US3465674A - Process for generating an explosion - Google Patents
Process for generating an explosion Download PDFInfo
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- US3465674A US3465674A US679208A US3465674DA US3465674A US 3465674 A US3465674 A US 3465674A US 679208 A US679208 A US 679208A US 3465674D A US3465674D A US 3465674DA US 3465674 A US3465674 A US 3465674A
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- United States
- Prior art keywords
- alcohol
- explosion
- chloro
- primary
- sulfoxide
- 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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- 238000004880 explosion Methods 0.000 title description 12
- 238000000034 method Methods 0.000 title description 5
- -1 -halo amides Chemical class 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000002360 explosive Substances 0.000 description 5
- 150000002440 hydroxy compounds Chemical class 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 2
- QBZXNCTYNYRTIJ-UHFFFAOYSA-N 3-chloro-1,3-oxazolidin-2-one Chemical compound ClN1CCOC1=O QBZXNCTYNYRTIJ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229950009390 symclosene Drugs 0.000 description 2
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- FCWAYYDINOPRFJ-UHFFFAOYSA-N 1-chloroazepan-2-one Chemical compound ClN1CCCCCC1=O FCWAYYDINOPRFJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- VTRRCXRVEQTTOE-UHFFFAOYSA-N 1-methylsulfinylethane Chemical compound CCS(C)=O VTRRCXRVEQTTOE-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- UUHRGIQMWDHGRU-UHFFFAOYSA-N 3-bromo-5-methyl-1,3-oxazolidin-2-one Chemical compound CC1CN(Br)C(=O)O1 UUHRGIQMWDHGRU-UHFFFAOYSA-N 0.000 description 1
- KXQNUBKHVULQFK-UHFFFAOYSA-N 3-chloro-5-methyl-1,3-oxazolidin-2-one Chemical compound CC1CN(Cl)C(=O)O1 KXQNUBKHVULQFK-UHFFFAOYSA-N 0.000 description 1
- YGZVAQICDGBHMD-UHFFFAOYSA-N 3-methylhexan-1-ol Chemical compound CCCC(C)CCO YGZVAQICDGBHMD-UHFFFAOYSA-N 0.000 description 1
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AZLIQMOCLWNKBE-UHFFFAOYSA-N n,n-dichloro-2-[2-(dichlorosulfamoyl)phenoxy]benzenesulfonamide Chemical compound ClN(Cl)S(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1S(=O)(=O)N(Cl)Cl AZLIQMOCLWNKBE-UHFFFAOYSA-N 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HBXNJMZWGSCKPW-UHFFFAOYSA-N octan-2-amine Chemical compound CCCCCCC(C)N HBXNJMZWGSCKPW-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06C—DETONATING OR PRIMING DEVICES; FUSES; CHEMICAL LIGHTERS; PYROPHORIC COMPOSITIONS
- C06C5/00—Fuses, e.g. fuse cords
- C06C5/06—Fuse igniting means; Fuse connectors
-
- 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
- the present invention relates to spontaneously explosive compositions and to a method for generating an explosion under predetermined conditions.
- Combinations of certain materials are known to be hypergolic, that is, ignition or explosion occurs on contact of the components. Such combinations are useful in rocketry and they are also sometimes employed to trigger a mechanical action or a larger explosion. The action is substantially instantaneous. Delayed action initiators such as the familiar black powder fuse of fireworks or other explosives are also known. Mechanically timed initiating devices have also been used to produce delayed explosions. The present invention provides a means whereby predetermined timed explosions can be produced by a novel chemical process.
- N-halo amides of the invention are defined herein by that term as including any carboxamide, sulfonamide,
- Representative compounds include N- chloroacetamide, N-bromosuccinimide, mono, di, and trichloroisocyanuric acid, 1,Z-dichloro-5,5-dimethyl-hydantoin, 1-bromo-3-chloro 5,5 dimethylhydantoin, N-N-dichloro-p-toluenesulfonamide, p,p oxybis(N,N-dichlorobenzenesulfonamide), N-chloro-Z-pyrrolidone, N-chloro- S-methyl-Z-oxazolidinone, N-chloro-2-morpholinone, N- chlorocaprolactam, and the like. Mixtures of such compounds may be employed. Particularly preferred are N- chloro-2-oxazolidinone and its lower alkyl substituted derivatives.
- Organic hydroxy compounds of the present invention include primary and secondary alkanols of 2-7 carbon atoms, benzyl alcohol, phenol, and lower alkyl substituted phenols.
- Representative of the class of alkanols are ice ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, isoamyl alcohol, and heptyl alcohol.
- Alkanols such as methanol, tert-butyl alcohol, and cyclohexanol are not operative.
- the class of lower alkyl substituted phenols includes thecresols, isopropylphenol, tert-butylphenol, xylenol, and their isomers.
- Amines useful in the present invention are alkyl primary amines of 3 to about 8 carbon atoms wherein the alkyl group is of primary or secondary configuration.
- Such amines include propylamine, isopropylamine, n-butylamine, 2-aminooctane, and the like.
- Lower alkyl sulfoxides which are operable include dimethyl sulfoxide, diethyl sulfoxide, methyl ethyl sulfoxide, dibutyl sulfoxide, and the like, wherein the alkyl groups are of primary or secondary configuration.
- the term lower alkyl is used herein in its usual sense to mean alkyl groups of 14 carbon atoms.
- Proportions of reactants which are operative in this invention are 0.02-50 parts by weight of di lower alkyl sulfoxide or an active hydrogen compound per part of N- chloro compound. When proportions of reactants outside this range are employed, the large excess of the one reactant tends to muffie the reaction so that no explosion takes place even though a reaction may occur.
- N-chloro-2-oxazolidinones and N-chloro-Z-morpholinone and their N-bromo analogs are new compounds which are the invention of one of us and these are described and claimed in copending application Ser. No. 679,254, filed concurrently herewith and now abandoned. They may be prepared by halogenating the parent com pounds with a haloisocyanuric acid as set forth in that application or by reacting the heterocycle with chlorine in the presence of an alkali as described by Tafel et al. Berichte 33, 2224 (1900).
- the utility of the present invention to generate sudden pressure, initiate a mechanical action, or detonate a conventional explosive is evident, particularly where it is desired to have a short delay between action and reaction.
- Examples 1-9 A series of tests were conducted wherein one gram of an N-haloamide was contacted with a small amount of isopropyl alcohol and the interval between this contact and explosion of the mixture was measured. During these tests, the mixtures characteristically showed little or no change in appearance or temperature for a definite time, then they suddenly and violently decomposed with an explosive evolution of gas and sometimes with a visible flame.
- Trichloroisocyanuric acid a 114 N-chloro-5-methyl-2-oxazo1idinone about 1 213 N -bromo-5-methyl-2-oxazolidinone 210 Results comparable to those of Examples 25-27 are obtained when the isopropylamine is replaced by other primary amines as previously defined as n-butylamine, propylamine, n-hexylamine, or Z-aminooctane.
- the N-halo amide can be any of other such compounds as shown in Examples 1-10 and as herein defined with similar results.
- Example 28 By the procedure of the foregoing examples, 1.0 gram of N-chloro-5-methyl-2-oxazolidinone was intimately contacted with 0.1 ml. of dimethyl sulfoxide. The mixture exploded after a lapse of 1.5 seconds, the exploding mixture attaining a maximum temperature of 165 C.
- a process for generating an explosion which comprises intimately contacting at least one N-halo amide, where the halogen is chlorine or bromine, and 0.02 parts based on the weight of N-halo amide of a reactive component which is at least one of a di lower primary or secondary alkyl sulfoxide, a primary or secondary alkyl primary amine of 3-8 carbon atoms, or an organic hydroxy compound which is a primary or secondary alkanol of 2-7 carbon atoms, phenol, a lower alkyl phenol, or benzyl alcohol.
- a reactive component which is at least one of a di lower primary or secondary alkyl sulfoxide, a primary or secondary alkyl primary amine of 3-8 carbon atoms, or an organic hydroxy compound which is a primary or secondary alkanol of 2-7 carbon atoms, phenol, a lower alkyl phenol, or benzyl alcohol.
- N-halo amide is an N-chloro-Z-oxabolidinone and the reactive component is a primary or secondary alkanol of 2-7 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
United States Patent O ABSTRACT OF THE DISCLOSURE N-halo amides react explosively with alkyl sulfoxides and active hydrogen compounds such as certain hydroxy compounds and amines. Delayed explosive decompositions occurring after a predetermined time can be produced by selection of components and variation of their proportions.
BACKGROUND OF THE INVENTION The present invention relates to spontaneously explosive compositions and to a method for generating an explosion under predetermined conditions.
Combinations of certain materials are known to be hypergolic, that is, ignition or explosion occurs on contact of the components. Such combinations are useful in rocketry and they are also sometimes employed to trigger a mechanical action or a larger explosion. The action is substantially instantaneous. Delayed action initiators such as the familiar black powder fuse of fireworks or other explosives are also known. Mechanically timed initiating devices have also been used to produce delayed explosions. The present invention provides a means whereby predetermined timed explosions can be produced by a novel chemical process.
SUMMARY OF THE INVENTION It has now been found that when a di lower alkyl sulfoxide or an active hydrogen compound such as any of certain alcohols and amines is intimately contacted with an N-halo amide or N-halo imide, the halogen being bromine or chlorine, the mixture remains substantially unchanged in appearance and temperature for a measurable time ranging from a second or two to several minutes, and in some cases, as long as several hours or even days, then it suddenly decomposes explosively with flame formation and generation of considerable gas and vapor. By choice of particular components and proportions of these, the interval between contact and explosion can be adjusted to a predetermined desired length.
DETAILED DESCRIPTION The N-halo amides of the invention are defined herein by that term as including any carboxamide, sulfonamide,
or corresponding carboximide or sulfonimide having at least one chlorine or bromine atom attached to the amide nitrogen atom. Representative compounds include N- chloroacetamide, N-bromosuccinimide, mono, di, and trichloroisocyanuric acid, 1,Z-dichloro-5,5-dimethyl-hydantoin, 1-bromo-3-chloro 5,5 dimethylhydantoin, N-N-dichloro-p-toluenesulfonamide, p,p oxybis(N,N-dichlorobenzenesulfonamide), N-chloro-Z-pyrrolidone, N-chloro- S-methyl-Z-oxazolidinone, N-chloro-2-morpholinone, N- chlorocaprolactam, and the like. Mixtures of such compounds may be employed. Particularly preferred are N- chloro-2-oxazolidinone and its lower alkyl substituted derivatives.
Organic hydroxy compounds of the present invention include primary and secondary alkanols of 2-7 carbon atoms, benzyl alcohol, phenol, and lower alkyl substituted phenols. Representative of the class of alkanols are ice ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, isoamyl alcohol, and heptyl alcohol. Alkanols such as methanol, tert-butyl alcohol, and cyclohexanol are not operative. The class of lower alkyl substituted phenols includes thecresols, isopropylphenol, tert-butylphenol, xylenol, and their isomers.
Amines useful in the present invention are alkyl primary amines of 3 to about 8 carbon atoms wherein the alkyl group is of primary or secondary configuration. Such amines include propylamine, isopropylamine, n-butylamine, 2-aminooctane, and the like.
Lower alkyl sulfoxides which are operable include dimethyl sulfoxide, diethyl sulfoxide, methyl ethyl sulfoxide, dibutyl sulfoxide, and the like, wherein the alkyl groups are of primary or secondary configuration. The term lower alkyl is used herein in its usual sense to mean alkyl groups of 14 carbon atoms.
Mixtures of alcohols, of amines, of sulfoxides, or combinations of these classes can be used effectively in the invention.
Proportions of reactants which are operative in this invention are 0.02-50 parts by weight of di lower alkyl sulfoxide or an active hydrogen compound per part of N- chloro compound. When proportions of reactants outside this range are employed, the large excess of the one reactant tends to muffie the reaction so that no explosion takes place even though a reaction may occur.
The N-chloro-2-oxazolidinones and N-chloro-Z-morpholinone and their N-bromo analogs are new compounds which are the invention of one of us and these are described and claimed in copending application Ser. No. 679,254, filed concurrently herewith and now abandoned. They may be prepared by halogenating the parent com pounds with a haloisocyanuric acid as set forth in that application or by reacting the heterocycle with chlorine in the presence of an alkali as described by Tafel et al. Berichte 33, 2224 (1900).
The utility of the present invention to generate sudden pressure, initiate a mechanical action, or detonate a conventional explosive is evident, particularly where it is desired to have a short delay between action and reaction. The occasion often arises where it is desirable to provide a known time between the triggering action, as by crushing a capsule of one component in the other component, and the explosion without having to depend on a burning fuse or action of a mechanical timer.
Examples 1-9 A series of tests were conducted wherein one gram of an N-haloamide was contacted with a small amount of isopropyl alcohol and the interval between this contact and explosion of the mixture was measured. During these tests, the mixtures characteristically showed little or no change in appearance or temperature for a definite time, then they suddenly and violently decomposed with an explosive evolution of gas and sometimes with a visible flame.
3 Examples 11-24 A series of tests were run substantially as described above wherein 0.3 ml. (or other quantity as noted) of a hydroxy compound was added to 1 ml. of N-chloro-S- methyl-2-oxazolidinone and the time before explosion was noted.
Hydroxy compound: Time, seconds Ethyl alcohol 78 Propyl alcohol 39 Isopropyl alcohol 4 Butyl alcohol 67 Isobutyl alcohol 39 Sec-butyl alcohol 3 n-Amyl alcohol 34 Isoamyl alcohol 79 n-Hexyl alcohol (0.1 ml.) 32 n-Heptyl alcohol 127 Isoheptyl alcohol 343 3-methyl-1-hexanol 231 Benzyl alcohol 24 o-Cresol (0.1 ml.) 3
Examples 25-27 Tests were run as in the foregoing examples wherein one gram quantities of an N-halo amide was contacted with 0.2 ml. of isopropylamine. In each case, the maximum temperature measured in the exploding mixture was determined.
Time, Maximum N-halo amide seconds temp., C.
Trichloroisocyanuric acid a. 114 N-chloro-5-methyl-2-oxazo1idinone about 1 213 N -bromo-5-methyl-2-oxazolidinone 210 Results comparable to those of Examples 25-27 are obtained when the isopropylamine is replaced by other primary amines as previously defined as n-butylamine, propylamine, n-hexylamine, or Z-aminooctane. In the same way, the N-halo amide can be any of other such compounds as shown in Examples 1-10 and as herein defined with similar results.
Example 28 By the procedure of the foregoing examples, 1.0 gram of N-chloro-5-methyl-2-oxazolidinone was intimately contacted with 0.1 ml. of dimethyl sulfoxide. The mixture exploded after a lapse of 1.5 seconds, the exploding mixture attaining a maximum temperature of 165 C.
Similar results are obtained when another di lower primary or secondary alkyl sulfoxide is employed in place of dimethyl sulfoxide or when the N-halo amide is another as previously defined.
We claim:
1. A process for generating an explosion which comprises intimately contacting at least one N-halo amide, where the halogen is chlorine or bromine, and 0.02 parts based on the weight of N-halo amide of a reactive component which is at least one of a di lower primary or secondary alkyl sulfoxide, a primary or secondary alkyl primary amine of 3-8 carbon atoms, or an organic hydroxy compound which is a primary or secondary alkanol of 2-7 carbon atoms, phenol, a lower alkyl phenol, or benzyl alcohol.
2. The process of claim 1 wherein the N-halo amide is an N-chloro-Z-oxabolidinone and the reactive component is a primary or secondary alkanol of 2-7 carbon atoms.
References Cited UNITED STATES PATENTS 2,149,694 3/1939 Vollrath 149-109 2,769,304 11/1956 Burton 149-109 X 2,771,737 11/1956 Scott et al 149-109 X 2,771,738 11/1956 Scott et al. 149-109 X 2,823,515 2/1958 Webb 149-109 X 2,826,037 3/1958 Scott et al 149-109 X 2,835,106 5/1958 Carter 149-109 X 2,859,587 11/1958 Scott et al. 149-109 X 2,869,320 1/1959 Burton 149-109 X 2,874,535 2/1959 Ayers et a1 149-109 X 2,932,941 4/1960 Ayers et al. 149-109 X CARL D. QUARFORTH, Primary Examiner S. J. LECHERT, Assistant Examiner U.S. Cl. X.R. -211; 149-109
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US67920867A | 1967-10-30 | 1967-10-30 |
Publications (1)
Publication Number | Publication Date |
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US3465674A true US3465674A (en) | 1969-09-09 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US679208A Expired - Lifetime US3465674A (en) | 1967-10-30 | 1967-10-30 | Process for generating an explosion |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4009178A (en) * | 1975-06-16 | 1977-02-22 | Interx Research Corporation | Brominating and oxidizing agent and method of using same |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2149694A (en) * | 1937-08-09 | 1939-03-07 | Richard E Vollrath | Spontaneously inflammable flashlight composition and method of preparation |
US2769304A (en) * | 1954-07-06 | 1956-11-06 | Phillips Petroleum Co | Hypergolic fuel and the method of using it |
US2771738A (en) * | 1951-10-01 | 1956-11-27 | Phillips Petroleum Co | Morpholines as hypergolic fuels |
US2771737A (en) * | 1951-12-04 | 1956-11-27 | Phillips Petroleum Co | Piperidines as hypergolic fuels |
US2823515A (en) * | 1954-04-09 | 1958-02-18 | California Research Corp | Auto-ignition method |
US2826037A (en) * | 1951-11-09 | 1958-03-11 | Phillips Petroleum Co | Polycyclic aldehydes as hypergolic fuels |
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US2869320A (en) * | 1954-07-06 | 1959-01-20 | Phillips Petroleum Co | Hypergolic fuel and its method of use in developing thrust |
US2874535A (en) * | 1951-11-08 | 1959-02-24 | Phillips Petroleum Co | Substituted furans as hypergolic fuels |
US2932941A (en) * | 1951-11-08 | 1960-04-19 | Phillips Petroleum Co | Sulfenamides and thiosulfenamides as hypergolic fuels |
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1967
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US2149694A (en) * | 1937-08-09 | 1939-03-07 | Richard E Vollrath | Spontaneously inflammable flashlight composition and method of preparation |
US2835106A (en) * | 1946-07-20 | 1958-05-20 | Aerojet General Co | Method of jet propulsion by spontaneous combustion of furfural |
US2771738A (en) * | 1951-10-01 | 1956-11-27 | Phillips Petroleum Co | Morpholines as hypergolic fuels |
US2874535A (en) * | 1951-11-08 | 1959-02-24 | Phillips Petroleum Co | Substituted furans as hypergolic fuels |
US2932941A (en) * | 1951-11-08 | 1960-04-19 | Phillips Petroleum Co | Sulfenamides and thiosulfenamides as hypergolic fuels |
US2826037A (en) * | 1951-11-09 | 1958-03-11 | Phillips Petroleum Co | Polycyclic aldehydes as hypergolic fuels |
US2771737A (en) * | 1951-12-04 | 1956-11-27 | Phillips Petroleum Co | Piperidines as hypergolic fuels |
US2859587A (en) * | 1953-06-08 | 1958-11-11 | Phillips Petroleum Co | Hypergolic fuel and method of propelling rockets |
US2823515A (en) * | 1954-04-09 | 1958-02-18 | California Research Corp | Auto-ignition method |
US2769304A (en) * | 1954-07-06 | 1956-11-06 | Phillips Petroleum Co | Hypergolic fuel and the method of using it |
US2869320A (en) * | 1954-07-06 | 1959-01-20 | Phillips Petroleum Co | Hypergolic fuel and its method of use in developing thrust |
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US4009178A (en) * | 1975-06-16 | 1977-02-22 | Interx Research Corporation | Brominating and oxidizing agent and method of using same |
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