Reaction #1382969

Reaction equation

di-(n-decyl)cyclopentadiene

1,10-decanediol

KOH

triglyme

→

Di-(n-decyl)cyclopentane

Conditions

Workup

1. 1
   OtherIn a one-liter three-necked flask fitted with a mechanical stirrer
2. 2
   Othertopped with a condenser
3. 3
   Otherdeoxygenated with a stream of nitrogen
4. 4
   TemperatureThe mixture was then heated
5. 5
   Temperatureto reflux under nitrogen for two hours
6. 6
   TemperatureThe mixture was cooled
7. 7
   Washwashed with water
8. 8
   Otherto remove base and triglyme
9. 9
   OtherThe product was dried
10. 10
    workup.ADDITIONcontaining a higher number of crosslinked di(n-decyl)cyclopentadienes
11. 11
    Otherwere formed
12. 12
    Otherat 100°

Procedure

In a one-liter three-necked flask fitted with a mechanical stirrer and a Soxhlet extractor packed with 3A molecular sieves (about 15 g) and topped with a condenser, 25.1 g of di-(n-decyl)cyclopentadiene (73 mmol), 12.6 g of 1,10-decanediol (73 mmol), 5 g of KOH, and 250 g of triglyme were stirred and deoxygenated with a stream of nitrogen. The mixture was then heated to reflux under nitrogen for two hours. The mixture was cooled and washed with water to remove base and triglyme. The product was dried and hydrogenated over palladium on carbon. The resulting product was characterized by gel permeation chromatography to determine the molecular weight. The number average molecular weight was 1250, indicating that on average about 3 di(n-decyl)cyclopentadienes had been crosslinked. The weight average molecular weight of 2250 indicates that molecules containing a higher number of crosslinked di(n-decyl)cyclopentadienes were formed. The measured viscosity at 100°, 40 cSt, is consistent with these high molecular weights.

Source