Cyclopentadiene: The impact of storage conditions on thermal stability

Organic Process Research and Development

Volumn 11, Issue 6, 2007, Pages 1141-1146

  Amende, David J ^a   Whritenour, David C ^a   Coe, Jotham W ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049021979     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op6002727     Document Type: Article

References (16)

1. (a) Varenicline tartrate (Chantix in the US, Champix elsewhere; Pfizer, Inc.).
2. (b) Coe, J. W.; Brooks, P. R.; Vetelino, M. G.; Wirtz, M. C.; Arnold, E. P.; Sands, S. B.; Davis, T. I.; Lebel, L. A.; Fox, C. B.; Shrikhande, A.; Schaeffer, E.; Rollema, H.; Lu, Y.; Mansbach, R. S.; Chambers, L. K.; Rovetti, C. C.; Schulz, D. W.; Tingley, F. D., III; O'Neill, B. T. J. Med. Chem. 2005, 48, 3474-3477.
3. (c) Coe, J. W.; Wirtz, M. C.; Bashore, C. G.; Candler, J. Org. Lett 2004, 6, 1589-1592.
4. (d) Brooks, P. R.; Caron, S.; Coe, J. W.; Ng, K. K.; Singer, R. A.; Vazquez, E.; Vetelino, M. G.; Watson, H. H., Jr.; Whritenour, D. C.; Wirtz, M. C. Synthesis 2004, 11, 1755-1758.
5. Moffett, R. B. Org. Synth. 1963, IV, 238-243.
6. Cheung, P. Cyclopentadiene and dicylopentadiene. In Kirk-Othmer Encyclopedia of Chemical Technology, 5th ed.; John Wiley & Sons: New York, 2001; Vol. 8, pp 219-235.
7. Bretherick's Handbook of Reactive Chemical Hazards, 6th ed.; Butterworth-Heinemann: Oxford, 1999.
8. Starkie, A.; Rowe, S. Chem. Br. 1996, Feb, 34-38.
9. The specific thermocouple calibration used during the VSP experiment does not accurately track temperature below 24 °C in this case, so only temperatures above 24 °C were recorded.
10. Heat of dimerization = MW × Phi × cp × ΔT MW = (66.1 g/mol)(1.16)(1.8 J/gC)(260 °C)KJ/1000J = 35.9 kJ/mol assuming an initial temperature of -20 °C where ΔT = 260 °C or 30 kJ/mol assuming an initial temperature of 20 °C.
11. Wilson, P. J.; Wells, J. H. Chem. Rev. 1944, (34), 1-50.
12. Other solvents have not been evaluated.
13. Janna, W. S. Engineering Heat Transfer, PWS Publishers: Boston, 1986.
14. Ferguson, H. D. J. Hazard. Maler. 1994, 37, 285-302.
15. The heat generation rate was corrected for the Phi Factor of the test cell. The Phi Factor was 1.16.
16. Boudart, M. Kinetics of Chemical Processes; Butterworth-Heinemann: Woburn, MA, 1991.