Synthesis of 1,3,5-trinitro-1,3,5-triazacyclohexane (USH0000447)
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Del.icio.us| IP.com Number | IPCOM000000443D |
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| Dated | Mar 1, 1988 UTC | ||
| Size | 2 page(s) (308.1 KB) | ||
| Disclosed by |
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Publication Summary
A process of preparing 1,3,5-trinitro-1,3,5-triazacyclohexane of high teccal purity by a one-step direct liquid nitrolysis of hexamethylenetetramine with dinitrogen pentoxide in 100% nitric acid under a separate chlorinated hydrocarbon phase.| Country | United States |
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| Language | English (United States) |
| Related Person(s) |
(OWNER) The United States of America as represented by the Secretary of the Navy (INVENTOR) Fischer, John W. (INVENTOR) Atkins, Ronald L. (ATTORNEY) Townsend, William C. (ATTORNEY) Skeer, W. Thom |
| Related Document(s) |
(PATENT) USH000447
(PATENT) US02355770 (PATENT) US02398080 (PATAPP) US07/024437 |
About this Publication
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United States Patent |
USH0000447 |
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Fischer , et al. |
March 1, 1988 |
Synthesis of 1,3,5-trinitro-1,3,5-triazacyclohexane
Abstract
A process of preparing 1,3,5-trinitro-1,3,5-triazacyclohexane of high teccal purity by a one-step direct liquid nitrolysis of hexamethylenetetramine with dinitrogen pentoxide in 100% nitric acid under a separate chlorinated hydrocarbon phase.
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Inventors: |
Fischer; John W. (Ridgecrest, CA), Atkins; Ronald L. (Ridgecrest, CA) |
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Assignee: |
The United States of America as represented by the Secretary of the Navy (Washington, DC) |
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Appl. No.: |
07/024,437 |
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Filed: |
March 11, 1987 |
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Current U.S. Class: |
544/180 |
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Current International Class: |
C07D 251/00 (20060101); C07D 251/06 (20060101); C07D 251/06 () |
References Cited
U.S. Patent Documents
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2355770 |
August 1944 |
Wyler |
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2398080 |
April 1946 |
Caesar |
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Primary Examiner: Miller; Edward A.
Assistant Examiner: Wolffe; Susan
Attorney, Agent or Firm:
Townsend; William C. Skeer; W. Thom
Claims
What is claimed is:
1. A process of preparing pure 1,3,5-trinitro-1,3,5-triaza cyclohexane having
the step of reacting hexamethylenetetramine with dinitrogen pentoxide as a
primary nitrating agent, the improvement comprising the steps of:
dissolving dinitrogen pentoxide in 100% nitric acid to form a nitrating
solution;
contacting said nitrating solution with hexamethylenetetramine under nitrating
conditions;
neutralizing said mixture with sodium bicarbonate and extracting said product
with a suitable solvent; and
removing said solvent and isolating pure
1,3,5-trinitro-1,3,5-triazacyclohexane.
2. A process as in claim 1 wherein said nitrating solution comprises about 25%
by weight dinitrogen pentoxide in 100% nitric acid.
3. A process as in claim 1 wherein contacting of said nitrating solution with
hexamethylenetetramine comprises stirring said hexamethylenetetramine into said
nitrating solution kept at -20.degree. C. under a separate CCl4 phase.
4. A process as in claim 1 wherein said solvent for extracting said product is
ethyl acetate.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a method of preparing pure
1,3,5-trinitro-1,3,5-triazacyclohexane by the direct liquid phase nitration of
hexamethylenetetramine.
2. Description of the Prior Art
1,3,5-trinitro-1,3,5-triazacyclohexane is currently prepared by a two-step
procedure known in the art as the Bachman process. In this process, a mixture
of ammonium nitrate and hexamine nitrate is added to a solution of nitric acid
in acetic anhydride. While the product yield is about 70%, the intermediates
and the final product contain about 10% of the contaminant
1,3,5,7-tetraaza-1,3,5,7-tetranitrocyclooctane. Further purification steps are
required to reduce the presence of the contaminant to acceptable levels. These
purification steps diminish the final yield of
1,3,5-trinitro-1,3,5-triazacyclohexane.
It is also known to prepare 1,3,5-trinitro-1,3,5-triazacyclohexane by direct
liquid n...