headerpos: 9513
 
 
  Oil Shale

ISSN 1736-7492 (electronic)  ISSN 0208-189X (print)
Published since 1984

Oil Shale

ISSN 1736-7492 (electronic)  ISSN 0208-189X (print)
Published since 1984

Publisher
Journal Information
» Editorial Policy
» Editorial Board
Extra
Guidelines for Authors
» For Authors
» Instructions to Authors
» Copyright Transfer Form
Guidelines for Reviewers
» For Reviewers
» Review Form
Subscription Information
Support & Contact
List of Issues
» 2019
Vol. 36, Issue 2S
Vol. 36, Issue 2
Vol. 36, Issue 1
» 2018
» 2017
» 2016
» 2015
» 2014
» 2013
» 2012
» 2011
» 2010
» 2009
» 2008
» Back Issues
» Back issues (full texts)
  in Google
Publisher
» Other journals
» Staff

PHENOLS TO PORES TO ADSORPTION. A POTENTIAL ROUTE TOWARDS NEW METHODS FOR EXTRACTING VALUE FROM SHALE OIL SIDE STREAM; pp. 128–141

(Full article in PDF format) https://doi.org/10.3176/oil.2019.2S.04


Authors

ALLAN NIIDU

Abstract

side stream of shale oil production contains alkylresorcinols as main constituents, which could prove to be useful intermediates to highly porous and versatile materials – metal-organic frameworks (MOFs). The latter structures have been used as adsorbents for various organic and inorganic compounds, including organic sulfur containing molecules. In the current work, a pathway from phenolic compounds in shale oil toward metal-organic framework linkers was indicated and its utility was proved by using related metal-organic frameworks as effective adsorbents for sulfur from model fuels exemplified in the form of benzothiophene (BT) and isooctane, respectively.

Keywords

shale oil, alkylresorcinol, metal-organic framework, adsorption, sulfur.

References

1.      Kreek , K. , Kriis , K. , Maaten , B. , Uibu , M. , Mere , A. , Kanger , T. , Koel , M. Organic and carbon aerogels containing rare-earth metals: Their properties and application as catalysts. J. Non-Cryst. Solids. 2014 , 404 , 43–48.
https://doi.org/10.1016/j.jnoncrysol.2014.07.021

2.      Kamal , A. , Robertson , A. , Tittensor , E. Hydroxy-carbonyl compounds. Part XIV. The syntheses of some isocoumarins. J. Chem. Soc. Resumed , 1950 , No. 0 , 3375–3380. https://doi.org/10.1039/JR9500003375

3.      Samokhvalov , A. Adsorption on mesoporous metal–organic frameworks in solution: Aromatic and heterocyclic compounds. Chem. Eur. J. , 2015 , 21(47) , 16726–16742.
https://doi.org/10.1002/chem.201502317

4.      Khan , N. A. , Jhung , S. H. Scandium-triflate/metal-organic frameworks: Remarkable adsorbents for desulfurization and denitrogenation. Inorg. Chem. , 2015 , 54(23) , 11498–11504.
https://doi.org/10.1021/acs.inorgchem.5b02118

5.      Ahmed , I. , Jhung , S. H. Adsorptive desulfurization and denitrogenation using metal-organic frameworks. J. Hazard. Mater. , 2016 , 301 , 259–276.
https://doi.org/10.1016/j.jhazmat.2015.08.045

6.      Hu , Z. , Zhao , D. De facto methodologies toward the synthesis and scale-up production of UiO-66-type metal–organic frameworks and membrane materials. Dalton T. , 2015 , 44 , 19018–19040.
https://doi.org/10.1039/C5DT03359D

7.      Rubio-Martinez , M. , Avci-Camur , C. , Thornton , A. W. , Imaz , I. , Maspoch , D. , Hill , M. R. New synthetic routes towards MOF production at scale. Chem. Soc. Rev. , 2017 , 46(11) , 3453–3480.
https://doi.org/10.1039/C7CS00109F

8.      Kandiah , M. , Nilsen , M. H.; Usseglio , S. , Jakobsen , S. , Olsbye , U. , Tilset , M. , Larabi , C. , Quadrelli , E. A. , Bonino , F. , Lillerud , K. P. Synthesis and stability of tagged UiO-66 Zr-MOFs. Chem. Mater. , 2010 , 22(24) , 6632–6640.
https://doi.org/10.1021/cm102601v

9.      DeCoste , J. B. , Peterson , G. W. , Jasuja , H. , Glover , T. G. , Huang , Y. , Walton , K. S. Stability and degradation mechanisms of metal–organic frameworks containing the Zr6O4(OH)4 secondary building unit. J. Mater. Chem. A , 2013 , 1(18) , 5642–5650.
https://doi.org/10.1039/C3TA10662D

10. Liu , X. , Demir , N. K. , Wu , Z. , Li , K. Highly water-stable zirconium metal–organic framework UiO-66 membranes supported on alumina hollow fibers for desalination. J. Am. Chem. Soc. , 2015 , 137(22) , 6999–7002.
https://doi.org/0.1021/jacs.5b02276

11. Valenzano , L. , Civalleri , B. , Chavan , S. , Bordiga , S. , Nilsen , M. H. , Jakobsen , S. , Lillerud , K. P. , Lamberti , C. Disclosing the complex structure of UiO-66 metal organic framework: A synergic combination of experiment and theory. Chem. Mater. , 2011 , 23(7) , 1700–1718.
https://doi.org/10.1021/cm1022882

12. Krtschil , U. , Hessel , V. , Kost , H.-J. , Reinhard , D. Kolbe-Schmitt flow synthesis in aqueous solution – from lab capillary reactor to pilot plant. Chem. Eng. Technol ,. 2013 , 36(6) , 1010–1016.
https://doi.org/10.1002/ceat.201200633

13. Tomás , R. A. F. , Bordado , J. C. M. , Gomes , J. F. P. p-Xylene oxidation to terephthalic acid: A literature review oriented toward process optimization and development. Chem. Rev. , 2013 , 113(10) , 7421–7469.
https://doi.org/10.1021/cr300298j

14. Li , J.-R. , Sculley , J. , Zhou , H.-C. Metal–organic frameworks for separations. Chem. Rev. , 2012 , 112(2) , 869–932.
https://doi.org/10.1021/cr200190s

15. Farrusseng , D. , Aguado , S. , Pinel , C. Metal–organic frameworks: opportunities for catalysis. Angew. Chem. Int. Edit. , 2009 , 48(41) , 7502–7513.
https://doi.org/10.1002/anie.200806063

16. Crombie , L. , Games , D. E. , James , A. W. G. Reactions of fused and unfused α-pyrones with magnesium alkoxide , sodium alkoxide and water as the nucleophile: effects of chelation. J. Chem. Soc. , Perk. 1 , 1996 , 22 , 2715–2724.
https://doi.org/10.1039/P19960002715

17. Qu , R.-Y. , Liu , Y.-C. , Wu , Q.-Y. , Chen , Q. , Yang , G.-F. An efficient method for syntheses of functionalized 6-bulkysubstituted salicylates under microwave irradiation. Tetrahedron , 2015 , 71(42) , 8123–8130.
https://doi.org/10.1016/j.tet.2015.08.040

18. Fadzil , N. A. M. , Rahim , M. H. A. , Maniam , G. P. A brief review of para-xylene oxidation to terephthalic acid as a model of primary C–H bond activation. Chinese J. Catal. , 2014 , 35(10) , 1641–1652.
https://doi.org/10.1016/S1872-2067(14)60193-5

19. Wuensch , C. , Glueck , S. M. , Gross , J. , Koszelewski , D. , Schober , M. , Faber , K. Regioselective enzymatic carboxylation of phenols and hydroxystyrene derivatives. Org. Lett. , 2012 , 14(8) , 1974–1977.
https://doi.org/10.1021/ol300385k

20. Wuensch , C. , Schmidt , N. , Gross , J. , Grischek , B. , Glueck , S. M. , Faber , K. Pushing the equilibrium of regio-complementary carboxylation of phenols and hydroxystyrene derivatives. J. Biotechnol. , 2013 , 168(3) , 264–270.
https://doi.org/10.1016/j.jbiotec.2013.07.017

21. Harris , C. M. , Kibby , J. J. , Fehlner , J. R. , Raabe , A. B. , Barber , T. A. , Harris , T. M. Amino acid constituents of ristocetin A. J. Am. Chem. Soc. , 1979 , 101(2) , 437–445.
https://doi.org/10.1021/ja00496a028

22. Sakurai , J. , Kikuchi , T. , Takahashi , O. , Watanabe , K. , Katoh , T. Enantioselective total synthesis of (+)-stachyflin: A potential anti-influenza A virus agent isolated from a microorganism. Eur. J. Org. Chem. , 2011 , 2011(16) , 2948–2957.
https://doi.org/10.1002/ejoc.201100173

23. Katz , M. J. , Brown , Z. J. , Colon , Y. J. , Siu , P. W. , Scheidt , K. A. , Snurr , R. Q. , Hupp , J. T. , Farha , O. K. A facile synthesis of UiO-66 , UiO-67 and their derivatives. Chem. Commun. 2013 , 49(82) , 9449–9451.
https://doi.org/10.1039/C3CC46105J

24. Rimoldi , M. , Howarth , A. J. , De Stefano , M. R. , Lin , L. , Goswami , S. , Li , P. , Hupp , J. T. , Farha , O. K. Catalytic zirconium/hafnium-based metal–organic frameworks. ACS Catal. , 2017 , 7(2) , 997–1014.
https://doi.org/10.1021/acscatal.6b02923

25. Wang , C. , Volotskova , O. , Lu , K. , Ahmad , M. , Sun , C. , Xing , L. , Lin , W. Synergistic assembly of heavy metal clusters and luminescent organic bridging ligands in metal–organic frameworks for highly efficient X-ray scintillation. J. Am. Chem. Soc. , 2014 , 136(17) , 6171–6174.
https://doi.org/10.1021/ja500671h

26. Cliffe , M. J. , Wan , W. , Zou , X. , Chater , P. A. , Kleppe , A. K. , Tucker , M. G. , Wilhelm , H. , Funnell , N. P. , Coudert , F.-X. , Goodwin , A. L. Correlated defect nanoregions in a metal–organic framework. Nat. Commun. , 2014 , 5(1) , 4176–4183.
https://doi.org/10.1038/ncomms5176

27. Shearer , G. C. , Chavan , S. , Bordiga , S. , Svelle , S. , Olsbye , U. , Lillerud , K. P. Defect engineering: Tuning the porosity and composition of the metal–organic framework UiO-66 via modulated synthesis. Chem. Mater. , 2016 , 28(11) , 3749–3761.
https://doi.org/10.1021/acs.chemmater.6b00602

28. Ho , Y.-S. Second-order kinetic model for the sorption of cadmium onto tree fern: A comparison of linear and non-linear methods. Water Res. , 2006 , 40(1) , 119–125.
https://doi.org/10.1016/j.watres.2005.10.040

29. Nouri , L. , Ghodbane , I. , Hamdaoui , O. , Chiha , M. Batch sorption dynamics and equilibrium for the removal of cadmium ions from aqueous phase using wheat bran. J. Hazard. Mater. , 2007 , 149(1) , 115–125.
https://doi.org/10.1016/j.jhazmat.2007.03.055

30. Van de Voorde , B. , Hezinova , M. , Lannoeye , J. , Vandekerkhove , A. , Marszalek , B. , Gil , B. , Beurroies , I. , Nachtigall , P. , De Vos , D. Adsorptive desulfurization with CPO-27/MOF-74: an experimental and computational investigation. Phys. Chem. Chem. Phys. , 2015 , 17(16) , 10759–10766.
https://doi.org/10.1039/C5CP01063B

31. Bolster , C. H. , Hornberger , G. M. On the use of linearized Langmuir equations. Soil Sci. Soc. Am. J. 2007 , 71(6) , 1796–1806.
https://doi.org/10.2136/sssaj2006.0304

32. Bagheri , M. , Masoomi , M. Y. , Morsali , A. High organic sulfur removal performance of a cobalt based metal-organic framework. J. Hazard. Mater. , 2017 , 331 , 142–149.
https://doi.org/10.1016/j.jhazmat.2017.02.037

33. Zuyi , T. , Taiwei , C. On the applicability of the Langmuir equation to estimation of adsorption equilibrium constants on a powdered solid from aqueous solution. J. Colloid Interf. Sci. , 2000 , 231(1) , 8–12.
https://doi.org/10.1006/jcis.2000.7057

34. He , W.-W. , Yang , G.-S. , Tang , Y.-J. , Li , S.-L. , Zhang , S.-R.; Su , Z.-M. ,
Lan , Y.-Q. Phenyl groups result in the highest benzene storage and most efficient desulfurization in a series of isostructural metal–organic frameworks. Chem. Eur. J. , 2015 , 21(27) , 9784–9789.
https://doi.org/10.1002/chem.201500815

 

 
Back

Current Issue: Vol. 36, Issue 2S, 2019




Publishing schedule:
No. 1: 20 March
No. 2: 20 June
No. 3: 20 September
No. 4: 20 December