New approaches to the development of high-performance hydrocarbon propellants

Article abstract of DOI:10.1134/S1070427207010065

An approach to express screening of promising hydrocarbon propellants, based on the calculation of the specific impulse of an engine from the results of quantum-chemical calculation of their heats of combustion, was suggested. The approach ensures high accuracy irrespective of the composition and structure of the compounds under consideration. Polycyclic and framework hydrocarbons with small rings were suggested as promising propellants.

Full text of DOI:10.1134/S1070427207010065

ISSN 1070-4272, Russian Journal of Applied Chemistry, 2007, Vol. 80, No. 1, pp. 31 37. Pleiades Publishing, Ltd., 2006.
Original Russian Text M.V. Savos’kin, L.M. Kapkan, G.E. Vaiman, A.N. Vdovichenko, O.A. Gorkunenko, A.P. Yaroshenko, A.F. Popov,
A.N. Mashchenko, V.A. Tkachev, M.L. Voloshin, Yu.F. Potapov, 2007, published in Zhurnal Prikladnoi Khimii, 2007, Vol. 80, No. 1, pp. 32 38.
PHYSICOCHEMICAL STUDIES
OF SYSTEMS AND PROCESSES
New Approaches to the Development
of High-Performance Hydrocarbon Propellants
M. V. Savos’kin, L. M. Kapkan, G. E. Vaiman, A. N. Vdovichenko, O. A. Gorkunenko,
A. P. Yaroshenko, A. F. Popov, A. N. Mashchenko, V. A. Tkachev,
M. L. Voloshin, and Yu. F. Potapov
Litvinenko Institute of Physical Organic and Coal Fuel Chemistry, National Academy of Sciences of Ukraine,
Donetsk, Ukraine
Yangel’ Yuzhnoe State Design Office, National Space Agency of Ukraine, Dnepropetrovsk, Ukraine
Received August 4, 2006
Abstract An approach to express screening of promising hydrocarbon propellants, based on the calculation
of the specific impulse of an engine from the results of quantum-chemical calculation of their heats of combus-
tion, was suggested. The approach ensures high accuracy irrespective of the composition and structure of the
compounds under consideration. Polycyclic and framework hydrocarbons with small rings were suggested as
promising propellants.
DOI: 10.1134/S1070427207010065
The development of new hydrocarbon propellants
for environmentally clean rockets is a priority research
field, because the use of energetic propellants in-
creases the pay load of carrier rockets and makes their
launch more cost-efficient.
heats of formation and hence higher heats of combus-
tion. The suggested propellants based on 1-methyl-
1,2-dicyclopropylcyclopropane [9] and dicyclobutyl
[10 13] are characterized by record-breaking heats of
combustion.
We believe that the use of polycyclic and frame-
work hydrocarbons with small rings as propellants can
further enhance the energy characteristics of rockets
owing to high density and increased heat of combus-
tion of such propellants.
One of approaches to enhancing the performance of
hydrocarbon propellants is increasing their density by
using cyclic and framework compounds [1 7]. Such
propellants are usually prepared by hydrogenation of
dicyclopentadiene followed by catalytic rearrangement
of the product from the endo to exo form, which is re-
quired for decreasing the melting point. Such propel-
lants as, e.g., JP-10, RJ-4, and RJ-41 with a density of
Studies on synthesis and determination of the char-
acteristics of new fuels require considerable expenses;
therefore, it is appropriate to start searching for com-
pounds having the required properties with the calcu-
lation of the relevant physicochemical characteristics.
With the modern computers, the existing quantum-
chemical methods allow quick screening of the poten-
tially promising compounds with incommensurably
lower time and money expenses compared to experi-
mental studies. This approach also allows calculation
of the characteristics of difficultly available and even
hypothetical substances.
3
0.94 g cm were prepared by this procedure. With
norbornane taken as starting compound, a propellant
3
(RJ-5) with a still higher density, 1.08 g cm , was
prepared. Another way to increase the density is the
condensation of dicyclopentadiene with adamantane
derivatives; however, this leads to a significant in-
crease in the melting point.
To enhance the performance of hydrocarbon pro-
pellants, their heat of combustion is increased, in
particular, by using structurally strained hydrocarbons
containing three- and four-membered rings [8]. These
compounds contain fragments with strongly distorted
C C bond angles, which leads to appreciably larger
Various empirical additive schemes for calculating
the heat of combustion require the knowledge of such
molecular parameters as the bond energies or force
constants. Additive schemes give particularly inaccu-
31

32
SAVOS’KIN et al.
rate results when applied to compounds of different
types, e.g., in going from normal hydrocarbons to
cyclic hydrocarbons, especially those with small rings.
Therefore, such calculations do not ensure the level
of versatility and accuracy required for comparing the
parameters of compounds with diverse chemical struc-
tures. Molecular mechanics methods suffer from the
same drawback.
thermochemical corrections to their enthalpies at 25 C
are 70.43, 42.80, and 20.64 kJ mol , respectively.
1
The calculated heats of combustion in oxygen of
saturated hydrocarbons of different chemical struc-
tures and several unsaturated hydrocarbons in the gas
phase are listed in the table.
To evaluate the accuracy of calculating the heat
of combustion within the framework of the above-
described scheme, we calculated the total energies of
aliphatic hydrocarbons for which these quantities are
well-known. As follows from the table, the relative
errors of the calculated heats of combustion of the
homologous series of hydrocarbons (from methane to
octane) are within 0.12 0.37%. Appreciably higher
accuracy is attained for molecules containing small
rings. In this case, the error does not exceed 0.1% and
in most cases is within 0.03 0.04%. The experimental
heats of combustion presented in the table refer to the
gas phase.
Since the heat of combustion of the compounds of
interest varies in a relatively narrow range (10% at
maximum and 2 3% in most cases), the only method
giving the reliable and comparable data is direct ab
initio calculation of the heat of combustion.
The overall reaction equation for the combustion of
hydrocarbon propellants in oxygen at a stoichiometric
component ratio,
CnHm + (n + m/4)O2 = m/2H2O + nCO2,
(1)
corresponds to the real calorimetric experiment. Al-
though the error in calculating the heat of combustion,
Note that, when comparing the power intensity of
various compounds, the heat of combustion is usually
referred to 1 g of the combustible but not of the fuel
(combustible + oxidant), which can lead to wrong
conclusions when choosing the most efficient fuel.
Indeed, assume that combustion of fuel of mass m
results in evolution of Q J of heat. Then, neglecting
the thermal dissociation of combustion products, we
can determine the velocity of their outflow v from the
law of energy preservation:
1
as will be shown below, is 4 8 kJ mol and some-
what exceeds the error of experimental determina-
tions, the calculation accuracy attained is quite suffi-
cient for comparing the power intensity of various
hydrocarbons.
The calculations reported in this paper were per-
formed ab initio using the GAMESS program package
[14] which allows, in particular, calculation of the
total energies of molecules and of the correlation and
thermodynamic corrections to them. The molecular
geometries were fully optimized within the framework
of the restricted Hartree Fock (RHF) method in the
TZV(d,p) basis set [15] with the polarization d func-
tions on the C atoms and p functions on the H atoms.
To determine the thermochemical correction at 25 C,
the harmonic vibration problem [16] was solved in
the same approximation. For the molecular geometry
corresponding to the total energy minimum in the
TZV(d,p) basis set, the electron correlation was taken
into account according to the Møller Plesset pertur-
bation theory (MP2) [17, 18] in a wider basis set,
TZV(2df,2p). Several test calculations of small mole-
cules showed that the geometry optimization in this
basis set did not lead to appreciable decrease in the
total energy. The oxygen molecule in the ground tri-
plet state was calculated by the restricted open-shell
Hartree Fock (ROHF) method, and the MP2 electron
correlation correction for this molecule was deter-
mined according to [19]. The required total energies
with the MP2 correction, calculated in the TZV(2df,p)
mv2/2 = Q,
(2)
where
Hence,
is the engine efficiency factor.
v = (2 H)1/2
(3)
(4)
(Glushko’s formula), where
H = Q/m
is the heat of combustion per unit mass of the fuel
1
(J kg ), which, as seen from formula (3), is the major
factor determining the outflow rate and hence the
engine thrust.
Let us illustrate these reasonings by a simple exam-
ple. Judging from the specific heat of combustion per
kilogram of combustible h, methane is the most effi-
cient (see table); however, its H value is relatively
low, determining its moderate power characteristics
as propellant. In the combustion of methane,
basis set (in atomic energy units) are as follows: H O
2
76.3204, CO 188.3156, and O 150.1218. The
CH4 + 2O2 = CO2 + 2H2O,
(5)
2
2
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 80 No. 1 2007

NEW APPROACHES TO THE DEVELOPMENT
33
Calculated heats of combustion of hydrocarbons and specific engine impulses
Specific heat of combustion,
1
Com-
pound
no.
Heat of combustion, kJ mol
caculation experiment*
Specific im-
pulses,**
s
1
kJ kg
Hydrocarbon
Formula
of combustible, h of fuel, H
1
2
3
4
Methane
CH4
C2H6
C3H8
C4H10
797
1423
2037
2650
794 [20]
1419 [21]
2040 [21]
2658 [22]
49657
47312
46184
45595
9953
10014
9978
339.1
340.2
339.6
339.2
Ethane
Propane
Butane
9959
5
6
Octane
C8H18
5106
4911
5112 [20]
4909
44696
44561
9929
338.7
344.5
Dicyclobutyl
10269
7
8
exo-Tetrahydrodicyc-
lopentadiene (JP-10)
Tetracyclo-
5780
5195
5770 [5]
42421
43225
9893
338.1
345.1
5193 [23]
10305
[3.3.1.02,4 6,8
0 ]nonane
9
-Pinene
5893
5905
6024
5347
5332
5544
4113
4139
4623
4199
4239
5891 [24]
5899 [24]
43253
43343
43571
43754
43631
45366
43682
43957
49096
44595
45020
10086
10108
10003
10240
10211
10617
10330
10395
11610
10546
10647
341.4
341.8
340.0
344.0
343.5
350.3
345.5
346.6
366.3
349.1
350.7
10
-Pinene
11 Pinane
12 Tricyclo[5.2.0.02,5]-
nonane I***
13 Tricyclo[5.2.0.02,5]-
nonane II***
14 Tricyclo[5.2.0.02,5]-
nonane III***
15 Tricyclo[4.1.0.02,4]-
heptane I***
4113 [25]
16 Tricyclo[4.1.0.02,4]-
heptane II***
17 Tricyclo[4.1.0.02,4]-
heptane III***
18 Tricyclo[3.2.0.02,4]-
heptane I***
19 Tricyclo[3.2.0.02,4]-
heptane II
20 4,7,7-Trimethyltricyc-
lo[4.1.1.02,4]octane****
6558
6556
5384
43644
43629
44057
10148
10145
10311
342.4
342.4
345.2
21 1,4,4-Trimethyltricyc-
lo[5.1.1.03,5]octane****
22 2,6-Dimethyl2ricyclo-
[3.1.1.03,6]heptane
23 Tricyclo[3.3.1.0]nonane
24 Tricyclo[3.3.2.0]decane
5239
5834
42870
42825
10033
9987
340.5
339.7
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 80 No. 1 2007

34
SAVOS’KIN et al.
Table. (Contd.)
Specific heat of combustion,
1
Com-
pound
no.
Heat of combustion, kJ mol
Specific im-
pulses,**
s
1
kJ kg
Hydrocarbon
Formula
caculation experiment*
of combustible, h of fuel, H
25 Bicyclo[1.1.0]butane
2520
3087
46592
46699
10954
11262
355.8
360.7
26 Tricyclo[2.1.0.02,5]-
pentane
27 Bicyclo[2.1.0]pentane
3089
3595
45342
44864
10574
10696
349.5
351.6
28 Tricyclo[3.1.0.02,4]hex-
ane
29 Prismane
3646
3550
4050
46678
44301
43956
11462
10561
10655
363.9
349.3
350.9
30 Tricyclo[3.1.0.02,6]hex-
ane
31 Quadricyclane
32 Cubane
4733
3115
45439
45731
11158
10664
363.9
351.0
33 Spiropentane
34 Norbornane
4139
43040
9947
339.0
35 Norbornene
36 Norbornadiene
37 Nortricyclene
4043
3968
4023
42936
43065
42731
10154
10439
10105
342.5
347.3
341.7
38 Adamantane
5720
41986
9791
336.4
* For the gas phase.
** Calculation by Glushko’s formula (8) at
= 0.556.
*** Bold dots denote hydrogen atoms located over the molecular plane.
**** Because of the large molecular size, the calculations were performed in a somewhat less accurate basis set TZV(df,2p),
which leads to 1-s underestimation of the specific impulse.
the oxygen consumption is 3.9891 mass units per
mass uinit of methane. Therefore, for complete com-
bustion of methane in oxygen, we have
the oxygen consumption is as low as 3.339 mass units
per mass unit of the combustible; hence,
1
H
h/(1 + 3.339) = 44561/4.339 = 10269 kJ kg .
1
H = h/(1 + 3.9891) = 49657/4.9891 = 9953 kJ kg .
Thus, although the heat of combustion per kilogram
1
of combustible (h) of methane, 49.657 kJ kg , appre-
Similarly, in combustion of, e.g., dicyclobutane,
1
ciably exceeds that of dicyclobutyl, 44.561 kJ kg ,
C8H14 + 11.5O2 = 8CO2 + 7H2O
(6)
methane is less efficient because of the lower heat of
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 80 No. 1 2007

NEW APPROACHES TO THE DEVELOPMENT
1
35
combustion per kilogram of fuel (H): 9953 kJ kg
The specific impulses given in the table range from
336.4 for adamantane to 366.3 for stereoisomer III of
1
against 10269 kJ kg for dicyclobutyl. Note that the
2,4
reasonings given here and below refer exclusively to
the stoichiometric ratio of the fuel components, com-
bustible and oxidant. Actually, to attain the maximal
performance of a specific type of propellant, the opti-
mal amounts of the oxidant are determined experi-
mentally, and they are usually appreciably lower than
the stoichiometric amount. In this case, our approach
to assessing the performance of propellants can be
used as a preliminary estimate.
tricyclo[4.1.0.0 ]heptane (no. 17). Note that the spe-
cific impulses of adamantane and JP-10 propellant are
close to that of kerosene, 337.9 s [10 12]. The natural
terpenes - and -pinene present in turpentine exhibit
higher specific impulse, 341.4 341.8 s. Still higher
values, 345 350 s, are attained, e.g., with 2,6-dimeth-
3,6
yltricyclo[3.1.1.0 ]heptane (no. 22), norbornadiene
2,6
(no. 36), tricyclo[3.1.0.0 ]hexane (no. 30), and bicy-
clo[2.1.0]pentane (no. 27). Note that tetracyclo[3.3.1.-
2,4 6,8
0
0
]nonane (no. 8) suggested in [23] as a promis-
To convert the specific heat of combustion of a
hydrocarbon h to the specific heat of combustion of
a fuel H, it is convenient to use a formula following
from Eq. (1):
ing aviation fuel, according to our calculations, has a
specific impulse of 345.1 s, only slightly exceeding
that of dicyclobutyl (344.5 s).
The highest values of the specific impulse (exceed-
ing 350 s) are characteristic of such strained frame-
work hydrocarbons as quadricyclane (no. 31), spiro-
pentane (no. 33), bicyclobutane (no. 25), cubane
H = h(11.91 + x)/(43.66 + 8.936x),
(7)
where x = m/n is the H/C atomic ratio in the given
hydrocarbon C H .
2,5
n
m
(no. 32), tricyclo[2.1.0.0 ]pentane (no. 26), and pris-
An important conclusion follows from Eq. (7):
With a decrease in the H/C ratio x in a hydrocarbon,
the conversion factor from h to H increases. Thus, a
propellant with a low hydrogen content can exhibit a
higher specific impulse, even despite lower power
intensity h per kilogram of the hydrocarbon.
mane (no. 29). Many of these compounds are hypo-
thetical and have not been synthesized up to now.
The synthesis of the other compounds of this group is
extremely difficult and labor-consuming, and it can
hardly be realized on the commercial scale in the near
future. Furthermore, such compounds have high mo-
lecular symmetry and hence should have high melting
point at relatively low boiling point, which is hardly
acceptable for propellants.
By multiplying the outflow velocity of gaseous
products v from formula (3) by the fuel consumption
1
rate (kg s ), we obtain the tractive force in newtons.
In the literature on rocket engines, the specific im-
The three series of stereoisomers of tricyclo-
2,4
2,5
pulse p , measured in kilogram-force (kgf) units and
[3.2.0.0 ]heptane (nos. 18, 19), tricyclo[5.2.0.0 ]-
sp
2,4
equal to the tractive force at a fuel consumption rate
nonane (nos. 12 14), and tricyclo[4.1.0.0 ]heptane
1
of 1 kg s , is commonly used. Conversion of formu-
(nos. 15 17) deserve particular consideration. As seen
from the table, in going from the transoid chair-like
to cisoid boat-like molecular configuration, the spe-
cific impulse increases by only 0.5 1.6 s. However, a
striking result was obtained with the skewed iso-
mers: the specific impulse increased by 6.8 s for tricy-
la (3) to p gives
sp
psp = (2 H)1/2/g,
(8)
1
i.e., the dimension of p is kgf kg s or simply s
sp
after the cancellation of kgf and kg, which is a
common practice. The results of calculation by formu-
la (8) are given in the table. The efficiency factor
was taken equal to 0.556 to bring the calculated and
experimental [10 12] specific impulses of dicyclobu-
tyl to coincidence; this value of was also applied to
calculate the specific impulses of all the other com-
pounds listed in the table. Thus, the parameter plays
the role of a calibration factor taking into account, to a
first approximation, the nonstoichiometric ratio of the
combustible and oxidant, partial dissociation of com-
bustion products, etc. It is assumed that these factors
affect the specific impulse of the examined substances
to approximately the same extent as that of dicyclo-
butyl.
2,5
clo[5.2.0.0 ]nonane III (no. 14) and even by 20.8 s
2,4
fir tricyclo[4.1.0.0 ]heptane III (no. 17) (relative to
the coresponding transoid structures). Compound
no. 17 even exceeds prismane (no. 29) in the specific
impulse, being a champion among the structures
chosen.
Analysis of data in the table, taking into account
the set of requirements to propellants (melting and
boiling points, density, viscosity, stability, etc.) shows
that the most promising for further experimental
studies are terpene derivatives (nos. 20, 21) and tri-
cycloheptanes (nos. 15 17), the more so as the raw
materials for their synthesis (turpnetine oil and cyclo-
pentadiene) are cheap and readily available.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 80 No. 1 2007

36
SAVOS’KIN et al.
For primary estimation of properties of potentially (103 C [25]). Unfortunately, the other stereoisomers
(nos. 16, 17) were not detected in the product.
promising propellants, we synthesized laboratory sam-
ples of some of them. Tricyclo[4.1.0.0 ]heptane was
2,4
Apparently, the purposeful synthesis of highly
strained stereoisomers like nos. 14 and 17 requires
a higher level of preparative organic chemistry. Such
a synthesis may involve the use of coordinating mat-
rices or catalysts ensuring formation and preservation
of the required strained steric configuration.
prepared by the Simmons Smith reaction [26] used
for obtaining three-membered hydrocarbon rings.
Cyclopentadiene prepared by thermal depolymeriza-
tion of dicyclopentadiene was treated with methylene
iodide in the presence of silver-plated zinc dust; in
the process, it was smoothly converted to tricyclo-
For chemical modification of natural terpenes, it
appeared feasible to use a two-step synthesis scheme
involving addition of dichlorocarbene to the double
bond of the substrate under phase-transfer conditions
(with triethylbutylammonium chloride, TEBAC, as
phase-transfer catalyst), followed by reductive dehalo-
genation of the intermediate product with sodium in
liquid ammonia. This scheme is preferable over the
Simmons Smith reaction because of the availability
of the reagents and solvents and high yield and purity
of the products.
2,4
[4.1.0.0 ]heptane:
1
The product was identified by H NMR spectros-
2,4
copy as transoid stereoisomer I of tricyclo[4.1.0.0 ]-
heptane (no. 15); its calculated specific impulse is
345.5 s. The compound synthesized has a density of
With -pinene used as precursor, this scheme leads
3
2,4
0.908 g cm (0.8912 according to [25]); its freezing
to 4,7,7-trimethyltricyclo[4.1.1.0 ]octane (no. 20)
point is below 103 C, and the boiling point is 104 C
whose calculated specific impulse is 342.4 s:
Na(NH )
3
CHCl , NaOH, TEBAC
3
phase-transfer catalysis
3,5
and from carene, 1,4,4-trimethyltricyclo[5.1.0.0 ]octane (no. 21) having the same specific impulse is obtained:
Na(NH )
3
CHCl , NaOH, TEBAC
3
phase-transfer catalysis
Since the above-described two-step synthesis with
individual turpentine components occurs very smooth-
ly and with high product yields, we made an attempt
to use as starting reagent turpentine oil, a multicom-
ponent mixture of natural terpenes. By so doing, we
heat of combustion of hydrocarbon propellants, is an
efficient approach to their express screening. This
approach ensures high accuracy when applied to hy-
drocarbons of diverse compositions and structures.
(2) The use of polycyclic and framework hydro-
carbons with small rings as propellants can ensure
further enhancement of the power characteristics of
rocket engines due to high densities and high heats of
combustion of such compounds.
3
obtained a propellant with a density of 0.882 g cm ,
freezing point below 90 C, and boiling onset point
of 186 C. The expected specific impulse should be
342 343 s.
(3) The power characteristics of strained polycy-
clic hydrocarbons essentially depend on their steric
configuration. For example, the stereoisomers of tri-
cyclo[4.1.0.0 ]heptane differ in the specific impulse
by more than 20 s.
CONCLUSIONS
2,4
(1) Evaluation of the specific impulse of a rocket
engine, based on quantum-chemical calculation of the
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 80 No. 1 2007

NEW APPROACHES TO THE DEVELOPMENT
37
(4) Strained polycyclic and framework hydrocar-
bons selected according to the calculation results were
synthesized by addition of carbenes to double bonds
of natural terpenes and cyclopentadiene. The products
obtained exhibit increased specific umpulse and densi-
ty; they also meet other requirements to propellants.
14. Schmidt, M.W., Baldridge, K.K., Boatz, J.A., et al.,
J. Comput. Chem., 1993, vol. 14, no. 5, pp. 1347
1365.
15. Dunning, T.H., J. Chem. Phys., 1971, vol. 55, no. 2,
pp. 716 723.
16. Boatz, J.A. and Gordon, M.S., J. Phys. Chem., 1989,
vol. 93, no. 5, pp. 1819 1826.
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