[en] Short chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw material. Three different strategies were used to synthesise uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1H-RMN and 13C-RMN). The best one, using an acid chloride as synthetic intermediate, furnished the expected amides as a mixture of anomers in 46 to 58 % global yield. Surface-active properties (CMC, g cmc, Tmax, Amin) of homologous series of uronic acid N-alkylamides from C8 to C18 were also assessed. In general, these sugar-based surfactants exhibited good surface-activities, and appeared as valuable non ionic surfactants compared to Triton X-100, the most well-known non ionic surfactant. Increasing the alkyl chain length influenced the CMC values for both glucuronic and galacturonic N-alkylamide derivatives. The galacturonic N-alkylamides decreased g cmc at slower values than their counterpart's glucuronic N-alkylamides.
Disciplines :
Chemistry
Author, co-author :
Laurent, Pascal ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Razafindralambo, Hary ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Wathelet, Bernard ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Blecker, Christophe ; Université de Liège - ULiège > Chimie et bio-industries > Technologie des industries agro-alimentaires
Wathelet, Jean-Paul ; Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Paquot, Michel ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Language :
English
Title :
Synthesis and Surface-Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials
VA Timoshchuk 1995 Uronic acids: synthesis and reactions Rus Chem Rev 64 675 703 10.1070/RC1995v064n07ABEH000169
DG Allen BY Tao 1999 Carbohydrate-alkyl ester derivatives as biosurfactants J Surfact Detergents 2 383 390 1:CAS:528:DyaK1MXkslKhurk%3D 10.1007/s11743-999-0093-4
Y Queneau S Chambert C Besset R Cheaib 2008 Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose Carbohydr Res 343 1999 2009 1:CAS:528:DC%2BD1cXnsFOgt74%3D 10.1016/j.carres.2008.02.008
R Sun JM Lawther WB Banks 1996 Fractional and structural characterization of wheat straw hemicelluloses Carbohydr Polym 29 325 331 1:CAS:528:DyaK2sXlsVKg 10.1016/S0144-8617(96)00018-5
MC Jarvis W Forsyth H Duncan 1988 A survey of the pectic content of nonlignified monocot cell walls J Plant Physiol 88 309 314 1:CAS:528: DyaL1MXkslWg 10.1104/pp.88.2.309
H Razafindralambo C Blecker S Mezdour C Deroanne JM Crowet R Brasseur L Lins M Paquot 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 1:CAS:528: DC%2BD1MXntVGjsLw%3D 10.1021/jp903187f
C Blecker S Picciuto G Lognay C Deroanne M Marlier M Paquot 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 1:CAS:528:DC%2BD38XhsVCht7w%3D 10.1006/jcis.2001.8154
B Moreau G Lognay C Blecker JC Brohée F Chéry P Rollin M Paquot M Marlier 2004 Synthesis of novel d-glucuronic acid fatty esters using Candida antartica lipase in tert-butanol Biotechnol Lett 26 419 424 1:CAS:528:DC%2BD2cXhslChtLw%3D 10.1023/B:BILE.0000018262.57902.68
B Moreau G Lognay C Blecker J Destain P Gerbaux F Chéry P Rollin M Paquot M Marlier 2007 Chromatographic, Spectrometric and NMR Characterization of a New Set of Glucuronic Acid Esters Synthesized by Lipase Biotechnol Agron Soc Environ 11 9 17 1:CAS:528:DC%2BD2sXltlSqtLg%3D
C Blecker S Danthine M Petre G Lognay B Moreau L Vander Elst M Paquot C Deroanne 2008 Enzymatically prepared n-alkyl esters of glucuronic acid: the effect of freeze-drying conditions and hydrophobic chain length on thermal behaviour J Colloid Interface Sci 321 154 158 1:CAS:528:DC%2BD1cXjvFOht78%3D 10.1016/j.jcis.2008.02.002
M Fieser LF Fieser E Toromanoff Y Hirata H Heymann M Tefft S Bhattacharya 1956 Synthetic emulsifying agents J Am Chem Soc 78 2825 2832 1:CAS:528:DyaG28XnslGhsQ%3D%3D 10.1021/ja01593a049
L Falkowski B Stefanska E Bylec P Kolodziejczyk 1980 An improved method of synthesis of glucuronamides Polymer J Chem 54 599 603 1:CAS:528: DyaL3cXlvVKksrs%3D
C Vogel U Jeschke V Vill H Fisher 1992 d-galacturonic acid derivatives with liquid crystalline properties Liebiegs Annalen der Chemie 11 1171 1177 10.1002/jlac.1992199201192
Perrin DD, Armarego WLF (1988) Purification of laboratory chemicals, 3rd edn. Pergamon Press Oxford, New York
J Sumner S Howell 1935 A method for determination of saccharase activity J Biol Chem 108 51 54 1:CAS:528:DyaA2MXhs12qug%3D%3D
H Razafindralambo C Blecker S Delhaye M Paquot 1995 Application of the quasi-static mode of the drop volume technique to the determination of fundamental surfactant properties J Colloid Interface Sci 174 373 377 1:CAS:528:DyaK2MXotVOmtbY%3D 10.1006/jcis.1995.1404
Boons GJ, Hale KJ (2000) Organic synthesis with carbohydrates; postgraduate chemistry series. Sheffield Academic Press, Sheffield
M Tosin PV Murphy 2002 Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group Org Lett 4 3675 3678 1:CAS:528:DC%2BD38XntVahtb4%3D 10.1021/ol026629j
M Tosin C O'Brien GM Fitzpatrick H Müller-Bunz W Kenneth Glass PV Murphy 2005 Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding J Org Chem 70 4096 4106 1:CAS:528:DC%2BD2MXjtlWkurk%3D 10.1021/jo0501994
D Goffin P Bystricky AS Shashkov M Lynch E Hanon M Paquot A Savage 2009 A systematic NMR determination of α-d-glucooligosaccharides, effect of linkage type, anomeric configuration and combination of different linkages type on 13C chemical shifts for the determination of unknown isomaltooligosaccharides Bull Korean Chem Soc 30 1 7 10.5012/bkcs.2009.30.1.001
JW Kuo DA Swann GD Prestwich 1991 Chemical modification of hyaluronic acid by carbodiimides Bioconjug Chem 2 232 241 1:CAS:528:DyaK3MXkslaisrw%3D 10.1021/bc00010a007
N Follain S Montanari I Jeacomine S Gambarelli MR Vignon 2008 Coupling of amines with polyglucuronic acid: evidence for amide bond formation Carbohydr Polymers 74 333 343 1:CAS:528:DC%2BD1cXhtVWksrfJ 10.1016/j.carbpol.2008.02.016
TC Baddeley RA Howie JMS Skakle JL Wardell 2005 1,2,3,4-Tetra-O-acetyl- β-D-glucopyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K Acta Cryst C61 o711 o714 1:CAS:528:DC%2BD2MXht1Oht7fF
DE Ward CK Rhee 1991 A simple method for the microscale preparation of Mosher's acid chloride Tet Lett 32 7165 7166 1:CAS:528:DyaK38Xht1ygsrw%3D 10.1016/0040-4039(91)80466-J
B Boyd C Drummond I Krodkiewska F Grieser 2000 How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behaviour and the air- water interfacial adsorption of glucose-based surfactants Langmuir 16 7359 7367 1:CAS:528:DC%2BD3cXlslGqtb8%3D 10.1021/la991573w