USH270H - Chemical warfare simulant - Google Patents
Chemical warfare simulant Download PDFInfo
- Publication number
- USH270H USH270H US06/784,718 US78471887A USH270H US H270 H USH270 H US H270H US 78471887 A US78471887 A US 78471887A US H270 H USH270 H US H270H
- Authority
- US
- United States
- Prior art keywords
- simulant
- chemical
- nerve gas
- decontamination
- properties
- 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.)
- Abandoned
Links
- 239000000126 substance Substances 0.000 title abstract description 15
- 239000003958 nerve gas Substances 0.000 claims abstract description 14
- 238000005202 decontamination Methods 0.000 claims abstract description 9
- 230000003588 decontaminative effect Effects 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- LSHFNMNSLRXFIM-UHFFFAOYSA-N (dimethyl-lambda4-sulfanylidene)-[2-[di(propan-2-yl)amino]ethoxy]methanol Chemical group CC(C)N(C(C)C)CCOC(O)=S(C)C LSHFNMNSLRXFIM-UHFFFAOYSA-N 0.000 claims 2
- MVQTWSDKEGWVPG-UHFFFAOYSA-N o-[2-[di(propan-2-yl)amino]ethyl] n,n-dimethylcarbamothioate Chemical compound CC(C)N(C(C)C)CCOC(=S)N(C)C MVQTWSDKEGWVPG-UHFFFAOYSA-N 0.000 abstract description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 10
- 238000011160 research Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000011161 development Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002575 chemical warfare agent Substances 0.000 description 2
- 230000003278 mimic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- -1 2-(diisopropylamino) ethyl dimethylthiocarbamate Chemical compound 0.000 description 1
- UTPHRZRWMXLNIK-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethanethiol;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCS UTPHRZRWMXLNIK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
Definitions
- This invention relates to a novel simulator of a chemical warfare agent.
- this invention relates to a chemical which may be used to simulate nerve gas in an improved manner during decontamination procedures.
- Another object is to provide a simulator of VX which is safe to use but mimics the physical and chemical properties of the cited dangerous toxic agent itself.
- the simulator of VX must be liquid, should have a solubility similar to VX, and in solution should be destroyed by oxidation and hydrolysis in a manner and rate similar to VX.
- the three main properties of a simulant are state, solubility, and reactivity.
- a fourth requirement of a decreased amount of toxicity when compared to VX is highly important.
- the properties of a necessary simulant in place of VX are shown. It has been found that as a result of this comparison, the simulant of this invention could replace VX in various studies which have to be made. In particular, the simulant besides having properties, which are substantially equivalent to that of VX, is less toxic than the nerve gas and could be used to study decontamination procedures. As shown, the simulant has no significant anti-cholinesterate properties which make it less dangerous. Thus, a low toxicity substitute has been found for VX.
- the simulant 2-(diisopropylamino) ethyl dimethylthiocarbamate is prepared from equimolar amounts of dimethylcarbamayl chloride and 2-(diisopropylamino)ethanethiol hydrochloride. The latter two chemicals are refluxed for about 20 hours in a five-fold molar excess of pyridine. The pyridine is evaporated, and the residue dissolved in chloroform. This solution is washed with dilute sodium hydroxide solution, dried over magnesium sulfate, and the chloroform is evaporated under vacuum. The product is then purified by vacuum distillation, and is collected at 118°-120° C. at 0.55 torr. The distillate, a colorless liquid, was confirmed as a pure compound by nmr spectroscopy, elemental analysis, and gas chromatography.
- simulant of this invention and VX nerve gas were reacted with a five-fold molar excess of sodium N, N-dichloroisocyanurate in water. At intervals of two to ten minutes, aliquots of each of the materials were removed and analyzed iodimetrically for active chlorine concentration.
- VX nerve gas under the above reaction conditions, consumed chlorine in two kinetically distinct processes. In the first few minutes, there was a rapid consumption of about 1.5 mole equivalent of hypochlorite per mol of VX nerve gas. This was followed by a slower but nearly linear consumption of chlorine over a substantially two hour period.
- the chlorine consumption of the simulant of this invention followed a similar two-stage pattern when compared to VX. During the period of 15 minutes to 60 minutes after mixing, their relative chlorine consumptions are within 10 percent of each other.
- VX is a liquid, so it is the simulant of this invention. VX could never be mimicked by a solid. VX and the cited simulant of this invention have similar solubilities in water and both are pH dependent in similar ways. Once in solution, VX nerve gas may be destroyed by oxidation or hydrolysis, and such is the chemical reactivity of the simulant of this invention.
- simulant of this invention has been prepared and its physical properties, slow hydrolysis, and behavior toward hypochlorite make this a suitable simulant for VX.
- the homologues of the simulant of this invention do not exhibit the desired properties.
- the cited simulant of this invention may be added to a catalog of compounds which may be used as simulants for specific agents under specific conditions.
- the simulant of this invention may be used in the testing of chemically active liquid decontaminants in place of VX for research, development, test, and evaluation of new systems.
Abstract
A chemical 2-(diisopropylamino)ethyl dimethylthiocarbamate as a simulant use in place of VX nerve gas in decontamination studies.
Description
The invention described herein may be manufactured, used and licensed by or for the Government for governmental purposes without the payment to me of any royalties thereon.
1. Field of the Invention
This invention relates to a novel simulator of a chemical warfare agent.
More particularly, this invention relates to a chemical which may be used to simulate nerve gas in an improved manner during decontamination procedures.
2. Description of the Prior Art
Difficulties of a technical and administrative nature prevent the use of nerve gas in research, development, and testing procedures due to the hazards involved. Current safety and security regulations which govern the use of toxic chemical warfare agents preclude most research, development, and testing of nerve gas such as VX in most laboratories. For example, no outdoor testing may be done with the actual nerve gas itself. Thus, in order to facilitate chemical defense research, development, testing and evaluation, it is vital to have an inventory of chemical simulants for such nerve gas for specific purposes. It can be seen where simulants are vital to sustained progress in the improvement of our defensive posture relative chemical warfare. As one can see, simulants are used in every major area of the research operation of chemical warfare agents. They are necessary in every stage of the life cycle of a system from conception through basic research, development, testing, evaluation and training.
To date, the only compound used to mimic the chemical behavior of VX is O-ethyl S-ethyl methylphosphonothiolate. However, the solubility and reactivity of this compound preclude the valid performance study of VX at varying pH levels.
It is known that each of the areas of study in testing and evaluation set their own parameters relative the experimental or operating stages. These parameters dictate what properties are essential for an effective simulant in the areas under study. In the past, experimenters had to use their individual judgement in selecting simulants and, many times, a simulator was a material which was used because it was readily available or because of prior use in another stage of the cycle. Many times, the material used for one specific purpose was not altogether satisfactory for a second specific purpose because of its properties.
There has been a long standing need in the research community of chemical defense for a catalog of compounds which might be used as simulants for specific chemical agents under specific conditions particular decomposition or decontamination. In particular, a search for a simulant of VX under decontamination studies is extremely important.
It is therefore an object of this invention to provide a simulant for VX nerve gas for use in research, development, evaluation and testing of chemically active liquid decontaminants.
Another object is to provide a simulator of VX which is safe to use but mimics the physical and chemical properties of the cited dangerous toxic agent itself.
Other objects and many of the attendant advantages of this invention will become more apparent to those skilled in the art from a reading of the detailed specification which follows.
In general, the simulator of VX must be liquid, should have a solubility similar to VX, and in solution should be destroyed by oxidation and hydrolysis in a manner and rate similar to VX. Thus the three main properties of a simulant are state, solubility, and reactivity. However, a fourth requirement of a decreased amount of toxicity when compared to VX is highly important.
We have found that the chemical 2-(diisopropylamino)ethyl dimethylthiocarbamate is the preferred stimulant for use in place of VX nerve gas in decontamination studies.
The formula for this simulator is, viz. ##STR1##
The table I which follows sets forth a comparison of the physical and chemical properties of this simulator as compared to VX.
TABLE I
______________________________________
VX Cited Simulator
______________________________________
Formula Weight
267.4 232.4
Boiling Point
298° C. 320° C.
Density-25° C.
1.008 g/Cm.sup.3
0.978 g/Cm.sup.3
Viscosity-25° C.
9.96 cP 9.75 cP
Solubility in
0.11 M/liter 0.015 M/liter
H.sub.2 O - 25° C.
Hydrolysis 40 hours @ pH 10
60 hours @ pH 10
Toxicity 500,00 M.sup.-1 sec.sup.-1
17 M.sup.-1 sec.sup.-1
K.sub.I (eel ACHE)
______________________________________
As seen in Table I, the properties of a necessary simulant in place of VX are shown. It has been found that as a result of this comparison, the simulant of this invention could replace VX in various studies which have to be made. In particular, the simulant besides having properties, which are substantially equivalent to that of VX, is less toxic than the nerve gas and could be used to study decontamination procedures. As shown, the simulant has no significant anti-cholinesterate properties which make it less dangerous. Thus, a low toxicity substitute has been found for VX.
The simulant 2-(diisopropylamino) ethyl dimethylthiocarbamate is prepared from equimolar amounts of dimethylcarbamayl chloride and 2-(diisopropylamino)ethanethiol hydrochloride. The latter two chemicals are refluxed for about 20 hours in a five-fold molar excess of pyridine. The pyridine is evaporated, and the residue dissolved in chloroform. This solution is washed with dilute sodium hydroxide solution, dried over magnesium sulfate, and the chloroform is evaporated under vacuum. The product is then purified by vacuum distillation, and is collected at 118°-120° C. at 0.55 torr. The distillate, a colorless liquid, was confirmed as a pure compound by nmr spectroscopy, elemental analysis, and gas chromatography.
In separate experiments, the simulant of this invention and VX nerve gas were reacted with a five-fold molar excess of sodium N, N-dichloroisocyanurate in water. At intervals of two to ten minutes, aliquots of each of the materials were removed and analyzed iodimetrically for active chlorine concentration.
VX nerve gas under the above reaction conditions, consumed chlorine in two kinetically distinct processes. In the first few minutes, there was a rapid consumption of about 1.5 mole equivalent of hypochlorite per mol of VX nerve gas. This was followed by a slower but nearly linear consumption of chlorine over a substantially two hour period.
The chlorine consumption of the simulant of this invention followed a similar two-stage pattern when compared to VX. During the period of 15 minutes to 60 minutes after mixing, their relative chlorine consumptions are within 10 percent of each other.
In comparison, VX is a liquid, so it is the simulant of this invention. VX could never be mimicked by a solid. VX and the cited simulant of this invention have similar solubilities in water and both are pH dependent in similar ways. Once in solution, VX nerve gas may be destroyed by oxidation or hydrolysis, and such is the chemical reactivity of the simulant of this invention.
There has been a long-standing need in the chemical defense research community for a simulant which would satisfactorily mimic the physical and chemical properties of VX. The simulant of this invention has been prepared and its physical properties, slow hydrolysis, and behavior toward hypochlorite make this a suitable simulant for VX. The homologues of the simulant of this invention do not exhibit the desired properties. The cited simulant of this invention may be added to a catalog of compounds which may be used as simulants for specific agents under specific conditions. For example, the simulant of this invention may be used in the testing of chemically active liquid decontaminants in place of VX for research, development, test, and evaluation of new systems.
Sodium N, N-dichloroisocyanurate (Fichlor reagent) was used in the comparison of the hypochlorite oxidation reaction. When VX was added to an unbuffered solution of the Fichlor reagent in water at a 5 molar excess relative VX, there was an immediate reaction. Within 1 minute, the VX was destroyed. The data for the simulant in Fichlor exhibited a similar pattern. There was an initial rapid burst of chloring consumption by the simulant which was followed by a slower steady-state consumption. The correlation of VX and simulant relative Kinetics is highly satisfactory for the intended purpose of testing and evaluation of the decontamination procedure.
Claims (2)
1. In the process of simulating the decontamination of VX nerve gas, the improvement consisting essentially of substituting 2-(diisopropylamino)ethyl dimethylthiocarbonate for said VX in said decontamination.
2. The process of claim 1 wherein said 2-(diisopropylamino)ethyl dimethylthiocarbonate has the following properties, viz.
(a) molecular weight of 232.4,
(b) boiling point of 320° C.,
(c) density of 0.978 g/cm3 at 25° C.,
(d) viscosity of 9.75 cP at 25° C.,
(e) solubility in water of 0.015M at 25° C., and
(f) hydrolysis in t1/2 greater than 60 hours at pH10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/784,718 USH270H (en) | 1987-05-05 | 1987-05-05 | Chemical warfare simulant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/784,718 USH270H (en) | 1987-05-05 | 1987-05-05 | Chemical warfare simulant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH270H true USH270H (en) | 1987-05-05 |
Family
ID=25133322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/784,718 Abandoned USH270H (en) | 1987-05-05 | 1987-05-05 | Chemical warfare simulant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH270H (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090062386A1 (en) * | 2007-08-30 | 2009-03-05 | Clean Earth Technologies, Llc | Simulants of Toxants for Training and Testing |
| US20090057622A1 (en) * | 2007-08-31 | 2009-03-05 | Clean Earth Technologies, Llc | Simulant of Radiological Contamination |
| RU2585027C1 (en) * | 2014-12-11 | 2016-05-27 | Федеральное государственное казённое военное образовательное учреждение высшего профессионального образования "Военная академия радиационной, химической и биологической защиты имени Маршала Советского Союза С.К. Тимошенко" | Simulator of o-isobutyl-s-2-(n,n-diethylamino)ethylmethylphosphonate for studying removal of droplets thereof from textile materials with powder formulations |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075006A (en) | 1976-07-30 | 1978-02-21 | Ppg Industries, Inc. | S-aryl N-alkynylthiolcarbamates |
-
1987
- 1987-05-05 US US06/784,718 patent/USH270H/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075006A (en) | 1976-07-30 | 1978-02-21 | Ppg Industries, Inc. | S-aryl N-alkynylthiolcarbamates |
Non-Patent Citations (1)
| Title |
|---|
| Mori et al., Chem. Abstracts, vol. 72, No. 9. Mar. 2, 1970. |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090062386A1 (en) * | 2007-08-30 | 2009-03-05 | Clean Earth Technologies, Llc | Simulants of Toxants for Training and Testing |
| US20090057622A1 (en) * | 2007-08-31 | 2009-03-05 | Clean Earth Technologies, Llc | Simulant of Radiological Contamination |
| RU2585027C1 (en) * | 2014-12-11 | 2016-05-27 | Федеральное государственное казённое военное образовательное учреждение высшего профессионального образования "Военная академия радиационной, химической и биологической защиты имени Маршала Советского Союза С.К. Тимошенко" | Simulator of o-isobutyl-s-2-(n,n-diethylamino)ethylmethylphosphonate for studying removal of droplets thereof from textile materials with powder formulations |
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