Ionic Liquids as Hypergolic Fluids

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1 Ionic Liquids as Hypergolic Fluids Jean ne M. Shreeve Department of Chemistry University of Idaho Moscow, ID Advanced Energetic Materials Synthesis Workshop University of Maryland College Park April 5,

2 Contents Definition Cations/Anions Summary Acknowledgment References 2

3 Hypergolic Ionic Liquids Hypergolic spontaneous reaction of one chemical (fuel) when contacted with another (oxidizer) Hypergolic bipropellants - fuel and oxidizer combinations that react chemically to release enough heat to spontaneously ignite, eliminating the need for an additional ignition source. Why hypergols? efficient propellants to replace volatile and carcinogenic hydrazines. Desirable properties low vapor pressure - low toxicity high thermal and hydrolytic stability short ignition delay time (< 5 msec) low impact sensitivity low viscosity - high density high specific impulse (> 300 s) environmentally friendly 3

4 Commonly Used Oxidizers IRFA inhibited, red-fuming nitric acid (83% HO % 2 O 4 + ~ 2% H 2 O + 0.6% HF) WFA white fuming nitric acid (~100% HO 3 ) 2 O 4 4

5 Azolium itrocyanamide and Dicyanamide Salts R AgY / CH 3 OH R X - AgX Y X = Cl, Br, or I Y = (C) 2, (O 2 )(C) Y = (C) 2 ; R = propargyl (1), allyl (2) Y = (O 2 )(C); R = ethyl (3), n-butyl (4), allyl (5), 2-methoxyethyl (6) 5

6 Properties of azolium nitrocyanamide and dinitrocyanamide salts Compd T g (T m ) a [ o C] T d b [ o C] d c [g/cm 3 ] η d [cp] ID e [ms] ΔH f f [kj/g] 1 h -61(17) h i (-73) i (-90) i (-91) i (-82) h,j h,i,k -6(-90) (20 o C) 9 h,l h,m 37 a glass transition (melting point); b decomposition onset; c density; d viscosity, 25 ºC; e ignition delay (WFA); f enthalpy of formation; g specific impulse (Cheetah 5); h Ref. (1, 2); i Ref. (5); j 1-methyl-4-amino-1,2,4-triazolium; k 1-butyl-3-methylimidazolium; l 1- butyl-1-methyl-pyrrolidinium; m n-butyl-3-methylpyridinium. I sp g [s] 6

7 Energetic 2,2-dimethyltriazanium Salts H 2 ether H 2 C l 0 o C H 2 C l H 2 (1) A g Ag A g Ag C C O 2 C C C O 2 O 2 C O 2 C C C H 2 H 2 H 2 H 2 H 2 H 2 H 2 H 2 C C O 2 C C C O 2 O 2 C O 2 C C (2) (3) (4) (5) A g C C C H 2 H 2 C C C C (6) Ag O 3 H 2 H 2 O 3 (7) 7

8 Properties of energetic 2,2-dimethyltriazanium salts Salts Density g cm -3 T m T d C C Ignition Delay [ms] 2 O 4 WFA H f kj mol 1 P GPa D m s -1 I sp S IS J not hy > > SH > >60 IL A* IL B* * 1-(2-propargyl)-3-methylimidazolium dicyanamide; 1-methyl-4-amino-1,2,4-triazolium dicyanamide Schneider, S. et al. Energy & Fuels 2008, 22,

9 Mono- and Diazidoethyl Tri and Dimethyl Ammonium Salts 3 CH3 I I 3 Ag(C) 2 or Ag(C)(O 2 ) C C O 2 C 3 3 C H 3 I 3 3 I Ag (C ) 2 or Ag (C )( O 2 ) C C 3 O 2 C 4 9

10 Properties of Mono- and Diazidoethyl Tri and Dimethyl Ammonium Salts 3 C C 3 O 2 C 3 3 C C 3 3 O 2 C Salts Density cm -3 T m T d C C Ignition Delay [ms] 2 O 4 WFA H f kj mol 1 I sp s IS J not hy > not hy > not hy > not hy >60 10

11 Hypergolic ionic liquids with azide anion H 3 H 3 H 3 H 3 H ypergolic in 2 O 4 11

12 ,-dimethylhydrazinium salts H 3 C H 3 C H 2 RX H 3 C H 3 C H AgY 2 H 3 C R H X 3 C H 2 R Y R X C 4 H 9 I 15, 19 CH 2 CHCH 2 Cl 16, 20 CH 2 CCH Br 17, 21 CH 2 CH 2 OH Cl 18, 22 Y = (O 2 )(C) (15-18) Y = (C) 2 (19-22) 12

13 Properties of,-dimethylhydrazinium salts Compd T d a (ºC) d b (g/cm 3 ) η c (cp) ID d (ms) ΔH f e (kj/g) I sp f (s) a decomposition onset; b density; c viscosity, 25 ºC; d ignition delay (WFA); e enthalpy of formation; f specific impulse 13

14 14

15 Generalizations Property Impact 1) asymmetrically substituted cation lower melting point 2) < seven carbon atoms encourages hypergolicity 3) unsaturated side chains, e. g., enhance tendency toward acetylenic hypergolicity 4) secondary or tertiary amines alternative to monomethyl hydrazine and unsymmetric dimethyl hydrazine 5) higher positive heat of formation higher specific impulse 6) oxygen balance in fuel unimportant - oxidizer provides 7) high specific impulse and density improve density-impulse measure of fuel performance 8) absence of - single bonds reduces toxicity but decreases enthalpy 9) low viscosity enhances flow characteristics and mixing with oxidizer 10) additives increases density/decreases viscosity 11) anions may govern viscosity 15

16 Hypergolic Borohydride Salts a and K H H B H H H H B H H -based ionic liquids hypergolic w ith w hite-fum ing nitric acid (W F A ) 16

17 Borohydride-Based Ionic Liquids BH C 4 4 H 9 B r B r ab H 4 C 4 H 9 C H 2 Cl 2 C 4 H 9 [B m im ]Br [Bm im ]B H 4 Hypergolic (white fuming nitric acid) Very water-sensitive BH 4 2 H 2 O BO 2 4 H 2 17

18 Cyanoborate-Based Salts B r ab H 3 C B H 3 C C 4 H 9 C H 2 C l 2 C 4 H 9 [Bm im ]Br [Bm im ]B H 3 C Hypergolic (white fuming nitric acid) Less water-sensitive BH 3 C 2 H 2 O BO 2 H C 3 H 2 18

19 Dicyanoborate-Based Salts ab H 3 C ac abh 2 (C ) 2 A g O 3 A gbh 2 (C ) 2 B r abh 2 (C ) 2 or A gbh 2 (C ) 2 C 4 H H 9 2 O B H 2 (C ) 2 C 4 H 9 [B m im ]B r [B m im ]B H 2 (C ) 2 Hypergolic (white fuming nitric acid) Water stable 19

20 B H 4 B H 3 C B H 2 (C ) 2 C 4 H 9 C 4 H 9 C 4 H 9 H 2 O -sensitive le ss H 2 O -sensitive H 2 O -stable B -H H O 3 hypergolic ignition 20

21 Synthesis M C 4 H 9 B r C H 2 C H C H 2 C l M C l (or M B r ) AgB H 2 (C ) 2 M B H 2 (C ) 2 M = H 3 C H 3 C H 2 C 4 H 9 H 3 C H 3 C H 2 C H 2 C H C H 2 H 3 C C 4 H 9 H 3 C C H 2 C H C H 2 C H 3 C 4 H 9 C H 2 C H C H 2 C 4 H 9 C H 3 C H 2 C H C H H 3 C C 4 H 9 H 3 C C H 2 C H C H

22 Properties O T m ( o C) T d ( o C) d (gcm -3, 25 o C) η (cp, 25 o C) ID (ms) H 3 C H 2 H 3 C R H 3 C R R C H 3 R H 3 C R 1 < < < < < < < < < < R group: butyl (black), allyl (red). 22

23 Properties of dicyanoborate-based salts compared with corresponding nitrocyanamide and dicyanamide analogues - BH 2 (C) 2 Compd. 1 f 1 (CA) g 1 (DCA) h T m /T g a o C < T d b o C d c g cm η d cp ID e ms f 2 (CA) g 2 (DCA) h < f 3 (CA) g 3 (DCA) h < f 4 (CA) g 4 (DCA) h < a Phase-transition temperature; b Decomposition temperature (onset); c Density (25 o C); d Viscosity (25 o C); e Ignition delay time (WFA). f - BH 2 (C) 2 ; g [CA] nitrocyanamide as anion with common cation; h [DCA] dicyanamide as anion with common cation

24 SUMMARY Several hypergolic salts with a variety of cations and a few different anions have been synthesized. Anions seem to be controlling although cations appear to have marginal influence on hypergolic properties. In general, with a common cation, dicyanamide anions tend to give salts with lower ignition delay times; however nitrocyanamide sometimes wins. Borohydride, cyanoborate, and dicyanoborate-based ionic liquids are hypergolic with WFA. Dicyanoborate-based ionic liquids with good properties (wide liquid range, low viscosity, high stability, and short ignition delay time), exhibit serious potential as bipropellants. 24

25 ACKOWLEDGMETS Office of aval Research ational Science Foundation 25

26 REFERECES S. Schneider, T. Hawkins, M. Rosander, G. Vaghjiani, S. Chambreau, G. Drake, Energy Fuels, 22, 2871 (2008). S. D. Chambreau, S. Schneider, M. Rosander, T. Hawkins, C. J. Gallegos, M. F. Pastewait, G. L. Vaghjiani, J. Phys. Chem. A, 112, 7816 (2008). H. Gao, Y.-H. Joo, B. Twamley, Z. Zhuo, J. M. Shreeve, Angew. Chem. Int. Ed. 48, 2792 (2009). Y. Zhang, H. Gao, Y. Guo, Y.-H. Joo, J. M. Shreeve, Chem. Eur. J., 16, 3114 (2010). L. He, G.-H.Tao, D. A. Parrish, J. M. Shreeve, Chem. Eur. J., 16, 5736 (2010). Y.-H. Joo, H. Gao, Y. Zhang, J. M. Shreeve, Inorg. Chem., 49(7), 3282 (2010). Y. Zhang, J. M. Shreeve, Angew. Chem. Int. Ed. 50, 935 (2011). 26

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