US3288867A - Stable nitromethane composition - Google Patents
Stable nitromethane composition Download PDFInfo
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- US3288867A US3288867A US433519A US43351965A US3288867A US 3288867 A US3288867 A US 3288867A US 433519 A US433519 A US 433519A US 43351965 A US43351965 A US 43351965A US 3288867 A US3288867 A US 3288867A
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- Prior art keywords
- weight
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- stabilizing amount
- stabilizing
- nitromethane
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- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 title claims description 16
- 239000000203 mixture Substances 0.000 title claims description 14
- 230000000087 stabilizing effect Effects 0.000 claims description 54
- 239000007788 liquid Substances 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- 230000035939 shock Effects 0.000 claims description 9
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 6
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 claims description 4
- 238000005474 detonation Methods 0.000 claims description 3
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002360 explosive Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- -1 l-nitropropane Chemical compound 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 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
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
- C06B23/005—Desensitisers, phlegmatisers
-
- 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
- C06B25/36—Compositions containing a nitrated organic compound the compound being a nitroparaffin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/02—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of a saturated carbon skeleton
Definitions
- a combination of nitromethane and a specific minimum amount of a stabilizing liquid selected from the group consisting of acetone, toluene, benzene, 1,2-butylene oxide, cyclohexanone, 1,4- dioxane, l-nitropropane, methanol Z-nitropropane, methylene chloride, methyl chloroform, and nitroethane are stable to extreme shock and provide a safe method for bulk transportation of nitromethane.
- liquid combinations of this invention have the following compositions:
- Combinations containing at least the minimum volume of stabilizer are not detonated when confined in a heavywalled vessel and subjected to severe shock.
- a special test which will subsequently be described in detail has been devised to measure the degree of stability of chemicals which do not detonate in any of the tests previously used.
- the new test has been devised to measure the amount of energy released when a material which cannot be detonated is subjected to severe shock
- a solid cylinder of cold rolled steel having a diameter of 5 inches and a length of 6 inches
- a hole 1 inch in diameter and 4 inches in depth having the same axis as the cylinder.
- the face of the cylinder is grooved by a single radial cut Ms inch wide and inch deep.
- the opening of the hole is covered with a 5 lb. test weight cut from .a cylindrical steel rod having a diameter of approximately 2% inches. It length will be about 3 inches.
- the cylinder is placed on an unyielding support at the foot of a perpendicular measuring board 20 ft. high marked in 1 it. increments.
- a liquid sample size of 4 milliliters is delivered to a test tube 13 x 100 mm. and placed in the hole bored in the cylinder.
- a No. 8 electric dynamite cap is placed in the test tube with sample and the lead wires are placed in the groove cut in the face of the cylinder.
- the test weight is centered over the hole, the cap is fired, and the height to which the weight is flung by the energy released is observed visually. Five determinations are made for each test substance. Data are given in Table 1 showing the results obtained on a number of commercial materials.
- Example 1 Commercial grade toluene 21 g. and nitromethane 79 g. were mixed. A 4 ml. sample was tested according to the described method. The weight was flung to an average height of 13 feet in five trials and the combination was adjudged stable for bulk transportation.
- Examples 2-12 In a manner similar to Example 1, other combinations of nitromethane and stabilizing amounts of a second component were tested. The weights were flung to an average height of no more than 13 feet and the combinations were adjudged safe for shipment.
- a liquid composition having improved stability to detonation by shock comprising liquid nitromethane .and a stabilizing amount of a stabilizing liquid, said stabilizing amount and said stabilizing liquid being:
- composition of claim 1 wherein the stabilizing liquid is toluene in a stabilizing amount of not less than 21% by weight.
- composition of claim 1 wherein the stabilizing liquid is benZene in a stabilizing amount of not less than 24% by Weight.
- composition of claim 1 wherein the stabilizing liquid is acetone in a stabilizing amount of not less than 24% by weight.
- composition of claim 1 wherein the stabilizing liquid is cyclohexanone in a stabilizing amount of not less than 23% by weight.
- composition of claim 1 wherein the stabilizing liquid is l-nitropropane in a stabilizing amount of not less 0 than 31% by weight.
- composition of claim 1 wherein the stabilizing liquid is 2-nitropropane in a stabilizing amount of not less than 45% by weight.
- composition of claim 1 wherein the stabilizing liquid is methylene chloride in a stabilizing amount of not less than 42% by weight.
- composition of claim 1 wherein the stabilizing liquid is methyl chloroform in a stabilizing amount of not less than 50% by weight.
- a method for the stabilization of bulk quantities of liquid nitromethane to detonation by shock comprising adding to the liquid nitromethane a stabilizing amount of a stabilizing liquid, said stabilizing amount and said stabilizing liquid being:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,2$8,867 STABLE NITRGMETHANE CGMPOSITION Richard S. Egly, West Terre Haute, and Quentin R.
.leftries, Torre Hante, Ind, assignors to Commercial Solvents Corporation, New York, N.Y., a corporation of Maryland No Drawing. Filed Feb. 17, 1965, Ser. No. 433,519 Claims. (Cl. 260-644) confined in a heavy-walled vessel which Will Withstand the development of considerable internal pressure. An embargo is presently in existence on shipment of nitromethane in bulk containers by both the manufacturer and the Interstate Commerce Commission. The ordinary drum meeting ICC Specification 17E ruptures at low pressures and nitromethane is regularly shipped in this container with a layer of nitrogen in the head space to replace the air. This method of transportation, however, has resulted in financial hardship for the user and has in general restricted the use of nitromethane in many applications where it would be of considerable technical value.
It is an object of this invention to provide stable com ositions of nitromethane. It is another object of this invention to provide compositions of nitromethane having improved stability for bulk transportation. Another object is to provide a method of bulk transportation of nitromethane.
It has been discovered that a combination of nitromethane and a specific minimum amount of a stabilizing liquid selected from the group consisting of acetone, toluene, benzene, 1,2-butylene oxide, cyclohexanone, 1,4- dioxane, l-nitropropane, methanol Z-nitropropane, methylene chloride, methyl chloroform, and nitroethane are stable to extreme shock and provide a safe method for bulk transportation of nitromethane.
More particularly the liquid combinations of this invention have the following compositions:
Combinations containing at least the minimum volume of stabilizer are not detonated when confined in a heavywalled vessel and subjected to severe shock. A special test which will subsequently be described in detail has been devised to measure the degree of stability of chemicals which do not detonate in any of the tests previously used.
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The combinations of this invention provide a variation of properties so that a particular combination usually can be used directly without separation into the components. However, if separation is desirable, means for so doing can be readily devised by those skilled in the art.
The common tests employed to determine Whether or not a substance should be placed in the explosive category do not yield useful information on non-explosives. Many substances will exhibit energy release when subjected to sources of high energy such as the shock wave of a detonated high explosive, heat, a combination of heat and shock at ambient pressure, a combination of heat and shock'at elevated pressure, or adiabatic compression.
The new test has been devised to measure the amount of energy released when a material which cannot be detonated is subjected to severe shock Into a solid cylinder of cold rolled steel having a diameter of 5 inches and a length of 6 inches, is drilled a hole 1 inch in diameter and 4 inches in depth having the same axis as the cylinder. The face of the cylinder is grooved by a single radial cut Ms inch wide and inch deep. In use, the opening of the hole is covered with a 5 lb. test weight cut from .a cylindrical steel rod having a diameter of approximately 2% inches. It length will be about 3 inches.
To conduct the test, the cylinder is placed on an unyielding support at the foot of a perpendicular measuring board 20 ft. high marked in 1 it. increments. A liquid sample size of 4 milliliters is delivered to a test tube 13 x 100 mm. and placed in the hole bored in the cylinder. A No. 8 electric dynamite cap is placed in the test tube with sample and the lead wires are placed in the groove cut in the face of the cylinder. The test weight is centered over the hole, the cap is fired, and the height to which the weight is flung by the energy released is observed visually. Five determinations are made for each test substance. Data are given in Table 1 showing the results obtained on a number of commercial materials.
TABLE 1 Chemical Quantity, ml. Height, ft.
Nitromcthane 4. O 48 Hydrogen peroxide, 4. 0 39 Hydrazine 4. 0 39 Ethylene oxide... 4. (l 10 1.3-butadiene 4. (J 4 4. O 5 Bntylene oxide 4. 0 5 Cyclohexanone 4. O 4 Dioxane 4. (l 5 l'nitropropane 4. (l 8 2-nitropropane 4. 0 7 Methanol 4. 0 5 Methylene chloride 4. 0 l2 Methyl chloroform 4. 0 6 Nitroethaneun. 4. 0 11 Acetone 4. 0 6
Hydrogen peroxide 90% and hydrazine released sufficient energy in this test to hurl the weight to a height of 39 feet yet they are shipped regularly in tank cars and tank trucks without special regulation. T-his basis of experience is the support for the definition of stabilized nitromethane as that combination which releases no more energy in the special test described than does 90% hydrogen peroxide or hydrazine. However, as an added safety measure for transportation purposes the rule has been adopted that stable nitromethane combinations safe for shipment in bulk are those that yield an average test height no greater than 13 feet when tested as described.
The practice of this invention is further illustrated by the following examples:
Example 1 Commercial grade toluene 21 g. and nitromethane 79 g. were mixed. A 4 ml. sample was tested according to the described method. The weight was flung to an average height of 13 feet in five trials and the combination was adjudged stable for bulk transportation.
Examples 2-12 In a manner similar to Example 1, other combinations of nitromethane and stabilizing amounts of a second component were tested. The weights were flung to an average height of no more than 13 feet and the combinations were adjudged safe for shipment.
COMPOSITION OF C OMBINATTONS Having described this invention, what is claimed is: 1. In combination, a liquid composition having improved stability to detonation by shock comprising liquid nitromethane .and a stabilizing amount of a stabilizing liquid, said stabilizing amount and said stabilizing liquid being:
(a) toluene in a stabilizing amount of not less than 21% by Weight,
(b) benzene in a stabilizing amount of not less than 24% by Weight,
(c) acetone in .a stabilizing amount of not less than 24% by weight,
(d) cyclohexanone in a stabilizing amount of not less than 23% by weight,
(e) l-nitropropane in a stabilizing amount of not less than 31% by weight,
(f) 2-nitropropane in a stabilizing amount of not less than 45% by weight, g) methylene chloride in a stabilizing amount of not less than 42% by weight, or
(h) methyl chloroform in a stabilizing amount of not less than 50% by weight.
2. The composition of claim 1 wherein the stabilizing liquid is toluene in a stabilizing amount of not less than 21% by weight.
3. The composition of claim 1 wherein the stabilizing liquid is benZene in a stabilizing amount of not less than 24% by Weight.
4. The composition of claim 1 wherein the stabilizing liquid is acetone in a stabilizing amount of not less than 24% by weight.
5. The composition of claim 1 wherein the stabilizing liquid is cyclohexanone in a stabilizing amount of not less than 23% by weight.
6. The composition of claim 1 wherein the stabilizing liquid is l-nitropropane in a stabilizing amount of not less 0 than 31% by weight.
7. The composition of claim 1 wherein the stabilizing liquid is 2-nitropropane in a stabilizing amount of not less than 45% by weight.
8. The composition of claim 1 wherein the stabilizing liquid is methylene chloride in a stabilizing amount of not less than 42% by weight.
9. The composition of claim 1 wherein the stabilizing liquid is methyl chloroform in a stabilizing amount of not less than 50% by weight.
10. A method for the stabilization of bulk quantities of liquid nitromethane to detonation by shock comprising adding to the liquid nitromethane a stabilizing amount of a stabilizing liquid, said stabilizing amount and said stabilizing liquid being:
(a) toluene in a stabilizing amount of not less than 21% by weight,
(b) benzene in a stabilizing amount of not less than 24% by weight,
(c) acetone in a stabilizing amount of not less than 24% by weight,
(d) cyclohexanone in a stabilizing amount of not less than 23% by weight,
(e) l-nitropropane in a stabilizing amount of not less than 31% by weight,
(f) Z-nitropropane in a stabilizing amount of not less than 45 by weight,
(g) methylene chloride in a stabilizing amount of not less than 42% by weight, or
(h) methyl chloroform in a stabilizing amount of not less than 50% by weight.
References Cited by the Examiner UNITED STATES PATENTS 2,433,943 1/1948 Zwicky et al. L
2,673,793 4/1954 Brodhacker l49--9O 2,809,884 10/1957 Ratje 260-644 3,043,099 7/ 1962 Wilson 14989 X OTHER REFERENCES Bottomley et al., Australian J. Chem., vol. 16, pp. 16 (1963). V
BENJAMIN R. PADGE'IT, Primary Examiner.
CARL D. QUARFORTH, LEON D. ROSDOL,
Examiners.
A, SEBASTIAN, Assistant Examiner.
Claims (1)
1. IN COMBINATION, A LIQUID COMPOSITION HAVING IMPROVED STABILITY TO DETONATION BY SHOCK COMPRISING LIQUID NITROMETHANE AND A STABILIZING AMOUNT OF A STABILIZING LIQUID, SAID STABILIZING AMOUNT AND SAID STABILIZING LIQUID BEING: (A) TOLUNE IN A STABILIZING AMOUNT OF NOT LESS THAN 21% BY WEIGHT, (B) BENZENE IN A STABILIZING AMOUNT OF NOT LESS THAN 24% BY WEIGHT, (C) ACETONE IN A STABILIZING AMOUNT OF NOT LESS THAN 24% BY WEIGHT, (D) CYCLOHEXANONE IN A STABILIZING AMOUNT OF NOT LESS THAN 23% BY WEIGHT, (E) 1-NITROPROPANE IN A STABILIZING AMOUNT OF NOT LESS THAN 31% BY WEIGHT, (F) 2-NITROPROPANE IN A STABILIZING AMOUNT OF NOT LESS THAN 45% BY WEIGHT, (G) METHYLENE CHLORIDE IN A STABILIZING AMOUNT OF NOT LESS THAN 42% BY WEIGHT, OR (H) METHYL CHLOROFORM IN A STABILIZING AMOUNT OF NOT LESS THAN 50% BY WEIGHT.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US433519A US3288867A (en) | 1965-02-17 | 1965-02-17 | Stable nitromethane composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US433519A US3288867A (en) | 1965-02-17 | 1965-02-17 | Stable nitromethane composition |
Publications (1)
Publication Number | Publication Date |
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US3288867A true US3288867A (en) | 1966-11-29 |
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US433519A Expired - Lifetime US3288867A (en) | 1965-02-17 | 1965-02-17 | Stable nitromethane composition |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3318741A (en) * | 1965-04-08 | 1967-05-09 | Commercial Solvents Corp | Thickened nitroparaffin containing stabilizer |
US3383252A (en) * | 1967-03-13 | 1968-05-14 | Commercial Solvents Corp | Nitro-paraffins thickened with nu-cocohydroxybutyramide |
US3722410A (en) * | 1970-10-08 | 1973-03-27 | Kinetics Int Corp | Method of petonating an ammonium nitrate-fuel oil composition with a number 6 cap |
US3798092A (en) * | 1972-08-25 | 1974-03-19 | Commerical Solvents Corp | Low-temperature liquid explosive composition |
US3915768A (en) * | 1973-08-01 | 1975-10-28 | Commercial Solvents Corp | Sensitized nitromethane |
US4892597A (en) * | 1989-08-30 | 1990-01-09 | The United States Of America As Represented By The Secretary Of The Army | Dissolved trinitrotoluene in sensitized nitromethane |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2433943A (en) * | 1944-03-11 | 1948-01-06 | Aerojet Engineering Corp | Operation of jet propulsion motors with nitroparaffin |
US2673793A (en) * | 1950-02-03 | 1954-03-30 | Commercial Solvents Corp | Model engine fuel |
US2809884A (en) * | 1954-09-16 | 1957-10-15 | Phillips Petroleum Co | Apparatus for separation by crystallization |
US3043099A (en) * | 1955-02-14 | 1962-07-10 | Aerojetgeneral Corp | Monopropellant fuel |
-
1965
- 1965-02-17 US US433519A patent/US3288867A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2433943A (en) * | 1944-03-11 | 1948-01-06 | Aerojet Engineering Corp | Operation of jet propulsion motors with nitroparaffin |
US2673793A (en) * | 1950-02-03 | 1954-03-30 | Commercial Solvents Corp | Model engine fuel |
US2809884A (en) * | 1954-09-16 | 1957-10-15 | Phillips Petroleum Co | Apparatus for separation by crystallization |
US3043099A (en) * | 1955-02-14 | 1962-07-10 | Aerojetgeneral Corp | Monopropellant fuel |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3318741A (en) * | 1965-04-08 | 1967-05-09 | Commercial Solvents Corp | Thickened nitroparaffin containing stabilizer |
US3383252A (en) * | 1967-03-13 | 1968-05-14 | Commercial Solvents Corp | Nitro-paraffins thickened with nu-cocohydroxybutyramide |
US3722410A (en) * | 1970-10-08 | 1973-03-27 | Kinetics Int Corp | Method of petonating an ammonium nitrate-fuel oil composition with a number 6 cap |
US3798092A (en) * | 1972-08-25 | 1974-03-19 | Commerical Solvents Corp | Low-temperature liquid explosive composition |
US3915768A (en) * | 1973-08-01 | 1975-10-28 | Commercial Solvents Corp | Sensitized nitromethane |
US4892597A (en) * | 1989-08-30 | 1990-01-09 | The United States Of America As Represented By The Secretary Of The Army | Dissolved trinitrotoluene in sensitized nitromethane |
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