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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant Appendix C Information on Current Composition of Levenstein Mustard Agent at Blue Grass Army Depot Tables C-1 through C-5 provide a summary overview of what is known about the current condition of the Levenstein mustard agent (H) in the U.S. chemical stockpile, including that in the projectiles stored at Deseret Chemical Depot.1 This form of mustard agent has degraded from what was originally about 70 percent pure mustard agent (liquid) and 30 percent (liquid) impurities into a mixture that is, on average, 70 percent solids and 30 percent liquid. 1 E-mail communication from Yu-Chu Yang, ACWA, on April 12, 2005, to Robert A. Beaudet, committee chair.
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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant TABLE C-1 Composition of Liquid H (Levenstein Mustard), 16-42 wt% (Average = 31 wt%) of Agent Fill in the 10 155-mm H Projectiles Tested During Munitions Washout System Testinga,b Compound Name Structure Gas Chromatograph/Mass Spectrometry—Chemical Ionization (GC/MS–CI) (area%) Nuclear Magnetic Resonance (NMR) (wt%) Volatile impurities Neat CD3CN Solvent 1-Butene 0.067 (0.040-0.12) 2-Chlorobutane 0.034 (0.020-0.070) Diethyl ether 0.084 (0.030-0.20) 0.24 (0.070-0.40) Chloroform 0.037 (0.010-0.12) HD and degradation compounds 1,2-Dichloroethane ClCCCl 1.7 (1.1-2.6) 2.0 (1.4-2.9) 1,4-Dithiane 3.0 (2.0-3.6) 0.92 (0.45-1.2) Ethylene sulfide (Thiirane) 0.036 (0.020-0.060) Bis(2-chloroethyl) sulfide (HD) ClCCSCCCl 81 (78-84) 78 (74-81) 1,2-Bis(2-chloroethylthio)ethane (Q) ClCCSCCSCCCl 7.9 (6.6-9.4) 10.2 (8.7-12) C3/C4 HD analogs/impurities 2.0 (1.4-2.8) Bis(3-chloropropyl) sulfide 0.24 (0.20-0.30) 2-Chloroethyl-4-chlorobutyl sulfide 0.83 (0.70-1.0) 2-Chloroethyl-2-chlorobutyl sulfide 0.059 (0.030-0.080) 2-Chloropropyl-3-chloropropyl sulfide 0.41 (0.30-0.50) 2-Chloroethyl-3-chloropropyl sulfide 0.27 (0.20-0.30) Linear polysulfides of HD Bis(2-chloroethyl) disulfide, HS2 ClCC-S-S-CCCl 1.4 (0.80-2.4) 0.3 (0.14-0.41) 2-(Chloroethylthio) ethyl-2-chloroethyl disulfide ClCCSCC-S-S-CCCl 0.18 (0.090-0.30) Bis(2-chloroethyl) trisulfide, HS3 ClCC-S-S-S-CCCl 0.77 (0.20-1.5) 0.55 (0.27-0.95) Bis(2-chloroethyl) tetrasulfide, HS4 ClCCS4CCCl 0.89 (0.53-1.5) Bis(2-chloroethyl) polysulfide, HSx ClCCSxCCCl 1.1 (0.45-2.0) Cyclic polysulfides 1,2,3-Trithiolane 0.63 (0.20-1.4) 1,2,5-Trithiepane (7-membered ring) 0.77 (0.50-1.1) 1,2,3,4-Tetrathiane 0.21 (0.050-0.40) 1,2,3,4,5-Pentathiepane (7-membered ring) 0.16 (0.030-0.30) Cyclic sulfonium ion S-(2-chloroethyl)-1,4-dithianium ion 0.89 (0.31-1.6) Total 99.78 97.09 aResults are the average and range for seven samples. bGas chromatography/thermal conductivity detector quantitative results for HD using an internal standard were 84.6 wt% (81.8-87.7).
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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant TABLE C-2 Composition of H Heels, 58-84 wt% (Average = 69 wt%) of Agent Fill in the 10 155-mm Projectiles Tested During Munitions Washout System Testinga,b Compound Name Structure GC/MS–CI Analysis of CH2Cl2 Extract (area%) NMR Analysis of Three Extracts (wt%) HD and degradation compounds CHCl3 Extract 1,4-Dithiane 10 (7.4-15) 1.3 (0.64-2.9) 1,4-Thioxane 0.23 (0.10-0.50) Bis(2-chloroethyl) sulfide (HD) ClCCSCCCl 58 (52-64) 28 (10- 37) 1,2-Bis(2-chloroethylthio)ethane (Q) ClCCSCCSCCCl 17 (14-20) 4.1 (0.99-5.5) Bis(2-chloroethyl) sulfoxide 0.46 (0.20-0.60) 1,4-Dithiane-1-oxide 0.80 (0.30-1.6) 2-Chloroethyl vinyl sulfide ClCC-S-CH=CH2 0.33 (0.020-0.60) Bis[(2-chloroethylthio)ethyl] sulfide ClCCSCC-S-CCSCCCl 2.6 (1.4-4.3) (2-chloroethylthio)ethyl vinyl sulfide ClCCSCCSCH=CH2 2.2 (1.5-2.9) C3/C4 HD analogs/impurities Bis(3-chloropropyl) sulfide 0.13 (0.050-0.20) 2-Chloroethyl-4-chlorobutyl sulfide 0.71 (0.60-0.80) 2-Chloroethyl-2-chlorobutyl sulfide 0.057 (0.040-0.080) 2-Chloropropyl-3-chloropropyl sulfide 0.29 (0.12-0.40) 2-Chloroethyl-3-chloropropyl sulfide 0.18 (0.11-0.30) Linear polysulfides Bis(2-chloroethyl) disulfide, HS2 ClCC-S-S-CCCl 0.29 (0.15-0.50) 2-(Chloroethylthio) ethyl 2-chloroethyl disulfide ClCCSCC-S-S-CCCl 0.41 (0.30-0.50) Bis(2-chloroethyl) trisulfide, HS3 ClCC-S-S-S-CCCl 0.86 (0.40-1.2) Cyclic sulfides and polysulfides 2-Methyl-1,3-dithiolane 0.050 (one sample) 1,2,3-Trithiolane 1.0 (0.40-2.2) 1,2,5-Trithiepane (7-membered ring) 2.1 (1.1-4.4) 1,4,7-Trithionane 0.12 (0.080-0.15) 1,2,3,4-Tetrathiane 0.18 (0.080-0.40)
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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant Compound Name Structure GC/MS–CI Analysis of CH2Cl2 Extract (area%) NMR Analysis of Three Extracts (wt%) 1,2,3,4,5-Pentathiepane (7-membered ring) 0.15 (0.080-0.30) 2-Methyl-1,3-dithiolane 0.050 (one sample) 1,4,7,10,13-pentathiacyclopentadecane 0.26 (0.070-0.90) 1,4,7,10-tetrathiacyclododecane 0.49 (0.14-1.0) Elemental sulfur Sulfur S6 0.10 (0.040-0.15) Sulfur S8 6.0 (one sample) Unknown MW 118 0.18 (0.11-0.30) Cyclic thioethers 1-oxa-4,7,10,13-tetrathiacyclopentadecane 0.080 (0.060-0.10) 1-oxa-4,7,10-trithiacyclododecane 0.41 (0.30-0.50) 1-oxa-4,7-dithionane 0.30 (0.070-0.70)
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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant Compound Name Structure GC/MS–CI Analysis of CH2Cl2 Extract (area%) NMR Analysis of Three Extracts (wt%) Cyclic sulfonium ion CH3CN Extract S-(2-chloroethyl)-1,4-dithianium ion 36 (27-48) Cyclic sulfonium dication H2O Extract 1,4-Dithioniabicyclo[2.2.2]octane dication 1.4 (0.70-2.7) Total 99.81 70.8c a Results are the average and range for seven samples. bUsing n-hexane extraction and an internal standard, gas chromatography/thermal conductivity detector quantitative measurements gave 13 wt% (5.47-18.4 wt%) HD. cThe main elements in the residual were iron and sulfur. TABLE C-3 Liquid Chromatography–Electrospray Ionization–Mass Spectrometry Analysis of 14 Solid H Samplesa Name Structure Relative Intensity (%) Range Average S-(2-chloroethyl)-1,4-dithianium ion [30843-67-5] 64.2-96.8 87.8 Bis[2-(1,4-dithianium)-S-ethyl] sulfide 0.7-25.8 6.9 S-(5-chloro-3-thiapentyl)-1,4-dithianium ion 2.0-7.7 4.1 1,2-Bis[1-(1,4-dithianium)]ethane < 0.1-3.3 1.2 aSamples were extracted into 50 vol% methanol-water solutions.
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Interim Design Assessment for the Blue Grass Chemical Agent Destruction Pilot Plant TABLE C-4 Liquid Chromatography–Electrospray Ionization–Mass Spectrometry Analysis of Solids (Filtered from Liquid H Samples)a Compound Name Structure Relative Intensity (%) Sample 003A Sample 033A S-(2-chloroeethy)-1,4-dithianium ion 41.6 58.0 S-(5-chloro-3-thiapentyl)-1,4-dithianium ion 51.6 42.0 S-(8-chloro-3,6-dithiapentyl)-1,4-dithianium ion 6.8 Below detection limit aAn aliquot of 25 μL of each liquid H sample was added to 250 μL CH2Cl2. Solutions were filtered using Gelman 0.45-μm GHF acrodisc syringe filters and the filters rinsed with additional CH2Cl2. Methanol/water (50/50, 1 mL) was then passed through each filter to dissolve and elute CH2Cl2-insoluble residue. Methanol/water solution was analyzed by liquid chromatography-electrospray ionization-mass spectrometry on October 1, 2003. TABLE C-5 Estimated Total Iron Contents in Liquid and Solid Phases of H Mustard Agent Fill in 155-mm Projectilesa,b Phase Solid in Munition (wt%) Total Iron (wt%) Liquid 1.0 (0.59-1.4) Solid 69 (58-84) 6.6 (2.1-9.8) aThe total measured iron in the agent fill of the 155-mm projectiles is 4.92 weight percent. bBy inductively coupled plasma-mass spectrometry.
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