US3041382A - Method of preparing 2, 2, 4, 4-tetranitro-1, 5-pentanediol - Google Patents
Method of preparing 2, 2, 4, 4-tetranitro-1, 5-pentanediol Download PDFInfo
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- US3041382A US3041382A US662550A US66255057A US3041382A US 3041382 A US3041382 A US 3041382A US 662550 A US662550 A US 662550A US 66255057 A US66255057 A US 66255057A US 3041382 A US3041382 A US 3041382A
- Authority
- US
- United States
- Prior art keywords
- tetranitro
- pentanediol
- preparing
- formaldehyde
- salt
- 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
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- 238000000034 method Methods 0.000 title claims description 11
- JWECTHAYJISSCX-UHFFFAOYSA-N 2,2,4,4-tetranitropentane-1,5-diol Chemical compound OCC([N+]([O-])=O)([N+]([O-])=O)CC(CO)([N+]([O-])=O)[N+]([O-])=O JWECTHAYJISSCX-UHFFFAOYSA-N 0.000 title claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- RQDCCDCSDZMLKK-UHFFFAOYSA-N 2,2,4,4-tetranitrobutan-1-ol Chemical class [N+](=O)([O-])C(CO)(CC([N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] RQDCCDCSDZMLKK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- AJHXPGZHSCGGIP-UHFFFAOYSA-N 1,1,3,3-tetranitropropane Chemical class [O-][N+](=O)C([N+]([O-])=O)CC([N+]([O-])=O)[N+]([O-])=O AJHXPGZHSCGGIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002360 explosive Substances 0.000 description 6
- 229940043375 1,5-pentanediol Drugs 0.000 description 5
- -1 3,3,3-trinitropropyl amine Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PFHGNIMWELIXGP-UHFFFAOYSA-N 1-nitropiperidine Chemical class [O-][N+](=O)N1CCCCC1 PFHGNIMWELIXGP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QMJDKPFQFHNFKQ-UHFFFAOYSA-N 1-nitropentane-1,5-diol Chemical compound OCCCCC(O)[N+]([O-])=O QMJDKPFQFHNFKQ-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- VIEWPDYJCCPAFZ-UHFFFAOYSA-N [N+](=O)([O-])C(CO)(CC([N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-].[K] Chemical compound [N+](=O)([O-])C(CO)(CC([N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-].[K] VIEWPDYJCCPAFZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting 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
- 239000000203 mixture Substances 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Definitions
- 2,2,4,4-tetranitro-l,S-pentanediol can be prepared con- 3,041,382 Patented June 2 5, 1962 3 C. and then continued for two hours at room temperature. The solution was then filtered and the filtrate extracted with ether. The ether extracts were dried and the ether distilled ofi under reduced pressure leaving 5 behind an oil which soon crystallized. The mush mixpure material.
- M is an alkali or alkaline earth metal or ammonia.
- 2,2,4,4-tetranitro-1,S-pentanediol readily reacts with nitro-substituted amines, such as 3,3,3-trinitropropyl amine, to form nitroalkyl substituted tetranitropiperidine compounds as disclosed in assignees, copending U.S. patent application Ser. No. 628,949, filed December 12, 1956, now U.S. Patent No. 2,978,453.
- the nitropiperidine compounds thus prepared are excellent 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 nitro piperidine 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 propellant 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.
- any salt of the alkali metal or alkaline earth metal salts such as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as sodium, potassium, lithium, cesium, magnesium, calcium, etc.
- Potassium is the preferred salt due to its solubility characteristics which permit greater ease in separation of the product from the reaction mass.
- the reaction proceeds in accordance with Example I, differing only in the selection of the starting material.
- the starting materials can be conveniently prepared according to the methods disclosed in assignees copending application No. 371,149, filed July 29, 1953, now abandoned.
- the method of preparing 2,2,4,4-tetranitro-1,5- pentanediol which comprises reacting a compound selected from the group consisting of alkaline earth metal, alkali metal, and ammonium salts of 2,2,4,4-tetranitro 'butanol and di-alkaline earth metal, di-alkali metal, and di-ammonium salts of 1, l,3,3-tetranitropropane with a member of the group consisting of formaldehyde and formalin in acid media and subsequently recovering 2,2,4,4-tetranitro-1,5-pentanediol.
- K 2 The method of preparing 2,2,4,4-tetranitropentanediol which comprises reaction an alkali metal salt of 2,2, 4,4-tetranitrobutanol with formaldehyde in acid media, and subsequently recovering 2,2,4,4-tetranitro-1,5-pen- 45 tanediol.
- a method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting the potassium salt of 2,2,4,4-tetrauitrobutanol with one equivalent of formaldehyde in acid media and subsequently recovering 2,2,4,4-
- a method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting the ammonium salt of 2,2,4,4-tetranitrobutanol with one equivalent of formaldehyde in acid media and subsequently recovering 2,2,
- a method of preparing 2,2,4,4-tetranitro-l,5,-pen- UNITE STATES PATENTS tanediol which comprises reacting the di-ammdnium salt 25227959 Plant P 1950 of 1,1,3,3-tetranitropropane with two equivalents of form- 5 aldehyde in acid media and subsequently recovering 2,2, FOREIGN PATENTS 4,4-tetranitro 1,5-pentanediol. V 138,456 Sweden Dec. 23, 1952
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
This application is a continuation-in-part of our copending U.S. patent application Ser. No. 371,150, filed July 29, 1953, now abandoned.
2,2,4,4-tetranitro-l,S-pentanediol can be prepared con- 3,041,382 Patented June 2 5, 1962 3 C. and then continued for two hours at room temperature. The solution was then filtered and the filtrate extracted with ether. The ether extracts were dried and the ether distilled ofi under reduced pressure leaving 5 behind an oil which soon crystallized. The mush mixpure material.
veniently according to either of the general reaction 1 schemes set forth below wherein M is an alkali or alkaline earth metal or ammonia.
Preparation 1 The mono-salt of 2,2,4,4-tetranitrobutauol is reacted with one equivalent of formaldehyde in acid media to yield the tetranitropentanediol.
Preparation II No. No, No, No, ll 11 201120 oorr,-o 2 M+) F HO CHr-CCHrCCHiOH No2 No, N03 N02 The di-salt of tetranitropropane is reacted with two equivalents of formaldehyde in acid media to yield the tetranitropentanediol.
2,2,4,4-tetranitro-1,S-pentanediol readily reacts with nitro-substituted amines, such as 3,3,3-trinitropropyl amine, to form nitroalkyl substituted tetranitropiperidine compounds as disclosed in assignees, copending U.S. patent application Ser. No. 628,949, filed December 12, 1956, now U.S. Patent No. 2,978,453.
The nitropiperidine compounds thus prepared are excellent 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 nitro piperidine 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 propellant 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 following example is provided to more clearly illustrate our invention. This example is presented purely as a means of illustration and does not in any way define either the limits or the scope of our invention.
EXAMPLE I.PREPARATION OF 2,2,4,4-' TETRANITRO-LEi-PENTANEDIOL 16 grams (0.0438 M.) of damp potassium 2,2,4,4- tetranitrobutanol were placed in a 300 ml. flask with 109 ml. of distilled water in 3.75 ml. (0.0505 M.) of formalin. The mixture was then cooled to 3 C. and 13 ml. of 30% sulphuric acid were added dropwise with stirring. The stirring was continued for 30 minutes at ture weighed 9.3 gm. Recrystallization from 150 ml. chloroform yielded 3.0 gm. of pure diol, melting point 9799 C. Evaporation of the filtrate to ml. with chilling produced an additional 1.1 gm. of somewhat less Total yield was 33% of the theoretical yield.
In the preparation of the diol, any salt of the alkali metal or alkaline earth metal salts such as sodium, potassium, lithium, cesium, magnesium, calcium, etc., as
15 well as the ammonium salts are found to be suitable.
1,5-pentanediol.
Potassium is the preferred salt due to its solubility characteristics which permit greater ease in separation of the product from the reaction mass. The reaction proceeds in accordance with Example I, differing only in the selection of the starting material.
Similarly when the starting material utilized is the disalt 'of tetranitropropane, the reaction proceeds in the manner described in Example I, except that two equivalents of formaldehyde are added in place of one in order to effect complete alcoholation.
The starting materials can be conveniently prepared according to the methods disclosed in assignees copending application No. 371,149, filed July 29, 1953, now abandoned.
We claim:
1. The method of preparing 2,2,4,4-tetranitro-1,5- pentanediol which comprises reacting a compound selected from the group consisting of alkaline earth metal, alkali metal, and ammonium salts of 2,2,4,4-tetranitro 'butanol and di-alkaline earth metal, di-alkali metal, and di-ammonium salts of 1, l,3,3-tetranitropropane with a member of the group consisting of formaldehyde and formalin in acid media and subsequently recovering 2,2,4,4-tetranitro-1,5-pentanediol.
K 2. The method of preparing 2,2,4,4-tetranitropentanediol which comprises reaction an alkali metal salt of 2,2, 4,4-tetranitrobutanol with formaldehyde in acid media, and subsequently recovering 2,2,4,4-tetranitro-1,5-pen- 45 tanediol.
3. The method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting an alkaline earth metal salt of 2,2,4,4-tetranitrobutanol with formaldehyde in acid media and subsequently recovering 2,2,4,4-tetranitro- 4. The method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting a di-alkali metal salt of l,1,3,3-tetranitropropane with formaldehyde in acid media and subsequently recovering 2,2,4,4-tetranitro-1,5-
pentanediol.
nitro-1,5-pentanediol.
6. A method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting the potassium salt of 2,2,4,4-tetrauitrobutanol with one equivalent of formaldehyde in acid media and subsequently recovering 2,2,4,4-
tetranitro-1,5-pentanediol.
7. A method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting the ammonium salt of 2,2,4,4-tetranitrobutanol with one equivalent of formaldehyde in acid media and subsequently recovering 2,2,
4,4-tetranitro-1,5-pentanediol.
'8. A method of preparing 2,2,4,4-tetranitro-1,5-pentanediol which comprises reacting the di-potassium salt of l,1,3,3-tetranitropropane with two equivalents of form- .3 4 aldehyde in.:acid media and subsequently reeovering 2,2, References Cited in the file of this patent 4,4-tetranitro-1,5-pentanediol. v D
9. A method of preparing 2,2,4,4-tetranitro-l,5,-pen- UNITE STATES PATENTS tanediol which comprises reacting the di-ammdnium salt 25227959 Plant P 1950 of 1,1,3,3-tetranitropropane with two equivalents of form- 5 aldehyde in acid media and subsequently recovering 2,2, FOREIGN PATENTS 4,4-tetranitro 1,5-pentanediol. V 138,456 Sweden Dec. 23, 1952
Claims (1)
1. THE METHOD OF PREPARING 2,2,4,4-TETRANITRO-1,5PENTANEDIOL WHICH COMPRISES REACTING A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALKALINE EARTH METAL, ALKALI METAL, AND AMMONIUM SALTS OF 2,2,4,4-TETRANITROBUTANOL AND DI-ALKALINE EARTH METAL, DI-ALKALI METAL, AND DI-AMMONIUM SALTS OF 1,1,3,3-TETRANITROPROPANE WITH A MEMBER OF THE GROUP CONSISTING OF FORMALDEHYDE AND FORMALIN IN ACID MEDIA AND SUBSEQUENTLY RECOVERING 2,2,4,4-TETRANITRO-1,5-PENTANEDIOL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US662550A US3041382A (en) | 1957-05-29 | 1957-05-29 | Method of preparing 2, 2, 4, 4-tetranitro-1, 5-pentanediol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US662550A US3041382A (en) | 1957-05-29 | 1957-05-29 | Method of preparing 2, 2, 4, 4-tetranitro-1, 5-pentanediol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3041382A true US3041382A (en) | 1962-06-26 |
Family
ID=24658171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US662550A Expired - Lifetime US3041382A (en) | 1957-05-29 | 1957-05-29 | Method of preparing 2, 2, 4, 4-tetranitro-1, 5-pentanediol |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3041382A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011118462B4 (en) | 2011-11-14 | 2021-07-22 | Maximilian Born | Energetic polymers as reactive structural materials for use in weapon systems |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2522959A (en) * | 1949-01-22 | 1950-09-19 | Aerojet Engineering Corp | 2, 2-dinitro-1, 3-propanediol and method of preparing same |
-
1957
- 1957-05-29 US US662550A patent/US3041382A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2522959A (en) * | 1949-01-22 | 1950-09-19 | Aerojet Engineering Corp | 2, 2-dinitro-1, 3-propanediol and method of preparing same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011118462B4 (en) | 2011-11-14 | 2021-07-22 | Maximilian Born | Energetic polymers as reactive structural materials for use in weapon systems |
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