F• • • NSWC/WOL/TR 77-71 (2

ANALYSIS OF MERCURIC 5-NITROTETRAZOLE

Li BY DONALD J. GLOVER

RESEARCH AND TECHNOLOGY DEPARTMENT

19 JULY 1977

\ 'NAVAL SURFACE WEAPONS CENTERI: C -Dahlgren, Virginia 22448 * Silver Spring, Maryland 20910

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NSWC!/WOL/-TR-77-ý71 091'ANALYSIS OF MERCURIC 5-NlTROTETRAZOLEa IFinal

DONALD J. LýOVER

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16S SUPPLEMENTARY NOTES

19 EY WORDS (Continue on reverse side If necessary and identify by block number)

M9ercury (II) UV absorptionI -nitrotetrazole dichromate oxidationprimary explosives thiocyanate titrationj

2Cortiu Ar re5 -1-19verse side If necessary an'd idenr~fy br: bloefr num~ber.)

Mercury (II) in mercuric 5-nitrotetrazole may be determinedny atomic absorption using the unique-to-mercury absorption 'Lineat 25336.5 angstroms, with a precision of 1-3%. For a precision o1

t +it-ration with thicy~nte ion is rec,-wmended. Th41 5-nitrotetrazole anion may be determined by measuring the absorb-IIance due to the anion at 257 nm in the ultraviolet, with aprecision of + 1%. The anion may also be determined by oxidation'

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I NSWC/WOL/TR 77-71

NSWC/WOL/TR 77-71 19 July 1977

ANALYSIS OF MERCURIC 5-NITROTETRAZOLE

This report describes analytical procedures for the determinationof the mercury (II) cation, as well as the 5-nitrotetrazole anion,in mercuric 5-nitrotetrazole, in particular for use in a specifica-tion. The work was carried out under Task No. WRIIHA(OPN).

JLIUS W. ENIGBy direction

I

I• NSWC/WOL/TR 77-71

TABLE OF CONTENTS

Page

INTRODUCTION .................. ....................... 3

EXPERIMENTAL AND RESULTS ................... 4

DISCUSSION ................ ........................ 9

SUMMARY AND CONCLUSIONS .................

TABLESTable Title Page

I Mercuric 5-Nitrotetrazole, AnionDetermination ............ ................. 5

II Mercuric 5-Nitrotetrazole, Determination ofMercury and Copper ........... .............. 7

2

NSWC/WOL/TR 77-71

ANALYSIS OF MERCURIC 5-NITROTETRAZOLE

INTRODUCTION

Mercuric 5-nitrotetrazole (Hg(5-NT)2) is being studied at theNSWC, WOL as a possible replacement for lead azide (1). Unlike leadazide, Hg (5-NT)2 is stable to moisture and is compatible withdetonator construction materials, such as copper or brass.

Twelve batches of Hg (5-NT)2 ranging from 65 g to 600 g wererecently prepared (2) by the procedure of Gilligan and Kamlet (1),according to the following series of reactions:

NHH2 N+

I- ~ +aO - +2N N H NNaNO -N E N NO2 /Cu CuHNT(NT) 2 .4H 2 0 (i)

CuHNT(NT) 2 .4H 2 0 CuSO4 /en Cuen2 (NT) 2 HNO 3 Cu(NT) 2 (2)

Cu(NT) 2 + Hg(NO3 ) 2 > Hg(NT) 2 + Cu(N0 3 ) 2 (3)

where NT = T0 2 ,the nitrotetrazole anion, and en = H 2NCH 2CH2NH2

ethylenediamine. In addition to these desired reactions, the initialdiazo compound. (equation (1)) can also react to form the hydroxy-tetrazole (1):

+ OHCI NC\

1 HOH/Cu÷ 2 N

N--N

1. W. H. Gilligan and M. J. Kamlet, "Synthesis of Mercuric 5-nitro-tetrazole", NSWC/WOL/TR 76-146, 9 December 1976.2. R. S. rarncomb, M. chang, and e. J. Pisacane, "Process Scale-up forMercuric 5-nitrotetrazola", personal communication.

3

NSWC/WOL/TR 77-71

It is desirable to have analytical methods for both Hg(II) andtne anion, NT, in the final product, i as well as for any impurities.

A methcd is already described (3) for the anion, based on themaximum absorption in the ultraviolet at 257nm. This method israpid and works well. Another metnod for the anion, oxidationwith dichromate in sulfuric aciL, is presented here.

Of the numerous methods in the literature for Hg(II), two wereselected for evaluation. A method for determining Hq(II) by atomicabsorption (AA) would confirm that this is the element beingmeasured. For this reason, the AA method presented in this reportis recommended for specification purposes, even though the methodg±ves a precision of only 1 to 3%. Greater precisior may beobtained by the thiocyaaate procedure described here.

EXPERIMENTAL AND RESULTS

CAUTION: ANY SALT OF 5-NITROTETRAZOLE SHOULD BE CONSIDERED HAZARDOUSWHEN HANDLED. THE MERCURY (II) CALT HAS THE SAME IMPACTSENSITIVITY, 5 CM., EITHER WET OR DRY (reference 2).

Determination of 5-nitrotetrazole anion

UV Method

Accurately weigh approximately 2.5 mg of Hg (5-NT) 2 into a 25 mlvolumetric flask. Dissolve in 2.5 mi of 20% ammonium acetatesolution, dilute to volume with water, and mix. This is Solution A.

Pipet a two ml aliquot of Solution A into a 10 ml vol-imetricflask, dilute to volume with water, ntix, and read the absorbanceat 257nm. Frequently, acetone is used in cleaning volumetric glass-ware. Evert a trace of acetone will interfere at 257 nm and must notbe used with any glassware used in •nis determination.

The ammonium acetate solutf*n is necessary for dissolution ofthe Hg (5-NT) 2 in a reasonable time. Hg (5-NT) 2 is soluble in wateralone, but slowly, 89.7 mag/100ml dissolving in 3 days at 300, with95% of this dissolving in 7 hours.

Using the above procedure with a specially purified sample ofHg (5-NT) 2 , the molar absorbancy was found to be 5353 + 28 (averageand average deviation for four samples). NMR was used-to establish

F(3} 1N. J. M D. G. Cav:es D. C. Mul.enger, and R. j Rapley

"Silver Nitrotetrazole: Its Stability and Compatibility with OtherMaterials", ERDE Technical Repcrt No. 163, January 1974.

4

NSWC/WOL/TR 77-71

F- the absence of water and any material having hydrogen atoms. Asample of sodium 5-NT was recrystallized from acetone and air dried.If dried in a desiccator, this salt lost its water of hydration(NMR), but if left loosely stoppered on the lab bench, it was shownby NMR to be the di-hydrate. Four samples of this di-hydrate gave5329 + 10 for the molar absorbancy of the NT anion at 257nm.

Fourteen different samples of Hg (5-NT)2 were analyzed by theUV method and the results are shown in Table I.

Dichromate method (4)

Accurately weigh a 35-44 mg sample of Hg (5-NT) 2 and transferit to a 250 ml standard tapered Erlenmeyer flask, using 20 ml ofwater. Pipet 10 ml of 0.2500 N K2 Cr 2O7 into the flask, then add 30ml of 96% sulfuric acid, which contains 10 g of Ag2 SO 4 /liter. Mixthoroughly. Connect the flask to a-reflux condenser and reflux atleast 30 minutes. Carefully rinse the condenser with distilledwater, and cool the flask to room temperature. Dilute the solutionto about 125 ml, again cool, add 2 drops of ferroin indicator andtitrate with standardized 0.1 N ferrous ammonium sulfate solution.The end point is very sharp, 0.02 ml, going from green to lightbrown.

All glassware must be cleaned by using the above procedurewithout the sample. The distilled water must not be stored inplastic wash bottles. A blank must be run using everything exceptthe sample. The milliequivalents of dichromate consumed arecalculated by subtracting the sample titre from the blank titre, andmultiplying the difference by the normality of the Fe+2 . When themilliequalents thus found are divided by the millimoles of anion( = 2 x millimoles of Hg (5-NT) 2), a value of 6 is found, w-h-l-c-•corresponds to the expected electron change (see Discussion).

The Ag2SO4 is used as a catalyst (4), and if 1,t is omitted, thereaction is only 80-90% complete in 30 minutes. With the catalyst,the reaction is complete in 15 minutes.

The results using this procedure are given in Table I, for bothHg (5-NT) 2 and Na 5-NT.2HOH.

Determination of Mercury (II) cation

AAMethod

Prepare a standard solttion of 1.000 ppm of Hg(II) by dissolvinq1.080 g of mercuric oxide in 5 ml of 6 N nitric acid in a one litervolumetric flask, and diluting to volume with water. Do not use

(4) "Standard Methods for the Examination of Water and 'astewater",adite- %A &I. '. 0rland, 12Lh ea. 1365, p. 513, "Chemical OxygenDemand".

5

NSWC/'WOL/TR 77-71

IICý(\ UN Q (- Cý ( C')t(ý 0 ; Cý C ;J t

1ý C ;J Lr\ o ý r4 (\ m; L\ C 0 ý (Y ý Cý~Q 0 0 0 00 0 : : c\C\ \ \C ON0000 C

0 000

0

H - C.2)

Cc . Lr U\J o U-\ cm \) a. \0 ) \( CO ONr D '.0 C\C)0J

0 00 H 0 0 H 00 H 0 00 H C

-0 (U , 4.)1H N t'0" o~C'\ 0 C'.)c

0

H 0 N H~ (N _r C\j c CM J C~i H C'! L~C\J C'] fm --T ()NW

C..) 00

H .i

- ) 4'. \, : L _ - L - \L L )ý \D \0 4(ý 8 r ý r

Q~~~~~.- U 0ý0 ý0 ý ;C ý

E-4 0) LA.PHr-PA~P A4 CC

+ 0Vf. P4 . -

MR N r-~. i Z LA~D mHlCj0 m c) N t- m Cja -

c( m c12\ -:r -x t\ m Cj vN -r m () u -

I-NSWC/WOL/TR 77-71

Hg(I) compounds as standards, as they give erroneously high results(5). Dilute aliquots of this standard to give solutions containing30, 40, and 50 ppm of Hg(II). Read the absorbancy of Solution A

above at 2536.5 angstroms and compare with the diluted standards.The machine sensitivity must be adjusted so that the 50 ppm solutionreads about three-fourths of the dial. For the Varian TechtronAA-5, this reading is 75 using the times 10 ,control.

The results using this procedure on Hg (5-NT) 2 are given in

Table II.

Thiocyanate Method

Pipet an aliquot of Solution A into a suitable titration vessel(a 25 ml volumetric flask may be used), add 1 ml of 6 N nitric acid,1 Ml of 0.1 N ferric nitrate, mix and titrate with 1 X l0-3 y sodiumthiocyanate solution to the light brown end point. Determination ofthe end point is facilitated by comparison with the color of thestarting solution and a solution of the standard Hg(II) that hasbeen titrated. A solution that is 50 ppm in Hg(II) is 2.5 x 10-4 M.The end point occurs when two moles of SCN per mole of Eg(II) havebeen added. Consequently, an aliquot of 8 ml will require 4 ml ofSCN . A micro buret graduated to 0.01 ml is therefore required.

The resul's using this procedure are given in Table II.

The end point is easier to detect, if about 50 mg of Hg (5-NT) 2are titrated using 0,1 N SCN . The sample is dissolved in 2.5 mlof 20% ammonilmi acetate, and because ferric ion gives a red colorwith ammonium ion, 3 ml of 6 N HNO3 are required to discharge thiscolor. The more dilute solution above was used to avoid unnecessaryhandling of sensitive Hg (5-NT) 2 .

Determination of Copper (II) cation

AAMethod

Copper (II) is a likely impurity in Hg (5-NT)2, because it isused during the synthesis. A 1 ppm solution of Cu(II) gives a dialreading of 100 on the times 10 dial setting on the Varian TechtronAA-5, whereas 50 ppm Hg(II) gives a dial reading of 75. Therefore,up to 2% Cu(II) in Hg(II) can be determined using the same solution.On this instrument, the Cu and Hg lamps may be mounted at the sametime. After determining the absorption due to Hg(II), one changesthe lamp by rotating a disk, adjusts the wavelength, and thendetermines the absorption due to Cu(II).

The results using this procedure are given in Table II.

(5) D. N. Hingle, G. F. Kirkbright, and T. S. West, Analyst, 92, 759(1967); chem. Abstracts, 68, ili,10lg (1968).

7

[ NSWC/WOL/TR 77-71

I 'D H H HI CM N C V) _:r H H NM

0 00 00 0 0000

4., )) - o \ m \ m \ m \ M~ M 0-- m~ m\ ON 0 U\

P4 Cd'W- H H4 H

P-i 4-

C.) 00 U-LN~L\ Lr\ U.N Ch L\ NON z m O LC\U.NONm

CdCOý 00 0 00 000 0

>-4 ý-i= C0)' O0 0 0 t- 0 Lr\O Hm MC

0

E-4-P0- 0 \ Y 7-r -t () ( :

.0 0) 0 C) 0 0 0 H 0CM 0 CM\ HH ;E .H H ' (1M (1 ' H~C ' '.

PO E-iZ-!D.\OH

E-4 cd H 0 t

H= C)ý- $.ý 4 +ý 0ý C ý C 1 ;4

4- UO L-- 0c 0 0 - m 0

00 *C4 HZ 0) 4 t 1 ý C ti i\

P . 0- .0~ d _1~

H 0 HO ri HmC -t ~~: c i~* O C

j C) r- - T - C 1 r V) 0)

HH ('1)H 0

+' 0 E-- U-\ U.N U.N t-- UN- V\~ Vt\ \D U.N V\N UN\ U.N ON

0) C)- 0CM'Cd 0 00 0

IH

00 bo 0\I c C) co iCO

OCI a) CMl m 1 r\.O t- CT*\ H CMN 0C) ON.\ - H H

4- o 4 -d 0\C

\0 0H~- C) 0 c

8

NSWC/WOL/TR 77-71

DISCUSSION

For the dichromate oxidation of the 5-nitrotetrazole anion,

the equation may be written:

NO1jN +3HOH =C 2 +2N 2 +NO +6H + +6e (5)

Duplicate analyses for nitrate by a gas chromatographic procedure (6)gave 108% (+ 8%) of the value required by equation (5). Carbondioxide and-nitrogen were not determined. The dichromate oxidationnas been used successfully for other explosives in this laboratory(7). The 6 electron change shown above was verified by the experi-mental results for sample 96-8898-80 of Hg (5-NT) 2 , and for Na 5-NT.2HOH (Table I). The value of 6 was invariant for reflux times of15 minutes to 4 hours.

Comparing the results for the anion procedures in Table I, thevalues found by the dichromate procedure are generally 0-3% higherthan i-ho-_ found by the TUV proceodure (theo rccult rUr ..t.- 11 ;;i!!be considered separately below). This may be because the dichromateprocedure will measure any readily oxidizable material, for example,organic fibers, or Hg(I).

When the samples of Hg (5-NT) 2 were received, they were undeLwater. A portion was removed and placed in an open container, whichwas placed in a desiccator over concentrated sulfuric acid to removeany water. To insure that they were dry, the NMR spectrum indeuterated DMSO was observed. No water was found, nor any hydrogenatoms. Thus, organics, such as ethylenediamine, are absent. It isestimated that the NMR method will detect impurities, if present togreater than 3%.

When the results for mercury (II) by the two procedures givenin Table II are compared, and the larger average deviation of the AAmethod is considered, it is seen that the two procedures agree within0-2%, except for sample 5 where the difference is 2.5%. Generally,the values by AA are lower than those by thiocyanate. When the AAvalues are higher, it may mean that mercury (1) is present (samples2, 6, and 7), although there is no experimental proof of this (5).

(6) D. J. Glover and J. C. Hoffsommer, "Gas Chromatographic Analysisof Nitrae and Nitrite Ions in M!icrogram .uatiie by- Co-r-r~t

Nitrobenzene", J. Chromatography, 94 334 (1974).(7) For TNT: C7H5N306 + 17HOH = 7C02 + 3NOJ + 39H + 36e; found, 36.1.0.3, RDX: C3 H6 N60 6 + 9HOH = 3C0 2 + 3NOý + 3NHý + 12H+ + 12e; found,

+1.8 + ) .3

NSWC/WOL/TR 77-71

Comparing the data in Tables I and II, the values for the anionby UV appear to be greater than the Hg(II) values by AA, but again,when the deviations are considered, the values by these two metho-isare in agreement. Except for samples 6 and 7, the anion values bydichromate oxidation agree quite well with the Hg(II) values bythiocyanate. Sample 7 may have Hg(I) present as already mentioned.

Sample 6 is the only sample examined which gives differentresults for Hg and the 5-NT anion by all four procedures. Accordingto reference (2), during the preparation of sample 6, the desiredtemperature of 750 could not be reached, and this may account for itslow purity.

When treated with ammonium acetate solution, or water only, someof sample 6 did not dissolve. When a large sample of 6 (111 mg) wastriturated with a solution of 20% ammonium acetate, diluted withwater, and filtered, there was found 7.4% of a yellow solid residue.The filtrate from this solid was analysed for the 5-NT anion by UVand for Hg(II) by thiocyanate titration. 87.7% of the theoreticalamount of anion was found and 87.0% of Hg(II). When this percentageof Hg (5-NT) 2 , 87.4%, is added to the solid residue, 94.7% of thesample weight is accounted for. This means that 5.3% of the sampleweight in solution is not Hg(II) or 5-NT anion.

It is possible that the soluble 5.3% is a Hg(I) compound,because the AA analysis for Hg is 98.1%, and Hg(I) compounds givehigher absorptions than Hg(II) compounds (5).

It was also considered likely that a soluble nitrate could bethe impurity in sample 6. Consequently, a nitrate analysis wasdone according to (6). There was found 0.48% nitrate, whichcorresponds to 0.73% Cu(N03)2. Converting this value of Cu(N03)2to percent Cu, 0.25%, shows that the nitrate is present not only asthe copper salt, for Cu by AA is only 0.11%. Nitrate obviously doesnot account for the 5.3% soluble in sample 6.

Another possibility for the soluble impurity would be an acidicmaterial. When sample 6 was triturated with water, a pH of 2.99 wasfound, while the pure sample 96-8898-80 gave a pH of 3.27. Whenthese pH values are converted to H+ concentrations, there is foundfor sample 6, 10.23 x 10-4 IV, and for 96-8898-80, 5.37 x 10-4 M.The difference, 4.86 x 10-4 M, would be the normality of the acidicimpurity. If the acid impurity is hydroxytetrazole (molecularweight = 86), then the weight of hydroxytetrazole is 86 x 4.86 x 10-= 0.0418 g/liter. As the sample weight was 0.006467 g/10 ml,hydroxytetrazole content would be 6.5%. This value is in fairagreement with the experimental value of 5.3%.

Titration of sample 6 with thiocyanate without filtration of theinsoluble material, gave a first end point at 96% of the calcu~atedHg(II). This end point faded, and a final end point was found at102.9% of the calculated value. Since the end point did not fade

•- 10

NSWC/WOL/TR 77-71

when the insoluble material was filtered, the insoluble material isprobably a Hg(II) compound. Considering the value of 102.9%, themolecular weight of the insoluble material must be less than thatfor Hg (5-NT) 2 , 428.7 g/mole. It is noted that mercuric 5-hydroxy-tetrazole has a molecular weight of 370.6 g/mole.

The dichromate oxidation of sample 6 without filtration of theinsoluble material, gave a value of 94.2% of the sample weight, basedon the expected 6 electron change for 5-nitrotetrazole. If, indeed,hydroxytetrazole is present, either as the acid or Hg(II) salt, thenthe electron change expected is 4:

OH

E) I + 3/2HOH= CO2 + 2N 2 + 3H+ + 4e (6)N- N

This means hydroxytetrazole as an impurity would give low resultsby the dichromate oxidation. However, these results will be higherthan the anion by UV, if the 5-hydroxytetrazole anion absorbs lessthan the 5-NT anion, which is what is observed (Table I).

SUMMARY AND CONCLUSIONS

Mercury (II) in mercuric 5-nitrotetrazole may be determined byatomic absorption using the unique-to-mercury absorption line at253r.5 angstroms, with a precision of 1-3%. For a precision of0.1 to 0.6%, a titration with thiocyanate ion is recommended. The5-nitrotetrazole anion may be determined by measuring the absorbancedue to the anion at 257 nm in the ultraviolet, with a precision of+ 1%. The anion may also be determined by oxidation with dichromateion in sulfuric acid solution, with a precision of + 0.5%.

For specification purposes, there are advantages to using bothof the cation methods presented here, as well as using both anionmethods. The AA method for Hg depends on measuring the unique-to-mercury absorption line at 2536.5 angstroms. Hg(I), if presenteither from Hg(II) contamination, or by reduction of Hg(II), willshow up by giving higher than calculated values based on Hg (5-NT)2.The thiocyanate titration gives more precise values for Hg(II), andwill react with Hg(I) to give the insoluble salt, and thereby givelow results. The UV method for the anion is specific, but is subjectto interference by any material absorbing at 257 nm. The dichromateoxidation of the anion will also reflect any easily oxidizableimpurity.

[i

NSWC/WOL/TR 77-71

Examination of the results for the fourteen different samplesof Hg (5-NT) 2 presented in Tables I and II, show that one (Batch 6)gives analyses indicating a poor product. On the basis of all thedata, the following requirements are recommended:

Property Requirement

AssayHg (AA) 100 + 3%

Hg (thiocyanate) 99.5 + 0.5%

5-nitrotetrazole anionUV 100.0 + 1.0%

Dichromate oxidation 100.0 + 1.0%

Cu (AA) <0.05 + 0.01%

NO3 (ref. 6) <0.10 + 0.01%

Insoluble in 20% ammonium acetate 0.5% max.

pH (10 mg triturated with 10 ml water) 3.32 + 0.10

12

NSWC/WOL/TR 77-71

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