AD~ ;121C I• L

CHEMICALSYSTEMS

-- --- LABORATORY US Army Armament Research and Development Command

Aberdeen Proving Ground, Maryland 21010

TECHNICAL REPORT ARCSL-TR-82029

RIOT CONTROL AGENT DECONTAM!NATION: IEVALUATION OF COMMERCIAL PRODUCTS

by 7

Joseph W. Hovanec

:- Chemical BranchResearch Division

June 1983

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LAiI Approved for public release; distribution unlimited

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Disclaimer

The findings in this report are not to be construed as an official Department of the Armyposition unless so designated by other authorized documents.

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REPORT DOCUMENTATION PAGE READ INSTRUCTIONSBEFORE COMPLETING FORM

. REPORT NUMBER 2 GOVT ACCESSION NO. 3. RECIPIENT'S CATALOG NUMBERARCSL-TR-82029 hZ. ýi2 $-'"i;

4. TITLE (arnd S.L1,R-. S. TYPE OF REPORT & PERIOD COVEkED

Technical ReportRIOT CONTROL AGENT DECONTAMINATION t Report I0EVALUATION OF COMMERCIAL PRODUCTS

6. PERFORMING ORG. REPORT NUMBER

7. AUTHBR(q) S. CONTRACT OR GRANT NUMBER(e)

loseph W. Hovanec

S. PERFORMING ORGANIZATION NAME AND ADDRESS 10. PROGRAM ELEMENT. PROJECT, TASK .Commander, Chemical Systems Laboratory AREA & WORK UNIT NUMUERSATTN: DRDAR-CLB-CA Project IL161101A91A

Aberdeen Proving Ground, Maryland 21010i I. CONTROLLING OFFICE NAME AND ADDRESS 12. REPORT DATE

Commander, Chemical Systems Laboratory June 1983ATTN: DRDAR-CLJ-R 13. NUMBER OF PAGES

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II. SUPPLEMENTARY NOTES

Sl. KEY WORDS (Continue on rever.o aide it necesesay end identity by block nurnbo.)

CS Sodium DithioniteCN DetergentsCR Riot control

20, ABSTR ACT ICietstimU em reerse eili it neoomme ad iderMlf by block number)

A variety of commercial cleaning, bleaching and disinfecting products wereexamined for their potential utility in the decontamination of CN, CS, and CR. Some ofthese products weie found to be quite useful in reacting with or promoting the reactionsof these agents. Specific recommendations are made regarding the use of thesematerials.

DD "O" 1473 EDITION OF NOV CS ISOBSOLETE UNCLASSIFIED

SECURITY CLASSIFICATION OF THIS PAGE (Wh-en lete Entered)

[ PREFACE

The information in this report was generated by work funded through an In-HouseLaboratory Independent Research program, Project ILI6I1I0A9IA. This report is concernedwth decontamination of riot control agents. The experimental data are recorded in notebook

Ii no. 9831. The period covered was from August 1978 to August 1980.

.i The use of trade narnes it" this report does not constitute an official endorsement or

approval of the use of such commercial hardware or software. This report may not be cited forpurposes of advertisement.

ii Reproduction of this document in whole or in part is prohibited except with permis-4 sion of the Commander, Chemical Systems Laboratory, ATTN: DRDAR-CLJ-R, AberdeenProving Ground, Maryland 21010. However, the Defense Technical Information Center and theNational Technical Informat'ion Service are authorized to reproduce the document for UnitedStates Government purposes.

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CONTENTSPage

. INTRODUCTION ...................................................... 7

2. EXPERIMENTAL ...................................................... 7

3. RESULTS AND DISCUSSION ............................................ .

4. CONCLUSIONS ....................................................... 11

LITERATURE CITED .................................................. 13

APPENDIX ........................................................... 15

DISTRIBUTION LIST ................................................... 17

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h-iECýEOJN'G PAGE BLANK8-NOT n1UviXD

RIOT CONTROL AGENT DECONTAMINATION:EVALUATION OF COMMERCIAL PRODUCTS

1. INTRODUCTION

The deployment of riot control agents by either military or civilian law enforcementagencies is often the only viable method of preserving order while minimizing personal injuryand property damage during civil disorders. Unfortunately, this results in the contamination ofpublic areas with riot control chemicals which must be decontaminated as soon as order isrestored. The current recommendation for decontamination of areas contaminated with riotI •control agents is to scrub the affected areas throughly with detergent in water. While in somecases this is sufficient, it is not often possible to reach all the affected surfaces. Poroussurfaces will retain a significant amount of contamination after washing.

There have been s veral laboratory studies to develop che rigal decontaminants for-chloroacetohenone (CN), o-chlorobenzylidenemalononitrile (CS),' 0- and dibenz(d,f) (1,4)-

oxazepine (CR). ,* Several chemicals have been observed to react with these materials butnone are suitable for large-scale decontamination of public areas because they are expensive,noxious, difficult to store, difficult to use, or corrosive. This study was undertaken todetermine whether any commercially available cleaning products could be of value in thisdecontamination problem.

2. EXPERIMENTATION

All commercial products were obtained from local retail stores (see appendix). Inmany cases, equivalent products are available under several different brand names. An effortwas made to avoid duplicating product types, and most products are widely available in the US.

CS and CR were obtained from Munitions Division, CSL. The CS was purified by vacuumsublimation to produce large white crystals, m.p. 550 to 56 0 C. The CR was recrystallized fromisooctane, yielding yellow crystals, m.p. 72 to 73 0 C. CN (phenacyl chloride) was obtained fromcommercial sources and used without further purification.

To evaluate the reactivity of the various preparations, a solid deposit of the agentwas firs* formed in the bottom of a vial. This was done by preparing a solution containing theagent (1.0% w/v) and nonadecane (0.1% w/v) in chloroform. A 1.0-mI aliquot of this solutionwas placed in a 3-ml vial and allowed to evaporate to dryness leaving 10 mg of agent and 1 mgof nona~lecane as a film on the bottom. One ml of the potential decontaminant was then addedto the vial. After waiting a suitable length of time, 1.00 ml of chloroform and ca. 100 mg ofsodiur-i chloride were added to the vial and the mixture shaken. The chloroform layer was thenanalyzed for residual agent by gas chromatography.

All three agents were analyzed by the same gas chromatographic system. Thisconsisted of a Hewlett-Packard 5730A chromatograph with a 4-mm by 183-cm glass column.The column was packed with UC-W98 (5%) on 100/120 Chromasorb W. The carrier gas washelium flowing at 60 ml/min. The injection and flame ionization detector (FID) temperatureswere 2500 C. The oven temperatures were programmed as follows:

CN: 130 0 C for 2 min after injection followed by 130 to 230 0 C @ 160/minCS and CR: 150 to 2300C at 8g/min (no program delay).

The signal from the FID was processed by a Hewlett-Packard 33805 recorder/integrator.

*Unpublished 13K data, 1965-1967.

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3. RESULTS AND DISCUSSION ii

Table 1 summarizes the results of the tests for CN decontamination. These data areconsistent with .the previously reported observation that CN undergoes slow hydrolysis inalkaline solution. The most significant impediment to the alkaline hydrolysis of CN is its poorsolubility in aqueous systems. Thus, it is observed that in aqueous trisodium phosphate alone,CN shows no significant reaction in spite of the high alkalinity of the solution. In Fantastik,however, which is only moderately alkaline, CN undergoes a slow but quite measurablehydrolysis. When trisodium phosphate (TSP) is dissolved in Fantastik, the combination of thedetergency of the latter and the alkalinity of the former combine to produce substantialhydrolysis.

Table I. PBehavior of CN in Various MediaProduced from Commercial Products

Number Reactionof medium Medium in 5 hours

I. Fantastik (neat) 202. Fantastik saturated with 30 !Tintex color remover

3. Fantastik saturated with 10Clorox 2

3. Zephiran (0.s5% in (TSP)) 205. Trisodium phosphate (1%) 06. Fantastik with 1% (TSP) 657. Zephiran (0.85%) and TSP (1%) 35

in water 16

a. Fantastik saturated with Vanish 0

Table 2 •ummarizes the jesuilts of the test with CS. CS has been observed to under-go both hydrolysis and oxidation. Like CN, the use of a high detergent formulation such asFantastik is very effective in promoting CS hydrolysis although the reaction is still quite slo'v.Nonchlorine oxidants such as perborate (Clorox 2) and peroxysulfate (Vanish) were ineffectiveagainst CS. The most dramatic results were obtained with those formulations containing Tintexcolor remover (TCR). The active ingredient in this product is sodium dithionite (Na S2 04).Sodium dithionite is a crystalline solid which is stabe at room temperature in dry air. in acidsolution, it quickly decomposes into sulfate, sulfite and elemental sulfur. It is Ionsiderablymore stable in alkaline solution where it functions as a strong reducing agent. It is thisproperty of dithionite solutions which makes them useful for decolorizing fabrics tinted with vatdyes. Alkaline dithionite will also react quickly and quantitatively with dissolved oxygen aridhas been employed in the quantitation of the same. It was initially thought that dithionite waspromoting the reduction of the cyano gros in CS to amines. This, however, is inconsistentwith the known chemistry of nitriles" which require reactive hydrides or catalytichydrogenation to effect such reductions. Furthermore, the product(s) of the CS-dithionitereaction are very soluble in alkaline water which would not be expected of amine products.

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Table 2. Behavior of CS in Various MediaProduced from Commercial Products

Number Rvaction

of medium Medium irn 5 hours I

1. Fantastik (neat) 892. Fantastik saturated with 100

Tintex color remover3. Fantastik saturated with Clorox 2 54 Al4. Downy fabric softener (1% in water) 05. Downy (1%) saturated with Tintex color 100

remover6. Downy (1%) saturated with Clorox 2 117. Spic & Span (7%) in water 0S. Spic & Span (7%) saturated with too

Tintex color remover9. Spic & Span (7%) saturated with -

Clorox 210. Zephiran (0.85%) in water 01I. Zephiran (0.85%) saturated with 100*

Tintex color remover12. Zephiran (0.85%) and TSP (1%) 913. Fantastik saturated with Vanish 014. Zephiran (0.85%) saturated with Vanish 015. Tintex color remover (saturated in I00

water)

Reaction after 15 min was 30%** Reaction after 15 min was 78%

Kerber and Starnik'4 have reported that acrylonitrile reects with dithionite asfollows: -1

$2041= + " 2 0 • HS 2 OC- + OH- (1)

HS20- + H2 0 - + HSO- + H+ (2)

HSO2 + CH2 =CHCN--)-O 2 S-CH 2 -CH 2 CN (3)

"Y52S-CH 2 -CH2CN + CH 2 =CHCN-H.C2-HCH 2 CN (4)

02

CH7 -CI-' 2 CN

9I

While the analogy to the CS/dithionite system is obvious, a sulfone product would not be watersoluble. Kerber and Starnik, however, ran their reactions with the acrylonitrile in excess. Inthe studies reported here, the dithionite was maintained in large excess over CS. As such, jreaction (3) would predominate and the water soluble sulfinic acid would be the primaryproduct. At present the evidence in support of thW: -eaction pathway for CS/dithionite is onlycircumstantial. Studies are continuing in this laboratory to provide additional information unthis system.

As the data in table 3 indicates, C(R was very resistant to decontamination by thecommercial products tested. There is some indication that acid catalyzed hydrolysis in aqueous!

detergent or isopropanol will proceed slowly. The alkaline system of Fantastik and trisodium Aphosphate was ineffective. Likewise, perborate (Clorox 2) and peroxysulf ate (Vanish) oxidantsproduced no reaction. Fichlor, a chlorine bleaching powder, rapidly destroyed the CR. Mention

Table 3. Behavior of CR in Various MediaProduced from Commercial Products

Number Reaction Aof mediediumdium in 5 hours

%

1. Fantastik (neat) 02. Fantastik saturated with Tintex 12

color remover3. Fantastik saturated with Clorox 2 04. Zephiran (0.85% in water) 75. Fantastik saturated with Vanish 06. Fantastik with 1% TSP (1%) 07. Zephiran (0.85%) and TSP (1%) 58. Axion (saturated solution in water) 09. Isopropanol/water (7:3) saturated with 33

Fichlor10. lsopropanol/concentrated HCI (7:3) 30it. lsopropanol/water (7:3) with excess

Tintex color remover 5211.. Isoprooanol/water (7:3) with excess t,

Fichlor.3. Isopi 3panol/30% hydrogen peroxide (7:3) 014. \Vater/5,0% hydrogen peroxide with 30 a,b

excess Tintex color removerI15. lsopropanol/j0% hydrogen peroxide with 0 oa

excess Tintex color remover

"a "Excess" means 2 to 3 times the amount required for a saturated solution.

b Reaction after one minute was 100%.

is made in a 1969 report* that sodium dithionite was efficacious in reducing the irritation ofskin by rR but the observation does not appear to have been pursued. In this study, aqueousdithionite (TCR) showed some effect but complete reaction was never achieved. When solidTintex color remover is added to the vial containing the solid CR and a mixture of isopropanol

U Unpublished CSI, review.

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INand hydrogen peroxide added, a vigorous reaction occurs. Considerable heat is produced and afoul smelling gas is evolved. While much of this is undoubtedly due to the redox reaction of thedithionite and peroxide, analysis showed ':he CR to be destroyed within 1 minute. The gaschromatogram showed several product peaks which changed over a period of several hours.Likewise, the color of the reaction mixture changed from its initial yellow-orange color throughorange, dark red and finally to violet-brown over the same period of time. It is clear that thissystem is undergoing several concurrent and/or sequential reactions with a multitude ofproducts. No efforts were made to identify them.

4. CONCLUSIONS

The decontamination of CN may be effected by a strongly alkaline detergentsolution such as trisonium phosphate in Fantastik. Trisodium phosphate is somewhat corrosive,making skin protection essential. Some damage to aluminum, paint and finished wood surfacemay be expected.

Sodium dithionite-based products offer considerable promise in the decontaminationof CS. The reaction appears to be quite rapid, produces a highly soluble product and the excessdithionite will decompose into harmless products. BecaUse of its bleaching capabilities, somedamage to fabrics may be expected.

The problem of CR decontamination is a difficult one and will require furtherinvestigation. While Fichior is effective, its use is contraindicated for several reasons. Fichloris quite corrosive and may be expected to do considerable damage to environmental surfaces.Further, the reaction of CR with Fichlor may produce chlorinated aromatics which areconsidered undesirable environmental contaminants. Finally, CR is often deployed inconjunction with CS. It has already been observed that CS can react with strong oxidants toproduce epoxides of the type

Ocl0N R

CH~~

and that such compounds show vesicant activity. Sodium dithionite does appear to react withCR and further studies in this area may -esult in optimization of this reaction to the extent thatit may be useful in both CS and CR decontamination. Clearly, the promotion of theCR/dithionite reaction by peroxides is unsuitable for use in any location other than a laboratoryfume hood.

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LITERATURE CITEr'

t. Edgewood Arsenal Special Report. EASP 600-3. Decontamination of CS/CNRiot-Control Agents. February 1969. UNCLASSIFIED Report.

2. Noye, Floyd Wt. EASP 400-37. Riot Control Agents CS and CN: A Bibliography !-of References. September 1971. UNCLASSIFIED Report.

3. Rosenblatt, 1). H. and Broome, G. H. CWLTR 2358. Reactions of CS with

Chlorine Solutions. February 1960. UNCLASSIFIED Report.

4. Demek, M. M., et al. EATR 4195. Decontamination of CS and CS2. I.I-ebruary 1968. UNCLASSIFIED Report.

5. Brooks, M. E., et al. E-C-TR-76078. Demilitarization of CS. 1. ChemicalDisposal of CS by Hydrolysis. December 1976. UNCLASSIFIED Report.

6. Wolverton, R. C., et al. Air Force Armament Laboratory AFATL-TR-68-27.New CS rDecontamiinant. Marrh 1968. UNCLASSIFIFI Report.

7. Brewster, Keith, et al. Oxidation of Some Dibenz(b,f) (1,4) oxazepines byPeracetic Acid. 3. Chern. Soc. Perkin 1. 1291-6 (1976).

8. Eaborn, C. Interaction of Phenacyl Chloride and Aqueous Alkali. J. Chern. Soc.1935-6. (1957).

9. Patai, Saul, and Rappoport, Zvi. Nucleophilic Attacks on Carbon-CarbonDouble Bonds. Part II. Cleavage of Arylrmethylenemalononitriles by Water in 95% Ethanol. J.Chem. Soc. 383-391 (1962).

10. Fieser, Louis F., and Fieser, Mary A. Peagents for Organic Synthesis. pp 1081-3. John Wiley and Sons, Inc., New York, New York. 1967.

11. Roberts, D). J. and Caserio, M. C. PBasic Principles in Organic Chemistry. p659. W. A. Benjamin, Inc., New York, New York. 1964.

12. Kerber, R. and Starnick, J. Darstellunc, von symmetrischen Sulfonen durchAnlagerung von Sulfoxylsaurederivaten an aktivierte Doppelbindungen. Chem. Ber. 104, 2035-43(1971).

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APPENDIX

DESCRIPTION OtF COMMERCIAL PRODUCTS USEDIN THIS INVESTIGATION

- ~Detergents •

Fantastik: Trademark, Morton Norwich Products; an "all purpose" householdcleaning product consisting primarily of anionic detergents and mildorganic solvents.

Spic & Span: Trademark, Proctor & Gamble Co.; a gran.:Iar household cleanerconsisting of anionic detergents and phosphate salts which appear tobuffer the solution at pH ca. 9.

Zephiran: Trademark, Winthrop Laboratories; a disinfectant consistingprimarily of cationic detergents of the benzalkonium family. !

Downy: Trademark, Proctor & Gamble Co.; a fabric softener for homelaundry use. The primary component of most such products arecationic detergents.

Reactive products

Tintex color remover:Trademark, Knomark, Inc.; a color stripper for pretreating fabrics Iprior to dying. The active ingredicit is sodium dithionite (Na2S52 04with buffers (pH 8 to 9) and a small amount of detergent.

Vanish: Trademark, Drackett Products Co.; a toilet bowl cleaner anddisinfectant wtiose active ingredient is sodium monopersulfate 44(NaHSO 5 ).

Clorox 2; Trademark, The Clorox Co.; an "all fabric" laundry bleachcontaining sodium perborate as the oxidant.

Fichlor: Sodium N,N-dichloroisocyanurate; a chlorine bleaching powder

widely used in water treatment and commercial fabric bleaching.

TSP: Trisodium phosphate; offered in paint and hardware stores under a 4variety of trade names; aqueous solutions are strongly aklaline and Jtare used to clean and degloss surfaces prior to repainting.

Axion: Trademark, Colgate-Palmolive Co.; a home laundry pre-soakcontaining modified hydrolytic enzymes of bacterial origin.

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ATTN: AMR/ORD/DD/S&T 1

Washington, DC 20505

ADDITIONAL ADDRESSEES

CommandantAcademy of Health Sciences, US Army

ATTN: HSHA-CDH 1

ATTN: HSHA-IPM 1

Fort Sam Houston, TX 78234

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