Dichloromethane → Decalin

EXAMPLE 5 is the comparative example of EXAMPLE 4.65 g of endo-THDCPD crystals from the same source of EXAMPLE 4 are placed in a 250 ml of glass bottle, followed by adding 40 g of dichloromethane thereto to dissolve these crystals, purging with dry nitrogen and stirring in the ice bath. Subsequently, 10 g of AlCl3 is added to the dichloromethane solution of endo-THDCPD, followed by stirring for 2 hours in the ice bath, and continuously stirring for 16 hours at room temperature. The resulting mixture is washed with 100 ml of saturated KCl solution, followed by adding it to a separatory funnel, shaking to allow to separate into two layers and leaving the upper layer in the separatory funnel. The above saturated KCl solution washing procedure is repeated for three times. Subsequently, the mixture washed with the saturated KCl solution is washed with 100 ml of deionized water, followed by adding it to a separatory funnel, shaking to allow to separate into two layers and leaving the lower layer in the separatory funnel. The above deionized water washing procedure is repeated for three times. Subsequently, the lower layer is distilled to remove dichloromethane and water. The bottoms is collected, and determined by chemical analysis. The chemical analysis shows that the bottoms is composed of 85.7 wt % of exo-THDCPD, 0.5 wt % of endo-THDCPD, 1.2 wt % of Decalin, 5.8 wt % of adamantane, 1.3 wt % of exo-THMDCPD, and the other two-stage hydrotreated and saturated C11+ derivatives, namely CPD and/or MCPD diners. The bottoms has a volumetric heating value of 39.17 MJ/L, a density of 0.9339 at 15° C., and a viscosity of 3.52 cSt at 20° C. and more than 26.7 cSt at −20° C. In this example, the isomerization reaction is violent because isomerization reaction time is too long so that portions of exo-THDCPD is further isomerized to adamantane which will increase the viscosity of the high energy fuel. Under such a violent reaction conditions, a small amount of THDCPD will be ring opened by hydrogen to give decalin (the side product) with relatively less volumetric heating value as well as density. Therefore, the isomerization reaction of this example is not suitable for preparing the high energy fuels because the freezing point of the isomerization product is too high.

1. dissolutionto dissolve these crystals
2. custompurging with dry nitrogen
3. additionSubsequently, 10 g of AlCl3 is added to the dichloromethane solution of endo-THDCPD
4. stirringby stirring for 2 hours in the ice bath
5. stirringcontinuously stirring for 16 hours at room temperature
6. washThe resulting mixture is washed with 100 ml of saturated KCl solution
7. additionby adding it to a separatory funnel
8. stirringshaking
9. customto separate into two layers
10. customleaving the upper layer in the separatory funnel
11. washThe above saturated KCl solution washing procedure
12. washSubsequently, the mixture washed with the saturated KCl solution
13. washis washed with 100 ml of deionized water
14. additionby adding it to a separatory funnel
15. stirringshaking
16. customto separate into two layers
17. customleaving the lower layer in the separatory funnel
18. distillationSubsequently, the lower layer is distilled
19. customto remove dichloromethane and water
20. customThe bottoms is collected
21. customat 15° C.
22. customat 20° C.
23. customat −20° C
24. customis violent because isomerization reaction time
25. temperaturewill increase the viscosity of the high energy fuel
26. customUnder such a violent reaction conditions

ORD record

ord-2fa15d533fb44cfba2d7a797a9578056

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450544B2