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I.

AFRPL-TR-69-111

(TITLE UNCLASSIFIED)

INVESTIGATION OF THE THERMODYNAMIC

,PROPERTIES, OF PROPELLANT INGREDIENTS

QUARTERLY PROGRESS REPORT AFRPL-TR-69-111

(1 January 1969 to 31 March 1969)

. f 1-1,STATR=NT #2 CL'ASSI.FLO"'

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be made only . - -.:", ":_erts or.

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(Prepa.ed under Contract Hr. F04611-67-C-0025 byThe Dow Chemical Company,

Midland, Michigan 48640)

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Report Nr. T0025-1Q-69

QUARTERLY PROGRESS REPORT (U)

(1 January 1969 to 31 March 1969)

April 1969

AIR FORCE SYSTEMS COMMANDRESEARCH AND TECHNOLOGY DIVISIONROCKET PROPULSION LABORATORYEDWARDS, CALIFORNIA 93523

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DOWNGRADED AT 3 YEARINTERVALS; DECLASSIFIED

AFTER 12 YEARS

DOD DIR 5200.10

CHEMICALS LABORATORYTHE DOW CHEMICAL COMPANYMIDLAND, MICHIGAN 48640

UNCLASSIFIED

UNCLASSIFIED AFRPL-T-69-1l

FOREWORD

This report was prepared by The Dow Chemical Company,

Midland, Michigan, under USAF Contract Nr. F04611-67-C-0025. The

contract was initiated under Air Force Program Nr. 750 G, AFSC

Project Nr. 3148, "Investigation of the Thermodynamic Properties

of Propellant Ingredients and the Burning Mechanisms of Propel-

lants." The work was administered under the direction of the

Rocket Propulsion Laboratory, Edwards Air Force Base, with

Mr. Curtis C. Selph acting as Air Force Project Officer.

This quarterly report covers the work performed during

1 January 1969 through 31 March 1969. The Dow Report Number is

T0025-lQ-69.

This work was performed by Dr. G. C. Sinke and Dr. J. L.

Curnutt, under the technical supervision of Dr. D. R. Stull and

Dr. Harold Prophet and management supervision of Dr. K. 0. Groves.

This report has been reviewed and is approved.

W. H. Ebelke, Colonel, USAF

Chief, Propellant Division

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UNCLASSIFIED

CONFIDENTIAL AFRPL-TR-69-111

ABSTRACT

(C) The heat of formation of methylene bisoxyamine diper-chlorate (CHeN 2 02 '2HCl04 ) dissolved in ethylene glycol was deter-mined by oxygen bomb calorimetry as -104.4 kcal/mole. The heatof solution in glycol will be measured in order to derive the heatof formation of' neat methylene bisoxyamine diperchlorate.

(C) Other work in progress includes the heat of combustionof free methylene bisoxyamine and the heat of explosion ofCF2 (ONF2 )2 with oxygen and a promoter such as propane.

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CONFIDENTIAL AFRPL-TR-69-1ll

TABLE OF CONTENTS

(C) A. THE HEAT OF FORMATION OF METHYLENE BISOXYAMTNE DIPERCHLORATE. 1 1

(U) Introduction .... ............ . ......... 1

(U) Method . .................... 1(U) Equipment . . . . . . . .. .. . . . . .. . . . .

(U) Procedure ............................... 1

(U) Calculations .... ............ ........... 2

(U) Results . . .......... . . . . ......... 2

(U) B. WORK IN PROGRESS . . . ................... . 6(U) REFERENCES ..... .................... . ........ 7

(U) DD Form 1473 (Dated 1 Jan. 1964) ..... .............. .13,14

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CONFIDENTIAL AFRPL-TR-69-111

A. THE HEAT OF FORMTION OF METHYLENE BISOXYAMINE DIPERCHLORATE (C)

1. Introduction (U)

(C) A sample of methylene bisoxyamine diperchlorate(CHeN 202 -2HC104) was received from Dr. Claude Merrill of the AirForce Rocket Propulsion Laboratory, Edwards Air Force Base,California. The material was a white crystalline solid. Accord-ing to Dr. Merrill, elemental analyses for carbon, hydrogen, andnitrogen are in good accord with theory. The compound is some-what hygroscopic, and all transfer operations were carried out ina dry nitrogen atmosphere.

2. Method (U)

(C) Organic perchlorates can be thermochemically character-ized by the heat of combustion technique. Zimmer et al. (1)determined the heat of formation of hydroxylammonium perchlorateby combustion calorimetry. Diethyl oxalate was used as an addi-tive to provide a fuel for the excess oxygen. A determination ofthe heat of combustion of aniline hydrochloride in this labora-tory (2) showed good agreement with a value based on solutionthermochemistry. The technique adopted for methylene bisoxyaminediperchlorate was similar to these two investigations.

3. Equipment (U)

(U) A rotating bomb calorimeter and a platinum lined combus-tion bomb were employed.

4. Procedure (U)

(U) A long narrow bag open on both ends was fabricated from0.5 mil polypropylene film and accurately weighed. A clamp wasfastened across the middle of the bag and the assembly weighed.An appropriate amount of sample was added to one side of the bagin a dry nitrogen atmosphere and the end of the bag was sealed.The bag and contents were weighed. An appropriate amount of eth-ylene glycol was added to the other side of the bag which wasthen sealed and the assembly weighed. The clamp was removed andby gentle manipulation the sample was dissolved in the ethyleneglycol.

(U) The bag was next placed in a platinum crucible whichwas suspended in a gimbal in the combustion bomb. A cotton threadfuse was strung from a fine platinum ignition wire to the bag.Approximately 11 g of 0.08 M As2O solution was accurately meteredto the bomb by means of a weight buret. The bomb was closed andcharged with purified oxygen to 30 atm pressure. After thermal

CONFIDENTIAL

CONFIDENTIAL AFRPL-TR-69-11

equilibrium was established, the charge was fired by electricalheating of the fuse wire and the resulting temperature rise wasaccurately monitored by an automatic resistance bridge. Afterthe calorimetry the bomb was carefully discharged, opened, and thesolution recovered for analysis for nitrate, unoxidized arseniousoxide, and platinum.

(U) The heat of combustion of the polypropylene film andethylene glycol was determined separately by standard oxygen bombcalorimetry. The calorimeter equivalent was determined by combus-tion of benzoic acid standard sample 39i from the National Bureauof Standards.

5. Calculations (U)

(U) A number of corrections must be applied to the bomb cal-orimeter data in order to derive true heats of formation. Thesecorrections are calculated by means of a computer program basedon the outline of Hubbard et al. (3) for C-H-O compounds and ofBaroody et al. (4) for C-H-0-N-Cl compounds. Parameters forC-H-O compounds are reasonably well established, but forC-H-C-t"-Cl samples some estimates have to be made (2). Constantfactors specific for the individual compounds treated here aregiven in Table I.

(U) The calorimeter equivalent determined by benzoic acidcombustion is E(calor) = 3427.20 cal/deg. This value is an aver-age of numerous determinations over the past year. There is nodiscernible trend with time.

6. Results (U)

(C) Calorimetric data for ethylene glycol are given in TableII. The average value of -AE0/M is used in correcting for theglycol in the methylene bisox~amine diperchlorate runs. The gly-col was a shelf sample which contained some water, and theresults are not intended to define the heat of combustion of pureglycol.

(C) Calorimetric data for the heat of combustion of thesolution of methylene bisoxyamine diperchlorate are given inTable III. The average value of -E*/M and a molecular weight of278.988 yield:

AE0 = -276.86 kcal/mole

for the reaction:

CH8Cl2 N2 010 (in glycol)

C02 (g) + 2HCl(600 H20) + 3H2O(1) + N2 (g) + 5/2 02 (g)

-2-

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CONFIDENTIAL AFRPL-TR-69-11

TABLE I

(C) Constant Factors in Calorimetry of Ethylene Glycol and

Methylene Bisoxyamine Diperchloratea b

Empirical formula, glycol C2 He0 2

Empirical formula, perchlorate CH8 C12 N201 0

Density of glycol, g/cc 1.115

Density of perchlorate, g/cc (1.85)

Bomb volume, liter 0.349

Water added to bomb for glycol experiments, ml 1.0

Initial oxygen pressure at 250C, atm 30.3

Reference temperature, 0C 25.00

Final ratio, H2 0/HC1 600

(6E/6P)T of glycol, cal/g/atm -0.00397

(6E/6P)T of pefchlorate, ca)./g/atm (-0.001)

Cp of glycol, cal/g/0 C 0.577

Cp of perchlorate, cal/g/oC (0.26)E(Calor), cal/"C 3427.20

Additional platinum parts, g 47.33

aQuantities in parentheses are estimated.

bFor data on polypropylene film and cotton fuse,

see Reference 2.

-3-

CONFIDENTIAL

UNCLASSIFIED AFRPL-TR-69-111

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UNCLASSIFIED

CONFIDENTIAL AFRPL-TR-69-111

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-5-

CONFIDENTIAL

CONFIDENTIAL AFRPL-TR-69-111

Correcting to constant pressure conditions:

6HO -276.86 + 9/2 RT

= -274.20 kcal/mole

(C) With auxiliary heats of formation in kcal/mole of-94.052 for C02 (g), -39.823 for HCl(600 H2 0), and -68.315 forH20(1), there is derived for the heat of formation of methylenebisoxyamine diperchlorate dissolved in ethylene glycol:

aLfs2 9 8 -lo4.4±i.2 kcal/mole.

The heat of solution is expected to be a small positive value, sothe heat of formation of neat methylene bisoxyamine diperchloratewill be slightly more negative.

B. WORK IN PROGRESS (U)

(C) A sample of methylene bisoxyamine of higher purity thanthe last reported work (2) has been received and its heat of com-bustion will be determined. The heat of solution of methylenebisoxyamine diperchlorate in glycol will also be determined.

(C) The heats of solution of methylene bisoxyamine andmethylene bisoxyamine diperchlorate in dilute perchloric acid arebeing run. These data will serve to interrelate the two compoundsand provide a check on the accuracy of the heats of combustion.

(C) Some work on the heat of explosion of mixtures ofCFsCN, CsH8 , and 02 indicates that satisfactory heats of formationof gaseous C-F-N-0-H compounds can be obtained by explosion witha promoter, such as C3H8 , and oxygen. Time permitting, thisapproach will be used to measure the heat of formation of a sam-ple of CF2 (ONF2 )2 received from Rocketdyne Corporation.

-6-

CONFIDENTIAL

UNCLASSIFIED AFRPL-TR-69-111

REFERENCES

1. M. F. Zimmer, E. E. Baroody, G. A. Carpenter, and R. A. Robb,J. Chem. Eng. Data, 13, 212 (1968).

2. The Dow Chemical Company, Midland, Mich., Annual ProgressReport AFRPL-TR-69-31, January 1969, Contract F04611-67-C-0025.

3. W. Hubbard, D. W. Scott, and G. Waddington, Chapt. 5 of"Experimental Thermochemistry," Vol. I, Interscience,New York, 1956.

4. E. E. Baroody, G. J. Wynne, and M. F. Zimmer, U. S. NavalPropellant Plant, Indianhead, Md., NavWeps Report 8686,Technical Report 154, August 17, 1964.

-7-UNCLASSIFIED

CONFIDENTIAL AFRPL-TR-69-11

CONFIDEN1ALseculit C14u4111"IM

DOCUMINT CONTIOL DATA • 1idI Olflniwst 1w A¢tlloY tC.. bow t f) "*ti g*e IwhenT as a"IlP Iae

The Dow Chemical Company ConfidentialMidland, Michigan 48640 * GOU -

Group IV

"nveutigation of the Thermodynamic Properties of PropellantIngredients and the Burning Mechaniams of Propellants

R4 OEICS11101-1 11 tO'p. ef N,.g.e .. d.E .* *I'* ..

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S, (C) The heat of formation of methylene bisoxyamine diper-chlorate (CHeN2o2O2HCO 4 ) dissolved in ethylene glycol was deter-mined by oxygen bomb calorimetry as -lo.4 kcal/mole. The heatof solution in glycol will be measured in order to derive the heatof formation of neat methylene bisoxyamine diperchlorate.

(C) Other work in progress includes the heat of combustionof free methylene bioxyamine and the heat of explosion ofCFa(ONP2 )2 with oxygen and a promoter such as propane.

,,

DD .-. 1473 .._FIDENTIAL• cutI. Cl gjsihee~on

-13-

CONFIDENTIAL

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