Synthesis of mono-substituted cyclopentadienes
Synthesis of mono-substituted alkylcyclopentadienes by mixing alkyl iodides with cyclopentadienyl magnesium chloride in tetrahydrofuran is described.
1. A process for reacting an organoiodide RI with an ethereal solution of cyclopentadienylmagnesium halide to produce a monosubstituted cyclopentadiene RCp according to the equation
RI+CpMgX→RCp+IMgX
wherein R comprises a C 1 to C 20 alkyl group, a C 3 to C 20 alkenyl group, or a C 7 to C 20 alkylaryl group, and X comprises a halide; said process further comprising the addition of a hydrocarbon diluent; and wherein said reaction takes place at a temperature ranging from about 20° C. to about 66° C.
2. The process of claim 1 further comprising said reaction occurring at a temperature ranging from about 30° C. to about 50° C.
3. The process of claim 1 , wherein the ethereal solution comprises tetrahydrofuran.
4. The process of claim 1 , wherein the halide further comprises chloride.
5. The process of claim 1 , wherein R is selected from the group consisting of ethyl, n-propyl, n-butyl, and butenyl.
6. A method for producing a monosubstituted cyclopentadiene RCp, said method comprising:
forming a first solution according to the equation
RI+CpMgX→RCp+IMgX
wherein R comprises a C 1 to C 20 alkyl group, a C 3 to C 20 alkenyl group, or a C 7 to C 20 alkylaryl group, and X comprises a halide; said reaction taking place at a temperature ranging from about 20° C. to about 66° C.;
treating said first solution with a hydrocarbon diluent to form a second solution; and
isolating a mono-substituted cyclopentadiene as distillate from said hydrocarbon-diluted second solution.
7. The method of claim 6 , wherein said first solution ranges in temperature between about 30° C. and about 50° C.
8. The method of claim 6 , wherein said hydrocarbon diluent further comprises a high boiling hydrocarbon oil, essentially free of volatile components.
9. The method of claim 6 , wherein said hydrocarbon diluent further comprises a high boiling hydrotreated hydrocarbon oil, essentially free of olefinic components.
10. The method of claim 6 , wherein said first solution further comprises an ethereal solution of CpMgX.
11. The method of claim 10 , wherein said first solution further comprises tetrahydrofuran.
12. The method of claim 6 , wherein the halide X further comprises chloride.
13. The method of claim 6 , wherein R is selected from the group consisting of ethyl, n-propyl, n-butyl, and n-but-1-enyl.
14. The method of claim 6 further comprising a one-pot process.
15. A method for producing a mono-substituted reaction product of the formula
R
-
I
+
CpMgX
→
THF
R
-
Cp
+
IMgX
wherein R comprises a C 1 to C 20 alkyl group, a C 3 to C 20 alkenyl group, or a C 7 to C 20 alkylaryl group, and X comprises halogen, said method comprising the step of treating said mono-substituted reaction product with a hydrocarbon diluent and isolating a mono-substituted distillate diluted in said THF.
16. The method of claim 15 , wherein said diluent further comprises a high boiling hydrocarbon oil, essentially free of volatile components.
17. The method of claim 15 , wherein said reaction takes place at a temperature ranging from about 30° C. to about 50° C.
18. A one-pot process for synthesizing a monosubstituted cyclopentadiene in tetrahydrofuran, said process comprising:
treating cyclopentadienyl magnesium chloride in tetrahydrofuran with an alkyl iodide to form a reaction mixture comprising mono-substituted alkylcyclopentadiene; and
treating said reaction mixture with a diluent and isolating said mono-substituted cyclopentadiene in tetrahydrofuran.
19. The process of claim 18 , wherein said first treating step takes place at a temperature ranging from about 20° C. to about 66° C.