US514838A - Nitro compound and process of making same - Google Patents
Nitro compound and process of making same Download PDFInfo
- Publication number
- US514838A US514838A US514838DA US514838A US 514838 A US514838 A US 514838A US 514838D A US514838D A US 514838DA US 514838 A US514838 A US 514838A
- Authority
- US
- United States
- Prior art keywords
- nitro
- compounds
- making same
- urea
- nitro compound
- 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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- 150000002828 nitro derivatives Chemical class 0.000 title description 13
- 238000000034 method Methods 0.000 title description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 24
- 239000004202 carbamide Substances 0.000 description 12
- 235000013877 carbamide Nutrition 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 241000702021 Aridarum minimum Species 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920013662 Zylonite Polymers 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- -1 cellu oid Polymers 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940079938 nitrocellulose Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C06B23/04—Compositions characterised by non-explosive or non-thermic constituents for cooling the explosion gases including antifouling and flash suppressing agents
Definitions
- the object of my invention is to produce a method of preventing the decomposition or of securing the chemical stability of nitro-compounds,-it being a wellknown fact that such compounds when sto"ed for a long' period of time often undergo decompositionwhich, slight at first, gradually increases until the whole compound has become more or less decomposed and otherwise chemically changed.
- nitratesof polyatomic alcohols such as glycerine and mannite and of related-compounds as. the carbohydrates for example starch, cellulose and the like, are especially susceptible to decomposition unless they are produced in an absolutely pure state, which is seldom the case-in manufacturing these compounds for commercial use; and whenever traces of acid or of impurities of an unstable character remain in the finished product, de-
- diphcnylamine and aniline compounds with nitrous acid whieh'is a constant product of the decomposition of these nitro derivatives, are themselves 'unstablein character, their introduction in many cases is inadmissible because of the discoloration which they are apt to produce.
- the nitrocompounds are freed as far as possible from all adherent acids by repeated washings, and they are subsequently dried, if necessary, after which I add the urea in suitable proportionsaccordiug to thequautity of nitro-compound and the purpose for which the finished product is intended to be used,the urea itself being dissolved in'a stable menstruum or flux compatible with the solvents employed in the respective manufactures of nitro-compounds which'solvents are usually methyl or ethyl alcohol.
- the quantity of urea which is mixed ditions above-mentioned and varies from one half per cent. (1 ⁇ to two per cent. (2 y This solution of urea and solvent penetrates every particle of the nitro-compounds and.
- the acids which have to be neutrio and nitrous acids which may be found in faint traces in the adherent wash-water.
- the nitrate and sulphate of urea are perfectly stable and colorless substances the product resulting from its use with nitro-compounds becomes absolutely stable, and no discoloration whatever occurs as with the use of the 8 amass substanceshere'totore added to preventthedefor which the resulting product is to be used;
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
"UNITED STATES PAT NT. Current,
ROBERT o; SOHUPPHAUS,.OF BROOKLYN, NEW YORK;
NITRO COMPOUND-AND PRocess'or'r'nAKmo sAME.
BPEOIFIOATIORforming partof Lettera'Patent a 514,838, dat ed February 18, 1894.
Application and. Jnly'fl, 1898.- smart. 450,192. (so npeoimenn.)
: To all. whom it mayooncernga Be it known that I, ROBER'T G. SoHI'iPPHA'U's,-; acitizen of the United States, residing in the.
city of Brooklyn, in the county of Kings and State of New York, have invented a certain new and useful Method of Securing the Chemical Stability of Nit-r0 Compounds, ofwhich the following is a specification.
The object of my invention is to produce a method of preventing the decomposition or of securing the chemical stability of nitro-compounds,-it being a wellknown fact that such compounds when sto"ed for a long' period of time often undergo decompositionwhich, slight at first, gradually increases until the whole compound has become more or less decomposed and otherwise chemically changed.
The nitratesof polyatomic alcohols such as glycerine and mannite and of related-compounds as. the carbohydrates for example starch, cellulose and the like, are especially susceptible to decomposition unless they are produced in an absolutely pure state, which is seldom the case-in manufacturing these compounds for commercial use; and whenever traces of acid or of impurities of an unstable character remain in the finished product, de-
-.'composition always occurs after the lapse of a more or less short period of time. To pre 3 vent this decomposition in the finished product of nitro-compounds, various means have been devised and employed as in :the' manufacture of gun cotton or nitro-cellulose, it is not unusual to incorporate a small quantity of an alkaline substance, such as silicate of soda, to the compound in course of its manufacture to prevent its decomposition; and in the manufacture of dynamite it is not unusual to add carbonate of lime or magnesia for the same purpos and in .the manufacture of pyralin, cellu oid, zylonite and similar compounds of pyroxyline and camphor, carbonate of magnesia is frequently added during the process of manufacture. In preparing high explosives diphcnylamine and aniline compounds with nitrous acid, whieh'is a constant product of the decomposition of these nitro derivatives, are themselves 'unstablein character, their introduction in many cases is inadmissible because of the discoloration which they are apt to produce.
' All of the above mentioned difiiculties and many others are overcome by the use of urea or carbamide as a ueutralizer, which substance I'havediscovered isaneliectual neutralizer of impurities in nitro compounds aud' abso lutely prevents their decomposition. In practice the nitrocompounds are freed as far as possible from all adherent acids by repeated washings, and they are subsequently dried, if necessary, after which I add the urea in suitable proportionsaccordiug to thequautity of nitro-compound and the purpose for which the finished product is intended to be used,the urea itself being dissolved in'a stable menstruum or flux compatible with the solvents employed in the respective manufactures of nitro-compounds which'solvents are usually methyl or ethyl alcohol. As above stated the quantity of urea which is mixed ditions above-mentioned and varies from one half per cent. (1} to two per cent. (2 y This solution of urea and solvent penetrates every particle of the nitro-compounds and.
neutralizes any acids or other impurities that "with the compound is regulated,by the conmay 'bepresent while the surplus remains evenly distributed throughout thewhole mass. The complete neutralization thus attained is an absolute safeguard against decomposition, but should however. any part ofthe mass be subjected to disturbing influences of any character and decomposition set in the additional quantity or surplus of the neutr izer, which as stated remains evenly distributed throughout the whole mass counteracts this incipient decomposition and prevents its spreading. tralized' in such compounds are sulphuric, m-
The acids which have to be neutrio and nitrous acids which may be found in faint traces in the adherent wash-water. As the nitrate and sulphate of urea are perfectly stable and colorless substances the product resulting from its use with nitro-compounds becomes absolutely stable, and no discoloration whatever occurs as with the use of the 8 amass substanceshere'totore added to preventthedefor which the resulting product is to be used;
composition of the nitrocompoundsas abovebut I mentioned. Furthermore as nitrous acid is What I olaimas myinvention, and desire to acts with ureain a remarkable manner, yieldsecure by Letters Patent, is-
5 ing carbonic acid, nitrogen and water, any ni- 1. In the process of securing the chemical r 115 aol that maybepresent or become genstability of nitro-compounds, the improveemted gfl c process'ot manufacture is ment which consists in adding to or incorpothereby rendered absolutely harmless. As rating therewith urea, as set forth. i requires a. minimum of oxygen to s set 2. As a new article ot manufacture an ex- 30 to complete combustion it is a perfect neu relplosive compound, composed of a nitro comnor in the manufacture of high explosives and pound having urea incorporated therewith, owing to its low molecular weight a smaller as set forth. quantity will neutralize a given amountof 3. Asa new article of manufacture, a py-' free acid than any other organic base heretoroxyline composition having urea mcorpo- 35 15 fore used for the same or similar purposes. rated therewith, as set forth.
- I do not limit myself to the quantity ofnrea This specification signed and witnessed this or'carbamide which may be introduced-into 2d day of December, A. D. 1892. the nitro-compounds for the purpose above" ROBERT C. SCHUPPHAUS. v stated, since as above-mentioned theflqnsn- 'In presence oty JO tity of urea will ,vary according to the char- M. GIBSON,
acterof the nitro-compound and the purpose E. MJTAYLQB.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US514838A true US514838A (en) | 1894-02-13 |
Family
ID=2583646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US514838D Expired - Lifetime US514838A (en) | Nitro compound and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US514838A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070203354A1 (en) * | 2006-02-03 | 2007-08-30 | Ramirez Jose E | Chemical Compositions and Methods of Making Them |
-
0
- US US514838D patent/US514838A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070203354A1 (en) * | 2006-02-03 | 2007-08-30 | Ramirez Jose E | Chemical Compositions and Methods of Making Them |
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