Skip to main content
SpringerLink
Log in

Copper(II) and iron(II) tetraamino- and tetrasulfophthalocyanines supported on cellulose: synthesis, characterization and catalytic activity on aerobic oxidation of alkyl arenes and alcohols

  • Original Paper
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

Functionalized cellulose with copper(II) and iron(II) tetraamino- and tetrasulfophthalocyanines (CuTAPc@cellulose, CuTSPc@cellulose, FeTAPc@cellulose, and FeTSPc@cellulose) have been synthesized and their structures characterized by FT-IR, elemental analysis, UV–Vis, X-ray diffraction, flame atomic absorption spectroscopy, thermogravimetric analysis, and scanning electron microscopy. The catalytic activity of synthesized catalysts was examined for the aerobic oxidation of alkyl arenes and alcohols to their corresponding carbonyl compounds. We found the best catalyst is the CuTSPc@cellulose from the solvent, conversion, temperature, and reaction time point of views. These catalysts can be readily recycled and reused for several runs without any significant loss of efficiency.

Graphical Abstract

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

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

Similar content being viewed by others

References

  • Alzeer J, Roth PJC, Luedtke NW (2009) An efficient two-step synthesis of metal-free phthalocyanines using a Zn(II) template. Chem Commun 15:1970–1971

    Article  Google Scholar 

  • Atalla RH, Nagel SC (1974) Cellulose: its regeneration in the native lattice. Science 185:522–523

    Article  CAS  Google Scholar 

  • Burke D, Danheiser RL (1999) Handbook of reagents for organic synthesis, oxidizing and reducing agents. Wiley, Chichester

    Google Scholar 

  • Chen SL, Huang XJ, Xu ZK (2011) Functionalization of cellulose nanofiber mats with phthalocyanine for decoloration of reactive dye wastewater. Cellulose 18:1295–1303

    Article  CAS  Google Scholar 

  • Chen SL, Huang XJ, Xu ZK (2012) Effect of a spacer on phthalocyanine functionalized cellulose nanofiber mats for decolorizing reactive dye wastewater. Cellulose 19:1351–1359

    Article  CAS  Google Scholar 

  • Chtchigrovsky M, Lin Y, Ouchaou K, Chaumontet M, Robitzer M, Quignard F, Taran F (2012) Dramatic effect of the gelling cation on the catalytic performances of alginate-supported palladium nanoparticles for the Suzuki–Miyaura reaction. Chem Mater 24:1505–1510

    Article  CAS  Google Scholar 

  • Cornils B, Herrmann WA (1996) Applied homogeneous catalysis with organometallic compounds. VCH, Weinheim

    Book  Google Scholar 

  • DeOliveira E, Neri CR, Ribeiro AO, Garcia VS, Costa LL, Moura AO, Prado AGS, Serra OA, Iamamoto Y (2008) Hexagonal mesoporous silica modified with copper phthalocyanine as a photocatalyst for pesticide 2,4-dichlorophenoxiacetic acid degradation. J Colloid Interface Sci 323:98–104

    Article  CAS  Google Scholar 

  • Firouzabadi H, Iranpoor N, Ghaderi A (2011) Gelatin as a bioorganic reductant, ligand and support for palladium nanoparticles. Application as a catalyst for ligand- and amine-free Sonogashira–Hagihara reaction. Org Biomol Chem 9:865–871

    Article  CAS  Google Scholar 

  • Fleysher MH, Richards WB (1963) Process of preparing metal-containing phthalocyanine sulfonic acids. US Patent 3091618 A

  • Geraskin IM, Luedtke MW, Neu HM, Nemykin VN, Zhdankin VV (2008) Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols. Tetrahedron Lett 49:7410–7412

    Article  CAS  Google Scholar 

  • Guibal E (2005) Heterogeneous catalysis on chitosan-based materials: a review. Prog Polym Sci 30:71–109

    Article  CAS  Google Scholar 

  • Hamza A, Srinivas D (2009) Selective oxidation of benzyl alcohol over copper phthalocyanine immobilized on MCM-41. Catal Lett 128:434–442

    Article  CAS  Google Scholar 

  • Huang J, Xiao H, Li B, Wang J, Jiang D (2006) Immobilization of Pycnoporus sanguineus laccase on copper tetra-aminophthalocyanine–Fe3O4 nanoparticle composite. Biotechnol Appl Biochem 44:93–100

    Article  CAS  Google Scholar 

  • Klenke EF (1962) Preparation of sulfonated phthalocyanines, US Patent 3041347 A

  • Lengke MF, Fleet ME, Southam G (2007) Synthesis of palladium nanoparticles by reaction of filamentous cyanobacterial biomass with a palladium(II) chloride complex. Langmuir 23:8982–8987

    Article  CAS  Google Scholar 

  • Lindner O, Rodefeld L (2005) Benzenesulfonic acids and their derivatives. Ullmann’s Encyclopedia of Industrial Chemistry. Wiley, Weinheim

    Google Scholar 

  • Mahyari M, Shaabani A (2014) Graphene oxide-iron phthalocyanine catalyzed aerobic oxidation of alcohols. Appl Catal A Gen 469:524–531

    Article  CAS  Google Scholar 

  • Mahyari M, Laeini MS, Shaabani A (2014) Aqueous aerobic oxidation of alkyl arenes and alcohols catalyzed by copper(II) phthalocyanine supported on three-dimensional nitrogen-doped graphene at room temperature. Chem Commun 50:7855–7857

    Article  CAS  Google Scholar 

  • Moon RJ, Martini A, Nairn J, Simonsen J, Youngblood J (2011) Cellulose nanomaterials review: structure, properties and nanocomposites. Chem Soc Rev 40:3941–3994

    Article  CAS  Google Scholar 

  • Muzart J (2006) Ionic liquids as solvents for catalyzed oxidations of organic compounds. Adv Synth Catal 348:275–295

    Article  CAS  Google Scholar 

  • Rahn K, Diamantoglou M, Klemm D, Berghmans H, Heinze T (1996) Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamidel/LiCl solvent system. Die Angew Makromol Chem 238:143–163

    Article  CAS  Google Scholar 

  • Rezaeifard A, Jafarpour M, Naeimi A, Salimi M (2012) Efficient and highly selective aqueous oxidation of alcohols and sulfides catalyzed by reusable hydrophobic copper(II) phthalocyanine. Inorg Chem Commun 15:230–234

    Article  CAS  Google Scholar 

  • Safari N, Jamaat PR, Pirouzmand M, Shaabani A (2004) Synthesis of metallophthalocyanines using microwave irradiation under solvent free and reflux conditions. J Porphyr Phthalocyanines 8:1209–1213

    Article  CAS  Google Scholar 

  • Seyyedhamzeh M, Ganji N, Shaabani A (2012) Controlled microwave-assisted synthesis of metallophthalocyanines. J Porphyr Phthalocyanines 16:1110–1113

    Article  CAS  Google Scholar 

  • Shaabani A (1998) Synthesis of metallophthalocyanines under solvent-free conditions using microwave irradiation. J Chem Res (S) 10:672–673

    Article  Google Scholar 

  • Shi J (2013) On the synergetic catalytic effect in heterogeneous nanocomposite catalysts. Chem Rev 113:2139–2181

    Article  CAS  Google Scholar 

  • Sorokin AB (2013) Phthalocyanine metal complexes in catalysis. Chem Rev 113:8152–8191

    Article  CAS  Google Scholar 

  • Su DS, Perathoner S, Centi G (2013) Nanocarbons for the development of advanced catalysts. Chem Rev 113:5782–5816

    Article  CAS  Google Scholar 

  • Taylor RJK, Reid M, Foot J, Raw SA (2005) Tandem oxidation processes using manganese dioxide: discovery, applications, and current studies. Acc Chem Res 38:851–869

    Article  CAS  Google Scholar 

  • Verma S, Jain SL, Sain B (2011) Starch immobilized ruthenium trichloride catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide. ChemCatChem 3:1329–1332

    Article  CAS  Google Scholar 

  • Yu HY, Chen GY, Wang YB, Yao JM (2015) A facile one-pot route for preparing cellulose nanocrystal/zinc oxide nanohybrids with high antibacterial and photocatalytic activity. Cellulose 22:261–273

    Article  CAS  Google Scholar 

  • Zalomaeva OV, Zaikovskii VI, Kovalenko KA, Kaichev VV, Chesalov YA, Sorokin AB, Mel’gunov MS, Kholdeeva OA, Fedin VP (2011) Iron tetrasulfophthalocyanine immobilized on metal organic framework MIL-101: synthesis, characterization and catalytic properties. Dalton Trans 40:1441–1444

    Article  CAS  Google Scholar 

  • Zhang J, Xia CG (2003) Natural biopolymer-supported bimetallic catalyst system for the carbonylation to esters of Naproxen. J Mol Catal A Chem 206:59–65

    Article  CAS  Google Scholar 

  • Zhang Y, Mo G, Li X, Ye J (2012) Iron tetrasulfophthalocyanine functionalized graphene as a platinum-free cathodic catalyst for efficient oxygen reduction in microbial fuel cells. J Power Sources 197:93–96

    Article  CAS  Google Scholar 

  • Zhong JP, Fan YJ, Wang H, Wang RX, Shen XC, Shi ZJ, Fan LL (2013) Copper phthalocyanine functionalization of graphene nanosheets as support for platinum nanoparticles and their enhanced performance toward methanol oxidation. J Power Sources 242:208–215

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support from the Iran National Science Foundation (INSF) and Research Council of Shahid Beheshti University.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani & Zeinab Hezarkhani

Authors
  1. Ahmad Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zeinab Hezarkhani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad Shaabani.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shaabani, A., Hezarkhani, Z. Copper(II) and iron(II) tetraamino- and tetrasulfophthalocyanines supported on cellulose: synthesis, characterization and catalytic activity on aerobic oxidation of alkyl arenes and alcohols. Cellulose 22, 3027–3046 (2015). https://doi.org/10.1007/s10570-015-0708-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-015-0708-x

Keywords

Search

Navigation