Skip to main content
SpringerLink
Log in

Optimization of guar gum galactomannan sulfation process with sulfamic acid

  • Original Article
  • Published:
Biomass Conversion and Biorefinery Aims and scope Submit manuscript

Abstract

Galactomannans are plant polysaccharides with the beneficial properties, which have a wide range of industrial application. The most important galactomannan derivatives are sulfates, which exhibit the anticoagulant and other biological activities. Here, we report on the results of investigations of the effect of urea-based solvents and activators on the sulfation of galactomannan guar gum with sulfamic acid. It has been shown that 1,4-dioxane is the most effective solvent, while urea is the most effective activator of the sulfation process. The numerical optimization (the Box‒Behnken design) of sulfation of galactomannan guar gum with sulfamic acid in the presence of the most effective activator has been carried out. It has been established that the optimal conditions for obtaining the galactomannan sulfates are a sulfamic acid amount of 34 mmol per 1 g of galactomannan, a temperature of 85 °C, and a time of 2.6 h. The introduction of a sulfate group into a galactomannan molecule has been proven by Fourier transform infra-red spectroscopy. It has been found that the Fourier transform infra-red spectrum of sulfated galactomannan contains absorption bands at 1249 and 817 cm‒1, which correspond to vibrations of the sulfate group. It has been demonstrated using gel permeation chromatography that, during sulfation of guar gum galactomannan by a complex of sulfamic acid and 1,4-dioxane, the molecular weight decreases from 8.5 × 105 to 3.0 × 105 g/mol and the polydispersity value increases from 1.816 to 2.049.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Thombare N, Jha U, Mishra S, Siddiqui MZ (2016) Guar gum as a promising starting material for diverse applications: a review. Int J Biol Macromol 88:361–372. https://doi.org/10.1016/j.ijbiomac.2016.04.001

    Article  Google Scholar 

  2. Reddy K, Mohan GK, Satla S, Gaikwad S (2011) Natural polysaccharides: versatile excipients for controlled drug delivery systems. Asian J Pharm Sci 6(6):275–286

    Google Scholar 

  3. Liu J, Willför S, Xu C (2015) A review of bioactive plant polysaccharides: biological activities, functionalization, and biomedical applications. Bioact Carbohydr Diet Fibre 5(1):31–61. https://doi.org/10.1016/j.bcdf.2014.12.001

    Article  Google Scholar 

  4. Ahmad S, Ahmad M, Manzoor K, Purwar R, Ikram S (2019) A review on latest innovations in natural gums-based hydrogels: preparations & applications. Int J Biol Macromol. https://doi.org/10.1016/j.ijbiomac.2019.06.113

    Article  Google Scholar 

  5. Nussinovitch A (2010) Plant gum exudates of the world: sources, distribution, properties, and applications CRC Press/Taylor & Francis, Boca Raton

  6. Williams PA (2011) Renewable resources for functional polymers and biomaterials. Polysaccharides, proteins and polyesters. RSC Polymer Chemistry Series. Royal Society of Chemistry, Cambridge.

  7. Mudgil D, Barak S, Khatkar BS (2011) Guar gum: processing, properties and food applications—a review. J Food Sci Technol 51(3):409–418. https://doi.org/10.1007/s13197-011-0522-x

    Article  Google Scholar 

  8. Yamamoto Y (2001) Hypolipidemic effects of a guar gum-xanthan gum mixture in rats fed high sucrose diet. J Jpn Soc Nutr Food Sci 54:139–145

    Article  Google Scholar 

  9. Zhang L-M, Zhou J-F, Hui PS (2005) A comparative study on viscosity behavior of water-soluble chemically modified guar gum derivatives with different functional lateral groups. J Sci Food Agric 85(15):2638–2644. https://doi.org/10.1002/jsfa.2308

    Article  Google Scholar 

  10. Hasan AMA, Abdel-Raouf ME (2018) Applications of guar gum and its derivatives in petroleum industry: a review. Egypt J Pet. https://doi.org/10.1016/j.ejpe.2018.03.005

    Article  Google Scholar 

  11. Jano A, Lame GA, Kokalari TE (2012) Use of extracted green inhibitors as a friendly choice in corrosion protection of low alloy carbon steel Kemija u industriji. J Chem Chem Eng 61(11–12):497–503. https://doi.org/10.15255/KUI.2012.013

    Article  Google Scholar 

  12. About S, Zouarhi M, Chebabe D, Damej M, Berisha A, Hajjaji N (2020) Galactomannan as a new bio-sourced corrosion inhibitor for iron in acidic media. Heliyon 6(3):e03574. https://doi.org/10.1016/j.heliyon.2020.e03574

    Article  Google Scholar 

  13. Adewole JK, Muritala KB (2019) Some applications of natural polymeric materials in oilfield operations: a review. J Petroleum Exploration Prod Technol 9(3):2297–2307. https://doi.org/10.1007/s13202-019-0626-9

    Article  Google Scholar 

  14. Mothé CG, Correia DZ, de França FP, Riga AT (2006) Thermal and rheological study of polysaccharides for enhanced oil recovery. J Therm Anal Calorim 85:31–36. https://doi.org/10.1007/s10973-005-7339-7

    Article  Google Scholar 

  15. Dodi G, Hritcu D, Popa M (2011) Carboxymethylation of guar gum: synthesis and characterization. Cellul Chem Technol 45:171

    Google Scholar 

  16. Gong H, Liu M, Chen J, Han F, Gao C, Zhang B (2012) Synthesis and characterization of carboxymethyl guar gum and rheological properties of its solutions. Carbohyd Polym 88(3):1015–1022. https://doi.org/10.1016/j.carbpol.2012.01.057

    Article  Google Scholar 

  17. Shaikh T, Kumar SS (2011) Pharmaceutical and pharmacological profile of guar gum an overview. Int J Pharm Pharm Sci 3:38–40

    Google Scholar 

  18. Lapasin R, De Lorenzi L, Pricl S, Torriano G (1995) Flow properties of hydroxypropyl guar gum and its long-chain hydrophobic derivatives. Carbohyd Polym 28(3):195–202. https://doi.org/10.1016/0144-8617(95)00134-4

    Article  Google Scholar 

  19. Shi H-Y, Zhang L-M (2007) New grafted polysaccharides based on O-carboxymethyl-O-hydroxypropyl guar gum and N-isopropylacrylamide: synthesis and phase transition behavior in aqueous media. Carbohyd Polym 67(3):337–342. https://doi.org/10.1016/j.carbpol.2006.06.005

    Article  Google Scholar 

  20. Shenoy MA, D’Melo DJ (2010) Synthesis and characterization of acryloyloxy guar gum. J Appl Polym Sci 117:148–154. https://doi.org/10.1002/app.31872

    Article  Google Scholar 

  21. Mestechkina NM, Egorov AV, Shcherbukhin VD (2006) Synthesis of galactomannan sulfates. Appl Biochem Microbiol 42:326. https://doi.org/10.1134/S0003683806030185

    Article  Google Scholar 

  22. Zhang Z, Wang H, Chen T, Zhang H, Liang J, Kong W, Yao J, Zhang J, Wang J (2019) Synthesis and structure characterization of sulfated galactomannan from fenugreek gum. Int J Biol Macromol 125:1184–1191. https://doi.org/10.1016/j.ijbiomac.2018.09.113

    Article  Google Scholar 

  23. Wang X, Wang J, Zhang J, Zhao B, Yao J, Wang Y (2009) Structure-antioxidant relationships of sulfated galactomannan from guar gum. Int J Biol Macromol 46(1):59–66. https://doi.org/10.1016/j.ijbiomac.2009.10.004

    Article  Google Scholar 

  24. Kazachenko AS, Akman F, Sagaama A, Issaoui N, Malyar YN, Vasilieva NY, Borovkova VS (2021) Theoretical and experimental study of guar gum sulfation. J Mol Model 27(1):5. https://doi.org/10.1007/s00894-020-04645-5

    Article  Google Scholar 

  25. Kazachenko AS, Malyar YUN, Vasilyeva NYU, Bondarenko GN, Korolkova IV, Antonov AV, Karacharov AA, Fetisova OYU, Skvortsova GP (2020) Green synthesis and characterization of galactomannan sulfates obtained using sulfamic acid. Biomass Conv Bioref. https://doi.org/10.1007/s13399-020-00855-2

    Article  Google Scholar 

  26. Vasilyeva NYu, Levdansky AV, Kuznetsov BN, Skvortsova GP, Kazachenko AS, Djakovitch L, Pinel C (2015) Sulfation of arabinogalactan by sulfamic acid in dioxane. Russ J Bioorg Chem 41:725–731. https://doi.org/10.1134/S1068162015070158

    Article  Google Scholar 

  27. Kazachenko AS, Vasilyeva NYU, Sudakova IG, Levdansky VA, Lutoshkin MA, Kuznetsov BN (2020) Numerical optimization of the abies ethanol lignin sulfation process with sulfamic acid in 1 4 dioxane medium in the presence of urea. J Sib Fed Univ Chem 13(2):232–246. https://doi.org/10.17516/1998-2836-0178

    Article  Google Scholar 

  28. Pen RZ (2014) Planning an experiment at Statgraphics Centurion. Krasnoyarsk: SibSTU, 2014. 293.

  29. Wang X, Wang J, Zhang J, Zhao B, Yao J, Wang Y (2010) Structure–antioxidant relationships of sulfated galactomannan from guar gum. Int J Biol Macromol 46(1):59–66. https://doi.org/10.1016/j.ijbiomac.2009.10.004

    Article  Google Scholar 

  30. Al-Horani RA, Desai UR (2010) Chemical sulfation of small molecules – advances and challenges. Tetrahedron 66(16):2907–2918. https://doi.org/10.1016/j.tet.2010.02.015

    Article  Google Scholar 

  31. Akman F, Kazachenko AS, Vasilyeva NYu, Malyar YuN (2020) Synthesis and characterization of starch sulfates obtained by the sulfamic acid-urea complex. J Mol Struc 1208:127899. https://doi.org/10.1016/j.molstruc.2020.127899

    Article  Google Scholar 

  32. Spillane W, Malaubier JB (2014) Sulfamic acid and its N- and O-substituted derivatives chemical reviews. 114(4):2507–2586. https://doi.org/10.1021/cr400230c

  33. Kuznetsov BN, Vasilyeva NYU, Kazachenko AS, Skvortsova GP, Levdansky VA, Lutoshkin MA (2018) Development of the method of Abies Wood ethanol lignin sulfation using sulfamic acid. J Sib Fed Univ Chem 1(11):122–130. https://doi.org/10.17516/1998-2836-0063

    Article  Google Scholar 

  34. Kuznetsov BN, Levdansky VA, Kuznetsova SA, Garyntseva NV, Sudakova IG, Levdansky AV (2018) Integration of peroxide delignification and sulfamic acid sulfation methods for obtaining cellulose sulfates from aspen wood. Eur J Wood Prod 76(3):999–1007. https://doi.org/10.1007/s00107-017-1262-z

    Article  Google Scholar 

  35. Kazachenko AS, Malyar YuN, Vasilyeva NYu, Fetisova OYu, Chudina AI, Sudakova IG, Antonov AV, Borovkova VS, Kuznetsova SA (2021) Isolation and sulfation of galactoglucomannan from larch wood (Larix Sibirica). Wood Sci Technol. https://doi.org/10.1007/s00226-021-01299-1

    Article  Google Scholar 

  36. Johny LC, Kudre TG, Suresh PV (2021) Production of egg white hydrolysate by digestion with pineapple bromelain: optimization, evaluation and antioxidant activity study. J Food Sci Technol. https://doi.org/10.1007/s13197-021-05188-0

    Article  Google Scholar 

  37. Kazachenko AS, Tomilin FN, Pozdnyakova AA, Vasilyeva NYu, Malyar YuN, Kuznetsova SA, Avramov PV (2020) Theoretical DFT interpretation of infrared spectra of biologically active arabinogalactan sulfated derivatives. Chem Pap. https://doi.org/10.1007/s11696-020-01220-3

    Article  Google Scholar 

  38. Sirviö JA, Ukkola J, Liimatainen H (2019) Direct sulfation of cellulose fibers using a reactive deep eutectic solvent to produce highly charged cellulose nanofibers. Cellulose 26:2303–2316. https://doi.org/10.1007/s10570-019-02257-8

    Article  Google Scholar 

Download references

Acknowledgements

This study was carried out using the equipment of the Krasnoyarsk Regional Center for Collective Use, Krasnoyarsk Science Center, Siberian Branch of the Russian Academy of Sciences.

Funding

This study was supported by the Russian Foundation for Basic Research, Government of the Krasnoyarsk Territory, and Krasnoyarsk Territorial Foundation for Support of Scientific and R&D Activities, project no. 20–43-243001. This study was carried out within the budget project #0287–2021-0017 for the Institute of Chemistry and Chemical Technology, Siberian Branch of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology, Federal Research Center Krasnoyarsk Science Center, Siberian Branch , Russian Academy of Sciences, Akademgorodok 50, bld. 24, Krasnoyarsk, 660036, Russia

    Aleksandr S. Kazachenko, Yuriy N. Malyar, Natalya Yu. Vasilyeva & Valentina S. Borovkova

  2. Siberian Federal University, pr. Svobodny 79, Krasnoyarsk, 660041, Russia

    Aleksandr S. Kazachenko, Yuriy N. Malyar, Natalya Yu. Vasilyeva & Valentina S. Borovkova

  3. Laboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, University of Monastir, 5079, Monastir, Tunisia

    Noureddine Issaoui

Authors
  1. Aleksandr S. Kazachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuriy N. Malyar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Natalya Yu. Vasilyeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Valentina S. Borovkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Noureddine Issaoui
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aleksandr S. Kazachenko.

Ethics declarations

Ethics approval

N/A. This article does not contain any studies with human participants or animals performed by any of the authors.

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher's note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kazachenko, A.S., Malyar, Y.N., Vasilyeva, N.Y. et al. Optimization of guar gum galactomannan sulfation process with sulfamic acid. Biomass Conv. Bioref. 13, 10041–10050 (2023). https://doi.org/10.1007/s13399-021-01895-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13399-021-01895-y

Keywords

Search

Navigation