US1419027A - High explosive and process - Google Patents
High explosive and process Download PDFInfo
- Publication number
- US1419027A US1419027A US1419027DA US1419027A US 1419027 A US1419027 A US 1419027A US 1419027D A US1419027D A US 1419027DA US 1419027 A US1419027 A US 1419027A
- Authority
- US
- United States
- Prior art keywords
- high explosive
- pentanitronaphthole
- mixture
- nitronaphtholes
- naphthalene
- 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
- 239000002360 explosive Substances 0.000 title description 26
- 238000000034 method Methods 0.000 title description 22
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229940075566 Naphthalene Drugs 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 229910001987 mercury nitrate Inorganic materials 0.000 description 12
- DRXYRSRECMWYAV-UHFFFAOYSA-N nitrooxymercury Chemical compound [Hg+].[O-][N+]([O-])=O DRXYRSRECMWYAV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000006396 nitration reaction Methods 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003517 fume Substances 0.000 description 6
- 230000005484 gravity Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000000802 nitrating Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- BFMBQYIQQLBGJA-UHFFFAOYSA-N 1,3,6,8-tetranitronaphthalene Chemical group [O-][N+](=O)C1=CC([N+]([O-])=O)=CC2=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C21 BFMBQYIQQLBGJA-UHFFFAOYSA-N 0.000 description 4
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 230000002378 acidificating Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 229940114148 picric acid Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 229950002929 trinitrophenol Drugs 0.000 description 2
- 239000000015 trinitrotoluene Substances 0.000 description 2
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
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Definitions
- the subject of this invention is a high explosive and process of preparing the same.
- the main object of the invention is the production of a high explosive from naphthalene and the use of mercury nitrate as a rea ent in the nitration of naphthalene.
- i aphthalene provides an abundant raw material for the preparation of high explosives.
- the most powerful explosive which has heretofore been prepared from it is tetranitronaphthalene (containing 18.18% nitrogen) which, while not as powerful as trinitrotoluene or picric acid, has nevertheless found some use, alone or in a mixture, as a filling for high explosive shells.
- the process may be carried out as follows I describe the two step process though the process may equally be carried out in one step or in three. 10 kilograms of naphthalene is treated, with stirring, with 30 liters of commercial nitric acid (specific gravity 1.42) in which half a kilogram of mercury nitrate has been dissolved and the mixture is melted until red fumes begin to come oii' abundantly. This occurs at about 75 0., and the mixture is kept at 70 to 80 C. until the vigorous evolution of'gas has subsided. The spent acid contains the mercury nitrate and may be fortified and used again for the first step of the process.
- the oil contains about 8.9% of nitrogen and consists largely of nitronaphtholes together with a small quantity of nitronaphthalenes.
- This oil is submitted directly to the second step of the nitration. While stirred and cooled, it is treated with 82.4 liters of concentrated sulphuric acid (specific gravity 1.82). 100 liters of nitric acid (specific gravity 1.49) is then added. A vigorous reaction takes place, copious red fumes are evolved and it is necessary to cool the reaction mixture. When the evolution of red fumes has subsided the mixture is heated for an hour at 110 to 115.
- the pen tanitronaphthole which is so obtained is purified in the usual way by boiling with water. It is an almost colorless crystalline substance which does not melt but decomposes at about 257. It contains about 19% nitrogen and has the acidic properties which are characteristic of nitrophenols.
- a yellowish orange mass is precipitated. This material melts at from to 105 and consists of the lower nitronaphtholes together with a quantity of nitronaphthalenes. It contains about 17.7% of nitrogen, and may be used as a high explosive alone or in mixtures.
- the method of preparing pentanitronaphthole comprising treating naphthalene with a mixture of nitric acid and mercury nitrate to produce nitronaphtholes, treating the nitronaphtholes with sulfuric acid, treating the mixture with nitric acid, filtering the resultant mixture to recover the crystals of penta-nitronaphthole and purifying the pentanitronaphthole.
- a high explosive consisting of pentanitronaphthole.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENT OFFICE.
TENNEY L. DAVIS, OF SOMERVILLE, MASSACHUSETTS.
HIGH EXPLOSIVE AND PROCESS OF PREPARING THE SAME.
N 0 Drawing.
Specification of Letters Patent.
Application filed April 18, 1221.
Patented June 1922.
Serial No. 462,031.
(FILED UNDER THE AGT 0?? MARCH 3, 1883, 22 STAT. L, 625.)
T0 alien/ 10m it may concern:
Be it known that I, TENNEY L. DAVIS, a citizen of the United States, and a resident of Somerville, county of Middlesex, and State of Massachusetts, have invented an Improvement in High Explosives and Processes of Preparing the Same, of which the following is a specification.
The invention described herein may be used by the Government, or any of its officers or employees in rosecution of work for the Government, or by any other person in the United States, without payment to me of any royalty thereon.
The subject of this invention is a high explosive and process of preparing the same.
The main object of the invention is the production of a high explosive from naphthalene and the use of mercury nitrate as a rea ent in the nitration of naphthalene.
i aphthalene provides an abundant raw material for the preparation of high explosives. The most powerful explosive which has heretofore been prepared from it is tetranitronaphthalene (containing 18.18% nitrogen) which, while not as powerful as trinitrotoluene or picric acid, has nevertheless found some use, alone or in a mixture, as a filling for high explosive shells.
I have discovered that the use of mercury nitrate as a reagent in nitration of naphtha lene leads to the production of nitronaphtholes. Naphthole nitrates more readily than naphthalene itself and I have succeeded in preparing by this method explosives which. contain more nitrogen than tetranitronaphthalene and which are more powerful. While I have worked out a satisfactory process for the preparation of this explosive, I do not desire to make the details of that process the object of the present application. I do, however, consider myself the inventor or discoverer of the general use of mercury nitrate as a reagent for the preparation of high explosives from naphthalene. The ex plosive which is produced by this process is a crude pentanitronaphthole which substance I also claim as my invention or discovery.
The process may be carried out as follows I describe the two step process though the process may equally be carried out in one step or in three. 10 kilograms of naphthalene is treated, with stirring, with 30 liters of commercial nitric acid (specific gravity 1.42) in which half a kilogram of mercury nitrate has been dissolved and the mixture is melted until red fumes begin to come oii' abundantly. This occurs at about 75 0., and the mixture is kept at 70 to 80 C. until the vigorous evolution of'gas has subsided. The spent acid contains the mercury nitrate and may be fortified and used again for the first step of the process. The oil contains about 8.9% of nitrogen and consists largely of nitronaphtholes together with a small quantity of nitronaphthalenes. This oil is submitted directly to the second step of the nitration. While stirred and cooled, it is treated with 82.4 liters of concentrated sulphuric acid (specific gravity 1.82). 100 liters of nitric acid (specific gravity 1.49) is then added. A vigorous reaction takes place, copious red fumes are evolved and it is necessary to cool the reaction mixture. When the evolution of red fumes has subsided the mixture is heated for an hour at 110 to 115. It is then allowed to stand over night and the crystals of pentanitronaphthole which have separated are filtered off from the strongly acid liquid by means of an asbestos or filtrose filter. The pen tanitronaphthole which is so obtained is purified in the usual way by boiling with water. It is an almost colorless crystalline substance which does not melt but decomposes at about 257. It contains about 19% nitrogen and has the acidic properties which are characteristic of nitrophenols. When the spent acids from the second step of nitration are diluted with water, a yellowish orange mass is precipitated. This material melts at from to 105 and consists of the lower nitronaphtholes together with a quantity of nitronaphthalenes. It contains about 17.7% of nitrogen, and may be used as a high explosive alone or in mixtures.
Having described my invention what I claim as new and desire to secure by Letters Patent, is:
1. The method of preparing pentanitronaphthole, comprising treating naphthalene with a mixture of nitric acid and mercury nitrate to produce nitronaphtholes, treating the nitronaphtholes with sulfuric acid, treating the mixture with nitric acid, filtering the resultant mixture to recover the crystals of penta-nitronaphthole and purifying the pentanitronaphthole.
2. The method of preparing pentanitronephtliole comprising nitrating naphtha- 5 lene, recovering the resulting nitronaphtholes nitrating the nitronaphtholes and then removing the pentanitronaphthole.
3. The method of preparing pentanitronaphthole, comprising nitrating naphthalene and then removing the resulting pentanitronapht-hole.
41-. A new article of manufacture, consisting of pentanitronaphthole.
5. A high explosive consisting of pentanitronaphthole.
TENNEY L. DAVIS.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1419027A true US1419027A (en) | 1922-06-06 |
Family
ID=3401630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1419027D Expired - Lifetime US1419027A (en) | High explosive and process |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1419027A (en) |
-
0
- US US1419027D patent/US1419027A/en not_active Expired - Lifetime
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