US3288867A - Stable nitromethane composition - Google Patents

Stable nitromethane composition Download PDF

Info

Publication number
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
Authority
US
United States
Prior art keywords
weight
less
stabilizing amount
stabilizing
nitromethane
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
Application number
US433519A
Inventor
Richard S Egly
Quentin R Jeffries
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Commercial Solvents Corp
Original Assignee
Commercial Solvents Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Commercial Solvents Corp filed Critical Commercial Solvents Corp
Priority to US433519A priority Critical patent/US3288867A/en
Application granted granted Critical
Publication of US3288867A publication Critical patent/US3288867A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/16Separation; Purification; Stabilisation; Use of additives
    • CCHEMISTRY; METALLURGY
    • C06EXPLOSIVES; MATCHES
    • C06BEXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B23/00Compositions characterised by non-explosive or non-thermic constituents
    • C06B23/005Desensitisers, phlegmatisers
    • CCHEMISTRY; METALLURGY
    • C06EXPLOSIVES; MATCHES
    • C06BEXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00Compositions containing a nitrated organic compound
    • C06B25/36Compositions containing a nitrated organic compound the compound being a nitroparaffin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/01Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
    • C07C205/02Compounds 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.
3,28%,dii7
"ice
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.
US433519A 1965-02-17 1965-02-17 Stable nitromethane composition Expired - Lifetime US3288867A (en)

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
US3288867A true US3288867A (en) 1966-11-29

Family

ID=23720417

Family Applications (1)

Application Number Title Priority Date Filing Date
US433519A Expired - Lifetime US3288867A (en) 1965-02-17 1965-02-17 Stable nitromethane composition

Country Status (1)

Country Link
US (1) US3288867A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
Kamlet The relationship of impact sensitivity with structure of organic high explosives. I. Polynitroaliphatic explosives
US2325064A (en) Explosive composition
US3288867A (en) Stable nitromethane composition
US3153606A (en) Aqueous explosive composition containing flake aluminum and ammonium nitrate
US5014623A (en) Binary munition system
US1992217A (en) Ammonium nitrate explosive
Yılmaz et al. Effect of inert plasticizers on mechanical, thermal, and sensitivity properties of polyurethane‐based plastic bonded explosives
Makovky et al. Nitromethane-physical properties, thermodynamics, kinetics of decomposition, and utilization as fuel
US3279965A (en) Ammonium nitrate explosive compositions
Krabbendam-La Haye et al. Compatibility testing of energetic materials at TNO-PML and MIAT
US3133844A (en) Ammonium nitrate explosives containing nitroalkanes
US3239395A (en) Stabilized explosive containing nitromethane and amine
Comtois et al. Linear burning rate and erosivity properties of nitrocellulose propellant formulations plasticized by glycidyl azide polymer and nitroglycerine
US2355817A (en) Explosive compositions
US4946521A (en) Selectively activated explosive
US4925505A (en) Foamed nitroparaffin explosive composition
US2338120A (en) Explosive composition
US3255057A (en) Sensitized ammonium nitrate explosives containing a hydrogen ion indicator
US3728174A (en) Gelatin explosive containing hollow resinous plastic spheres
Toan et al. Thermal decomposition and shelf-life of PETN and PBX based on PETN using thermal methods
US2371879A (en) Explosive charge
US3012868A (en) Enhanced organic explosives
US3819429A (en) Blasting agent for blasting in hot boreholes
US2312752A (en) Explosive composition
US3579392A (en) Nitroglycerin-nitroglycol blasting composition