Liquid Carbon-Boron Cluster Additives for Mixed Amine-50
Abstract
:1. Introduction
2. Experimental
2.1. Reagents and Instruments
2.2. Synthesis and Characterization
2.2.1. Synthesis of C,C′-Bis(2-ethylhexanoylmethyl)-o-carborane
- (1)
- Bis(hydroxymethyl)-o-carborane (1, BHMCB)A solution of 5 g (34.67 mmol) of ortho-carborane (OCB) in 60 mL of super-dry tetrahydrofuran was prepared. Under nitrogen protection and at −78 °C, 30 mL of n-butyllithium (2.4 mol/L) was slowly added dropwise to the carborane solution, followed by stirring for 2 h. Subsequently, 2.19 g (72.81 mmol) of paraformaldehyde was added to the mixture in one portion at room temperature, and the reaction system was stirred for an additional 10 h. The reaction was quenched using a 10% HCl aqueous solution. After evaporating the solvent and water using a rotary evaporator, the residue was extracted with diethyl ether. The organic layer was washed three times with deionized water and dried over anhydrous sodium sulfate. After removing the solvent, the residue was recrystallized using a mixture of dichloromethane and n-hexane (Vdichloromethane/Vn-hexane, 1:5). The crystallized product was washed extensively with n-hexane to yield a white solid with a yield of 87%. Chemical shifts attributed for BHMCB: 1H NMR (400 MHz, CDCl3) δ (ppm): 4.23 (4H, d), 2.87 (2H, s), 1.39–3.48, (10H, br m); 13C NMR (101 MHz, CDCl3) δ (ppm): 78.18, 64.48; 11B (128 MHz, CDCl3) δ (ppm): −3.28 (d, J = 149.2 Hz), −11.15 (dd, J = 165.2, 89.9 Hz).
- (2)
- C,C’-Bis(2-ethylhexanoylmethyl)-o-carborane (2, BEMCB):A mixture of 5 g (24.48 mmol) of BHMCB and 5.59 mL (56.30 mmol) of triethylamine was dissolved in super-dry dichloromethane. Under nitrogen protection and at −5 °C, 8.9 mL (53.85 mmol) of 2-ethylhexanoyl chloride was added dropwise to the solution. After the addition was complete, the reaction was allowed to warm to room temperature and stirred for 5 h. The reaction was then quenched with deionized water. The solvent and water were evaporated using a rotary evaporator, and the residue was extracted with diethyl ether. The organic layer was washed three times with deionized water and dried over anhydrous sodium sulfate. After removing the solvent, the residue was purified by column chromatography using a mixture of dichloromethane and n-hexane (1:10) to yield a pale yellow liquid with a yield of 80%. The synthetic route is shown in Figure 1.Chemical shifts attributed for BEMCB: 1H NMR (400 MHz, Chloroform-d) δ (ppm): 4.66 (q, J = 7.1, 6.2 Hz, 4H), 2.32 (tt, J = 13.2, 5.7 Hz, 2H), 1.55 (dddd, J = 53.5, 31.7, 13.4, 6.4 Hz, 10H), 1.32–1.23 (m, 4H), 0.91–0.85 (m, 12H). 1.39–3.48, (10H, br m); 13C NMR (101 MHz, CDCl3) δ (ppm): 174.45, 75.87, 62.42, 46.93, 31.25, 29.46, 25.02, 22.53, 13.83, 11.71; 11B (128 MHz, CDCl3) δ (ppm): −3.03 (d, J = 149.7 Hz), −10.29 (d, J = 162.4 Hz).
2.2.2. Preparation of Cluster Liquid Propellant
2.2.3. Characterization Methods and Testing Conditions
3. Results and Discussion
3.1. Characterization and Analysis
3.1.1. Structural Characterization of C,C′-Bis(2-ethylhexanoylmethyl)-o-carborane (BEMCB)
3.1.2. Thermal Stability Analysis
3.2. Performance Characterization and Analysis of Composite Fuels
3.2.1. Compatibility and Stability Testing
3.2.2. Physicochemical Properties
3.2.3. Thermal Stability Analysis
3.3. Theoretical Calculation of Isp
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
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Fuel | Components | wt. % | |
---|---|---|---|
A | Mixed Amine-50 | - | 0 |
B | BHMCB | 20 | |
C | BEMCB | 20 |
Fuel | ρ (20 °C)/g·cm−3 | FP/°C | μ/mPa·s | Qv/kJ·cm−3 |
---|---|---|---|---|
A | 0.855 | <−55 | 1.02 | 35.97 |
B | 0.884 | <−55 | 2.26 | 36.36 |
C | 0.884 | <−55 | 2.32 | 36.43 |
Fuel | ρ (20 °C)/g·cm−3 | Isp/s | D-Isp/N·s·m−3 |
---|---|---|---|
A | 0.855 | 338 | 2.88 × 106 |
B | 0.884 | 344 | 2.96 × 106 |
C | 0.884 | 347 | 2.99 × 106 |
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Mu, X.; Wang, S.; Yang, F.; Li, H. Liquid Carbon-Boron Cluster Additives for Mixed Amine-50. Molecules 2025, 30, 2037. https://doi.org/10.3390/molecules30092037
Mu X, Wang S, Yang F, Li H. Liquid Carbon-Boron Cluster Additives for Mixed Amine-50. Molecules. 2025; 30(9):2037. https://doi.org/10.3390/molecules30092037
Chicago/Turabian StyleMu, Xiaogang, Shenghui Wang, Fanzhi Yang, and Hao Li. 2025. "Liquid Carbon-Boron Cluster Additives for Mixed Amine-50" Molecules 30, no. 9: 2037. https://doi.org/10.3390/molecules30092037
APA StyleMu, X., Wang, S., Yang, F., & Li, H. (2025). Liquid Carbon-Boron Cluster Additives for Mixed Amine-50. Molecules, 30(9), 2037. https://doi.org/10.3390/molecules30092037