USH270H - Chemical warfare simulant - Google Patents

Chemical warfare simulant Download PDF

Info

Publication number
USH270H
USH270H US06784718 US78471887A USH270H US H270 H USH270 H US H270H US 06784718 US06784718 US 06784718 US 78471887 A US78471887 A US 78471887A US H270 H USH270 H US H270H
Authority
US
Grant status
Grant
Patent type
Prior art keywords
vx
simulant
chemical
invention
nerve gas
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
Application number
US06784718
Inventor
Joseph W. Hovanec
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
US Secretary of Army
Original Assignee
US Secretary of Army
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02Monothiocarbamic acids; Derivatives thereof
    • C07C333/04Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms

Abstract

A chemical 2-(diisopropylamino)ethyl dimethylthiocarbamate as a simulant use in place of VX nerve gas in decontamination studies.

Description

GOVERNMENTAL INTEREST

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.

BACKGROUND OF THE INVENTION

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.

SUMMARY OF THE INVENTION

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.

DESCRIPTION OF THE PREFERRED EMBODIMENT

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          232.4Boiling Point       298° C. 320° C.Density-25° C.       1.008 g/Cm.sup.3                      0.978 g/Cm.sup.3Viscosity-25° C.       9.96 cP        9.75 cPSolubility in       0.11 M/liter   0.015 M/literH.sub.2 O - 25° C.Hydrolysis  40 hours @ pH 10                      60 hours @ pH 10Toxicity    500,00 M.sup.-1 sec.sup.-1                      17 M.sup.-1 sec.sup.-1K.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.

PREPARATION

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.

COMPARISON REACTION TO AQUEOUS HYPOCHLORITE

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.

HYPOCHLORITE OXIDATION

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)

I claim:
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.
US06784718 1987-05-05 1987-05-05 Chemical warfare simulant Abandoned USH270H (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US06784718 USH270H (en) 1987-05-05 1987-05-05 Chemical warfare simulant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06784718 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
US06784718 Abandoned USH270H (en) 1987-05-05 1987-05-05 Chemical warfare simulant

Country Status (1)

Country Link
US (1) USH270H (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090057622A1 (en) * 2007-08-31 2009-03-05 Clean Earth Technologies, Llc Simulant of Radiological Contamination
US20090062386A1 (en) * 2007-08-30 2009-03-05 Clean Earth Technologies, Llc Simulants of Toxants for Training and Testing
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Mori et al., Chem. Abstracts, vol. 72, No. 9. Mar. 2, 1970.

Cited By (3)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
Smith et al. Simple alkanethiol groups for temporary blocking of sulfhydryl groups of enzymes
Fina et al. The alpha effect. A review
Neely Estimating rate constants for the uptake and clearance of chemicals by fish
Hermens Electrophiles and acute toxicity to fish.
Nannipieri et al. Ecological significance of the biological activity in soil
Antonijevic et al. Unequal efficacy of pyridinium oximes in acute organophosphate poisoning
Lunn et al. Destruction of hazardous chemicals in the laboratory
Wagner et al. Reactions of VX, HD, and their simulants with NaY and AgY zeolites. Desulfurization of VX on AgY
Kim et al. Kinetic analysis of a protein tyrosine kinase reaction transition state in the forward and reverse directions
Wagner et al. Reactions of VX, GD, and HD with nanosize CaO: autocatalytic dehydrohalogenation of HD
Jurek et al. Phosphate diester hydrolysis by mono-and dinuclear lanthanum complexes with an unusual third-order dependence
Uetrecht Reactivity and possible significance of hydroxylamine and nitroso metabolites of procainamide.
Watanabe et al. Modulation of calcium binding in sarcoplasmic reticulum adenosinetriphosphatase
US20040022867A1 (en) Decontamination formulation with sorbent additive
Bryantsev et al. Computational study of copper (II) complexation and hydrolysis in aqueous solutions using mixed cluster/continuum models
US3810788A (en) Method for decontaminating chemical warfare agents
Stock et al. Effects of ionic liquids on the acetylcholinesterase–a structure–activity relationship consideration
Spanggord et al. Mutagenicity in Salmonella typhimurium and structure‐activity relationships of wastewater components emanating from the manufacture of trinitrotoluene
Draper et al. Solar photooxidation of pesticides in dilute hydrogen peroxide
US5032291A (en) Catalytic reduction of nitro- and nitroso- substituted compounds
Marlier Multiple isotope effects on the acyl group transfer reactions of amides and esters
Worek et al. Kinetic analysis of reactivation and aging of human acetylcholinesterase inhibited by different phosphoramidates
Kirby et al. Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester
Zamecnik et al. Analogues of diadenosine 5', 5'''-P1, P4-tetraphosphate (Ap4A) as potential anti-platelet-aggregation agents
Hayden et al. Cysteine conjugate toxicity, metabolism, and binding to macromolecules in isolated rat kidney mitochondria.