Skip to main content
SpringerLink
Log in

Palladium-Catalyzed Telomerization of Butadiene with Polyols: From Mono to Polysaccharides

  • Chapter
  • First Online:
Carbohydrates in Sustainable Development II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 295))

Abstract

The telomerization of butadiene with alcohols is an elegant way to synthesize ethers with minimal environmental impact since this reaction is 100% atom efficient. Besides telomerization of butadiene with methanol and water that is industrially developed, the modification of polyols is still under development. Recently, a series of new substrates has been involved in this reaction, including diols, pure or crude glycerol, protected or unprotected monosaccharides, as well as polysaccharides. This opens up the formation of new products having specific physicochemical properties. We will describe recent advances in this field, focusing on the reaction of renewable products and more specifically on saccharides. The efficient catalytic systems as well as the optimized reaction conditions will be described and some physicochemical properties of the products will be reported.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

CMC:

Critical micelle concentration

CTAB:

Cetyltrimethyl ammonium bromide

dba:

Dibenzylideneacetone

DMAc:

Dimethyacetamide

DMI:

Dimethyl isosorbide

DPPM:

Diphenylphosphine methane

DS:

Degree of substitution

HLB:

Hydrophilic lipophilic balance

IMes.HCl:

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride

MEK:

Methyl ethyl ketone

MIBK:

Methyl isobutyl ketone

PEG:

Poly ethylene glycol

POEA:

Polyethoxylated tallow amine

TOMPP:

Tris(2-methoxyphenyl)phosphine

TON:

Turnover number

TPPMS:

(m-Sulfonato-phenyl) diphenyl phosphine monosodium salt

TPPTS:

Tris(m-sulfonato-phenyl) phosphine trisodium salt

References

  1. Wurzburg OB (1984) Modified starches: properties and uses. CRC, Boca Raton

    Google Scholar 

  2. Boursier B (2005) Techniques de l'ingénieur F 4 690

    Google Scholar 

  3. Richardson S, Gorton L (2003) Anal Chim Acta 497:27

    Article  CAS  Google Scholar 

  4. Smutny EJ (1967) J Am Chem Soc 89:6793–6794

    Article  CAS  Google Scholar 

  5. Takahashi S, Shibano T, Hagihara N (1967) Tetrahedron Lett 8:2451–2455

    Article  Google Scholar 

  6. Behr A, Becker M, Beckmann T, Johnen L, Leschinski J, Reyer S (2009) Angew Chem Int Ed 48:3598–3614

    Article  CAS  Google Scholar 

  7. Palkovits R, Nieddu I (2008) Klein Gebbink RJM, Weckhuysen BM. ChemSusChem 1:193–196

    Article  CAS  Google Scholar 

  8. Palkovits R, Nieddu I, Kruithof CA, Klein Gebbink RJM, Weckhuysen BM (2008) Chem Eur J 14:8995–9005

    Article  CAS  Google Scholar 

  9. Behr A, Leschinski J, Awungacha C, Simic S, Knoth T (2009) ChemSusChem 2:71–76

    Article  CAS  Google Scholar 

  10. Grotevendt A, Jackstell R, Michalik D, Gomez M, Beller M (2009) ChemSusChem 2:63–70

    Article  CAS  Google Scholar 

  11. Gruber B, Weese K, Mueller HP, Hill K, Behr A, Tucker J, Hoagland S (1992) WO1991US0005214 Henkel Corporation Zucker Aktiengesellschaft Uelzen-Braunschweig

    Google Scholar 

  12. Behr A, Urschey M (2003) J Mol Catal A 197:101–113

    Article  CAS  Google Scholar 

  13. Jackstell R, Grotevendt A, Andreu MG, Beller M (2009) Org Process Res Dev 13:349–353

    Article  CAS  Google Scholar 

  14. Palkovits R, Parvulescu AN, Hausoul PJC, Kruithof CA, Klein Gebbink RJM, Weckhuysen BM (2009) Green Chem 11:1155–1160

    Article  CAS  Google Scholar 

  15. Gordillo A, Pachón LD, de Jesus E, Rothenberg G (2009) Adv Synt Catal 351:325–330

    Article  CAS  Google Scholar 

  16. Behr A, Urschey M (2003) Adv Synt Catal 345:1242–1246

    Article  CAS  Google Scholar 

  17. Behr A, Urschey M, Brehme VA (2003) Green Chem 5:198–204

    Article  CAS  Google Scholar 

  18. Pennequin I (1993) Thèse Université des Sciences et Technologies de Lille, n° 1117

    Google Scholar 

  19. Pennequin I, Mortreux A, Petit F, Mentech J, Thiriet B (1994) FR2693188 (Eridania Beghin-Say)

    Google Scholar 

  20. Valerio C, Pinel C. Unpublished results

    Google Scholar 

  21. Hénin F, Bessmertnykh A, Serra-Muns A, Muzart J, Baillia H (2004) Eur J Org Chem 511–520

    Google Scholar 

  22. Bessmertnykh A, Hénin F, Serra-Muns A, Muzart J, Baillia H (2006) Carbohydr Res 341:153–159

    Article  CAS  Google Scholar 

  23. Vollmüller F, Krause J, Klein S, Mägerlein W, Beller M (2000) Eur J Org Chem 1825–1832

    Google Scholar 

  24. Benvenuti F, Carlini C, Lami M, Marchionna M, Patrini R, Galletti AMR, Sbrana G (1999) J Mol Catal A 144:27–40

    Article  CAS  Google Scholar 

  25. Bessmertnykh A, Hénin F, Muzart J (2004) Carbohydr Res 339:1377–1380

    Article  CAS  Google Scholar 

  26. Bertho JN, Mathaly P, Dubois V, Baynast RD (1997) PCT Int Appl WO 9729115 (ARD)

    Google Scholar 

  27. Bertho JN, Mathaly P, Dubois V, Baynast RD (1999) Eur Pat EP 995805 (ARD)

    Google Scholar 

  28. Muzart J, Hénin F, Estrine B, Bouquillon S (2001) Fr patent 0116363

    Google Scholar 

  29. Estrine B, Bouquillon S, Hénin F, Muzart J (2004) Eur J Org Chem 2914–2922

    Google Scholar 

  30. Bessmertnykh A, Hénin F, Muzart J (2005) J Mol Catal A 238:199–206

    Article  CAS  Google Scholar 

  31. Damez C, Estrine B, Bessmertnykh A, Bouquillon S, Hénin F, Muzart J (2006) J Mol Catal A 244:93–98

    Article  CAS  Google Scholar 

  32. Estrine B, Bouquillon S, Hénin F, Muzart J (2007) Appl Organomet Chem 21:945

    Article  CAS  Google Scholar 

  33. Ferroud D, Genêt JP, Muzart J (1984) Tetrahedron Lett 25:4379–4382

    Article  CAS  Google Scholar 

  34. Muzart J, Genêt JP, Denis A (1987) J Organomet Chem 326:C23–C25

    Article  CAS  Google Scholar 

  35. Goux C, Lhoste P, Sinou D, Muzart J (1994) Sulfur Lett 18:1

    CAS  Google Scholar 

  36. Roy O, Riahi A, Hénin F, Muzart J (2000) Tetrahedron 56:8133

    Article  CAS  Google Scholar 

  37. Estrine B, Soler R, Damez C, Bouquillon S, Hénin F, Muzart J (2003) Green Chem 5:686–689

    Article  CAS  Google Scholar 

  38. Hausoul PJC, Bruijnincx PCA, Klein Gebbink RJM, Weckhuysen BM (2009) ChemSusChem 2:855–858

    Article  CAS  Google Scholar 

  39. Hill K, Gruber B, Weese KJ (1994) Tetrahedron Lett 35:4541–4544

    Article  CAS  Google Scholar 

  40. Estrine B, Bouquillon S, Hénin F, Muzart J (2005) Green Chem 7:219–223

    Article  CAS  Google Scholar 

  41. Grushin VV, Alper H (1993) Organometallics 12:1890–1901

    Article  CAS  Google Scholar 

  42. Muzart J (2003) Tetrahedron 59:5789–5816

    Article  CAS  Google Scholar 

  43. Amatore C, Blart E, Genet JP, Jutand A, Lemaire-Audoire S, Savignac M (1995) J Org Chem 60:6829–6839

    Article  CAS  Google Scholar 

  44. Hegedus LS (1988) Angew Chem Int Ed 27:1113–1126

    Article  Google Scholar 

  45. Trzeciak AM, Ciunik Z, Ziółkowski JJ (2002) Organometallics 21:132–137

    Article  CAS  Google Scholar 

  46. Muzart J (2009) J Mol Cat A 308:132–137

    Article  Google Scholar 

  47. Prinz T, Driessen-Hölscher B (1999) Chem Eur J 5:2069–2076

    Article  CAS  Google Scholar 

  48. Prinz T, Keim W, Driessen-Hölscher B (1996) Angew Chem Int Ed 35:1708–1710

    Article  CAS  Google Scholar 

  49. Pennequin I, Meyer J, Suisse I, Mortreux A (1997) J Mol Catal A 120:139–142

    Article  CAS  Google Scholar 

  50. Desvergnes-Breuil V, Pinel C, Gallezot P (2001) Green Chem 3:175–177

    Article  CAS  Google Scholar 

  51. Kshirsagar AC, Singhal RS (2007) Carbohydr Polym 69:455

    Article  CAS  Google Scholar 

  52. Donzé C, Pinel C, Gallezot P, Taylor PL (2002) Adv Synth Catal 344:906–910

    Article  Google Scholar 

  53. Mesnager J, Quettier C, Lambin A, Rataboul F, Pinel C (2009) ChemSusChem 2:1125–1129

    Google Scholar 

  54. Mesnager J, Kuntz E, Pinel C (2009) J Organomet Chem 694:2513–2518

    Article  CAS  Google Scholar 

  55. Mesnager J (2008) Développement d’amidon hydrophobe par télomérisation du butadiène en milieu aqueux. Etudes et applications catalytiques de complexes de palladium, Université Lyon n°215-2008

    Google Scholar 

  56. Monflier E, Bourdauducq P, Couturier JL, Kervennal J, Mortreux A (1995) Appl Catal A 131:167–178

    Article  CAS  Google Scholar 

  57. Monflier E, Bourdauducq P, Couturier JL, Kervennal J, Mortreux A (1995) J Mol Catal A 97:29–33

    Article  CAS  Google Scholar 

  58. Monflier E, Bourdauducq P, Couturier JL, Kervennal J, Suisse I, Mortreux A (1995) Catal Lett 34:201–212

    Article  CAS  Google Scholar 

  59. Pinel C, Donze C, Gallezot P (2003) Catal Commun 4:465–468

    Article  CAS  Google Scholar 

  60. Tsuji J, Kobayashi Y, Takahashi T (1980) Tetrahedron Lett 21:483–486

    Article  CAS  Google Scholar 

  61. Tsuji J, Shimizu I, Suzuki H, Naito Y (1979) J Am Chem Soc 101:5070–5072

    Article  CAS  Google Scholar 

  62. Tsuji J, Yasuda H, Mandai T (1978) J Org Chem 43:3606–3607

    Article  CAS  Google Scholar 

  63. Rodriguez A, Normen M, Spur BW, Godfroid JJ, Lee TH (2000) Eur J Org Chem 2991–3000

    Google Scholar 

  64. Yoshimura N (2004) Hydrodimerization. In: Cornils B, Hermann WA (eds) Aqueous-phase organometallic chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  65. Benvenuti F, Carlini C, Raspolli Galletti AM, Sbrana G, Marchionna M, Patrini R (1999) J Mol Catal A 137:49–55

    Article  CAS  Google Scholar 

  66. von Rybinski W, Hill K (1998) Angew Chem Int Ed 37:1328–1345

    Article  Google Scholar 

  67. Falbe J, Bahrmann H, Lipps W, Mayer D (1985) In: Gerhartz W, Yamamoto YS, Campbell FT, Pfefferkorn R, Rounsaville JF (eds) Ullmann’s encyclopedia of industrial chemistry, vol A1. VCH, Weinheim

    Google Scholar 

  68. Urata K, Takaishi N (1996) J Am Oil Chem Soc 73:819–830

    Article  CAS  Google Scholar 

  69. Müller R, Gruber B, Wangmann F, Seidel K, Hollenberg D (1993), Ger Offen DE 4203490 (Henkel KGAA)

    Google Scholar 

  70. Gruber B, Fabry B, Giesen B, Müller R, Wangmann F (1993) Tenside Surfact Det 30:422–426

    CAS  Google Scholar 

  71. Meixner J, Pedain J, Büchel KH, Träckner HJ (1993) EP 522400

    Google Scholar 

  72. Hadad C, Damez C, Bouquillon S, Estrine B, Hénin F, Muzart J, Pezron I, Komunjer L (2006) Carbohydr Res 341:1938–1944

    Article  CAS  Google Scholar 

  73. Hill K (1993) Hydrophobic alkyl glucosides: synthetic methods and properties. In: Descotes G (ed) Carbohydrates as organic raw materials II. VCH, Weinheim

    Google Scholar 

  74. Zhou J, Ren L, Tong J, Ma Y (2009) J Appl Polym Sci 114:940–948

    Article  CAS  Google Scholar 

  75. Chi H, Xu K, Wu X, Chen Q, Xue D, Song C, Zhang W, Wang P (2007) Food Chem 106:923–928

    Article  Google Scholar 

  76. Chi H, Xu K, Xue D, Song C, Zhang W, Wang P (2007) Food Res Int 40:232–238

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut de Chimie Moléculaire de Reims, UMR 6229/CNRS – Université de Reims Champagne-Ardenne, 1039, 51687, Reims Cedex 2, France

    Sandrine Bouquillon & Jacques Muzart

  2. Université de Lyon, 69622, Lyon, France

    Catherine Pinel & Franck Rataboul

  3. Institut de Recherches sur la Catalyse et l’Environnement de Lyon, Université Lyon 1 CNRS, UMR 5256, 2 Avenue Albert Einstein, 69626, Villeurbanne, France

    Catherine Pinel & Franck Rataboul

Authors
  1. Sandrine Bouquillon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jacques Muzart
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Catherine Pinel
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Franck Rataboul
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Catherine Pinel .

Editor information

Editors and Affiliations

  1. Fac. Ciências, Depto. Química e Bioquímica, Universidade de Lisboa, Campo Grande, Lisboa, 1749-016, Portugal

    Amélia P. Rauter

  2. , EPFL ICMB LGSA, Swiss Federal Inst. of Technology, Bat BCH, Lausanne, 1015, Switzerland

    Pierre Vogel

  3. Labo. Chimie Organique (LCO), INSA Lyon, av. Albert Einstein 20, Villeurbanne CX, 69621, France

    Yves Queneau

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer

About this chapter

Cite this chapter

Bouquillon, S., Muzart, J., Pinel, C., Rataboul, F. (2010). Palladium-Catalyzed Telomerization of Butadiene with Polyols: From Mono to Polysaccharides. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development II. Topics in Current Chemistry, vol 295. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_53

Download citation

Publish with us

Policies and ethics

Search

Navigation