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- NAVORD REPORT 3979

SEMI-PILOT SCALE PRODUCTION OF TETRANITROMETHANE

15 MAY 1955

U. So NAVAL ORDNANCE LABORATORYWHITE OAK, MARYLAND

_ _ _ _ _ AUG 2 1955

55 AA 36762y/ . -s

SEMI-PILOT SCALE PRODUCTION OF TETRANITROMETHANW

IkPrepared by:

Francis Taylor, Jr.

Approved by: D. V. SiokmanChief, Chemistry Division

ABSTRACT: Tetranitromethane is at present an essentialstarting material for new experimental high explosives con-taining the trinitromethyl group. Several hundred poundshave been prepared by the reaction of 96-98% nitric acid withacetic anhydride on a semi-pilot scale. This somewhathazardous reaction requires care and many precautions toconduct safely on an enlarged scale. The yields averaged50% based on nitric acid and 35% based on acetic anhydride.The direct cost was $2.40 for chemicals and $9.85 for labor,

:4 largely skilled, per pound of 99.9% tetranitromethane.

N

EXPLOSIVES RESEARCH DEPARTMENTU.S. NAVAL ORDNANCE LABORATORY

WHITE OAK, MARYLAND

!iCONFIDENTIAL

55A A 36762

NAVORD Report 3979 15 May 1955

This report is a description of the semi-pilot scaleproduction of tetranitromethane performed under Task NOL-B2c-19-1-55. The reliability of the work and the validityof the conclusions are the responsiblity of the author andthe Chemistry Division of the U. S. Naval Ordnance Laboratory.

JOHN T. HAYWARDCaptain, USNCommander

S E. LA D Deputy Chiefplosives Research Department

ii I

CONFIDENT IALNAVORD Report 3979

TABIE OF CONTENTS

Page

Abstract ... .............. r, .. . . . . . ...... . . iIntroduction ..... .......... . .... ...................... 1Experimental ... .......... . ......... ....... . ....... 3

A. Developmental Experiments ........................ 3B. Preferred Pilot Scale Procedure .................

Physical Properties ... .................... . .......... . 7Explosive Properties ............... ................ 7Health, Safety and Sanitation ......................... 8Acknowledgments .............. ...... . ...... . .......... . 9References ....... .. ... .......... 0-ii

I LLUS TRAT IONS

Table 1 - Summary of Experimental Development Data .... 12Table 2 - Impact Sensitivity of TNM Mixed With

Combustible Material ........................ 13Figure 1 -Schematic Layout of Pilot PlantFigure 2 -NitratorFigure 3 -Aging KettlesFigure 4 -Effect of Aging Temperature on TNM YieldFigure 5 -Impact Sensitivity of TNM Mixed With Hydrocarbons

i55AA 36762CONFIDENTIAL

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NAVORD Report 3979

SEMI-PILOT SCALE PRODUCTION OF TETRANITROMETHANE

INTRODUCTI ON

Tetranitromethane (TNM) is an essential raw material forthe preparation of new explosive compounds containing thetrinitromethyl group. Until February 1953 an adequate supplyof TNM was available for the Navy's research and pilot plantnew explosive program from the Nitroform Company, East Orange,New Jersey. In February 1953 the Nitroform Company wasdestroyed by an accidental explosion which killed all of thekey personnel. The only other commercial supplier was Johnsonand Scudder, Bloomfield, New Jersey, and their production wasvery limited and they were not interested in supplying TNM inlarge quantities.

This lack of a commercial source of TNM threatened toseriously hinder the experimental development of new highexplosives. The Bureau of Ordnance (Re2c) recognized theimuediate need and asked the Chemistry Division of the

Explosives Research Department to start making TNM on ascale as large as was feasible with the equipment available.About this same time the Polynitro Chemical Company, CollegePark, Maryland started producing TNM on a limited scale.

Much work on the preparation of TNM on a laboratory scalehas been reported since the beainning of the century. Onlytwo of these reactions reported in the literature seem practicalfor a safe and convenient laboratory preparation of TNM, thereaction of acetic anhydride with nitric acid (1, 2), and thatof acetylene with nitric acid (3,4,5), although both haveserious drawbacks for large industrial scale use.

Until World War II TNM was only prepared on a laboratoryscale. During the recent war both in Germany and this countryTNM was prepared on a large scale. Schimmelschmidt, workingat I. G. Farbenindustrie, developed a continuous process inan all glass apparatus for the nitration of acetylene to TNMon a scale of one kilogram per hour based on the work of Ortonand McKie (5,6). In this country the Trojan Powder Companyprepared a thousand pounds of TNM during thn last war for theAir Force using the acetic anhydride-nitric acid procedure (7).

1

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It has also been known for many years that TNM is aby-product from the manufacture of trinitrotoluene(8), butvery little work has been done toward separating and re-covering the TNM. The Evans Research and Development .Corporation (9) and this Laboratory have made some preliminaryinvestigations of this source. We are planning to extend thework. A study of the original work of Orton and McKie hasbeen made by the Naugatuck Chemical Division, United StatesRubber Company (10), Evans Research and Development Corporation(11), and at present work is being done at this Laboratory (12).

Of the two practical methods available for the preparationsof TNM in the pilot plant, we chose the acetic anhydride-nitricacid procedure. This was the most convenient to adapt to ourequipment and thus start semi-pilot scale production with thef minimum delay. Our equipment consisted of four Pt audlerSeries "P" ten-gallon stainless steel reactors complete withagitators and fitted with a 3/4" aluminum cooling coil inaddition to the full jacket around the kettle. All of thekettles were equipped with a solenoid dump valve as a safetyfeature. These were controlled from behind a concretebarricade. One kettle was used as a nitrator and the otherthree as aging kettles. The reactants were loaded into astainless steel feed tank which was fitted with a deliveryline to the nitrator. The acetic anhydride was transferred tothe nitrator under nitrogen pressure. The nitric acid (96-98%)was added to the reaction mixture in the same manner but meteredthrough a Brooks Full-View Rotameter.

The temperature was controlled during the addition ofnitric acid with circulating chilled water. The flow wasarranged so that one could circulate the cooling water throughthe reactor or by-lass it as the reaction required. The waterwas chilled to 3-5 C by a three horsepower Freon compressor.

After the nitric acid addition was completed the reactionmixture was transferred by gravity flow to another kettle forthe five day aging cycle. The kettles used for the aging cyclewere similar to the nitrator, but they were equipped for coolingby circulating tap water only. The temperature during theaging cycle was controlled at 25*C by automatically controllingthis water flow to govern thm heat of the reaction by twoAmerican Instrument Company "Quickset" bimetal thermoregulatorsmounted in wells and an Emil Greimer Company Electronic Relay

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Model G 24875 which controlled a normally open solenoidwater valve. This arrangement was necessary especiallyfor winter-time operation when our tap water got as lowas 7'C during the period from November to April. Thereaction mixture was drowned in thirteen-gallon glasscarboys. Three liter three-neck flasks fitted with abottom draining stop-cock, stainless steel agitator, andthermometer were used for the purification of the crudeTNM. Figure 1 shows a schematic layout of our equipment.Figures 2 and 3 are photographs of our equipment.

EXPERI MENTAL

A. Developmental Experiments

Chattaway has suggested the following equation for thereaction (2):

4(CH 3 0)2 0 + hHNO 3 --oC(N02 )4 + 7CH 3COOH + 002

Various methods have been suggested for carrying out thenitration. These involve differences in the reaction tempertureduring nitration, the use of a diluent, the concentration ofnitric acid used as well as its N204 content, ratio of reactants,the presence of particles of glass, use of a catalyst, thelength of time allowed for completion of the reaction and-thetemperature during the aging cycle. Numerous experiments wereconducted in this Laboratory to determine the effects of some

h of the above variables on the yield of TNM.

Various concentrations of nitric acid were investigated.In general, it appeared that the more concentrated the aicdthe higher the yield of TNM based upon nitric acid. It isreported that 70% nitric acid yielded no TNM (13), 90% C.P.grade acid yielded 36% TNM, 95% C.P. grade acid yielded 40%TNM, 96-98% technical acid manufactured by the U. S. NavalPowder Factory, Indian Head, Maryland by the ammonia oxidationprocess, yielded on an average 50% TNM under comparableconditions. Red fuming nitric acids containing 6% and 20%nitrogen dioxide, were tried. Both mixtures gave about thesame yields as obtained with 98% technical acid but the timecould be reduced somewhat. White fuming nitric acid, 95%,decolorized with urea gave no TNM.

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The literature claims that the addition of small amountsof phosphorus pentoxide, sulfuryl chloride, and sulfuric acidwill show an increased yield of TNM (7). All of these materialswere tried but we were unable to substantiate these claims andin addition the reaction was difficult to control. Wyler alsoclaimed that the use of quartz or pieces of chipped glass alsoincreased the yield (7). We did not investigate this claimin our Laboratory. One reaction using a catalytic amount ofboron trifluoride was tried which resulted in a "fume-off",

As to ratio of reactants, it was found that nitric acidin a 10% excess or 15% excess acetic anhydride gave equivalentand maximum yields. We chose excess acid for economicalreasons. We purchased the acid for $0.06/pound and 99% aceticanhydride was supplied in drums by Carbide and CarbonChemicals Company at a cost of $0.16/pound.

Table 1 gives a summary of our experimental data. Nosubstantial improvement was obtained. However, comparableyields to present process could be obtained in a shorteraging cycle by the use of either red fuming nitric acid orsulfuric acid. The latter increased the hazard from self-heating and was also detrimental to the aluminum cooling coils.The addition of red fuming nitric acid to the 99.3% nitricacid helped. The yields given in the table are for crude TNM.

We have run the reaction by adding the nitric acid to theacetic anhydride and by the reverse procedure. The yields werethe same by either order of addition. We feel that it is saferto add the acid to the anhydride rather than adding a potentialfuel to a powerful oxidizing agent. If the anhydride is addedto the acid, one passes through a composition during theaddition of a good Sprengel-type explosive mixture which mightbe hard to control if the reaction temperature should accidentallybecome too high. Temperatures up to 400C for a moderate timewere not considered too hazardous during the aging cycle butduring the initial mixing cycle such temperatures were usuallyassociated with a rapid rate of increase which was dangerousand difficult to control. The incipient "fume-off" temperaturewas estimated at about 70eC as a result of a near accident bythe Polynitro Chemical Company.

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All of our earlier nitrations were carried out at l0-15oC.We have noted recently that nitration temperatures of 15-200 Cincreased the yield of TNM. We also found that an agingtemperature of 350C offered some advantage over 250C but wasmore hazardous and difficult to control. Figure 4 shows theeffect of the aging temperature on the yield.

We have always agitated the reaction mixture during theaging cycle and experienced no difficulties. Aerojet GeneralCorporation reported "fume-offs" during the aging cycle, butthey do not agitate the reaction mixture during this period (14).

B. Preferred Pilot Scale Procedure

We modified the procedure reported in Organic Synthesis,which is essentially that of the Chattaway (2,15); and scaledit up to 190 moles for pilot plant production from the 0.5 molesdescribed. A typical run in our pilot plant was as follows:

1. Preparation of TNM

a. Chemicals

4 "Acetic Anhydride, 90%

I Nitric Acid, 96-98% (oxides of nitrogen as HNO 2.3 to .4%)

b. Procedure

The feed tank was charged with 20,700 ml of 99% aceticanhydride and then transferred to the nitrator under 20 psiof nitrogen gas. The acetic anhydride was agitated and

k chilled to 5C by circulating chilled water through the coilsinside the nitrator and through the jacket. The feed tank wasnext charged with 9,031 ml of 96-98% nitric acid. The acid wasadded to the anhydride by metering it through a rotometer atabout 75 ml/minute. At this rate the reaction mixture selfheated slowly and was controlled at 15-200 C by circulating thechilled water as needed. It usually required two hours tocomplete the addition.

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After the nitric acid addition, the reaction mixturewas exothermic and the temperature was controlled at 25*Cmanually in the nitrator for several hours as a safetyprecaution before transferring by gravity flow to an agingkettle which was equipped for cooling by tap water only tocontrol the temperature of the reaction mixture.

Standing instructions for emergency drowning of thenitration mixture called for the temperature to reach 35'Cor to pass 300C at a rate greater than 1V per minute. Thishad to be done only once.

The reaction mixture was transferred to one of threeaging kettles by gravity flow. The temperature was controlledautomatically at 250C and the mixture agitated for a minimumof three days and preferably five days. After aging, thereaction was drowned with water by running both simultaneouslyinto a thirteen-gallon glass carboy. The TNM separated as alayer on the bottom and the aqueous acid layer was siphonedoff, diluted with capious quantities of water and discarded.

The crude TNM, 3225 mi, was transferred to a three-gallonglass bottle and washed and agitated with a continuous streamof water until acid free, allowing the wash water to overflowto the drain. When the TNM was acid free it was necessary toremove the water since we observed it to hydrolyze slowly.The batch was divided in half and each portion transferred toa three liter three-neck flask fitted with a thermometer,agitator, and bottom drain stopcock. 1050 Ml of 40% sulfuricacid was added to each flask and agitated for several minutesand then allowed to separate. The TNM was removed through thebottom stopcock and transferred to a similar flask where it waswashed with three-five hundred-twenty-five ml portions ofconcentrated sulfuric acid. Occasional batches were found toevolve considerable heat and turn black if allowed to standover the sulfuric acid for longer than 10-15 minutes. Afterthe last washing the major portion of the acid was removed andthe mixture allowed to stand overnight to insure completeseparation. The yield was 3982 grams, a conversion of 43%based on nitric acid, m.p. 14.1OC (corr.). having a minimumpurity of 99.9 mole percent.

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The rurity of each lot of TNM prepared was checked byfreezing point measured as follows: A 25 ml sample of TNMwas placed in an unsilvered Dewar jacketed tube, fitted withan agitator and narrow range mercury thermometer which hadbeen calibrated by the National Bureau of Standards, surroundedwith an ice bath. The sample was agitated and a freezing pointcurve plotted. The temperature recorded was that obtained byextrapolation to the time of separation of tho first solidmaterial. *

PHYSICAL PROPERTIES

The physical properties of TNM were measured on a samplehaving purity of 99.996 mole percent. They are as follows

Fraezing Point 14.1360C

Boiling Point 126 0c (760 mmn)25

Index of Refraction nD 1.4351

Density 1.65

Heat of Fusion 2250.6 ± cal/mole

Cryoscopic Constant 14.3C mole solute/kg TNM

EXPLOSIVE PROPERTIES

Pure TNM is a relatively non-explosive liquid. The impactsensitivity on the ERL drop-weight impact machine with 2.50 kgweight is above 320 cm (TNT = 160 cm). Mixtures of TNM withhydrocarbons like toluene have been reported as being explosiveand more sensitive to shock than nitroglycerine (18). TNH hasbeen reported to form more sensitive mixtures with aromatichydrocarbons than with aliphatic hydrocarbons.

I We have made a preliminary study of the sensitivity ofTNM when mixed with nitromethane and nitrobenzene. The impactsensitivities of these mixturas do not bear out the extremesensitivity reported in the literature. Mixtures of TNM andnitrobenzene were found to be much more sensitive than mixtureswith nitromethanes, With both substances the maximum sensitivityoccurred at the stioohiometric composition for explosion to CO2

7CONFIDENTIAL

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and water. We don't feel that this method of measuringsensitivity is a good criterion. Gap-sensitivity measurementswould probably be a better method. However, we do not feelthat it warrants the effort at this time.

The impact sensitivities of TNM with nitromethane andnitrobenzene in various proportions are listed in Table 2 andFigure 5.

The impact sensitivity of the reaction mixture wasmeasured immediately after the addition of nitric acid, oneday later, five days later, and that of the crude productafter drowning and separation. All of these materials appearedto be insensitive and gave no explosion on our drop weightmachine with a 2.5 kg weight up to 320 cm.

HEALTH, SAFETY AND SANITATION

TNM, itself, is a violent poison (19). The preliminaryeffecto of exposure to TNM vapors are characterized by a verypenetrating odor and an irritating effect on the membranes ofthe eyes and nose. -In the interest of health and safety,exposure to fumes of TNM-above 5 ppm should be carefully avoided.Suitable gas masks should be used when it becomes necessary towork near any fumes. During our drowning operations concentrationsof 10-15 ppm were encountered even with good ventilation (20).We have found the Mine Safety Appliance Co. all-service gas maskfitted with an all-service carister model "S" very satisfactory.We tested the cannister by preparing a solution containing53 ppm TNM and pulling the vapors from the TNM through the p.cannister for thirty minutes. At the end of this period 0.01 ppmTNM was detected in the filtered air, and this was deemedsuitable protection for our needs. A detailed report on thetoxic effects of TNM has been published by the U. S. PublicHealth Service (19).

TNM can be produced by the acetic anhydride-nitric acidprocedure in pilot plant equipment safely. With a five daytotal reaction cycle with a 10 gallon nitrator and three agingkettles we could produce seventy pounds per month minimum andusing a three day cycle a maximum of about one hundred-sixtypounds per month under ideal conditions. TNM can be producedon this scale at a labor and material cot of #12.25/pound ofwhich $2.40 are for materials. This is not a cheap chemical,

8CONFIDENTIAL

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but it is a reasonable price for a research intermediate.On a larger scale it would be cheaper, but for productionpurposes the nitration of acetylene or recovery of TNM as aby-product from the manufacture of TNT would probably bemore feasible. Both of these routes are under investigationat the present time.

ACKNOWLEDGMENTS

The helpful suggestions of Drs. D. V. Sickman and0. H. Johnson in the layout and design of the pilot plantare acknowledged. B. 0. Wilkerson assisted in the productionoperations. Dr. 0. H. Johnson and M. E. Hill performed aportion of the developmental work.

t

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REFERENCES

1. Ch.attaway, F. D., Chemical News, 1022, 307 (1910).

2. Chattaway, F. D., J. Chem. Soc., 97, 2100.

3. McKie, P. V., J. Chem. Soc., 1927, 962.

4• Orton, K. J. P., Brit. Patent 125,000 (Aug 3 1918).

5. Orton, K. J. P., and McKie, P. V., J. Chem. Soc., 117,283 (1920).

6. The Production of Tetranitromethane and Nitroform atI. G. Farbenindustrie, B.I.O.S. Final Report 709,3 July 1946.

7. Wyler, Joseph A., U. S. Patent 2,057,076 (13 Oct 1936).

8. Claessen, L., Ger. Patent 184,229 (5 Nov 1905).

9. Evans Research and Development Corporation, Contract No.DA-30-O69-ORD-103, 12 June 1951.

10. Sundholm, N. K., Richards, T. C., and Schoene, D. L.,NORD 10,121, Naugatuck Chemical DivisionUnited StatesRubber Company, Progress Report, April-July 1951.

11. Evans Research and Development Corporation, Summary

Report on the Nitration of Acetylene, 15 April 19;4.

12. Southworth, R. W., Nitroform from Nitration of Acetylene,NavOrd 3903 (to be published later).

13. Hurd, C. D., OSRD No. 334 (20 Jan 1942).

14. Private communication from Dr. Karl Klager of AerojetGeneral Corporation, Azusa, California.

15. Liang, P., Organic Synthesis, Volume 21 (1941).

16. Johnson, 0. H., Preparation of Pure Tetranitromethane,U. S. Naval Ordnance Laboratory Memorandum 10,898(26 April 1950).

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NAVORD Report 3979

REFERENCES (Cont'd)

17. Hu, Jih-Heng and Harris, P. M., The Ohio State UniversityResearch Foundation Report No. 5, Contract No. N6ONR 22517 NR 017 406 (Sep 1953).

18. Schultheis, W., Halstead Explorating Center, Report onWork in Connection with Explosives. B.I.O.S/Gp.II/H.E.C5741.

19. Sievers, R. F., Rashings E., Gray, H., and Monaco, A.,Toxic Effects of Tetranitromethane, U. S. Public HealthReports, 62, 1048 (1947).

20. Glover, D. J., and Landsman, S. G., Determination ofSmall Amounts of Tetranitromethane in the Atmosphere,

4NavOrd in preparation.

I

I 11

C ONFIDENTI AL

CONFIDENTIALNAVORD Report 3979

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CONFIDENTIALNAVORD Report 3979

TABLE 2

Impact Sensitivity of TNM Mixed WithCombustible Material

ImPaQt Sensitivity OxygenDiluent Wt.% TNM (2.5. kit wt) Balance

Nitromethane 44.6 109 cm CO2

21.2 196 cm CO

65 180 C 02ft 85 210 cm C02

Nitrobenzene 42.6 264 cm 4 CO

61.7 44cm CO

76.3 22 cm CO2

82.8 47 cm ,CO 2

2,4-dinitrobutulene 95 300 cm

Reference Nitroglycerin 4-5 cm

Sensitivities )RDX 22 cmjTNT 160 cmPure TNM > 320 cm

13CONFIDENTIAL

CONFIDENTIALNAVORD REPORT 3979

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CONFIDENTIALNAVORD REPORT 3979

FIG. 2 NITRATOR

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CONFIDENTIALNAVORD REPORT 3979

FIG. 3 AGING KETTLES

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CONFIDENTIALNAVORD REPORT 3979

FIG. 4 EFFECT OF TEMPERATURE ON YIELDOF TNIVI

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130

120

110

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TEMPERATURE (C

CONFIDENTIAL

FIG. 5 IMPACT SENSITIVITY OF TNM MIXED WITH HYDROCARBONS

250

225

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WEIGHT (PERCENT TNM)

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