US3000928A - Polynitro nitrate compounds and method of preparation - Google Patents
Polynitro nitrate compounds and method of preparation Download PDFInfo
- Publication number
- US3000928A US3000928A US715988A US71598858A US3000928A US 3000928 A US3000928 A US 3000928A US 715988 A US715988 A US 715988A US 71598858 A US71598858 A US 71598858A US 3000928 A US3000928 A US 3000928A
- Authority
- US
- United States
- Prior art keywords
- preparation
- polynitro
- pentanitro
- undecane
- nitric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 7
- 150000002823 nitrates Chemical class 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 4
- -1 alkylene radical Chemical class 0.000 description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 239000002360 explosive Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BZMSHGYVEUFSEL-UHFFFAOYSA-N 4,4,6,6,8,8-hexanitroundecane-1,11-diol Chemical compound [N+](=O)([O-])C(CCCO)(CC(CC(CCCO)([N+](=O)[O-])[N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] BZMSHGYVEUFSEL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- MHWLNQBTOIYJJP-UHFFFAOYSA-N mercury difulminate Chemical compound [O-][N+]#C[Hg]C#[N+][O-] MHWLNQBTOIYJJP-UHFFFAOYSA-N 0.000 description 1
- XDBPKWWDUBMCPW-UHFFFAOYSA-N n,n-bis(4-hydroxy-2,2-dinitrobutyl)nitramide Chemical compound OCCC([N+]([O-])=O)([N+]([O-])=O)CN([N+]([O-])=O)CC([N+]([O-])=O)([N+]([O-])=O)CCO XDBPKWWDUBMCPW-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 102220095346 rs876658161 Human genes 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/40—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups and esterified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
Definitions
- This invention relates to new and useful polynitro nitrates and a method for their preparation. Inparticu lar it relates to aliphatic polynitro nitrates having the general formula: Y
- A is an alkylene radical and Z is a nitromethylene, dinitromethylene or nitramine radical.
- the nitro compounds of this invention are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge.
- An example of such a missile is disclosed in U.S. Patent No. 2,470,162, issued May 17, 1949.
- One way of using the high explosives in a device such as that disclosed in U.S. Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed.
- a charge thus prepared is sufficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure developed from ignition of a propellent charge, and can be caused to explode on operation of an impactor time-fuse mechanism firing a detonating explosive such as lead azide or mercury fulminate.
- nitro alcohols used as starting materials in this invention are readily prepared by the reduction of the corresponding acyl halides with sodium borohydride, as disclosed in assignees copending application No. 392,- 471, now abandoned, filed November 16, 1953.
- any member of the nitro-containing aliphatic nitrate series may be prepared by merely selecting the appropriate nitro-containing alcohol and reacting it with nitric acid, in accordance with the teachings of this invention.
- compositions of matter having the formula:
- A is a lower alkylene radical and Z is a radical selected from the group consisting of nitromethylene, dinitromethylene and nitramine radicals.
- A is a lower alkylene radical and Z is a member of a group consisting of nit'mmethylene, dinitrom'ethylene' and nitramine radicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
This invention relates to new and useful polynitro nitrates and a method for their preparation. Inparticu lar it relates to aliphatic polynitro nitrates having the general formula: Y
wherein A is an alkylene radical and Z is a nitromethylene, dinitromethylene or nitramine radical.
The nitro compounds of this invention are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge. An example of such a missile is disclosed in U.S. Patent No. 2,470,162, issued May 17, 1949. One way of using the high explosives in a device such as that disclosed in U.S. Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed. A charge thus prepared is sufficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure developed from ignition of a propellent charge, and can be caused to explode on operation of an impactor time-fuse mechanism firing a detonating explosive such as lead azide or mercury fulminate.
The compounds of this invention are readily prepared by reacting the corresponding alcohols with nitric acid, in accordance with the general reaction scheme set forth below:
wherein A and Z are as defined above.
The nitro alcohols used as starting materials in this invention are readily prepared by the reduction of the corresponding acyl halides with sodium borohydride, as disclosed in assignees copending application No. 392,- 471, now abandoned, filed November 16, 1953.
To more clearly illustrate this invention, the following examples are presented. It is to be understood, however, that these examples are presented merely as a means of illustration and are not intended to limit the scope of the invention in any way.
EXAMPLE I Preparation of 4,4,6,8,8-pentanitr-1,II-undecane dinitmte The solid 4,4,6,8,8-pentanitro-l,1l-undecanediol was added to a tenfold excess of 100% commercial nitric acid at ice-bath temperature. The acid solution was stirred for a period of 15 minutes at a temperature of about 5- l0 C. and then poured over ice. The white solid was collected, washed with water and dried in vacuum over potassium hydroxide. The product was recrystallized from methanol in 96.1% yield and exhibited a melting atent I l 3,000,920 Patented Sept. 19, 1961 ice point of 73-75 "7 C. 'I'heelemental analysis of the compound is as follows:
Calculated f0I C1 H17N 1O15Z C, 26.25%; H, 3.41%; N, 19.48%. Found: C, 26.79%; H, 3.64%; N, 19.18%.
- Prep tzrat iori of 4,4,6,6,8,8-hexiinitro-1,II-undecane di trate By reacting 4,4,6,6,8,8 hexanitro 1,11 -undecanediol with nitric acid in'accordance with'the procedure in Example I, 4,4,6,6,8,8-hexanitro-1,lleundecane dinitrate 1 having a melting point of 100l01 C. was obtained in 95.2% yield. The elemental analysis of the product is as follows:
Calculated for C11H18N3013: C, H, N, 20.44%. Found: C, 24.54%; H, 2.99%; N, 19.91%. The explosive values of the product were calculated to be:
Lead block value 138 T.N.T.=
Ballistic mortar value 143 T.-N.T.= 100 EXAMPLE III Preparation of 4,4,6,8,8-pentaititro-6-aza-1,II-undecane dinitrate By reacting 4,4,6,8,8-pentanitro-6-aza-1,1l-undecanediol with nitric acid in accordance with the procedure in Example I, 4,4,6,8,8-pentanitro-6-aza-1,1l-undecane di-. nitrate having a melting point of 133-135 C. was obtained in 95.0% yield. The elemental analysis of the product is as follows:
Calculated for C H N O C, 23.82%; H, 3.20%; N, 22.22%. Found: C, 23.88%; H, 2.96%; N, 22.15%. The explosive values of the product were calculated to be:
Lead block value 135 T.N.T.= 100 Ballistic mortar value 142 T.N.T.-=100 I have also'found that the homologues of the above compounds, namely, 3,3,5,5,7,7-hexanitro-1,9-nonanediol, 3,3,5,7,7-pentanitro-1,9-nonanediol and 3,3,5,7,7-pentanitro-5-aza-1,9-nonanediol also react with nitric acid forming the nitrate esters 3,3,5,5,7,7-hexanitro-l,9-nonane dinitrate, 3,3,5,7,7-pentanitro-1,9-nonane dinitrate, and 3,3,5,7,7-pentanitro-5-aza-1,9-nonane dinitrate.
It is apparent that any member of the nitro-containing aliphatic nitrate series may be prepared by merely selecting the appropriate nitro-containing alcohol and reacting it with nitric acid, in accordance with the teachings of this invention.
This application is a continuation-in-part of my copending U.S. Patent Application Ser. No. 409,263, now abandoned, filed February 9, 1954.
I claim:
1 As compositions of matter, the aliphatic polynitronitrates having the formula:
wherein A is a lower alkylene radical and Z is a radical selected from the group consisting of nitromethylene, dinitromethylene and nitramine radicals.
2. As a composition of matter, 4,4,6,8,8-pentanitro-1, 11-undecane dinitrate having the structural formula:
0 11001 If): ITIO; N Or-CHzCHzCHa-C-CHr-CH-CHz-Ei-CHaCHaCHrN 03 N O: NO:
. t V 3 3. As a composition of matter, 4,4,6,6,8,8-hexanitro- 1",1'1'undecane' dinit'rate having the structural formula:
4. As acomposition of matter, 4,4,6,8-,8-pehtani;tro-6- aza-1,-1l-undecane dinitrate having the structural formula:
I 5. The method-0f preparingaliphatic polynitronitrates having the formula:
which comprises reacting nitric acid with a nitro-confai'nin'g'dioi havirig the formula:
wherein A is a lower alkylene radical and Z is a member of a group consisting of nit'mmethylene, dinitrom'ethylene' and nitramine radicals.
6. The method of. preparing 4,4,6,8,8pentanitro-I,11- undeca'n'e dinitra'te which comprises reacting 4,4,6,8,8- pentanitro-1,1l-undecariediol with nitric acid.
7. The method of preparing- 4,4,6 6,8,8-hexanitro=1',11- undecane dinitra-te which comprises reacting 4,4,6,6,8,8- hexanitro-Ll l-undecanediol ;withnitric acid.
8. The method of preparing 4,4,6,8,8-pentanitro-6 aza- 1,11-undecane dinitrate which comprises reacting 4,4,6,8, 8-pentanitro-6-aza-Lll-undecanediol with nitric acid.
No references cited.
Claims (1)
1. AS COMPOSITIONS OF MATTER, THE ALIPHATIC POLYNITRONITRATES HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US715988A US3000928A (en) | 1958-02-18 | 1958-02-18 | Polynitro nitrate compounds and method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US715988A US3000928A (en) | 1958-02-18 | 1958-02-18 | Polynitro nitrate compounds and method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3000928A true US3000928A (en) | 1961-09-19 |
Family
ID=24876271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US715988A Expired - Lifetime US3000928A (en) | 1958-02-18 | 1958-02-18 | Polynitro nitrate compounds and method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3000928A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010640A1 (en) * | 1990-01-17 | 1991-07-25 | Atlas Powder Company | Nitrate ester preparation |
-
1958
- 1958-02-18 US US715988A patent/US3000928A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991010640A1 (en) * | 1990-01-17 | 1991-07-25 | Atlas Powder Company | Nitrate ester preparation |
| US5089652A (en) * | 1990-01-17 | 1992-02-18 | Atlas Powder Company | Nitrate ester preparation |
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