US1029519A - Method of making unfreezable explosives. - Google Patents
Method of making unfreezable explosives. Download PDFInfo
- Publication number
- US1029519A US1029519A US525545A US1909525545A US1029519A US 1029519 A US1029519 A US 1029519A US 525545 A US525545 A US 525545A US 1909525545 A US1909525545 A US 1909525545A US 1029519 A US1029519 A US 1029519A
- Authority
- US
- United States
- Prior art keywords
- explosives
- glycerin
- acid
- making
- unfreezable
- 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 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229960003711 glyceryl trinitrate Drugs 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- 239000000006 Nitroglycerin Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000000802 nitrating effect Effects 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000020 Nitrocellulose Substances 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
- 229920001220 nitrocellulos Polymers 0.000 description 3
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical group CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- -1 nitro sulfuric acid Chemical compound 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000012550 audit Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229940079938 nitrocellulose Drugs 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N palmityl palmitate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 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
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/02—Compositions containing a nitrated organic compound the nitrated compound being starch or sugar
Definitions
- the present invention has for its objectprimarily to provide a method of making practically unfreezable explosives having a plastic and horny consistency and a low explosive temperature.
- the present invention relates to the preparation and the use of nitrate'd esters of glycerin with formic or acetic acid, nitroknown in that they are not volatile sub-' Y stances but arevery permanent, they do not contain clilorin, they are not hygroscopic and, moreover, are easy to make.
- nitracetin contains little nitracetin. 'It'has-beenfoundthat the sulfuric acid of the acid mixture separates acetyl, and that on the other hand, a good yield of pure nitracetin can be obtaincdhy nitrating the basic acetins with nitric acid of more than NO 'H or with nitro-sulturic acid containing more nitric than sulfuric acid, and that a good yield of mixtures of nitracetin and intro-glycerin can be obtained by nitrating acetin-glycerin mixtures, if acid mixtures are employed containing as much more nitric acid than sulfuric acid as there is acetin in propor-.
- Nitro-formins here: tofore unknown can also be obtained by nitrat-ing formin, and it has been found that these nitro-formins have'a great explosive power and they also lower the freezing point of nitroglycerin to such ail-extent that a mixture for-instance of about 25% clinit-ro-tormin with nitro-glycerin may be regarded as practically untreezable.
- Example No. 1 100 kgs. of glycerin 99%) are heated with 20 kgs. of anhydrous oxalic acid at 100 C. and the mixture is the'nlheated for about '20 hours at a temperature'ranging between 1&0 and 150 (1., the product obtained which consists of about 125 kgs. of a mixture of formin and glycerin is directly nitrated in 275' kgs. of nitric acid:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
"units VEZIO vnnnza n, or rattan; trans.
METHOD OI IIIAKING UNFREEZA'BLE EXZLOSIVES.
filed October 30, 1909.,
To (ZZZ whom it may} concern:
Be it known that I, Vnzro Yunnan, a'subject of the King of Italy, residing at Milan, Italy, have invented certain new and useful Improvements in Methods of Making U11 treezable Explosives, of which the following' is a specification.
The present invention has for its objectprimarily to provide a method of making practically unfreezable explosives having a plastic and horny consistency and a low explosive temperature.
At the present time it is regarded as essential that explosives and smokeless powder have a plastic and horny consistency, but such substances as have been heretofore made containing nitro-glycerin are objectionable in that they freeze at a temperature below 50 1 they lose their valuable'jprop crties and they are also slow of ignition and are very dangerous.
The present invention relates to the preparation and the use of nitrate'd esters of glycerin with formic or acetic acid, nitroknown in that they are not volatile sub-' Y stances but arevery permanent, they do not contain clilorin, they are not hygroscopic and, moreover, are easy to make.
' free OH} 7 3 I nitrating acetins (containing with ordinary 'nitro sulfuric acid for maliing nitro-glycerin, a Very poor' yield of nitroglycerin is obtainedwhich moreover Specification of Letters Fatent,
contains little nitracetin. 'It'has-beenfoundthat the sulfuric acid of the acid mixture separates acetyl, and that on the other hand, a good yield of pure nitracetin can be obtaincdhy nitrating the basic acetins with nitric acid of more than NO 'H or with nitro-sulturic acid containing more nitric than sulfuric acid, and that a good yield of mixtures of nitracetin and intro-glycerin can be obtained by nitrating acetin-glycerin mixtures, if acid mixtures are employed containing as much more nitric acid than sulfuric acid as there is acetin in propor-.
tion to lvccri. 13v obtainin 'iurc nitraceh c: tins, as nuntioncdabove, it has been drscox cred that these nitracetins possess certain valuable properties which areof especial Patented June 313, T932 Serial Ho. 525,545.
' no Drawing. ori inal application filed December a, was, Serial No. 346,961. named and this application 1 I I fll 'utility in the manufactureof explosives,
that to say, it has been found that ni tracetln does not freeze even. at- .very low temperatures nor does nitracetin'freeze at,
very low temperatures when mixedavith nitro-glycerin th atnitra-cetin is extremely nonsusceptible to heat and shock audit is so great a solvent for gun cotton even when cold that gun cotton'of'l3. l%;,N may be gelatinizedg Moreover, dinitra' cetin can not be exploded or ignited by means of a hammer or by striking 'ironaga'inst iron, but when expldcled with a suitable primer, it
possesses airexplosive power as great asnitro-g-lyceriualthough it has a lower ex- 'plosion temperature. Nitro-formins here: tofore unknown can also be obtained by nitrat-ing formin, and it has been found that these nitro-formins have'a great explosive power and they also lower the freezing point of nitroglycerin to such ail-extent that a mixture for-instance of about 25% clinit-ro-tormin with nitro-glycerin may be regarded as practically untreezable.
h Iore specifically, the invention may be disclosed more clearly by the following which are given as examples 4 Example No. 1: 100 kgs. of glycerin 99%) are heated with 20 kgs. of anhydrous oxalic acid at 100 C. and the mixture is the'nlheated for about '20 hours at a temperature'ranging between 1&0 and 150 (1., the product obtained which consists of about 125 kgs. of a mixture of formin and glycerin is directly nitrated in 275' kgs. of nitric acid:
(96%) and 90 kgs. of fuming sulfuric acid (25% S0 at 25? C. after which the oil separated after washing with water and a warm soda-solution'is of a pale yellow color vand has'a specific gravity of 1.57 at- 15 C. and aboutl5.7% N corresponding to a mixture'of initro-formin and 672 trinitroglycerin. ,100 kgs. of this intro-glycerin mixture is gelatinized with 10 kgs. of colic clion cotton to obtain-a blasting gelatin or with 200 lags. of nitro-cellulose to obtain horny explosives, the blasting gelatin. or
horny explosives thus obtained. remaining.
unfrozen even at a temperature of minus 17 C.
llixample No. 2: 100K kgs. orglycerin (9992) and Takes. acetic acid (99%;).336 boiled for about 2% hours and acetic acid is distilled off by heating to 240 0.; t" the raw monacetin obtained, l25.;hg-s:
are in tinted with 340 kgs. of nitric acid of and 110 kgs. fuming sulfuric acid (25%;:- SO at 25 C.; the whole'is poured into Water'and the separatedoil Washed with Water and a Warm soda solution. A pale yellow oil having a specific gravity of 1.45 at 15 C. is obtained which is insoluble in water; benzin and sulfid of carbon,' s0luble' r r .1n nitric acid, alcohol, acetone and n1tr0-' T /anzyl test an. expansion of about 450 glycerin, consisting in nitrating a suitable flbasicglycerin ester of a nonobesic acid of the acetic series with acidcontainlng not less tain iirzibtically. unfreczable explosives.
*2. A method of making mixed esters of glycerin, consisting in nitmting a suitable basic glycerin ester of 'a 'monobasic acid of 25 the acetic series With amixture of nitric and sulfuric acid, containing more nitric than Y sulfuric zicidJ In testirnony whereof I have hereunto set my hand in presence of two subscribing Wit 30 nesses.
I VEZIO VENDER.
\Vitnesses:
N. LYLE RoBB, CHAS. H. FLISCHER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US525545A US1029519A (en) | 1906-12-08 | 1909-10-30 | Method of making unfreezable explosives. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34696106A US946294A (en) | 1906-12-08 | 1906-12-08 | Method of making horny nitrocellulose bodies. |
| US525545A US1029519A (en) | 1906-12-08 | 1909-10-30 | Method of making unfreezable explosives. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1029519A true US1029519A (en) | 1912-06-11 |
Family
ID=3097812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US525545A Expired - Lifetime US1029519A (en) | 1906-12-08 | 1909-10-30 | Method of making unfreezable explosives. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1029519A (en) |
-
1909
- 1909-10-30 US US525545A patent/US1029519A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3388147A (en) | 2-fluoro-2, 2-dinitroethyl carbonates and production thereof | |
| US5205983A (en) | Energetic plasticizer and improved gas producing charges | |
| US1402693A (en) | Explosive | |
| US1936020A (en) | Method of nitrating organic substances | |
| Bulusu et al. | Synthesis of nitrogen‐15 labeled 1, 3, 5‐trinitro‐1, 3, 5‐triazacyclohexane (RDX) and 1, 3, 5, 7‐tetranitro‐1, 3, 5, 7‐tetraazacyclooctane (HMX) | |
| US3000939A (en) | N-nitro,n,n'-bis(trinitroalkyl)-urea | |
| US3097239A (en) | Condensation products of trinitromethane and dimethylolurea | |
| US3070473A (en) | Liquid propellants | |
| US1754417A (en) | Explosive and solvent therefor | |
| US3356714A (en) | 4-fluoro-4, 4-dinitrobutyric acids and esters thereof | |
| US1560427A (en) | Explosive and process of making same | |
| US1371215A (en) | Explosive and process of making explosives | |
| USRE12669E (en) | Anton mikolajczak | |
| US1206223A (en) | Process of making glycol dinitrate for explosive uses. | |
| US2978489A (en) | Nitro-dicarbamates | |
| US2934558A (en) | Nitrazaalkylnitrates | |
| US3014073A (en) | 1, 3-bis(nitroguanidino)-2-nitroxypropane, 1, 3-bis(guanidinium)-2-hydroxy propane and the preparation thereof | |
| US2978452A (en) | Pentanitropiperidine | |
| US3378576A (en) | Nitrate esters of tetrahydroxy-3, 6-dinitrocyclohexane | |
| US3197511A (en) | Nitropolystyrene | |
| US3000944A (en) | N,n'-polynitroalky-oxamides | |
| US855595A (en) | Process of manufacturing nitroglycerin explosives of reduced freezing-point. | |
| US1393623A (en) | Propellent smokeless-powder charge | |
| US2999099A (en) | Trinitroethylsuccinic acid and derivatives thereof | |
| US3270047A (en) | Organoboron urethanes |