US1685771A - Cyano nitrate explosive and process of producing the same - Google Patents
Cyano nitrate explosive and process of producing the same Download PDFInfo
- Publication number
- US1685771A US1685771A US219817A US21981727A US1685771A US 1685771 A US1685771 A US 1685771A US 219817 A US219817 A US 219817A US 21981727 A US21981727 A US 21981727A US 1685771 A US1685771 A US 1685771A
- Authority
- US
- United States
- Prior art keywords
- cyano
- nitrate
- producing
- explosive
- same
- 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 21
- 238000000034 method Methods 0.000 title description 12
- IBGCXOFOCKCBNQ-UHFFFAOYSA-N nitro cyanate Chemical compound [O-][N+](=O)OC#N IBGCXOFOCKCBNQ-UHFFFAOYSA-N 0.000 title description 6
- -1 cyano ethanol nitrate Chemical compound 0.000 description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NWIPPCMREQXKRU-UHFFFAOYSA-N ethanol nitrate Chemical compound CCO.[O-][N+]([O-])=O NWIPPCMREQXKRU-UHFFFAOYSA-N 0.000 description 2
- UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical class N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- ZBSGZSWGVZACES-UHFFFAOYSA-N cyanomethyl nitrate Chemical compound [O-][N+](=O)OCC#N ZBSGZSWGVZACES-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
Definitions
- This invention relates to explosives containrng one or morecyano groups and.one or more nitrate groups. It relates particularl to explosives comprising a hydrocarbon whic v l has attached thereto wcyano groups and nitrate groups, and also relates to the process of producing said explosives. a I
- One object of the invention is to provide a new type of explosive of the above char- 10 'acter combining in part the explosive group-' ings of nitroglvcerine and hydrocyanic acid.
- a further object of the invention is toprovide a product which may be used alone or in combination with the usual dynamite g 'ingredients to make a dynamite of; good strength and great insensitivene'ss to me- .chanical shock.
- e e I The product cya'no methanol nitrate,
- cyano methanol nitrate may thus be made by the nitratio'n Iof CNCH OH. j g Further'objects andadvanta es of'the in- 40 vention will appear from the ollowing des criptionand detailed examples of the inven- 'tion..
- Cyano nitrate explosives in which thecyano and nitrate groups are attached to the same carbon atom are acidic in character and relamethylene cyanohydrin,
- vent-ion is to' provide a novel, practical and.
- ouomomonogon ono cyano-and nitrate groups each ondifl'erent carbonatoms may bemade in any desired way. I prefer, however, to make them by treating .cyanohydrins with mixed acid.
- the 'cyanol nitrate explosives having the example of the way in which my process may I be-c arried out is the following. 7
- This oil while not quite as powerful as ethylene glycol dinitrate, has the desirable property of being-much less sensitive to mechanical shock than the latter.
- Cyano ethanol nitrate may be used alonei as an explosive or incombination with the usual dynamite ingredients tomake ja dylflmite of-good strength and great insensitiveness to mechanical shock. It may used nitroglycerine with in a dynamite com rising nitroglycerine or its substitutes, as, or example, mixtures of tetranitro'diglycerlne,
- the ollowing composition may be cited as a specific example of a dynamite in which the new explosive typical example, the cy'ano nitrate explosives may be used for the manufacture of gelati- In addition'to. its use in non-gelatinous explosives, of which the above formula is a nous explosives in which case it is gelatinized with mtrocellulose.
- ammonium nitrate ammonium perchlorate or POtflSSlIlIIlllltlfl-t.
- ammonium nitrate ammonium perchlorate
- POtflSSlIlIIlllltlfl-t ammonium perchlorate
- proportions may vary widely as to each andall of the ingredients, accordin to the particular uses to which the explosive isto be applied.
- V An explosive compound containing a cyano groupand a nitrate group.
- An explosive compound comprising an aliphatic ester containing a cyano group and a nitrate group.- f
- An explosive compound comprising an aliphatic ester containing a cyano group and a nitrate group, said groups bein each attached to difierent carbon atoms t erein.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
I Patented on. 2, 192
nnanx H. nnaenrm, or woonB nY, NEW Jan-say, AS$IGNOR won. I. no ron'r DE nniuonns & comranx, or wrnmmeron, DELAWARE, A oonrona'rron or DELA- WARE.
F CYANO mna'rn nxrnosxvn AND. rnocnss or rnonuome THE same.
No Drawing.
This invention relates to explosives containrng one or morecyano groups and.one or more nitrate groups. It relates particularl to explosives comprising a hydrocarbon whic v l has attached thereto wcyano groups and nitrate groups, and also relates to the process of producing said explosives. a I One object of the invention is to provide a new type of explosive of the above char- 10 'acter combining in part the explosive group-' ings of nitroglvcerine and hydrocyanic acid.
- to a hydrocarbon.-
A further object of the invention is toprovide a product which may be used alone or in combination with the usual dynamite g 'ingredients to make a dynamite of; good strength and great insensitivene'ss to me- .chanical shock. e e I The product cya'no methanol nitrate,
but by an expensive method involving t euse v of silver nitrate and potassium iodide, which is'impractical from the viewpoint of economy.
3 Accordingly, a still further object of my inrelatively inexpensive process for producing -this andother products. By the process of my invention, which has a wide application, a'c'yanohydrin is nitrated with mixedacid to give a cyano nitrate explojsive." The above mentioned explosive,
" cyano methanol nitrate, may thus be made by the nitratio'n Iof CNCH OH. j g Further'objects andadvanta es of'the in- 40 vention will appear from the ollowing des criptionand detailed examples of the inven- 'tion..
a Cyano nitrate explosives in which thecyano and nitrate groups are attached to the same carbon atom are acidic in character and relamethylene cyanohydrin,
. tively unstable; 1 have found that cyano nitrate explosives having the cyano and nigate groups enflditferent carbon atoms, in
vent-ion is to' provide a novel, practical and.
Application filed September 15, 1927. serial No. 219,817.
accordance with the present invention, as
for example cyano ethanol nitrate,
- CNCH CH ONO possess an unusually good stability; Another example of this type of explosive is that formed by the nitration of the cyanohydrin of glycerine,
ouonzofnonon on,
which gives cyano propanediol dinitrate,
ouomomonogon ono cyano-and nitrate groups each ondifl'erent carbonatoms may bemade in any desired way. I prefer, however, to make them by treating .cyanohydrins with mixed acid. One
The 'cyanol nitrate explosives having the example of the way in which my process may I be-c arried out is the following. 7
If the case of cytano ethanol nitrate, I may add one part by weight of cyano ethanol,
p prepared in anydesired way, to two and one- CNCH ONO has previously been "pre ared,
111g approximately 40% nitric acid and'60% all parts by-weight of mixed acid compris- 10" C. x 'The high solubility of the nitrated" product in the waste acid necessitates: drownjv 'mg' to obtain the explosive oil. This oil'may then be neutralized by washing with a weak- 1y alkaline solution such as a 5% solution of sodium carbonate. The product thus ,ob-
tained is a neutral, colorless oil of about the same viscosity as glycol dini'trate. It has been found to retain its neutrality over a period-of. several months storage. Analyzed for nitrate nitrogen by the nitrometer method, it gave a p value very near to the theoretical (12.07%).
This oil, while not quite as powerful as ethylene glycol dinitrate, has the desirable property of being-much less sensitive to mechanical shock than the latter.
Cyano ethanol nitrate may be used alonei as an explosive or incombination with the usual dynamite ingredients tomake ja dylflmite of-good strength and great insensitiveness to mechanical shock. It may used nitroglycerine with in a dynamite com rising nitroglycerine or its substitutes, as, or example, mixtures of tetranitro'diglycerlne,
nitro sugars, or nitroglycol. The ollowing composition may be cited as a specific example of a dynamite in which the new explosive typical example, the cy'ano nitrate explosives may be used for the manufacture of gelati- In addition'to. its use in non-gelatinous explosives, of which the above formula is a nous explosives in which case it is gelatinized with mtrocellulose. I
Furthermore, instead of the sodium nitrate, or in addition thereto, I may use various other oxidizing salts, as, for example,
ammonium nitrate, ammonium perchlorate or POtflSSlIlIIlllltlfl-t. Also, it will be understood that the various known carbonaceous the above compositions the proportions may vary widely as to each andall of the ingredients, accordin to the particular uses to which the explosive isto be applied.
- While I have described my invention in detail, it is to be understeod that many changes may be made in the examplesabove given without-departing from the invention as defined by tlga following claims.
I claim: V 1. An explosive compound containing a cyano groupand a nitrate group.
2. An explosive compound comprising an aliphatic ester containing a cyano group and a nitrate group.- f
3. An explosive compound comprising an aliphatic ester containing a cyano group and a nitrate group, said groups bein each attached to difierent carbon atoms t erein.
4. Asa new chemical compound, cyanoethanol-nitrate.
5. The, process which comprises producing a cyano nitrate by the nitration of a cyano alcohol. V
' 6. The process which com rises producing cyano ethanol nitrate by t -he nitration of cyano ethanol.
7. The process which comprises producing a cyano nitrate by,nitration of a cyano alcohol and washing'the separated product with an alkaline solution. 8. The process which comprises pioducing cyano ethanol nitrate by the mtration of cyano -ethanol-and washing the separated product -with an alkaline solution. a
' '9. The process which comprises producingcyano ethanol nitrate (by the nitration of i: ano ethanol with mix acid, and washing a t 1e separated product with an alkaline solu-l .tion.
In testimony whereof, I aflix my signature.
FRANK H. BERGEIM.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US219817A US1685771A (en) | 1927-09-15 | 1927-09-15 | Cyano nitrate explosive and process of producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US219817A US1685771A (en) | 1927-09-15 | 1927-09-15 | Cyano nitrate explosive and process of producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1685771A true US1685771A (en) | 1928-10-02 |
Family
ID=22820902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US219817A Expired - Lifetime US1685771A (en) | 1927-09-15 | 1927-09-15 | Cyano nitrate explosive and process of producing the same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1685771A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254109A (en) * | 1963-08-13 | 1966-05-31 | Gulf Research Development Co | Nitrate esters of aldehyde cyanohydrins |
-
1927
- 1927-09-15 US US219817A patent/US1685771A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254109A (en) * | 1963-08-13 | 1966-05-31 | Gulf Research Development Co | Nitrate esters of aldehyde cyanohydrins |
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