Skip to main content
SpringerLink
Log in

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

  • Living reference work entry
  • First Online:
Encyclopedia of Sustainability Science and Technology

Glossary

Amphiphiles:

Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups.

Bio-based chemicals:

Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, and terpenes.

Carbohydrates:

Carbohydrates are a family of biomolecules, are ubiquitous in nature, and are based on a common polyhydroxylated backbone. They vary in size (from small molecules to macromolecules) and in fine structure (configuration and functionalization) they possess a wide range of biological properties and roles, making them indispensable to life.

Surfactants:

Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension.

Definition of the Subject

Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life and must therefore be...

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

Access this chapter

Log in via an institution

Institutional subscriptions

References

  1. Rosen MJ, Kunjappu JT (2012) Surfactants and interfacial phenomena. Wiley, Hoboken

    Book  Google Scholar 

  2. Zoller U (2008) Handbook of detergents, part E: applications. Taylor & Francis, California

    Book  Google Scholar 

  3. Surfactants Market by Type (Anionic, Non-Ionic, Cationic, and Amphoteric), Substrate (Synthetic, and Bio-based), Application (Detergents, Personal Care, Textile, Elastomers & Plastics, Crop Protection, Food & Beverage) – Global Forecast to 2021 MarketsandMarkets.com; oct 2016, 170 pages

  4. Kjellin M, Johansson I (eds) (2010) Surfactants from renewable resources. Wiley, Stockholm

    Google Scholar 

  5. Holmberg K (2001) Natural surfactants. Curr Opin Colloid Interface Sci 6:148–159

    Article  CAS  Google Scholar 

  6. Hubbard A (2004) Novel surfactants: preparation, applications, and biodegradability. Marcel Dekker, New York

    Google Scholar 

  7. Jessop PG, Ahmadpour F, Buczynski MA, Burns TJ, Green NB II, Korwin R, Long D, Massad SK, Manley JB, Omidbakhsh N, Pearl R, Pereira S, Predale RA, Sliva PG, Van der Bilt H, Weller S, Wolf MH (2015) Opportunities for greener alternatives in chemical formulations. Green Chem 17:2664–2678

    Article  CAS  Google Scholar 

  8. Foley P, Kermanshahi-pour A, Beach ES, Zimmerman JB (2012) Derivation and synthesis of renewable surfactants. Chem Soc Rev 41:1499–1518

    Article  CAS  Google Scholar 

  9. Razafindralambo H, Blecker C, Paquot M (2012) Carbohydrate-based surfactants: structure-activity relationships. In: Advances in chemical engineering. InTech, Rijeka

    Google Scholar 

  10. Almeida MVD, Hyaric ML (2005) Carbohydrate-derived surfactants. Mini-Rev Org Chem 2:283–297

    Article  Google Scholar 

  11. Nakamura S (1999) Application of sucrose fatty acid esters as food emulsifiers. In: Karsa DR (ed) Industrial applications of surfactants IV, 1st edn. The Royal Society of Chemistry, Manchester, pp 73–87

    Chapter  Google Scholar 

  12. Hayes DG, Kitamoto D, Solaiman D, Ashby R (eds) (2009) Biobased surfactants and detergents: synthesis, properties, and applications. AOCS Press, Urbana

    Google Scholar 

  13. Pöhnlein M, Hausmann R, Lang S, Syldatk C (2015) Enzymatic synthesis and modification of surface-active glycolipids. Eur J Lipid Sci Technol 117:145–155

    Article  CAS  Google Scholar 

  14. Bogaert INAV, Saerens K, Muynck CD, Develter D, Soetaert W, Vandamme EJ (2007) Microbial production and application of sophorolipids. Appl Microbiol Biotechnol 76:23–34

    Article  CAS  Google Scholar 

  15. Besson M, Gallezot P, Pinel C (2014) Conversion of biomass into chemicals over metal catalysts. Chem Rev 114:1827–1870

    Article  CAS  Google Scholar 

  16. Bödiger M, Demharter S, Mülhaupt R (2007) Carbohydrates as organic raw materials III. Wiley-VCH, New York

    Google Scholar 

  17. Corma A, Iborra S, Velty A (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411–2502

    Article  CAS  Google Scholar 

  18. Queneau Y, Jarosz S, Lewandowski B, Fitremann J (2007) Sucrose chemistry and applications of sucrochemicals. In: Horton D (ed) Advances in carbohydrate chemistry and biochemistry. Elsevier, London, pp 217–292

    Google Scholar 

  19. Rauter AP, Vogel P, Queneau Y (eds) (2010) Carbohydrates in sustainable development I. Springer, Heidelberg

    Google Scholar 

  20. Rauter AP, Vogel P, Queneau Y (eds) (2010) Carbohydrates in sustainable development II. Springer, Heidelberg

    Google Scholar 

  21. Sheldon RA (2014) Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem 16:950–963

    Article  CAS  Google Scholar 

  22. Chatterjee C, Pong F, Sen A (2014) Chemical conversion pathways for carbohydrates. Green Chem 17:40–71

    Article  CAS  Google Scholar 

  23. Queneau Y, Fitremann J, Trombotto S (2004) The chemistry of unprotected sucrose: the selectivity issue. C R Chim 7:177–188

    Article  CAS  Google Scholar 

  24. Molinier V, Fenet B, Fitremann J, Bouchu A, Queneau Y (2005) PFGSE–NMR study of the self-diffusion of sucrose fatty acid monoesters in water. J Colloid Interface Sci 286:360–368

    Article  CAS  Google Scholar 

  25. Queneau Y, Chambert S, Besset C, Cheaib R (2008) Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose. Carbohydr Res 343:1999–2009

    Article  CAS  Google Scholar 

  26. Bethell D, Galsworthy PJ, Jones K (1988) Mutarotation of glucose derivatives in solutions of surfactants in organic solvents: co-operativity and bimodal catalytic behaviour. J Chem Soc Perkin Trans 2:2035–2043

    Article  Google Scholar 

  27. Thévenet S, Descotes G, Bouchu A, Queneau Y (1997) Hydrophobic effect driven esterification of sucrose in aqueous medium. J Carbohydr Chem 16:691–696

    Article  Google Scholar 

  28. Fitremann J, Queneau Y, Maître J-P, Bouchu A (2007) Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Lett 48:4111–4114

    Article  CAS  Google Scholar 

  29. Le Coënt A-L, Tayakout-Fayolle M, Couenne F, Briançon S, Lieto J, Fitremann-Gagnaire J, Queneau Y, Bouchu A (2003) Kinetic parameter estimation and modelling of sucrose esters synthesis without solvent. Chem Eng Sci 58:367–376

    Article  Google Scholar 

  30. Pierre R, Adam I, Fitremann J, Jérôme F, Bouchu A, Courtois G, Barrault J, Queneau Y (2004) Catalytic etherification of sucrose with 1,2-epoxydodecane: investigation of homogeneous and heterogeneous catalysts. C R Chim 7:151–160

    Article  CAS  Google Scholar 

  31. Villandier N, Adam I, Jérôme F, Barrault J, Pierre R, Bouchu A, Fitremann J, Queneau Y (2006) Selective synthesis of amphiphilic hydroxyalkylethers of disaccharides over solid basic catalysts: influence of the superficial hydrophilic–lipophilic balance of the catalyst. J Mol Catal A Chem 259:67–77

    Article  CAS  Google Scholar 

  32. Peyrot C, Lafite P, Lemiègre L, Daniellou R (2017) Low molecular weight carbohydrate-based hydrogelators. In: Rauter AP, Lindhorst TK, Queneau Y (eds) Carbohydrate chemistry-chemical and biological approaches, vol 43. The Royal Society of Chemistry, Cambridge, pp 245–265

    Chapter  Google Scholar 

  33. Renault L, Pessel F, Benvegnu T (2017) Surfactants based on green/blue sugars: towards new functionalities in formulations. In: Rauter AP, Lindhorst TK, Queneau Y (eds) Carbohydrate chemistry-chemical and biological approaches, vol 43. The Royal Society of Chemistry, Cambridge, pp 196–244

    Chapter  Google Scholar 

  34. Fischer E (1893) Ueber die Glucoside der Alkohole. Ber Dtsch Chem Ges 26:2400–2412

    Article  Google Scholar 

  35. Klotz W, Schmidt RR (1993) Anomeric O-alkylation, 11. Anomeric O-alkylation of O-unprotected hexoses and pentoses – convenient synthesis of decyl, benzyl, and allyl glycosides. Liebigs Ann Chem 1993:683–690

    Article  Google Scholar 

  36. El-Nokaly MA, El-Taraboulsy MA (1980) Preparation of O-dodecyl sucrose surfactant. J Dispers Sci Technol 1:373–392

    Article  CAS  Google Scholar 

  37. Bessmertnykh A, Hénin F, Muzart J (2005) Palladium-catalysed telomerization of butadiene with aldoses: a convenient route to non-ionic surfactants based on controlled reactions. J Mol Catal A Chem 238:199–206

    Article  CAS  Google Scholar 

  38. Damez C, Estrine B, Bessmertnykh A, Bouquillon S, Hénin F, Muzart J (2006) Effects of the reactants concentration in the butadiene telomerization with D-xylose and parallel influence of triethylamine as additive. J Mol Catal A Chem 244:93–98

    Article  CAS  Google Scholar 

  39. Hadad C, Damez C, Bouquillon S, Estrine B, Hénin F, Muzart J, Pezron I, Komunjer L (2006) Neutral pentosides surfactants issued from the butadiene telomerization with pentoses: preparation and amphiphilic properties. Carbohydr Res 341:1938–1944

    Article  CAS  Google Scholar 

  40. Estrine B, Bouquillon S, Hénin F, Muzart J (2004) Telomerization of butadiene with L-Arabinose and D-Xylose in DMF: selective formation of their monooctadienyl glycosides. Eur J Org Chem 2004:2914–2922

    Article  CAS  Google Scholar 

  41. Estrine B, Bouquillon S, Henin F, Muzart J (2005) Telomerization of butadiene with pentoses in water: selective etherifications. Green Chem 7:219–223

    Article  CAS  Google Scholar 

  42. Bouquillon S (2011) D-Xylose and L-Arabinose-based surfactants: synthesis, reactivity and physico-chemical properties. C R Chim 14:716–725

    Article  CAS  Google Scholar 

  43. Hausoul PJC, Bruijnincx PCA, Klein Gebbink RJM, Weckhuysen BM (2009) Base-free Pd/TOMPP-catalyzed telomerization of 1,3-butadiene with carbohydrates and sugar alcohols. ChemSusChem 2:855–858

    Article  CAS  Google Scholar 

  44. Toshima K, Tatsuta K (1993) Recent progress in O-glycosylation methods and its application to natural products synthesis. Chem Rev 93:1503–1531

    Article  CAS  Google Scholar 

  45. Schmidt RR, Michel J (1980) Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharides. Angew Chem Int Ed Engl 19:731–732

    Article  Google Scholar 

  46. Pougny J-R, Sinaÿ P (1976) Reaction d’imidates de glucopyranosyle avec l’acetonitrile. Applications synthetiques. Tetrahedron Lett 17:4073–4076

    Article  Google Scholar 

  47. von Rybinski W, Hill K (1998) Alkyl polyglycosides—properties and applications of a new class of surfactants. Angew Chem Int Ed 37:1328–1345

    Article  Google Scholar 

  48. Nickel D, Förster T, Rybinski W (2008) Alkyl polyglycosides: technology, properties and applications. Wiley-VCH, Weinheim

    Google Scholar 

  49. Guilbot J, Kerverdo S, Milius A, Escola R, Pomrehn F (2013) Life cycle assessment of surfactants: the case of an alkyl polyglucoside used as a self emulsifier in cosmetics. Green Chem 15:3337–3354

    Article  CAS  Google Scholar 

  50. Hill K (2005) Industrial development and application of biobased oleochemicals. In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries-industrial processes and products. Wiley-VCH Verlag GmbH, Potsdam, pp 291–314

    Chapter  Google Scholar 

  51. Geetha D, Tyagi R (2012) Alkyl Poly Glucosides (APGs) surfactants and their properties: a review. TSD 49:417–427

    Article  CAS  Google Scholar 

  52. Bertsch H, Rauchalles G, Akiengesellschaft B (1936) Verwendung von hochmolekularen synthetischen Glucosiden als Saponinersatz, als Emulgierungs-, Reinigungs- und Netzmittel. German Patent DE593422C

    Google Scholar 

  53. Fischer E, Helferich B (1911) Über neue synthetische glucoside. Justus Liebigs Ann Chem 383:68–91

    Article  CAS  Google Scholar 

  54. Cui J, Zheng J, Qiao W, Wan X (2008) Solvent-tuned multiple self-assembly of a new sugar-appended gelator. J Colloid Interface Sci 326:267–274

    Article  CAS  Google Scholar 

  55. Bao C, Lu R, Jin M, Xue P, Tan C, Zhao Y, Liu G (2004) Synthesis, self-assembly and characterization of a new glucoside-type hydrogel having a Schiff base on the aglycon. Carbohydr Res 339:1311–1316

    Article  CAS  Google Scholar 

  56. Jung JH, John G, Masuda M, Yoshida K, Shinkai S, Shimizu T (2001) Self-assembly of a sugar-based gelator in water: its remarkable diversity in gelation ability and aggregate structure. Langmuir 17:7229–7232

    Article  CAS  Google Scholar 

  57. Jung JH, Rim JA, Han WS, Lee SJ, Lee YJ, Cho EJ, Kim JS, Ji Q, Shimizu T (2006) Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group. Org Biomol Chem 4:2033–2038

    Article  CAS  Google Scholar 

  58. Maldonado OS, Lucas R, Comelles F, Jesús González M, Parra JL, Medina I, Morales JC (2011) Synthesis and characterization of phenolic antioxidants with surfactant properties: glucosyl- and glucuronosyl alkyl gallates. Tetrahedron 67:7268–7279

    Article  CAS  Google Scholar 

  59. Es DSV, Marinkovic S, Oduber X, Estrine B (2013) Use of furandicarboxylic acid and its decyl ester as additives in the fischer’s glycosylation of decanol by D-glucose: physicochemical properties of the surfactant compositions obtained. J Surfact Deterg 16:147–154

    Article  CAS  Google Scholar 

  60. Bergfeld DMJ, Seifert DJ (1994) Method for the continuous production of alkylglycosides. European Patent EP0617045A2

    Google Scholar 

  61. Oberholz DA, Kahsnitz DJ, Schmidt DS (1995) Process for manufacturing alkyl glycosides and alkyl oligoglycosides. European Patent EP0482325B1

    Google Scholar 

  62. Eskuchen R, Nitsche M (2008) Technology and production of alkyl polyglycosides in: alkyl polyglycosides: technology, properties and applications. Wiley-VCH, Weinheim

    Google Scholar 

  63. Roussel M, Benvegnu T, Lognoné V, Le Deit H, Soutrel I, Laurent I, Plusquellec D (2005) Synthesis and physico-chemical properties of novel biocompatible Alkyl-d-Mannopyranosiduronate surfactants derived from alginate. Eur J Org Chem 3085–3094

    Article  CAS  Google Scholar 

  64. Castro MJL, Kovensky J, Fernández Cirelli A (2002) New family of nonionic gemini surfactants. Determination and analysis of interfacial properties. Langmuir 18:2477–2482

    Article  CAS  Google Scholar 

  65. Liu S, Sang R, Hong S, Cai Y, Wang H (2013) A novel type of highly effective nonionic gemini alkyl O-glucoside surfactants: a versatile strategy of design. Langmuir 29:8511–8516

    Article  CAS  Google Scholar 

  66. Sari-Chmayssem N, Pessel F, Guégan JP, Taha S, Mawlawi H, Benvegnu T (2016) Direct and one-pot conversion of polyguluronates and alginates into alkyl-L-guluronamide-based surfactant compositions. Green Chem 18:6573–6585

    Article  CAS  Google Scholar 

  67. Villandier N, Corma A (2011) Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes. ChemSusChem 4:508–513

    Article  CAS  Google Scholar 

  68. Villandier N, Corma A (2010) One pot catalytic conversion of cellulose into biodegradable surfactants. Chem Commun 46:4408–4410

    Article  CAS  Google Scholar 

  69. Climent MJ, Corma A, Iborra S, Martínez-Silvestre S (2016) Transformation of cellulose into nonionic surfactants using a one-pot catalytic process. ChemSusChem 9:3492–3502

    Article  CAS  Google Scholar 

  70. Deng W, Liu M, Zhang Q, Tan X, Wang Y (2010) Acid-catalysed direct transformation of cellulose into methyl glucosides in methanol at moderate temperatures. Chem Commun 46:2668–2670

    Article  CAS  Google Scholar 

  71. Karam A, De Oliveira Vigier K, Marinkovic S, Estrine B, Oldani C, Jérôme F (2017) Conversion of cellulose into amphiphilic alkyl glycosides catalyzed by aquivion, a perfluorosulfonic acid polymer. ChemSusChem 10:3604–3610

    Article  CAS  Google Scholar 

  72. Zou M, Chen J, Wang Y, Li M, Zhang C, Yang X (2016) Alcoholysis of starch to produce alkyl polyglycosides with sub-critical isooctyl alcohol. J Surfact Deterg 19:879–884

    Article  CAS  Google Scholar 

  73. Marinkovic S, Bras JL, Nardello-Rataj V, Agach M, Estrine B (2011) Acidic pretreatment of wheat straw in decanol for the production of surfactant, lignin and glucose. Int J Mol Sci 13:348–357

    Article  CAS  Google Scholar 

  74. Sekine M, Kimura T, Katayama Y, Takahashi D, Toshima K (2013) The direct and one-pot transformation of xylan into the biodegradable surfactants, alkyl xylosides, is aided by an ionic liquid. RSC Adv 3:19756–19759

    Article  CAS  Google Scholar 

  75. Turner P, Svensson D, Adlercreutz P, Karlsson EN (2007) A novel variant of thermotoga neapolitana β-glucosidase B is an efficient catalyst for the synthesis of alkyl glucosides by transglycosylation. J Biotechnol 130:67–74

    Article  CAS  Google Scholar 

  76. Agach M, Moity L, Renault B, Marinkovic S, Estrine B, Nardello-Rataj V (2014) Succinylation of non-ionic surfactants: physicochemical characterization, functional properties, biodegradability and mathematical modeling of the polarity tuning. J Surfact Deterg 17:591–602

    Article  CAS  Google Scholar 

  77. Drouet P, Zhang M, Legoy MD (1994) Enzymatic synthesis of alkyl β-D-xylosides by transxylosylation and reverse hydrolysis. Biotechnol Bioeng 43:1075–1080

    Article  CAS  Google Scholar 

  78. Vic G, Thomas D, Crout DHG (1997) Solvent effect on enzyme-catalyzed synthesis of β-D-glucosides using the reverse hydrolysis method: application to the preparative-scale synthesis of 2-hydroxybenzyl and octyl β-D-glucopyranosides. Enzym Microb Technol 20:597–603

    Article  CAS  Google Scholar 

  79. Ochs M, Muzard M, Plantier-Royon R, Estrine B, Remond C (2011) Enzymatic synthesis of alkyl β-D-xylosides and oligoxylosides from xylans and from hydrothermally pretreated wheat bran. Green Chem 13:2380–2388

    Article  CAS  Google Scholar 

  80. Rather MY, Mishra S (2013) β-Glycosidases: an alternative enzyme based method for synthesis of alkyl-glycosides. Sustain Chem Process 1:7

    Article  CAS  Google Scholar 

  81. Papanikolaou S (2001) Enzyme-catalyzed synthesis of alkyl-β-glucosides in a water–alcohol two-phase system. Bioresour Technol 77:157–161

    Article  CAS  Google Scholar 

  82. Montiel C, Bustos-Jaimes I, Bárzana E (2013) Enzyme-catalyzed synthesis of heptyl-β-glycosides: effect of water coalescence at high temperature. Bioresour Technol 144:135–140

    Article  CAS  Google Scholar 

  83. Younis Rather M, Mishra S, Verma V, Chand S (2012) Biotransformation of methyl-β-D-glucopyranoside to higher chain alkyl glucosides by cell bound β-glucosidase of Pichia etchellsii. Bioresour Technol 107:287–294

    Article  CAS  Google Scholar 

  84. Bousquet M-P, Willemot R-M, Monsan P, Boures E (1998) Production, purification, and characterization of thermostable α-transglucosidase from Talaromyces duponti–application to α–alkylglucoside synthesis. Enzym Microb Technol 23:83–90

    Article  CAS  Google Scholar 

  85. Dahiya S, Ojha S, Mishra S (2015) Biotransformation of sucrose into hexyl-α-D-glucopyranoside and -polyglucosides by whole cells of Microbacterium paraoxydans. Biotechnol Lett 37:1431–1437

    Article  CAS  Google Scholar 

  86. Richard G, Morel S, Willemot R-M, Monsan P, Remaud-Simeon M (2003) Glucosylation of α-butyl- and α-octyl-D-glucopyranosides by dextransucrase and alternansucrase from Leuconostoc mesenteroides. Carbohydr Res 338:855–864

    Article  CAS  Google Scholar 

  87. Jin Z, Zhang J, Yang X, Zhou Y (2016) Synthesis of alkyl monoglucoside citric monoester and properties of its sodium salt. J Surfact Deterg 19:885–891

    Article  CAS  Google Scholar 

  88. Lin L-H, Lai Y-C, Chen K-M, Chang H-M (2015) Oxyethylene chain length affects the physicochemical properties of sugar-based anionic surfactants with phosphates groups. Colloids Surf A Physicochem Eng Asp 485:118–124

    Article  CAS  Google Scholar 

  89. Perusse D, Guegan JP, Rolland H, Guilbot J, Benvegnu T (2016) Efficient solvent-free cationization of alkylpolyglycoside based surfactant compositions using natural glycine betaine. Green Chem 18:1664–1673

    Article  CAS  Google Scholar 

  90. Tabor RF, Tan DD, Han SS, Young SA, Seeger ZLE, Pottage MJ, Garvey CJ, Wilkinson BL (2014) Reversible pH- and photocontrollable carbohydrate-based surfactants. Chem Eur J 20:13881–13884

    Article  CAS  Google Scholar 

  91. Szabó LZ, Hanrahan DJ, Jones EM, Martin E, Pemberton JE, Polt R (2016) Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis. Carbohydr Res 422:1–4

    Article  CAS  Google Scholar 

  92. Epoune Lingome C, Gadenne B, Alfos C, Queneau Y, Moebs-Sanchez S (2017) Ring opening of epoxidized methyl or ethyl oleate by alkyl glycosides. Eur J Lipid Sci Technol 119:1600413–1600421

    Article  CAS  Google Scholar 

  93. Potier P, Bouchu A, Descotes G, Queneau Y (2001) Lipase-catalysed selective synthesis of sucrose mixed diesters. Synthesis 3:458–462

    Article  Google Scholar 

  94. Miethchen R, Peters D (1988) Ultraschallforcierte Reaktionen; Synthese und Charakterisierung amphiphiler 4, 6-O (n-Alkyliden)-D-glucopyranosen. Z Chem 28:298–299

    Article  CAS  Google Scholar 

  95. Thiem J, Vill V, Miethchen R, Peters D (1991) Flüssigkristalline 4,6-O-(n-Alkyliden)-D-glucopyranosen. J Prakt Chem 333:173–175

    Article  CAS  Google Scholar 

  96. Ono D, Masuyama A, Okahara M (1990) Preparation of new acetal type cleavable surfactants from epichlorohydrin. J Org Chem 55:4461–4464

    Article  CAS  Google Scholar 

  97. Kida T, Masuyama A, Okahara M (1990) Preparation of trihydroxycarboxylates bearing a long-chain alkyl acetal group from glucono-1,5-lactone. Tetrahedron Lett 31:5939–5942

    Article  CAS  Google Scholar 

  98. Fanton E, Fayet C, Gelas J (1997) Long-chain acetals derived from sucrose as a new class of surfactants. Carbohydr Res 298:85–92

    Article  CAS  Google Scholar 

  99. Porwanski S, Salanski P, Panaud N, Descotes G, Bouchu A, Queneau Y (2000) Regioselectivity in acid- or base-catalysed acetalation of sucrose: selection of [OH-2, OH-3] or [OH-4, OH-6] diols. Top Catal 13:335–338

    Article  CAS  Google Scholar 

  100. Porwanski S, Salanski P, Descotes G, Bouchu A, Queneau Y (2000) Selective synthesis of 4,6-O-alkenylidene and -benzylidene acetals from unprotected sucrose by lanthanide(III) resin-catalyzed transacetalization. Synthesis 2000:525–528

    Article  Google Scholar 

  101. Gozlan C, Duguet N, Lemaire M, Queneau Y, Redl A (2016) Method for preparing long-chain alkyl cyclic acetals made from sugars. WIPO Patent WO2014199345A1

    Google Scholar 

  102. Belmessieri D, Gozlan C, Duclos M-C, Molinier V, Aubry J-M, Dumitrescu O, Lina G, Redl A, Duguet N, Lemaire M (2017) Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers. Eur J Med Chem 128:98–106

    Article  CAS  Google Scholar 

  103. Gozlan C, Lafon R, Duguet N, Redl A, Lemaire M (2014) Catalytic reductive cleavage of methyl α-D-glucoside acetals to ethers using hydrogen as a clean reductant. RSC Adv 4:50653–50661

    Article  CAS  Google Scholar 

  104. Ames GR, Blackmore HM, King TA (1964) The reaction of sugars with alkyl halogenomethyl ethers. J Appl Chem 14:503–506

    Article  CAS  Google Scholar 

  105. Ames GR, Blackmore HM, King TA (1964) Alkyloxymethyl ethers of sucrose and glucose as surfactants. J Appl Chem 14:245–249

    Article  CAS  Google Scholar 

  106. Gronwald O, Shinkai S (2001) “Bifunctional” sugar-integrated gelators for organic solvents and water-on the role of nitro-substituents in 1-O-methyl-4,6-O-(nitrobenzylidene)-monosaccharides for the improvement of gelation ability. J Chem Soc Perkin Trans 2:1933–1937

    Google Scholar 

  107. Kowalczuk J, Jarosz S, Tritt-Goc J (2009) Characterization of low molecular-weight gelator methyl-4,6-O-(p-nitrobenzylidene)-α-D-glucopyranoside hydrogels and water diffusion in their networks. Tetrahedron 65:9801–9806

    Article  CAS  Google Scholar 

  108. Chen Q, Lv Y, Zhang D, Zhang G, Liu C, Zhu D (2010) Cysteine and pH-responsive hydrogel based on a saccharide derivative with an aldehyde group. Langmuir 26:3165–3168

    Article  CAS  Google Scholar 

  109. Allen DK, Tao BY (1999) Carbohydrate-alkyl ester derivatives as biosurfactants. J Surfact Deterg 2:383–390

    Article  CAS  Google Scholar 

  110. Gumel AM, Annuar MSM, Heidelberg T, Chisti Y (2011) Lipase mediated synthesis of sugar fatty acid esters. Process Biochem 46:2079–2090

    Article  CAS  Google Scholar 

  111. Neta NS, Teixeira JA, Rodrigues LR (2015) Sugar ester surfactants: enzymatic synthesis and applications in food industry. Crit Rev Food Science Nutr 55:595–610

    Article  CAS  Google Scholar 

  112. Szűts A, Szabó-Révész P (2012) Sucrose esters as natural surfactants in drug delivery systems—a mini-review. Int J Pharm 433:1–9

    Article  CAS  Google Scholar 

  113. Plat T, Linhardt RJ (2001) Syntheses and applications of sucrose-based esters. J Surfact Deterg 4:415–421

    Article  Google Scholar 

  114. Baker IJA, Matthews B, Suares H, Krodkiewska I, Furlong DN, Grieser F, Drummond CI (2000) Sugar fatty acid ester surfactants: structure and ultimate aerobic biodegradability. J Surfact Deterg 3:1–11

    Article  CAS  Google Scholar 

  115. Drummond CJ, Fong C, Krodkiewska I, Boyd BJ, Baker IJA (2004) Sugar fatty acid esters. In: Hubbard A (ed) Novel surfactants: preparation, applications, and biodegradability. Marcel Dekker, New York, pp 95–128

    Google Scholar 

  116. Bromann R, König B, Fischer L (1999) Regioselective synthesis of sugar esters without catalyst using α-hydroxycarboxylic acids. Synth Commun 29:951–957

    Article  CAS  Google Scholar 

  117. Boyère C, Broze G, Blecker C, Jérôme C, Debuigne A (2013) Monocatenary, branched, double-headed, and bolaform surface active carbohydrate esters via photochemical thiol-ene/-yne reactions. Carbohydr Res 380:29–36

    Article  CAS  Google Scholar 

  118. Boyère C, Favrelle A, Broze G, Laurent P, Nott K, Paquot M, Blecker C, Jérôme C, Debuigne A (2011) Lipase catalysis and thiol-Michael addition: a relevant association for the synthesis of new surface-active carbohydrate esters. Carbohydr Res 346:2121–2125

    Article  CAS  Google Scholar 

  119. Nandi S, Altenbach H-J, Jakob B, Lange K, Ihizane R, Schneider MP, Gün Ü, Mayer A (2012) Amphiphiles based on D-glucose: efficient low molecular weight gelators. Org Lett 14:3826–3829

    Article  CAS  Google Scholar 

  120. Wang K, Jiang J, Liang X (2016) Design, synthesis and evaluation of novel glycosyl surfactant—lignocellulosic hydrolysate esters from shrub willow. Ind Crop Prod 92:127–135

    Article  CAS  Google Scholar 

  121. Zief M (1950) Unsaturated esters of sucrose. J Am Chem Soc 72:1137–1140

    Article  CAS  Google Scholar 

  122. Hass HB, Snell FD, York WC, Osipow LI (1959) Process for producing sugar esters. US Patent 2893990

    Google Scholar 

  123. Osipow L, Snell FD, York WC, Finchler A (1956) Methods of preparation fatty acid esters of sucrose. Ind Eng Chem 48:1459–1462

    Article  CAS  Google Scholar 

  124. Nelen BAP, Bax L, Cooper JM (2015) Sucrose esters. In: Norn V (ed) Emulsifiers in food technology, 2nd edn. Wiley, Juelsminde, pp 147–180

    Google Scholar 

  125. Marti-Mestres G (2000) Main surfactants used in the pharmaceutical field. In: Nielloud F (ed) Pharmaceutical emulsions and suspensions, 2nd edn. Marcel Dekker, New York, pp 1–18

    Google Scholar 

  126. Nakamura S, Nagahara H, Kawaguchi J (1999) Process for production of high-monoester sucrose higher fatty acid esters. European Patent EP0560081B1

    Google Scholar 

  127. Wilson DC (1999) Continuous process for the synthesis of sucrose fatty acid esters. US Patent 5872245

    Google Scholar 

  128. Parker KJ, James K, Hurford J (1977) Sucrose ester surfactants—a solventless process and the products thereof. In: Sucrochemistry. American Chemical Society, Washington D.C., pp 97–114

    Google Scholar 

  129. Liu X, Gong L, Xin M, Liu J (1999) The synthesis of sucrose ester and selection of its catalyst. J Mol Catal A Chem 147:37–40

    Article  CAS  Google Scholar 

  130. Thévenet S, Wernicke A, Belniak S, Descotes G, Bouchu A, Queneau Y (1999) Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity versus acyl- or alkyloxycarbonyl-group migrations. Carbohydr Res 318:52–66

    Article  Google Scholar 

  131. Molinier V, Wisniewski K, Bouchu A, Fitremann J, Queneau DY (2003) Transesterification of sucrose in organic medium: study of acyl group migrations. J Carbohydr Chem 22:657–669

    Article  CAS  Google Scholar 

  132. Molinier V, Kouwer PJJ, Fitremann J, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2006) Self-organizing properties of monosubstituted sucrose fatty acid esters: the effects of chain length and unsaturation. Chem Eur J 12:3547–3557

    Article  CAS  Google Scholar 

  133. Molinier V, Kouwer PJJ, Fitremann J, Bouchu A, Mackenzie G, Queneau Y, Goodby JW (2007) Shape dependence in the formation of condensed phases exhibited by disubstituted sucrose esters. Chem Eur J 13:1763–1775

    Article  CAS  Google Scholar 

  134. Goodby JW, Gortz V, Cowling SJ, Mackenzie G, Martin P, Plusquellec D, Benvegnu T, Boullanger P, Lafont D, Queneau Y, Chambert S, Fitremann J (2007) Thermotropic liquid crystalline glycolipids. Chem Soc Rev 36:1971–2032

    Article  CAS  Google Scholar 

  135. Molinier V, Kouwer PHJ, Queneau Y, Fitremann J, Mackenzie G, Goodby JW (2003) A bilayer to monolayer phase transition in liquid crystal glycolipids. Chem Commun 2860–2861

    Google Scholar 

  136. Muller A-S, Gagnaire J, Queneau Y, Karaoglanian M, Maitre J-P, Bouchu A (2002) Winsor behaviour of sucrose fatty acid esters: choice of the cosurfactant and effect of the surfactant composition. Colloids Surf A Physicochem Eng Asp 203:55–66

    Article  CAS  Google Scholar 

  137. Molinier V, Fenet B, Fitremann J, Bouchu A, Queneau Y (2006) Concentration measurements of sucrose and sugar surfactants solutions by using the 1H NMR ERETIC method. Carbohydr Res 341:1890–1895

    Article  CAS  Google Scholar 

  138. Wernicke A, Belniak S, Thevenet S, Descotes G, Bouchu A, Queneau Y (1998) Synthesis of sucrose carbonates in aqueous medium. J Chem Soc Perkin Trans 1:1179–1182

    Article  Google Scholar 

  139. Boyer A, Lingome CE, Condassamy O, Schappacher M, Moebs-Sanchez S, Queneau Y, Gadenne B, Alfos C, Cramail H (2013) Glycolipids as a source of polyols for the design of original linear and cross-linked polyurethanes. Polym Chem 4:296–306

    Article  CAS  Google Scholar 

  140. Cramail H, Boyer A, Lingome CE, Alfos C, Gadenne B, Cloutet E, Queneau Y, Moebs S (2014) Preparation of polyurethanes and polyesters from glycolipid type compounds. US Patent 20140235814A1

    Google Scholar 

  141. Ferrer M, Cruces MA, Plou FJ, Pastor E, Fuentes G, Bernabé M, Parra JL, Ballesteros A (2000) Chemical versus enzymatic catalysis for the regioselective synthesis of sucrose esters of fatty acids. In: Corma A, Melo FV, Mendioroz S, Fierro JLG (eds) Studies in surface science and catalysis. Elsevier, Amsterdam, pp 509–514

    Google Scholar 

  142. Potier P, Bouchu A, Descotes G, Queneau Y (2000) Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate. Tetrahedron Lett 41:3597–3600

    Article  CAS  Google Scholar 

  143. Potier P, Bouchu A, Gagnaire J, Queneau Y (2001) Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides. Tetrahedron Asymmetry 12:2409–2419

    Article  CAS  Google Scholar 

  144. Vemula PK, Li J, John G (2006) Enzyme catalysis: tool to make and break amygdalin hydrogelators from renewable resources: a delivery model for hydrophobic drugs. J Am Chem Soc 128:8932–8938

    Article  CAS  Google Scholar 

  145. Xu Y, Wang D, Mu XQ, Ni YQ (2003) Efficient esterification of sorbitan oleate by lipase in a solvent-free system. J Am Oil Chem Soc 80:647–651

    Article  CAS  Google Scholar 

  146. Sarney DB, Barnard MJ, Virto M, Vulfson EN (1997) Enzymatic synthesis of sorbitan esters using a low-boiling-point azeotrope as a reaction solvent. Biotechnol Bioeng 54:351–356

    Article  CAS  Google Scholar 

  147. Lavergne A, Moity L, Molinier V, Aubry J-M (2013) Volatile short-chain amphiphiles derived from isosorbide: hydrotropic properties of esters vs. ethers. RSC Adv 3:5997–6007

    Article  CAS  Google Scholar 

  148. Moreau B, Lognay GC, Blecker C, Brohée J-C, Chéry F, Rollin P, Paquot M, Marlier M (2004) Synthesis of novel D-glucuronic acid fatty esters using Candida antarctica lipase in tert-butanol. Biotechnol Lett 26:419–424

    Article  CAS  Google Scholar 

  149. Moreau B, Lognay G, Blecker C, Destain J, Gerbaux P, Chéry F, Rollin P, Paquot M, Marlier M (2007) Chromatographic, spectrometric and NMR characterization of a new set of glucuronic acid esters synthesized by lipase. Biotechnol Agron Soc Environ 11:9–17

    CAS  Google Scholar 

  150. Blecker C, Piccicuto S, Lognay G, Deroanne C, Marlier M, Paquot M (2002) Enzymatically prepared n-alkyl esters of glucuronic acid: the effect of hydrophobic chain length on surface properties. J Colloid Interface Sci 247:424–428

    Article  CAS  Google Scholar 

  151. Lu H, Drelich A, Omri M, Pezron I, Wadouachi A, Pourceau G (2016) Catalytic synthesis of a new series of alkyl uronates and evaluation of their physicochemical properties. Molecules 21:1301

    Article  CAS  Google Scholar 

  152. Richel A, Nicks F, Laurent P, Wathelet B, Wathelet J-P, Paquot M (2012) Efficient microwave-promoted synthesis of glucuronic and galacturonic acid derivatives using sulfuric acid impregnated on silica. Green Chem Lett Rev 5:179–186

    Article  CAS  Google Scholar 

  153. Xavier NM, Rauter AP, Queneau Y (2010) Carbohydrate-based lactones: synthesis and applications. In: Rauter AP, Vogel P, Queneau Y (eds) Carbohydrates in sustainable development II. Springer, Berlin/Heidelberg, pp 19–62

    Chapter  Google Scholar 

  154. Allam A, Behr J-B, Dupont L, Nardello-Rataj V, Plantier-Royon R (2010) Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from D-galacturonic acid. Carbohydr Res 345:731–739

    Article  CAS  Google Scholar 

  155. Auvray X, Labulle B, Petipas C, Bertho J-N, Benvegnu T, Plusquellec D (1997) Thermotropic liquid-crystalline properties of some novel hexuronic acid derivatives bearing a single or two alkyl chains. J Mater Chem 7:1373–1376

    Article  CAS  Google Scholar 

  156. Bertho J-N, Ferrières V, Plusquellec D (1995) A new synthesis of D-glycosiduronates from unprotected D-uronic acids. J Chem Soc Chem Commun 1391–1393

    Google Scholar 

  157. Razafindralambo H, Blecker C, Mezdour S, Deroanne C, Crowet J-M, Brasseur R, Lins L, Paquot M (2009) Impacts of the carbonyl group location of ester bond on interfacial properties of sugar-based surfactants: experimental and computational evidences. J Phys Chem B 113:8872–8877

    Article  CAS  Google Scholar 

  158. Gaertner VR (1961) Sucrose ether- and ester-linked surfactants. J Am Oil Chem Soc 38:410–418

    Article  CAS  Google Scholar 

  159. Raaijmakers HWC, Arnouts EG, Zwanenburg B, Chittenden GJF, van Doren HA (1995) The synthesis and properties of some mesogenic 3–O-alkyl derivatives of D-glucitol and D-mannitol. Recl Trav Chim Pays-Bas 114:301–310

    Article  CAS  Google Scholar 

  160. Goodby JW, Watson MJ, Mackenzie G, Kelly SM, Bachir S, Bault P, Gode P, Goethals G, Martin P, Ronco G, Villa P (1998) The dependence of mesomorphic behaviour on the extent of hydrogen-bonding in sugar derived polyols. Liq Cryst 25:139–147

    Article  CAS  Google Scholar 

  161. Houdier S, Pérez S (1995) Assessing sucrose hydroxyl acidities through semiempirical calculations. J Carbohydr Chem 14:1117–1132

    Article  CAS  Google Scholar 

  162. Lichtenthaler FW, Immel S, Pokinskyj P (1995) Molecular modeling of saccharides, 8. Selective 2-O-benzylation of sucrose: a facile entry to its 2-deoxy- and 2-keto-derivatives and to sucrosamine. Eur J Org Chem 1995:1939–1947

    Google Scholar 

  163. Hamann CH, Fischer S, Polligkeit H, Wolf P (1993) The alkylation of mono- and disaccharides via an initialising electrochemical step. J Carbohydr Chem 12:173–190

    Article  CAS  Google Scholar 

  164. Chauvin C, Baczko K, Plusquellec D (1993) New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses. J Org Chem 58:2291–2295

    Article  CAS  Google Scholar 

  165. Gérard E, Götz H, Pellegrini S, Castanet Y, Mortreux A (1998) Epoxide–tertiary amine combinations as efficient catalysts for methanol carbonylation into methyl formate in the presence of carbon dioxide. Appl Catal A Gen 170:297–306

    Article  Google Scholar 

  166. Gagnaire J, Toraman G, Descotes G, Bouchu A, Queneau Y (1999) Synthesis in water of amphiphilic sucrose hydroxyalkyl ethers. Tetrahedron Lett 40:2757–2760

    Article  CAS  Google Scholar 

  167. Gagnaire J, Cornet A, Bouchu A, Descotes G, Queneau Y (2000) Study of the competition between homogeneous and interfacial reactions during the synthesis of surfactant sucrose hydroxyalkyl ethers in water. Colloids Surf A Physicochem Eng Asp 172:125–138

    Article  CAS  Google Scholar 

  168. Queneau Y, Gagnaire J, West JJ, Mackenzie G, Goodby JW (2001) The effect of molecular shape on the liquid crystal properties of the mono-O-(2-hydroxydodecyl)sucroses. J Mater Chem 11:2839–2844

    Article  CAS  Google Scholar 

  169. Singh MK, Xu R, Moebs S, Kumar A, Queneau Y, Cowling SJ, Goodby JW (2013) Hydrophobic and hydrophilic balance and its effect on mesophase behaviour in hydroxyalkyl ethers of methyl glucopyranoside. Chem Eur J 19:5041–5049

    Article  CAS  Google Scholar 

  170. Dalpozzo R, Nardi M, Oliverio M, Paonessa R, Procopio A (2009) Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides. Synthesis 2009:3433–3438

    Article  CAS  Google Scholar 

  171. Likhar PR, Kumar MP, Bandyopadhyay AK (2001) Ytterbium trifluoromethanesulfonate Yb(OTf)3: an efficient, reusable catalyst for highly selective formation of β-alkoxy alcohols via ring-opening of 1,2-epoxides with alcohols. Synlett 2001:0836–0838

    Article  Google Scholar 

  172. Gruber B, Weese KJ, Mueller H, Hill K, Behr A, Tucker JR (1993) Octyl ethers and octadienyl ethers. US Patent 5236909

    Google Scholar 

  173. Hill K, Gruber B, Weese KJ (1994) Palladium catalyzed telomerization of butadiene with sucrose: a highly efficient approach to novel sucrose ethers. Tetrahedron Lett 35:4541–4542

    Article  CAS  Google Scholar 

  174. Pennequin I, Mortreux A, Petit F, Mentech J, Thiriet B (1994) Telomerization of conjugated dienes with polyols such as nonreducing sugars. French Patent FR 2693188 A1

    Google Scholar 

  175. Pennequin I, Meyer J, Suisse I, Mortreux A (1997) A further application of TPPTS in catalysis: efficient sucrose-butadiene telomerization using palladium catalysts in water. J Mol Catal A Chem 120:139–142

    Article  CAS  Google Scholar 

  176. Desvergnes-Breuil V, Pinel C, Gallezot P (2001) Green approach to substituted carbohydrates: telomerisation of butadiene with sucrose. Green Chem 3:175–177

    Article  CAS  Google Scholar 

  177. Lai J, Bigot S, Sauthier M, Molinier V, Suisse I, Castanet Y, Aubry J-M, Mortreux A (2011) Telomerisation of 1,3-butadiene with 1,4:3,6-dianhydrohexitols: an atom-economic and selective synthesis of amphiphilic monoethers from agro-based diols. ChemSusChem 4:1104–1111

    Article  CAS  Google Scholar 

  178. Donzé C, Pinel C, Gallezot P, Taylor PL (2002) Palladium-catalyzed telomerization of butadiene with starch. Adv Synth Catal 344:906–910

    Article  Google Scholar 

  179. Mesnager J, Quettier C, Lambin A, Rataboul F, Pinel C (2009) Telomerization of butadiene with starch under mild conditions. ChemSusChem 2:1125–1129

    Article  CAS  Google Scholar 

  180. Mesnager J, Quettier C, Lambin A, Rataboul F, Perrard A, Pinel C (2010) Telomerization of butadiene with starch in water: role of the surfactants. Green Chem 12:475–482

    Article  CAS  Google Scholar 

  181. Faßbach TA, Sommer FO, Behr A, Romanski S, Leinweber D, Vorholt AJ (2017) Non-ionic surfactants from renewables – amphiphilic ligands in biphasic reactions. Cat Sci Technol 7:1650–1653

    Article  CAS  Google Scholar 

  182. Mesnager J, Lambin A, Quettier C, Rataboul F, Pinel C (2010) Efficient telomerization of butadiene with starch in water: the role of the surfactant. Top Catal 53:1282–1284

    Article  CAS  Google Scholar 

  183. Bouquillon S, Muzart J, Pinel C, Rataboul F (2010) Palladium-catalyzed telomerization of butadiene with polyols: from mono to polysaccharides. In: Carbohydrates in sustainable development II. Springer, Berlin/Heidelberg, pp 93–119

    Chapter  Google Scholar 

  184. Queneau Y, Pinel C, Scherrmann M-C (2011) Some chemical transformations of carbohydrates in aqueous medium. C R Chim 14:688–699

    Article  CAS  Google Scholar 

  185. Pito DS, Castanheiro JE (2013) Reactions of sucrose in the presence of solid catalysts. In: Magazù S (ed) Sucrose: properties, biosynthesis and health implications. Nova Science, New York

    Google Scholar 

  186. Sauthier M, Mortreux A, Suisse I (2014) From conventional to greener catalytic approaches for carbohydrates etherification. In: Pilar Rauter A, Lindhorst T, Queneau Y (eds) Carbohydrate chemistry: volume 40. The Royal Society of Chemistry, Cambridge, pp 73–98

    Chapter  Google Scholar 

  187. Shi Y, Dayoub W, Favre-Réguillon A, Chen G-R, Lemaire M (2009) Straightforward selective synthesis of linear 1-O-alkyl glycerol and di-glycerol monoethers. Tetrahedron Lett 50:6891–6893

    Article  CAS  Google Scholar 

  188. Shi Y, Dayoub W, Chen G-R, Lemaire M (2010) Selective synthesis of 1-O-alkyl glycerol and diglycerol ethers by reductive alkylation of alcohols. Green Chem 12:2189–2195

    Article  CAS  Google Scholar 

  189. Moity L, Shi Y, Molinier V, Dayoub W, Lemaire M, Aubry J-M (2013) Hydrotropic properties of alkyl and aryl glycerol monoethers. J Phys Chem B 117:9262–9272

    Article  CAS  Google Scholar 

  190. Sutter M, Silva ED, Duguet N, Raoul Y, Métay E, Lemaire M (2015) Glycerol ether synthesis: a bench test for green chemistry concepts and technologies. Chem Rev 115:8609–8651

    Article  CAS  Google Scholar 

  191. Gozlan C, Deruer E, Duclos M-C, Molinier V, Aubry J-M, Redl A, Duguet N, Lemaire M (2016) Preparation of amphiphilic sorbitan monoethers through hydrogenolysis of sorbitan acetals and evaluation as bio-based surfactants. Green Chem 18:1994–2004

    Article  CAS  Google Scholar 

  192. Eellis GP, Honeyman J (1955) Glycosylamines. In: Wolfrom ML (ed) Advances in carbohydrate chemistry. Elsevier, New York, pp 95–168

    Google Scholar 

  193. Pestman JM (1998) Carbohydrate-derived surfactants containing an N-acylated amine functionality: fundamental aspects and practical applications. University of Groningen, Groningen

    Google Scholar 

  194. Zhu Y-P, Rosen MJ, Vinson PK, Morrall SW (1999) Surface properties of N-alkanoyl-N-methyl glucamines and related materials. J Surfact Deterg 2:357–362

    Article  CAS  Google Scholar 

  195. Hildreth JEK (1982) N-D-Gluco-N-methylalkanamide compounds, a new class of non-ionic detergents for membrane biochemistry. Biochem J 207:363–366

    Article  CAS  Google Scholar 

  196. Liberek B, Melcer A, Osuch A, Wakieć R, Milewski S, Wiśniewski A (2005) N-Alkyl derivatives of 2-amino-2-deoxy-D-glucose. Carbohydr Res 340:1876–1884

    Article  CAS  Google Scholar 

  197. Vega-Pérez JM, Espartero JL, Alcudia F (1993) Oxazolidinones from sugars. III. A new method for N-alkyl and N,N-dialkyl-D-glucosamine derivatives. J Carbohydr Chem 12:477–486

    Article  Google Scholar 

  198. Humphrey AJ, Fremann C, Critchley P, Malykh Y, Schauer R, Bugg TDH (2002) Biological properties of N-acyl and N-haloacetyl neuraminic acids: processing by enzymes of sialic acid metabolism, and interaction with influenza virus. Bioorg Med Chem 10:3175–3185

    Article  CAS  Google Scholar 

  199. Inouye Y, Onodera K, Kitaoka S, Hirano S (1956) Some fatty acid derivatives of D-glucosamine. J Am Chem Soc 78:4722–4724

    Article  Google Scholar 

  200. El Ghoul M, Latge P, Rico I, Lattes A, Godefroy L (1996) N-alkyl, n-acetylglycosylamines. US Patent 5539091A

    Google Scholar 

  201. Lockhoff O, Stadler P (1998) Syntheses of glycosylamides as glycolipid analogs. Carbohydr Res 314:13–24

    Article  CAS  Google Scholar 

  202. Neto V, Voisin A, Héroguez V, Grelier S, Coma V (2012) Influence of the variation of the alkyl chain length of N-alkyl-β-D-glycosylamine derivatives on antifungal properties. J Agric Food Chem 60:10516–10522

    Article  CAS  Google Scholar 

  203. Lubineau A, Augé J, Drouillat B (1995) Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents. Carbohydr Res 266:211–219

    Article  CAS  Google Scholar 

  204. Bogaert PMP, Langezaal WPC, Van Haveren J, Slaghek TM, van der Meeren P (1999) Non-reductive coupling of branched amino fatty acid esters with mono and disaccharides: synthesis of a new class of alkyl glycosylamines. Fett-Lipid 101:64–70

    Article  CAS  Google Scholar 

  205. Au V, Harichian B, Hung A, Vermeer R (1999) Compositions comprising glycosylamide surfactants. US Patent 5872111A

    Google Scholar 

  206. Bhattacharya S, Acharya SNG (1999) Pronounced hydrogel formation by the self-assembled aggregates of N-alkyl disaccharide amphiphiles. Chem Mater 11:3504–3511

    Article  CAS  Google Scholar 

  207. Epoune Lingome C, Pourceau G, Gobert-Deveaux V, Wadouachi A (2014) Efficient synthesis of glycosylamines in solventless conditions promoted by mechanical milling. RSC Adv 4:36350–36356

    Article  CAS  Google Scholar 

  208. Latge P, Rico I, Garelli R, Lattes A (1991) Synthesis of long chain N-alkyllactylahines from unprotected lactose a new series of non-ionic surfactants. J Dispers Sci Technol 12:227–237

    Article  CAS  Google Scholar 

  209. Laughlin RG, Fu Y-C, Wireko FC, Scheibel JJ, Munyon RL (2004) N-Alkanoyl-N-Alkyl-1-Glycamines in: novel surfactants: preparation, applications, and biodegradability. Marcel Dekker, New York, pp 1–34

    Google Scholar 

  210. Maugard T, Remaud-Simeon M, Petre D, Monsan P (1998) Enzymatic amidification for the synthesis of biodegradable surfactants: synthesis of N-acylated hydroxylated amines. J Mol Catal B Enzym 5:13–17

    Article  CAS  Google Scholar 

  211. Wang ZD, Sheikh SO, Cox S, Zhang Y, Massey K (2007) Direct Preparation of N-Glycosidic Bond-Linked Nonionic Carbohydrate-Based Surfactant (NICBS) via Ritter Reaction. Eur J Org Chem 2007:2243–2247

    Article  CAS  Google Scholar 

  212. Maugard T, Remaud-Simeon M, Petre D, Monsan P (1997) Enzymatic synthesis of glycamide surfactants by amidification reaction. Tetrahedron 53:5185–5194

    Article  CAS  Google Scholar 

  213. Gaber Y, Tornvall U, Orellana-Coca C, Ali Amin M, Hatti-Kaul R (2010) Enzymatic synthesis of N-alkanoyl-N-methylglucamide surfactants: solvent-free production and environmental assessment. Green Chem 12:1817–1825

    Article  CAS  Google Scholar 

  214. Guderjahn L, Kunz M, Schuettenhelm M (1994) New carbohydrate surfactants derived from Palatinose. Tenside Surfactants Deterg 31:146–150

    CAS  Google Scholar 

  215. Klein J, Behrens W, Kunz M (1989) Isomaltamines and their N-acyl derivatives, methods for their production, and their uses as surfactants and monomers. US Patent 4843154

    Google Scholar 

  216. Kunz MD, Guderjahn L, Schüttenhelm M, Kowalczyk JD (1997) N-alkylisomaltamines, their preparation from isomaltulose and their application as surfactants. European Patent EP0618216B1

    Google Scholar 

  217. Jäger M, Minnaard AJ (2015) Regioselective modification of unprotected glycosides. Chem Commun 52:656–664

    Article  CAS  Google Scholar 

  218. Pietsch M, Walter M, Buchholz K (1994) Regioselective synthesis of new sucrose derivatives via 3-ketosucrose. Carbohydr Res 254:183–194

    Article  CAS  Google Scholar 

  219. Fieser M, Fieser LF, Toromanoff E, Hirata Y, Heymann H, Tefft M, Bhattacharya S (1956) Synthetic emulsifying agents. J Am Chem Soc 78:2825–2832

    Article  CAS  Google Scholar 

  220. Pilakowska-Pietras D, Lunkenheimer K, Piasecki A (2004) Synthesis of novel N,N-di-n-alkylaldonamides and properties of their surface chemically pure adsorption layers at the air/water interface. J Colloid Interface Sci 271:192–200

    Article  CAS  Google Scholar 

  221. Laurent P, Razafindralambo H, Wathelet B, Blecker C, Wathelet J-P, Paquot M (2011) Synthesis and surface-active properties of uronic amide derivatives, surfactants from renewable organic raw materials. J Surfact Deterg 14:51–63

    Article  CAS  Google Scholar 

  222. Berchel M, Lemiègre L, Jeftić J, Benvegnu T (2008) Synthesis of unsymmetrical spin-labelled bolaamphiphiles. Tetrahedron Lett 49:4690–4692

    Article  CAS  Google Scholar 

  223. Berchel M, Lemiègre L, Trépout S, Lambert O, Jeftić J, Benvegnu T (2008) Synthesis of unsymmetrical saturated or diacetylenic cationic bolaamphiphiles. Tetrahedron Lett 49:7419–7422

    Article  CAS  Google Scholar 

  224. Guilbot J, Benvegnu T, Legros N, Plusquellec D, Dedieu J-C, Gulik A (2001) Efficient synthesis of unsymmetrical bolaamphiphiles for spontaneous formation of vesicles and disks with a transmembrane organization. Langmuir 17:613–618

    Article  CAS  Google Scholar 

  225. Bosco M, Rat S, Kovensky J, Wadouachi A (2010) Fast synthesis of uronamides by non-catalyzed opening of glucopyranurono-6,1-lactone with amines, amino acids, and aminosugars. Tetrahedron Lett 51:2553–2556

    Article  CAS  Google Scholar 

  226. Raaijmakers HWC, Zwanenburg B, Chittenden GJF (1994) The synthesis and properties of some long-chain alkyl-D-glucofuranosidurono-6,3-lactones, D-glucofuranosides and derivatives thereof. Recl Trav Chim Pays-Bas 113:79–87

    Article  CAS  Google Scholar 

  227. Pierre R, Chambert S, Alirachedi F, Danel M, Trombotto S, Doutheau A, Queneau Y (2008) Carboxymethyl glucosides and carboxymethyl glucoside lactones: a detailed study of their preparation by oxidative degradation of disaccharides. C R Chim 11:61–66

    Article  CAS  Google Scholar 

  228. Trombotto S, Bouchu A, Descotes G, Queneau Y (2000) Hydrogen peroxide oxidation of palatinose and trehalulose: direct preparation of carboxymethyl α-D-glucopyranoside. Tetrahedron Lett 41:8273–8277

    Article  CAS  Google Scholar 

  229. Listkowski A, Ing P, Cheaib R, Chambert S, Doutheau A, Queneau Y (2007) Carboxymethylglycoside lactones (CMGLs): structural variations on the carbohydrate moiety. Tetrahedron Asymmetry 18:2201–2210

    Article  CAS  Google Scholar 

  230. Mehltretter CL, Mellies RL, Rankin JC (1954) Substituted gluconamides. US Patents 2670345A

    Google Scholar 

  231. Au V, Vermeer R, Harichian B (1997) Sulfated polyhydroxy compounds as anionic surfactants and a process for their manufacture. US patent US5686603A

    Google Scholar 

  232. Arévalo MJ, Avalos M, Babiano R, Cabanillas A, Cintas P, Jiménez JL, Palacios JC (2000) Optically active sugar thioamides from δ-gluconolactone. Tetrahedron Asymmetry 11:1985–1995

    Article  Google Scholar 

  233. Plusquellec D, Lefeuvre M (1987) Sugar chemistry without protecting groups: a regioselective addition of the primary hydroxyl of monosaccharides to alkylisocyanates. Tetrahedron Lett 28:4165–4168

    Article  CAS  Google Scholar 

  234. Plusquellec D, Roulleau F, Brown E (1984) Chimie des sucres sans groupements protecteurs: synthèse de carbamates, d’urées et de thiourées en position 1 du lactose. Tetrahedron Lett 25:1901–1904

    Article  CAS  Google Scholar 

  235. Plusquellec D, Chevalier G, Talibart R, Wróblewski H (1989) Synthesis and characterization of 6-O-(N-heptylcarbamoyl)-methyl-α-D-glucopyranoside, a new surfactant for membrane studies. Anal Biochem 179:145–153

    Article  CAS  Google Scholar 

  236. Prata C, Mora N, Lacombe J-M, Maurizis JC, Pucci B (1997) Stereoselective synthesis of glycosyl carbamates as new surfactants and glycosyl donors. Tetrahedron Lett 38:8859–8862

    Article  CAS  Google Scholar 

  237. Christian D, Fitremann J, Bouchu A, Queneau Y (2004) Preparation of amphiphilic sucrose carbamates by reaction with alkyl isocyanates in water–alcohol mixtures. Tetrahedron Lett 45:583–586

    Article  CAS  Google Scholar 

  238. Rico-Lattes I, Blanzat M, Franceschi-Messant S, Perez É, Lattes A (2005) Catanionic sugar derived surfactants, polymers and dendrimers: from molecules to targeted self-organized systems. C R Chim 8:807–814

    Article  CAS  Google Scholar 

  239. Rico-Lattes I, Lattes A (1997) Synthesis of new sugar-based surfactants having biological applications: key role of their self-association. Colloids Surf A Physicochem Eng Asp 123–124:37–48

    Article  Google Scholar 

  240. Ewan HS, Muli CS, Touba S, Bellinghiere AT, Veitschegger AM, Smith TB, Pistel WL, Jewell WT, Rowe RK, Hagen JP, Palandoken H (2014) Synthesis of sugar oxime ether surfactants. Tetrahedron Lett 55:4962–4965

    Article  CAS  Google Scholar 

  241. Padwa A (1984) 1,3-dipolar cycloaddition chemistry. Wiley, New York

    Google Scholar 

  242. Meldal M, Tornøe CW (2008) Cu-catalyzed azide−alkyne cycloaddition. Chem Rev 108:2952–3015

    Article  CAS  Google Scholar 

  243. Lim D, Brimble MA, Kowalczyk R, Watson AJA, Fairbanks AJ (2014) Protecting-group-free one-pot synthesis of glycoconjugates directly from reducing sugars. Angew Chem Int Ed 53:11907–11911

    Article  CAS  Google Scholar 

  244. Aich U, Loganathan D (2005) Synthesis of N-(β-Glycopyrano-syl)azidoacetamides. J Carbohydr Chem 24:1–12

    Article  CAS  Google Scholar 

  245. Paul KJV, Loganathan D (2008) Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides. Tetrahedron Lett 49:6356–6359

    Article  CAS  Google Scholar 

  246. Schuster T, Schellenberger S, Friedrich R, Klapper M, Müllen K (2013) Branched fluorinated amphiphiles based on carbohydrates. J Fluor Chem 154:30–36

    Article  CAS  Google Scholar 

  247. Latxague L, Ramin MA, Appavoo A, Berto P, Maisani M, Ehret C, Chassande O, Barthélémy P (2015) Control of stem-cell behavior by fine tuning the supramolecular assemblies of low-molecular-weight gelators. Angew Chem Int Ed 54:4517–4521

    Article  CAS  Google Scholar 

  248. Mangunuru HPR, Yerabolu JR, Liu D, Wang G (2015) Synthesis of a series of glucosyl triazole derivatives and their self-assembling properties. Tetrahedron Lett 56:82–85

    Article  CAS  Google Scholar 

  249. Sani FA, Heidelberg T, Hashim R, Farhanullah (2012) Alkyl triazole glycosides (ATGs)—a new class of bio-related surfactants. Colloids Surf B Biointerfaces 97:196–200

    Article  CAS  Google Scholar 

  250. Schmid W, Whitesides GM (1991) Carbon-carbon bond formation in aqueous ethanol: diastereoselective transformation of unprotected carbohydrates to higher carbon sugars using allyl bromide and tin metal. J Am Chem Soc 113:6674–6675

    Article  CAS  Google Scholar 

  251. Chan T-H, Li C-J (1992) A concise chemical synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). J Chem Soc Chem Commun 747–748

    Google Scholar 

  252. Lalitha K, Muthusamy K, Prasad YS, Vemula PK, Nagarajan S (2015) Recent developments in β-C-glycosides: synthesis and applications. Carbohydr Res 402:158–171

    Article  CAS  Google Scholar 

  253. Román Galán E, Galbis Pérez JA, Arévalo Arévalo MA (1983) New C-nucleoside analogs by dehydration of 1-benzyl-4,5,6,7-tetrahydro-6,6-dimethyl-2-(D-galacto-pentitol-1-yl)-indol-4-one. Carbohydr Res 116:255–262

    Article  Google Scholar 

  254. Gonzalez MA, Jimenez Requejo JL, Palacios Albarran JC, Gabis Perez JA (1986) Facile preparation of C-glycosylbarbiturates and C-glycosylbarbituric acids. Carbohydr Res 158:53–66

    Article  Google Scholar 

  255. Wulff G, Clarkson G (1994) On the synthesis of C-glycosyl compounds containing double bonds without the use of protecting groups. Carbohydr Res 257:81–95

    Article  CAS  Google Scholar 

  256. Kozikowski AP, Lin GQ, Springer JP (1987) An approach to bi-tetrahydrofurans from glucose and a correction of the literature. Tetrahedron Lett 28:2211–2214

    Article  CAS  Google Scholar 

  257. Rodrigues F, Canac Y, Lubineau A (2000) A convenient, one-step, synthesis of β-C-glycosidic ketones in aqueous media. Chem Commun 2049–2050

    Google Scholar 

  258. Philippe M, Semeria D (2002) Novel c-glycoside derivatives and use thereof. WIPO Patent WO/2002/051803A2

    Google Scholar 

  259. Hersant Y, Abou-Jneid R, Canac Y, Lubineau A, Philippe M, Semeria D, Radisson X, Scherrmann M-C (2004) One-step synthesis of β-C-glycolipid derivatives from unprotected sugars. Carbohydr Res 339:741–745

    Article  CAS  Google Scholar 

  260. Foley PM, Phimphachanh A, Beach ES, Zimmerman JB, Anastas PT (2011) Linear and cyclic C-glycosides as surfactants. Green Chem 13:321–325

    Article  CAS  Google Scholar 

  261. Ranoux A, Lemiègre L, Benoit M, Guégan J-P, Benvegnu T (2010) Horner-Wadsworth-Emmons reaction of unprotected sugars in water or in the absence of any solvent: one-step access to C-glycoside amphiphiles. Eur J Org Chem 2010:1314–1323

    Article  CAS  Google Scholar 

  262. Ranoux A, Lemiegre L, Benvegnu T (2010) Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents. Sci China Chem 53:1957–1962

    Article  CAS  Google Scholar 

  263. Werpy T, Petersen G (2004) Top value added chemicals from biomass: volume I – results of screening for potential candidates from sugars and synthesis gas. National Renewable Energy Lab, Golden

    Google Scholar 

  264. Bozell JJ, Petersen GR (2010) Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited. Green Chem 12:539–554

    Article  CAS  Google Scholar 

  265. Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793

    Article  CAS  Google Scholar 

  266. McElhanon JR, Zifer T, Kline SR, Wheeler DR, Loy DA, Jamison GM, Long TM, Rahimian K, Simmons BA (2005) Thermally cleavable surfactants based on furan−maleimide Diels−Alder adducts. Langmuir 21:3259–3266

    Article  CAS  Google Scholar 

  267. Stensrud K, Wicklund L (2016) Synthesis of non-ionic surfactants from 5-hydroxymethyl-2-furfural, furan-2,5-dimethanol and bis-2,5-dihydroxymethyltetrahydrofurans. WIPO Patent WO2016028845A1

    Google Scholar 

  268. Park DS, Joseph KE, Koehle M, Krumm C, Ren L, Damen JN, Shete MH, Lee HS, Zuo X, Lee B, Fan W, Vlachos DG, Lobo RF, Tsapatsis M, Dauenhauer PJ (2016) Tunable oleo-furan surfactants by acylation of renewable furans. ACS Cent Sci 2:820–824

    Article  CAS  Google Scholar 

  269. Hanemann T, Schumacher E, Haase W, Lichtenthaler FW (1997) Some novel disaccharide-derived liquid crystals. Liq Cryst 22:47–50

    Article  CAS  Google Scholar 

  270. Lichtenthaler FW, Martin D, Weber T, Schiweck H (1993) Studies on Ketoses, 7 – 5-(α-D-Glucosyloxymethyl)furfural: preparation from isomaltulose and exploration of its ensuing chemistry. Eur J Org Chem 1993:967–974

    Google Scholar 

  271. Müller C, Diehl V, Lichtenthaler FW (1998) Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose. Tetrahedron 54:10703–10712

    Article  Google Scholar 

  272. Tan J-N, Ahmar M, Queneaua Y (2014) Isomaltulose oxidation and dehydration products as starting materials towards fine chemicals. Curr Org Chem 18:1768–1787

    Article  CAS  Google Scholar 

  273. Tan J-N, Ahmar M, Queneau Y (2015) Glucosyloxymethylfurfural (GMF): a creative renewable scaffold towards bioinspired architectures. Pure Appl Chem 87:827–839

    Article  CAS  Google Scholar 

  274. Tan J-N, Ahmar M, Queneau Y (2013) HMF derivatives as platform molecules: aqueous Baylis–Hillman reaction of glucosyloxymethyl-furfural towards new biobased acrylates. RSC Adv 3:17649–17653

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246 CNRS, Univ Lyon 1, INSA Lyon, CPE Lyon, Université de Lyon, Villeurbanne, France

    Lianjie Wang & Yves Queneau

Authors
  1. Lianjie Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yves Queneau
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yves Queneau .

Editor information

Editors and Affiliations

  1. Ramtech Ltd., Larkspur, CA, USA

    Robert A. Meyers

Section Editor information

  1. Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

    Buxing Han

  2. Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

    Tianbin Wu

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer Science+Business Media, LLC, part of Springer Nature

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Wang, L., Queneau, Y. (2018). Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants. In: Meyers, R. (eds) Encyclopedia of Sustainability Science and Technology. Springer, New York, NY. https://doi.org/10.1007/978-1-4939-2493-6_1009-1

Download citation

  • DOI: https://doi.org/10.1007/978-1-4939-2493-6_1009-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4939-2493-6

  • Online ISBN: 978-1-4939-2493-6

  • eBook Packages: Springer Reference Earth and Environm. ScienceReference Module Physical and Materials ScienceReference Module Earth and Environmental Sciences

Publish with us

Policies and ethics

Search

Navigation