Synthesis of alkyl cyclopentadiene compounds

Patent metadata

Field	Value
Publication number	US-8975427-B2
Application number	US-201113635766-A
Country	US
Kind code	B2
Filing date	Apr 5, 2011
Priority date	Apr 28, 2010
Publication date	Mar 10, 2015
Grant date	Mar 10, 2015

Abstract

A method of synthesizing an alkyl cyclopentadiene compound is disclosed. The method includes contacting at least one cyclopentadienyl anion source and at least one alkyl group source to form at least one alkyl cyclopentadiene compound. The method further includes extracting the alkyl cyclopentadiene compound with a hydrocarbon solvent. The alkyl cyclopentadiene compound may be converted to a metallocene catalyst compound.

First claim

What is claimed is:

1. A method of synthesizing at least one alkyl cyclopentadiene compound, which includes alkyl cyclopentadiene and substituted alkyl derivatives thereof, comprising: contacting at least one cyclopentadienyl anion source which comprises at least one reagent selected from the group consisting of a cyclopentadienyl Grignard reagent, sodium cyclopentadienyl, lithium cyclopentadienyl, potassium cyclopentadienyl, and any combination thereof and at least one alkyl group source which comprises at least one reagent selected from the group consisting of an alkyl halide and an alkyl sulfonate, for 4 to 7 hours at the temperature of 50° C. to 65° C., to form at least one alkyl cyclopentadiene compound; and
extracting the alkyl cyclopentadiene compound with a hydrocarbon solvent wherein the mole ratio of the alkyl group source to the cyclopentadienyl anion source is in the range of from 0.5:1 to 0.9:1.

2. The method of claim 1 wherein the cyclopentadienyl anion source comprises a cyclopentadienyl Grignard reagent.

3. The method of claim 1 wherein the mole ratio of the alkyl group source to the cyclopentadienyl anion source is in the range of from 0.5:1 to 0.8:1.

4. The method of claim 1 wherein the mole ratio of the alkyl group source to the cyclopentadienyl anion source is 0.75:1.

5. The method of claim 1 wherein the alkyl cyclopentadiene compound comprises a C 3 to C 12 alkyl group.

6. The method of claim 1 wherein the alkyl cyclopentadiene compound comprises an alkyl group substituted with one or more heteroatoms or one or more heteroatom-containing groups.

7. The method of claim 1 wherein the alkyl cyclopentadiene compound comprises a substituted alkyl group, wherein the substituted alkyl group is formed by replacing one or more H atoms with an alkenyl radical, an alkynyl radical, a cycloalkyl radical, an aryl radical, an acyl radical, an aroyl radical, an alkoxy radical, an aryloxy radical, an alkythio radical, a dialkylamino radical, an alkoxycarbonyl radical, an arloxycarbonyl radical, a carbomoyl radical, an alkyl- or dialkyl-carbamoyl radical, an acyloxy radical, an acylamino radical, an aroylamino radical, a straight, branched or cyclic, alkylene radical, or any combination thereof.

8. The method of claim 1 wherein the alkyl cyclopentadiene compound comprises a compound selected from the group consisting of n-propylcyclopentadiene, n-butylcyclopentadiene, n-pentylcyclopentadiene, n-hexylcyclopentadiene, n-heptylcyclopentadiene, n-octylcyclopentadiene, n-nonylcyclopentadiene, n-decylcyclopentadiene, n-dodecyclopentadiene, 3-chloro-propylcyclopentadiene, 4-bromobutylcyclopentadiene, 3-phenoxypropylcyclopentadiene, 2-phenoxyethylcyclopentadiene, and any combination thereof.

9. The method of claim 1 wherein the extracting of the alkyl cyclopentadiene compound comprises adding the hydrocarbon solvent to a reaction mixture comprising the alkyl cyclopentadiene compound, filtering solids from the reaction mixture, and removing the hydrocarbon solvent from the reaction mixture.

10. The method of claim 9 comprising removing a solvent from the reaction mixture prior to the extracting of the alkyl cyclopentadiene compound.

11. The method of claim 9 comprising washing the filtered solids with the hydrocarbon solvent.

12. The method of claim 9 wherein the hydrocarbon solvent comprises pentane.

13. The method of claim 1 further comprising converting the alkyl cyclopentadiene compound to at least one metallocene catalyst compound.

14. The method of claim 13 wherein the conversion comprises:
reacting the alkyl cyclopentadiene compound with a base to form a cyclopentadiene anion; and
reacting the cyclopentadiene anion with a metal-containing compound to form the metallocene catalyst compound.

Assignees

• Harlan C Jeff
• Cao Xianyi
• Rix Francis C
• Univation Tech Llc

Inventors

• Harlan C Jeff
• Cao Xianyi
• Rix Francis C

Classifications

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• C07C17/32

  by introduction of halogenated alkyl groups into ring compounds · CPC title

• C07C2101/10

  Chemistry & Metallurgy · mapped topic

• C07C2/54 Primary

  by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring · CPC title

• C07F17/00

  Metallocenes · CPC title