US1560426A - Harold a - Google Patents
Harold a Download PDFInfo
- Publication number
- US1560426A US1560426A US1560426DA US1560426A US 1560426 A US1560426 A US 1560426A US 1560426D A US1560426D A US 1560426DA US 1560426 A US1560426 A US 1560426A
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- US
- United States
- Prior art keywords
- explosive
- product
- compound
- producing
- nitrate
- Prior art date
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- Expired - Lifetime
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- 239000002360 explosive Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000000802 nitrating effect Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- KYDXWCHDUCDNGR-UHFFFAOYSA-N 1-chloro-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1[N+]([O-])=O KYDXWCHDUCDNGR-UHFFFAOYSA-N 0.000 description 5
- 229910002651 NO3 Inorganic materials 0.000 description 5
- -1 nitro-chlor aromatic compound Chemical class 0.000 description 5
- YIWOOPQOYHKISC-UHFFFAOYSA-N [O-][N+](=O)CC(O)([N+]([O-])=O)OC1=CC=CC=C1 Chemical compound [O-][N+](=O)CC(O)([N+]([O-])=O)OC1=CC=CC=C1 YIWOOPQOYHKISC-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- AGUIVNYEYSCPNI-UHFFFAOYSA-N N-methyl-N-picrylnitramine Chemical group [O-][N+](=O)N(C)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O AGUIVNYEYSCPNI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005422 blasting Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-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
- USXDFAGDIOXNML-UHFFFAOYSA-N Fulminate Chemical compound [O-][N+]#[C-] USXDFAGDIOXNML-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- MMDJDBSEMBIJBB-UHFFFAOYSA-N [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] MMDJDBSEMBIJBB-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical class [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- My invention relates particularly to a process for producing a new explosive of advantageous character and the product thereof.
- the object of my invention is to provide a new and useful explosive compound suitable for use in detonators and so-called booster charges.
- My process furnishes a simple and economical means of producing explosives of the nitro-nitrate class where the nitric ester side chain is attached to. the benzene nucleus through oxygen.
- glycols such as propylene and trimethylene glycol can be treated in the same manner yielding the corresponding trinitrophenoxyalkyl nitrates, such substances constituting valuable explosive compounds.
- dinitrochlorbenzene condensed with a polyhydric alcohol such as ylcerol gives dinitrophenoxy-glycerol, w iich on nit-ration gives trinitrophenoxy-glycerol dinitrate.
- Trinitrophenoxy-ethyl. nitrate as produced by my process, is particularly well adapted for use in blasting caps or in socalled booster charges, or in any of the numerous explosive devices for which such explosives as trinitrotoluene, picric acid and tetryl have proved adapted.
- a compressed charge consisting of 3 grains of trinitrophenoXy-ethyl nitrate in the base of the shell, and a primer of t grains of a 90-10 mixture of fulminate and chlorate with a superimposed inner capsule exhibits an explosive force entirely comparable with that given by tetryl loaded and fired under the same conditions.
- a process or producing an explosive compound which comprises condensing a polyhydric alcohol, having not more than 3 'hydroxyl groups, with a. nitro-chlor aromatic compound and nitrating the product of condensation.
- a process of producing anexplosive compound which comprises condensing ethylene glycolwith dinitrochlorbenzene and nitrating the product of condensation.
- a process of producing an explosive compound which comprises'nitrating the product obtainable iby the condensation of a glycol with dinitrochlorbenzene.
- An explosive comprising an organic compound of the aromatic series, having a plurality of nitro groups attached to the ring and a side chain comprising a mono nitrate of an aliphatic alcohol attached to the ring through oxygen.
- An explosive comprising a nitro-eryloxy-alkyl nitrate.
- An explosive comprising a'polynitrophenyloxy-alkyl nitrate.
- An explosive comprising the compound obtainable by nitrating the product resulting from the condensation of a glycol containing less than five carbon atoms with a nitro-chlor aromatic compound of the-benzene series.
- An explosive comprising a nitrated dinitrophenoxy-ethanol.
- An explosive comprising trinitrophenoxy-ethyl nitrate.
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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
Patented Nov. 3, 1925.
UNITED STATES PATENT orrlce.
HAROLD A. LEWIS, OF WOODBURY, NEW JERSEY, ASSIGNOR TO E. I. DU PONT DE NEMOURS &, COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELA- WARE.
EXPLOSIVE COMPOUND AND PROCESS OF PRODUCING SAME.
N 0 Drawing.
To all whom it may concern:
Be it known that I, HAROLD A. LEWIS, a citizen of the United States, and a resident of \Voodbury. in the county of Gloucester and State of New Jersey, have invented certain new and useful Explosive Compounds and Processes of Producing Same, of which the following is a specification.
My invention relates particularly to a process for producing a new explosive of advantageous character and the product thereof. The object of my invention is to provide a new and useful explosive compound suitable for use in detonators and so-called booster charges. My process furnishes a simple and economical means of producing explosives of the nitro-nitrate class where the nitric ester side chain is attached to. the benzene nucleus through oxygen.
I have discovered that the condensation product of a nitro-chlor aromatic compound with a polyhydric alcohol nitrates readily in the presence of sulphuric and nitric acid, forming an aromatic compound having a plurality of nitro groups attached to- .the ring and a side chain comprised of a nitric ester of an aliphatic alcohol attached tothe ring through oxygen. For example, if I condense dinitrochlorbenzene with a dihvdric alcohol such as ethylene glycol, I obtain dinitrophenoxy-ethanol which on nitration yields trinitrophenoxy-ethyl nitrate. Other glycols such as propylene and trimethylene glycol can be treated in the same manner yielding the corresponding trinitrophenoxyalkyl nitrates, such substances constituting valuable explosive compounds. Likewise dinitrochlorbenzene condensed with a polyhydric alcohol such as ylcerol gives dinitrophenoxy-glycerol, w iich on nit-ration gives trinitrophenoxy-glycerol dinitrate. Although the exact details of the various steps of my process may be varied, I
have found the following to yielda very satisfactory explosive compound, starting with dinitrochlorbenzene and ethylene glycol 100 parts by weight of 2, 4-dinitrochlorbenzene are dissolved in 322 parts by weight of ethylene glycol. To this is added an ethylene glycol solution of NaOH made by dissolving parts of NaOH in 12 parts of water and adding 322-parts of glycol. The
Application filed January 26, 1925. Serial No. 4,961.
mixture is heated at 90 to 100 C. for hour, during which time sodium chloride crystallizes out. The hot mixture'is then drowned in about 600 parts of water and the dinitrophenoxy-ethanol separated. 100 parts by weightof this product, after drying, are then dissolved in 1000 parts by weight of 95% sulphuric acid and the solution slowly added to 300 parts of nitric acid (1.47 sp. gr.) which is constantly agitated and kept at 35 C. The temperature is then raised and kept at to for one hour, after which the mixture is drowned in water and the crystalline product separated and washed by any one of the well known methods; The crude product obtained by me in following the process, as described above, gave a product melting at 10l102 C. \Vhen recrystallized fro-m benzene it melted at l05106 C. The nitrate nitrogen as determined by nitromet/en was 4.23% as compared with the theoretical value of 4.40% for trinitrophenoxyethyl nitrate. The product flashed when heated on a steel spatula and detonated when primed with fulminate of mercury.
Trinitrophenoxy-ethyl. nitrate, as produced by my process, is particularly well adapted for use in blasting caps or in socalled booster charges, or in any of the numerous explosive devices for which such explosives as trinitrotoluene, picric acid and tetryl have proved adapted. For example, in a blasting cap shell, I have found that a compressed charge consisting of 3 grains of trinitrophenoXy-ethyl nitrate in the base of the shell, and a primer of t grains of a 90-10 mixture of fulminate and chlorate with a superimposed inner capsule exhibits an explosive force entirely comparable with that given by tetryl loaded and fired under the same conditions.
While I have described my process in detail only as a plied to the condensation and nitration of dmitrochlorbenzcne and ethylene glycol, it is understood that other nitrochloro aromatic compounds, such, for ex ample, as dinitrochlo-rotolueaie, may be used, as well as various polyhydric alcohols other than those specifically mentioned above. My process is also not confined to the particular method of condensation or nitration given in the specific example.
I claim: 7
1. A process or producing an explosive compound which comprises condensing a polyhydric alcohol, having not more than 3 'hydroxyl groups, with a. nitro-chlor aromatic compound and nitrating the product of condensation.
2. A process of producing an explosive compound which com rises condensing a glycol with a nitro-c lor aromatic compound and nitrating sation. 7
3. A process of producing anexplosive compound which comprises condensing ethylene glycolwith dinitrochlorbenzene and nitrating the product of condensation.
4. A process of producing an explosive compound which comprises'nitrating the product obtainable iby the condensation of a glycol with dinitrochlorbenzene.
5. A process 'of producing an explosive compound which-comprises nitrating :the product obtainable by condensing ethylene glycol with 2, 4-dinitrochlorbenzene.
6. A process of producing an explosive the product of condencompound which comprises nitrating dinitrophenoxy-ethanol. Y
'7. An explosive comprising an organic compound of the aromatic series, having a plurality of nitro groups attached to the ring and a side chain comprising a mono nitrate of an aliphatic alcohol attached to the ring through oxygen.
8. An explosive comprising a nitro-eryloxy-alkyl nitrate.
9. An explosive comprising a'polynitrophenyloxy-alkyl nitrate.
10. An explosive comprising the compound obtainable by nitrating the product resulting from the condensation of a glycol containing less than five carbon atoms with a nitro-chlor aromatic compound of the-benzene series. v
11. An explosive comprising a nitrated dinitrophenoxy-ethanol.
12. An explosive comprising trinitrophenoxy-ethyl nitrate.
In testimony whereof I aflix my signature.
. HAROLD A.-LEWIS.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1560426A true US1560426A (en) | 1925-11-03 |
Family
ID=3409285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1560426D Expired - Lifetime US1560426A (en) | Harold a |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1560426A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037057A (en) * | 1959-01-23 | 1962-05-29 | Union Carbide Corp | Production of aromatic aminoalcohols |
-
0
- US US1560426D patent/US1560426A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037057A (en) * | 1959-01-23 | 1962-05-29 | Union Carbide Corp | Production of aromatic aminoalcohols |
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