.8"; and that the said Letters Patent should be read with this eorrectiori therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 25th day of December, A. D. 19LL5.

Leslie Frazer (Seal) First Assistant Commissioner of Patents.

CERTIFICATE OF CORRECTION. Patent No. 2,581,uo6, August 7, 19L 5.

' HENRY s. HASS, ET AL.

, It is hereby certified that erroi' appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, in the tab1e, under the heading "Percent hydrogen' for "3 readr 5.8--; and that the saigL Letters Patent should be read with this correctiori therein that the same may conform to the record of the ease in the Patent Office.

Signed and sealed this 25th day of December, A. D. 1915.

Leslie Frazer (Seal) First Assistant Commissibner of Patents.