M4

l NSWC/WOL/TR 76-146

'7

WHITE OAK LABORATORY

SYNTHESIS OF MERCURIC 5-NITROTETRAZOLE

BYWilliam H. Gilligan

r-..

Motie J. TECHNICAL EMER97

" NAVRL SURFACE WEAPONS CENTERWHIT E OAK LABORATO RY

SYNTHERSISOP ECRICG MAYLND TR2ETR910

Mortproedfr J. i raeleaedit rbto 9uDECEMBERd197

NAVAL SURFACE WEAPONS CENTER

WHT A9SILVER SPRING, MARYLAND 20910

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NSWC/WdL/TR-76-146 ___

4 TITLE(apd Swbl14t4) 5 TYPE OF REPORT & PERIOD COVERED

SYNTHESIS OF MERCURIC 5-NITROTETRAZOLE,

S"- 6 PERrORMING ORG REPORT NUMBER

7 AUTHOR(s) - 8 CONTRACT OR GRANT NUMBER(a)

William H./Gilligan/and ', I - -,

Mortimer J.iKamlet _ _ _ __

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Naval Surface Weapons Center 0: 0.

White Oak Laboratory OPN;

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Initiators Lead AzidePrimary Explosives DetonatorsExplosivesSynthesis

20. ABSTRACT (Continue on reverse aide It necessary and Identify by block number)

Initial tests indicate Mercury 5-Nitrotecrazole is a promisingreplacement for lead azide in detonators. During the courseof preparation of this material for testing, several improvementsin the original synthesis were made. A reliable good yieldprocedure for mercury 5-nitrotetrazole is now a.vailable.

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NSWC/WOL/TR 76-146 9 December 1976

SYNTHESIS OF MERCURIC 5-11ITROTETRAZOLE

An improved synthesis of mercuric 5-nitrotetrazole is de!scribed.Mercuric: 5-nitrotetrazole is a very promising candidate for thereplacement of lead azide in detonators.

This task SF 33-354-316/8460 was funded by the Naval Sea SystemsCommand, SEA-0332.

ULIU-SW. TINIGBy direction

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llNSWC/WOL/TR 76-146

TABLE OF CONTENTS

Page

I. INTRODUCTION ................. 3........................3

"II. VON HERZ PROCEDURE FOR MERCURIC, 5-NITROTETRAZOLE ....... 3

III. ELIMINATION OF MINOR DETONATIONS ....................... 5

IV. SEPARATION OF THE COPPER ACID SALT OF5-NITROTETRAZOLE ....................................... 6

V. PURIFICATION OF 5-N'TROTETRAZOLE VIABIS(ETHYLENEDIAMINE) COPPER (I!)BIS(5-NITROTETRAZOLE) .... .............................. 6

VI. EXPERIMENTAL ........................................... 7

TABLE

STable Title Page

I- EFFECT OF SODIUM NITRITE CONCENTRATION ONACID COPPER SALT PREPARATION ........................ 8

A

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NSWC/WOL/TR 76-146

SYNTHESIS OF MERCURIC 5-NITROTETRAZOLE

I. INTRODUCTION

Lead azide is one of the most common primary explosives usedin detonators. it has been in widespread use for the past 50 yearsnot only in the United States but throughout the world. Despiteits almost universal acceptance, its service life is often shortenedbecause of ready hydrolysis in the presence of moisture and carbondioxide. One of the by-products of hydrolysis is hydrogen azidewhich in the presence of copper or copper alloys can form various

H 2 0/CO222 Pb(N-3)2/ PbCO Pb(OH)2 + 4HN 3

cooper azides some of which are even more sensitive, particularly toelectrostatic discharqe than lead azide itself.

1120Cu + HN3 C2 CuN + Cu(N 3 ) 2Cu(OH) 2 ...

The presence of copper azides is believed to have caused anumber of fatal accidents during the handling and storace ofmunitions, and is also thought to be a factor in premature firinas.

For these reasons a program was begun at the Naval SurfaceWeapons Center, White Oak Laboratory (NSWC/WOL) to find areplacement for lead azide that would be stable to hydrolysis,compatible with detonatli construction materials and would atleast equal lead azide in, performance. Before and during thisprogram, close cooperation was maintained with British personnelat the Explosive Research and Development Establishment (ERDE)at Waltham Abbey, Essex, England, who were conducting a similarinvestigation.

II. VON HERZ PROCEDURE FOR MERCURIC 5-NITROTETRAZOLE

Preliminary screening performed both here and by the Britishat Waltham Abbey indicated that mercuric 5-nitrotetrazole was apromising lead azide replacement. Our attention then was directedto an examination of the synthesis and properties of this compound.

3

NSWC/WOL/TR 76-146

Mercuric 5-nitrotetrazole was first reported in 1932 byVon Herz'. He prepared this material via the fo]lowing threesteps:

a. NH2"H2SO12 2 4

.CC CuSO4

N 'ON/N + 4 - uHTN),4

where NT = 5-nitrotetrazole anion.

b. (uHNT(NT). 2 "4H2 0 N CuO , +, C

N-N

C. NO. - NO 2

C +

2 N'bN -Na+ + Hg(NO3 ) 2 N Hg3

N- N N-2N-2

He proposed that the heavy metal salts and methyl esters of5-nitrotetrazole would be useful initiating explosives. Conversely,in 1952 it was reported that mercuric 5-nitrotetrazole was rejectedfrom consideration as a primary explosive because of excessivewater solubility2 , though no data as a basis for this decisionwere given.

1E. Von Herz, U.S. Pat. 2,066,954 (1-932).

2•F. Taylor, NAVORD 2468, Naval Ordnance Laboratory, Wnite Cak, 11D,3 Jun 1952.

3 The solubility of pure mercuric 5-nitrotetrazole in water wasdetermined by D. Glover of this Center, formerly the NavalOrdnance Laboratory, to be 0.09% at 30'C.

4

NSWC/WOL/TR 76-146

During initial experimentation with the Von Herz procedureseveral problems were encountered. During the diazotization therewas a continuous series of minor detonations, which while notharmful in themselves 4 , were pschologically disturbing and didon occasion break glassware. There was the possibility that thepotentially dangerous (in the dry state) acid copper nitrotetrazolesalt would be spilled over adjacent surfaces.

Upon completion of the diazotization the acid copper salt waspresent as a voluminous gel-like precipitate which required longperiods (six hours or longer) to separate by filtration and towash free of impurities. This would seriousl hamper scale-upoperations where large quantities would have to *,eprocessed. In addition, although Von Herz claimed yields ofaround 90% for this step, we were only able to obtain yields of60 to 65%.

The purity of the sodium 5-nitrotetrazole used for thereaction with mercuric nitrate had a marked effect on both theyield and the properties of the resultant mercuric 5-nitrotetrazole.When raw solutions of sodium 5-nitrotetrazole obtained by treatingthe acid copper salt with sodium hydroxide and filtering offthe cupric oxide were used the mercury salt dead pressed atmoderate pressures ( 20 kpsi) and so was unsuitable for detonatoruse.

It was necessary then to further purify the sodium 5-nitrotetrazole. This was done by recrystallizingthe sodium salttwice from water. This proved to be a time consuming procedurewhich requLred the evaporation of large volumes of watei. Also,because of the solubility of the sodium salt, yield losseswere high. The mercuric 5-nitrotetrazole prepared by the reactionof twice recrystallized sodium 5-nitrotetrazcle with mercuricnitrate did not dead press up to 80 kpsi, and had gooc JLetonantproperties, but even here there were batch to batch variations incrystal form and sizes

III. ELIMINATION OF MINOR DETONATIONS

5-Diazotetrazole will spontaneously detonate in aqueoussolution when the concentration exceeds i%6. It was reasoned then

'Private communication from Dr. J. Jenkins, ERDE, Waltham Abbey,Essex, England. An aqueous slurry of the copper acid salt of5-nitrotetrazole could not be exploded with a detonator cap.

SA more consistent product could be obtained by recrystallizingthe sodium salt two additional times from acetone but this, ofcourse, further increased both the yield losses and the timerequired for purification.

6F. R. Benson, "Heterocyclic Compoands," 8, p. 1 (1967).

5

INSWC/WOL/TR 76-146

that the detonations occurring during the diazotization werecaused by nitrogen oxide fumes arising from the reaction solutionand reacting with droplets of 5-aminotetrazole solution on varioussurfaces of the apparatus. Since copper salts catalyze thereaction of 5-diazotetrazole with nucleophiles, it was felt thatthe addition of small amounts of copper sulfate to the 5-aw.ino-tetrazole solution would eliminate any build-up of thediazotetrazole by catalyzing its conversion to 5-hydroxytetrazole.

C ++

NiOC N 2 N N + N.:,i0 / ý H 20/u++/ HC

N -- N N -N

This iproved to be the case since the addition of small amounts (%2q)of copper sulphate to the 5-aminotetrazole solution completelyeliminated the detonations previously experienced.

IV. SEPARATION OF THE COPPER ACID SALT OF 5-NITROTETRAZOLE

Table 1 summarizes the results of a number of experiments inwhich the sodium nitrite concentration was gradually increasedby the addition of excess sodium nitrite and by decrE~asing thereaction volume. There was a concomitant increase in the ,ieldof the acid copper salt from 62 to 85%. In addition, the physicalnature of the precipitate was markedly altered from gel-like toa more compact easily filtered material. The, filtration andwashing which were previously a major headache could now bequickly accomplished in about ten minutes. The substitution ofnitric acid for sulfuric acid under Von Herz conditions didappear to be somewhat advantageous (expt 3), however at highernitrite concentrationsthere was no discernible difference.

Because of the increased yield and the importance of easeof filtration the more favorable modifications were incorporatedinto a revised procedure for the preparation of the acid coppersalt (see Experimental).

V. PURIFICATION OF 5-NITROTETRAZOLE VIA BIS(ETHYLENEDIAMINE)COPPER (II) BIS(5-NITROTETRAZOLE)

As a result of investigations carried out at ERDE, WalthamAbbey, Essex, England7 , it was found that the copper acid salt

7 Private communication from Drs. J. Jenkins and R. McGuchan.English patent pending.

6

NSWC/WOL/TR 76-146

of 5-nitrotetrazole could be reacted with ethylenediamire togive bis(ethylenediamine)copper(II)bis(5-nitrotetrazole.,) This

2 CuHNT(NT) 2"4H2 0 + CuSO4 + 6 NH2CH 2CH 2NH2

3 Cuen2 (NT) 2

where en = NH2 CH2 CH2 NH,;

NT = anion of 5-nitrotetrazole

coordination compound could be readily purified by recrystallizationfrom water, was relatively non-sensitive 8 and so could be handledsafely in the dry state. Mercuric 5-nitrotetrazole could then beprepared by dissolving the Cuen 2 (NT) 2 in hot water adding nitricacid to tie up the ethylenediamine followed by the addition ofmercuric nitrate solution.

Cuen 2 (NT) 2 + 4 HNO 3 - Cu(NT) 2 + 2 (en- 2 11NO 3)

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

Mercuric 5-nitrotetrazole prepared in this manner was in the formof discrete well shaped crystals which showed little variancefrom run to run. The product showed excellent detonant propertiesas an initiator explosive. This procedure eliminated the necessityfor the time-consuming purification of sodium 5-nitrotetrazoleand was easily adaptable to scale-up operations.

With the adoption of the bis(ethylenediamine) Cu(II)bis(5-nitrotetrazole) purification method, all of the problemsassociated with the original Von Herz procedure were eliminated.A reliable good yield procedure for mercuric 5-nitrotetrazoleis now available.

During the course of this work, approximately 5 poundsof sodium 5-nitrotetrazole and about 2.5 pounds of mercuric5-nitrotetrazole were prepared in the laboratory for investigativepurposes without incident.

VI. EXPERIMENTAL

MERCURIC 5-NITROTETRAZOLE FROM SODIUM 5-NITROTETRAZOLE

I. Sodium 5-Nitrotetrazole

Cuen 2 (NT) gave evidernce of burning at 50 cm (2.5 kg wt) butdid n6t detonate up to 300 (m on the NSWC impact machine.

7

Fr~ ~ Fi -iiiiz ~-2;1 iSWI/.OL/TR 76-146

C\J PM -.

E-10

0 C

p, Cd Lf\

E-4 4-) Z)

4-)-

CC 3 0 0 .0 G0

04 0C

CC 0i

C-)

HZ E- I i OC)

UC 0 0 0 bC 0C -0 0CU-\ L)tx 0 L C* r 0 Ll

0 OH\ 0- Hr C-, C)* I,- -z , 0-1O Q .)Cr: ZM: +'~ +jD +C 0C '0

C+ H r + H + - HH.-1-11 0 E-' E-J 0- A- 0 - - U

<4 E4 H NO. 0.0 r 00 0\0 CC' 0 0 C 0 c Co- + ~ Ci (DCl CU) N ~ (D(U c~ Q)Uj 0l \

CC z ;R .12 CC'. =) Cd +v .-Cd Cl mE-4N- C ) :r c U -\ co L-1 H d U -, H 4 UN L Lr\\ C.)t- 4.)

0 00 b. CCO b*r *C LO 0 (D0(H) C) HoO 0 ' Hcoo ca0 HO (DJ HOC -iO CC 0

tr--U UU =0U L'NC uit.- UNCl UNOC uNC)--u 0

4C U

H ' C-UN'0 -

0 8

Oi I i

NSWC/WOL/TR 76-146

Reagents:

A. 104g (1.5 mol) NaNO2 and 55g (0.22 mol) CuSO 45H 20 in 300 mlwater.

B. 51.5g (0.5 mol) 5-aminotetrazole monohydrate, 2g CuSO 45H2 0and 64 ml 70% nitric acid in 700 ml H 20.

C. 70 ml 70% HNO3 in 30 ml H 20.

D. 50% NaOH solution (ca 30 ml).

Caution:

The copper acid salt of 5-nitrotetrazole, CuHNT(NT) 2, can behandled safely in the wet state; however in the dry state, it isvery sensitive to shock and electrostatic discharge. Air driedsodium 5-nitrotetrazole containing two or more mole-equivalentsof water of crystallization is relatively insensitive to shock;

= it cannot be detonated with a hammer blow. However when completelydry, it is also a sensitive explosive. Both compounds willdetonate violently if dropped on a hot plate. All precautionsconsistent with the handling of potentially dangerous explosivematerials should be observed throughout this operation.

~ Procedure:

Place solution A in a 2L beaker and cool to 50C. Adc solutionB to A dropwise with efficient stirring ovcr a period of about90 minutes holding the temperature at 150 to 181C (Note 1). Stirfor 15 minutes, add solution C drcpwise and then stir for anadditional 30 minutes. Filter with suction and wash the copperacid salt with 250 ml 1.8 N HNO3 and three times with 250 ml ofwater. Do not allow the cake to dry during the filtration andwashing. Transfer the wet cake to a 1500 ml beaker and adjustthe volume to about 600 ml with water.

Adjust the pH of the slurry to ca 9 with 50% sodium hydroxidesolution to precipitate copper hydroxide and then heat theefficiently stirred slurry to 70°C and digest fur 30 minutes(Note 2). Allow the precipitate to partially settle and filterwith suction through a packed layer of "celite" (Note 3) . Washthe precipitate twice with 100 ml of water.

Adjust the pH of the combined filtrate and washes to 4,with conc. TINO Reduce the volume to ca 350 ml using a rotovacat a bath temperature of 600C. Cool to 2°C and filter thesodium 5-nitrotetrazole (Note 4). Reduce the filtrate to 200 mland take a second crop... etc. Combine the crops, redissolvein water and recrystallize a second time. Air dry the product.

9

NSWC/WOL/TR 76-146

Dissolve the sodium 5-nitrotetrazole in acetone on a steambath and filter to remove inorganic salts. Cool the filtrate inan ice bath and remove the sodium 5-nitrotetrazole by filtration.Recrystallize a second time from acetone and air dry (Note 5).The yield is about 45-55% of theory based on 5-aminotetrazoie.

Notes:

1. During the diazotization of 5-aminotetrazole nitrogen oxideS~fumes are given off from the reaction solution. This step shouldbe carried out in an efficient hood.

2. The blue hydrated cupric hydroxide is converted to the[•,j brownish-black cupric oxide at 70 0 C.

3. Without "celite" the filtration and washing requires severalhours since the finely divided cupric oxide clogs the filtelr.

4. Sodium 5-nitrotetrazole crystallizes from water as avoluminous hydrated mass. After air drying, the salt contaLnstwo to five moles of water of crystallization depending on ambienthumidity.

5. Sodium 5-nitrotetrazole crystallizes from acetone as adihydrate. This appears to be stable at ambient conditions.

II. Mercuric 5-Nitrotetrazole from Sodium 5-Nitrotetrazole

2Na(NT) + Hg(N0 3 ) 2 \ Hg(NT) + 2NaNO322 3

where NT = anion of 5-nitrotetrazole

Reagents:

A. Hg(NO ) solution. Dissolve 54.0 g of red mercuric oxide in200 mi 9f 35% HNO0. Filter and dilute the filtrate tc 250 ml

S "with 35% HNO 3.

B. 70% HNO 3

C. Sodium 5-nitrotetrazole dihydrate.

Caution:

Sodium 5-nitrotetrazole containing two or more mole-equivalentsof water of hydration is relatively insensitive to shock; it cannotbe detonated with a hammer blow. However when completely dry,it is a sensitive explosive.

10

NSWC/WOL/TR 76-146

Mercuric 5-nitrotetrazole is a powerful primary explosive.It detonates at 7 cm (2.5 kg wt) on the NSWC impact machine. Itis also sensitive to friction. All operations should be carriedout behind a safety screen with minimum exposure, by experiencedpersonnel.

Procedure:

Dissolve 16.7 g of sodium 5-nitrotetrazole in 188 ml water.Add 12 ml 70% HNO and place a magnetic stirring bar in thesolution. In a s~parate container, add 60 ml of the Hg"NO•) 2solution to 140 ml of water. Heat both the tetrazole solu ionand the Hg(NO 3 ) 2 solution to 750C in a water bath.

SI Remove the solutions, quickly add the Hq(N0) solution to

the tetrazole solution and begin stirring at slowest speedpossible. Allow to cool gradually to ca 30 0 C with continuousstirring while the mercuric salt crvstallizes. a-op the stirring,allow the mercury sa]t to settle an, then decanL the supernatantAiquid. Transfer the solids to a "Nalgene" beaker by means of awater wash bottle. Add 200 ml of water, swirl, and again decant.

Transfer about 1/3 of the solids to a small "Nalgene"buchner funnel (#2 Whatman paper) by means of a water wash bottleand wash consecutively with 50 ml water, twice with 50 ml ofmethanol, and finally with 50 ml of methylene chloride. Aiir dryon the funnel. Carefully transfer the dried salt by gent'ypouring the contents into a weighed wide-mouth conductive plasticcontainer. After weighing place meicuric salt into a blast-proofcontainer. Repeat filtration and washing for remainder ofproduct. Yield is 75 to 80% of theory based on sodium 5-nitrotetrazole.

MERCURIC 5-NITROTETPAZOLE FROM BIS(ETHYLENEDIAMINE)COPPER(II)

1,BIS(5-NITROTETRAZOLE)

I. Bis(Ethylenediamine)Copper(II)Bis(5-Nitrotetrazole)

Reagents:

A. 104 g (1.5 mol) NaNO2 and 55 g (0.22 mol/ CuSO 4 51H20 in300 ml H20.

B. 51.5 g (0.5 mol) 5-aminotetrazole monohydrate, 2 g CuSO 45H 20 and 64 ml 70% nitric acid in 700 ml H2 0.

C. 70 ml 70% HNO3 in 30 ml 2° 0.

D. Ethylenediamine.

• •11

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NSWC/WOL/TR 76-146

Caution:

The copper acid salt of 5-nitrotetrazole [CuHNT(NT) 2 ] can behandled safely in the wet state, however when dried, it is verysensitive to shock and electrostatic discharge. Bis(ethylene-diamine)copper(II)bis(5-nitrotetrazole) has been routinelyhandled in the dry state without incident. On the NSWC impactmachine, it burns at 50 cm (2.5 kg wt) but does not detonate. Whenheated in a capillary, in an aluminum block, it begins meltingat 2100C and completely decomposes with a burst of gas at 225'Cleaving a brownish-black residue. Under these conditions, itdoes not detonate. Nevertheless, all precautions consistentwith the handling of potentially dangerous materials should beobserved throughout these operations.

Procedure:

Place solution A in a 2L beaker and cool to 50 C. Add solutionB to A dropwise, with efficient stirring over a period of about90 minutes holding the temperature at 15 - 18 0 C (Note 1). Stirfo" 15 minutes, add solution C dropwise and then stir for anadditional 30 minutes. Filter the copper acid salt with suctionand wash witi- 250 ml 1.8N HNO and three times with 250 ml water.Do not allow the cake to dry during the filtration and washing.Transfer the wet cake to a 1500 ml Erlenmeyer and make up thevolume to about 600 ml with water.

Heat the slurry (water bath) to 75 0 C with efficient stirringand add a solution of 21 q CuSO4- 5H 20 and 45 ml of ethylenedianine

th4 2ur a opeein 80 ml of H2 0. Stir until the slurry has completely dissolvedand then cool quickly with swirling in an ice bath. After coolingallow to remain in the i.e bath for 45 minutes to complete thecrystallization. Filter, wash twice with 200 ml cold water andair dry. The yield of Cuen 2 (NT) 2 is about 77 g; 75% based on"5-aminotetrazole.

Note 1. During the diazotization of 5-aminotetrazole, nitrogenoxide fumes are given off from the reaction solution. This stepshould be carried out in an efficient hood.

II. Mercuric 5-Nitrotetrazole frcm Bis(r~thylenediamine)Copper(II)

Bis(5-Nitrotetrazole)

Reagents:

A. 100 g Cuen2 (N]T) 2 in 1100 ml H 0 at 751C.2 2 2

SB. 65 ml 70% HNO 3 in 160 ml H20.

t C. 4 ml 70% HNO3 in 255 ml of 1.OM Hg(NO 3 ) 2.

12

NSWC/WOL/TR 76-146

Caution:

Mercuric 5-nitrotetrazole is a powerful primary explosive.It detonates at 7 cm (2.5 kg wt) on the NSWC impact machine andis also sensitive to friction. All operations should be carriedout behind a safety screen with minimum exposure, by experiencedpersonnel.

Procedure:

Add solution B to A, dropwise, w'ith stirring at 750 to 80'Cover a period of 15 minutes. Then add solution C in the samemanner over a period of 55 minutes. Stir for 15 minutes then allowto cool to 55 0 C. Decant the supernate from the solid productand wash by decantation 5 times with 500 ml H 0 Transfer the

2product to a plastic bottle with a water wash bottle and store* under water. Yield is about 92 g (89%).

Analysis of Mercuric 5-Nitrotetrazole

The 5-nitrotetrazole ring has a maximum in the ultravioletat 257 mwi, which can be used for analysis 9. The molecuLarextinction coefficient is 5.4 x 103.31

About 60 mg of mercuric 5-nitrotetrazole is dissolved in20 ml of 20% ammonium acetate solutico and then diluted to 250 mlwith water. A second dilution of about one to ten is then made with2% ammonium acetate solution and the absorption is measured at257 m•p against a reagent blank.

Sodium 5-nitrotetrazole dihydrate which was recrystallized§twice from water and three times from acetone and then air driedwas used to prepare a standard curve.

9 N. J. Blay, D. '. Davies, D. C. Mullinger and R. J. Rapley, TRDE,TR 163, Explosives Research and Development Establishment,Waltham Abbey, Essex, England, Jan 1974.

13

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