Skip to main content
Top
Published in: Cellulose 3/2017

01-02-2017 | Original Paper

Chitosan-modified Pd(II)-d-penicillamine: preparation, characterization, and catalyst application

Authors: Sajjad Keshipour, Farivar Ahmadi, Behnam Seyyedi

Published in: Cellulose | Issue 3/2017

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

A new derivative of chitosan was prepared via a chemical modification process which included chemical bonding of chitosan with d-penicillamine and anchoring of Pd(II) to the chitosan-d-penicillamine. Chitosan-modified Pd(II)-d-penicillamine was characterized by FT-IR, CHNS analysis, flame absorption atomic spectroscopy, energy dispersive X-ray spectroscopy, X-ray diffraction pattern and thermal gravimetric analysis. The importance of biopolymers in the catalytic transformation led us to use the synthesized compound as a catalyst in the oxidation reaction of benzyl alcohol to benzoic acid. High yield and excellent selectivity was achieved for the selective oxidation of benzyl alcohol in H2O at room temperature using H2O2 as a green oxidant during 24 h. The reaction has some advantages such as green and mild reaction conditions, high yield, excellent selectivity, green oxidant and short reaction conditions. Also, the catalyst is a stable compound and the recovered catalyst is usable for 4 times without any significant decrease in the yield.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Literature
go back to reference Baig RBN, Nadagouda MN, Varma RS (2014) Ruthenium on chitosan: a recyclable heterogeneous catalyst for aqueous hydration of nitriles to amides. Green Chem 16:2122–2127CrossRef Baig RBN, Nadagouda MN, Varma RS (2014) Ruthenium on chitosan: a recyclable heterogeneous catalyst for aqueous hydration of nitriles to amides. Green Chem 16:2122–2127CrossRef
go back to reference Barakat MA (2011) New trends in removing heavy metals from industrial wastewater. Arab J Chem 4:361–377CrossRef Barakat MA (2011) New trends in removing heavy metals from industrial wastewater. Arab J Chem 4:361–377CrossRef
go back to reference Chtchigrovsky M, Primo A, Gonzalez P, Molvinger K, Robitzer M, Quignard F, Taran F (2009) Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3 + 2] Huisgen cycloaddition. Angew Chem Int Ed 48:5916–5920CrossRef Chtchigrovsky M, Primo A, Gonzalez P, Molvinger K, Robitzer M, Quignard F, Taran F (2009) Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3 + 2] Huisgen cycloaddition. Angew Chem Int Ed 48:5916–5920CrossRef
go back to reference Dekamin MG, Azimoshan M, Ramezani L (2013) Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chem 15:811–820CrossRef Dekamin MG, Azimoshan M, Ramezani L (2013) Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chem 15:811–820CrossRef
go back to reference Doornbos D, Faber JS (1964) Studies on metal complexes of drugs. d-Penicillamine and N-acetyl-d-penicillamine. Pharm Weekbl 99:289–309 Doornbos D, Faber JS (1964) Studies on metal complexes of drugs. d-Penicillamine and N-acetyl-d-penicillamine. Pharm Weekbl 99:289–309
go back to reference Guibal E (2004) Interactions of metal ions with chitosan-based sorbents: a review. Sep Purif Technol 38:43–74CrossRef Guibal E (2004) Interactions of metal ions with chitosan-based sorbents: a review. Sep Purif Technol 38:43–74CrossRef
go back to reference Guibal E (2005) Heterogeneous catalysis on chitosan-based materials: a review. Prog Polym Sci 30:71–109CrossRef Guibal E (2005) Heterogeneous catalysis on chitosan-based materials: a review. Prog Polym Sci 30:71–109CrossRef
go back to reference Jiao TF, Zhou J, Zhou JX, Gao LH (2011) Synthesis and characterization of chitosan-based schiff base compounds with aromatic substituent groups. Iran Poly J 20:123–136 Jiao TF, Zhou J, Zhou JX, Gao LH (2011) Synthesis and characterization of chitosan-based schiff base compounds with aromatic substituent groups. Iran Poly J 20:123–136
go back to reference Karthikeyan P, Aswar SA, Muskawar PN, Bhagat PR, Kumar SS (2012) A novel CuCl2/BIL catalyst for direct oxidation of alcohol to acid at ambient temperature. Catal Commun 26:189–193CrossRef Karthikeyan P, Aswar SA, Muskawar PN, Bhagat PR, Kumar SS (2012) A novel CuCl2/BIL catalyst for direct oxidation of alcohol to acid at ambient temperature. Catal Commun 26:189–193CrossRef
go back to reference Keshipour S, Adak K (2016) Pd(0) supported on N-doped graphene quantum dot modified cellulose as an efficient catalyst for the green reduction of nitroaromatics. RSC Adv 6:89407–89412CrossRef Keshipour S, Adak K (2016) Pd(0) supported on N-doped graphene quantum dot modified cellulose as an efficient catalyst for the green reduction of nitroaromatics. RSC Adv 6:89407–89412CrossRef
go back to reference Keshipour S, Kalam Khalteh N (2016) Oxidation of ethylbenzene to styrene oxide in the presence of cellulose-supported Pd magnetic nanoparticles. Appl Organomet Chem 30:653–656CrossRef Keshipour S, Kalam Khalteh N (2016) Oxidation of ethylbenzene to styrene oxide in the presence of cellulose-supported Pd magnetic nanoparticles. Appl Organomet Chem 30:653–656CrossRef
go back to reference Keshipour S, Shaabani A (2014) Copper(I) and palladium nanoparticles supported on ethylenediamine-functionalized cellulose as an efficient catalyst for the 1,3-dipolar cycloaddition/direct arylation sequence. Appl Organometal Chem 28:116–119CrossRef Keshipour S, Shaabani A (2014) Copper(I) and palladium nanoparticles supported on ethylenediamine-functionalized cellulose as an efficient catalyst for the 1,3-dipolar cycloaddition/direct arylation sequence. Appl Organometal Chem 28:116–119CrossRef
go back to reference Keshipour S, Shojaei S, Shaabani A (2013) Palladium nano-particles supported on ethylenediamine functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water. Cellulose 20:973–980CrossRef Keshipour S, Shojaei S, Shaabani A (2013) Palladium nano-particles supported on ethylenediamine functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water. Cellulose 20:973–980CrossRef
go back to reference Kumar S, Singhal N, Singh RK, Gupta P, Singh R, Jain SL (2015) Dual catalysis with magnetic chitosan: direct synthesis of cyclic carbonates from olefins with carbon dioxide using isobutyraldehyde as the sacrificial reductant. Dalton Trans 44:11860–11866CrossRef Kumar S, Singhal N, Singh RK, Gupta P, Singh R, Jain SL (2015) Dual catalysis with magnetic chitosan: direct synthesis of cyclic carbonates from olefins with carbon dioxide using isobutyraldehyde as the sacrificial reductant. Dalton Trans 44:11860–11866CrossRef
go back to reference Li N, Bai R (2006) Development of chitosan-based granular adsorbents for enhanced and selective adsorption performance in heavy metal removal. Water Sci Technol 54:103–113CrossRef Li N, Bai R (2006) Development of chitosan-based granular adsorbents for enhanced and selective adsorption performance in heavy metal removal. Water Sci Technol 54:103–113CrossRef
go back to reference Ma J, Sahai Y (2013) Chitosan biopolymer for fuel cell applications. Carbohydr Polym 92:955–975CrossRef Ma J, Sahai Y (2013) Chitosan biopolymer for fuel cell applications. Carbohydr Polym 92:955–975CrossRef
go back to reference Mohanasrinivasan V, Mishra M, Singh S, Selvarajan E, Suganthi V, Devi CS (2014) Studies on heavy metal removal efficiency and antibacterial activity of chitosan prepared from shrimp shell waste. Biotech 4:167–175 Mohanasrinivasan V, Mishra M, Singh S, Selvarajan E, Suganthi V, Devi CS (2014) Studies on heavy metal removal efficiency and antibacterial activity of chitosan prepared from shrimp shell waste. Biotech 4:167–175
go back to reference Molnár Á, Papp A (2014) The use of polysaccharides and derivatives in palladium-catalyzed coupling reactions. Catal Sci Technol 4:295–310CrossRef Molnár Á, Papp A (2014) The use of polysaccharides and derivatives in palladium-catalyzed coupling reactions. Catal Sci Technol 4:295–310CrossRef
go back to reference Pillai CKS, Paul W, Sharma CP (2009) Chitin and chitosan polymers: chemistry, solubility and fiber formation. Prog Polym Sci 34:641–678CrossRef Pillai CKS, Paul W, Sharma CP (2009) Chitin and chitosan polymers: chemistry, solubility and fiber formation. Prog Polym Sci 34:641–678CrossRef
go back to reference Sahu PK, Gupta SK, Agarwal DD (2014) Chitosan: an efficient, reusable, and biodegradable catalyst for green synthesis of heterocycles. Ind Eng Chem Res 53:2085–2091CrossRef Sahu PK, Gupta SK, Agarwal DD (2014) Chitosan: an efficient, reusable, and biodegradable catalyst for green synthesis of heterocycles. Ind Eng Chem Res 53:2085–2091CrossRef
go back to reference Santilli C, Makarov IS, Fristrup P, Madsen R (2016) Dehydrogenative synthesis of carboxylic acids from primary alcohols and hydroxide catalyzed by a ruthenium N-heterocyclic carbene complex. J Org Chem 81:9931–9938CrossRef Santilli C, Makarov IS, Fristrup P, Madsen R (2016) Dehydrogenative synthesis of carboxylic acids from primary alcohols and hydroxide catalyzed by a ruthenium N-heterocyclic carbene complex. J Org Chem 81:9931–9938CrossRef
go back to reference Shaabani A, Keshipour S, Hamidzad M, Seyyedhamzeh M (2014a) Cobalt(II) supported on ethylenediamine-functionalized nanocellulose as an efficient catalyst for room temperature aerobic oxidation of alcohols. J Chem Sci 126:111–115CrossRef Shaabani A, Keshipour S, Hamidzad M, Seyyedhamzeh M (2014a) Cobalt(II) supported on ethylenediamine-functionalized nanocellulose as an efficient catalyst for room temperature aerobic oxidation of alcohols. J Chem Sci 126:111–115CrossRef
go back to reference Shaabani A, Keshipour S, Hamidzad M, Shaabani S (2014b) Cobalt(II) phthalocyanine covalently anchored to cellulose as are coverable and efficient catalyst for the aerobic oxidation of alkyl arenes and alcohols. J Mol Catal A 395:494–499CrossRef Shaabani A, Keshipour S, Hamidzad M, Shaabani S (2014b) Cobalt(II) phthalocyanine covalently anchored to cellulose as are coverable and efficient catalyst for the aerobic oxidation of alkyl arenes and alcohols. J Mol Catal A 395:494–499CrossRef
go back to reference Sun J, Wang J, Cheng W, Zhang J, Li X, Zhang S, She Y (2012) Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2. Green Chem 14:654–660CrossRef Sun J, Wang J, Cheng W, Zhang J, Li X, Zhang S, She Y (2012) Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2. Green Chem 14:654–660CrossRef
go back to reference Sundeesh N, Sharma SK, Shukla RS (2010) Chitosan as an eco-friendly solid base catalyst for the solvent-free synthesis of jasminaldehyde. J Mol Catal A 321:77–82CrossRef Sundeesh N, Sharma SK, Shukla RS (2010) Chitosan as an eco-friendly solid base catalyst for the solvent-free synthesis of jasminaldehyde. J Mol Catal A 321:77–82CrossRef
go back to reference Toffey A, Samaranayake G, Frazier CE, Glasser WG (1996) Chitin derivatives. I. Kinetics of the heat-induced conversion of chitosan to chitin. J Appl Polym Sci 60:75–85CrossRef Toffey A, Samaranayake G, Frazier CE, Glasser WG (1996) Chitin derivatives. I. Kinetics of the heat-induced conversion of chitosan to chitin. J Appl Polym Sci 60:75–85CrossRef
go back to reference Tojo G, Fernandez M (2007) Oxidation of primary alcohols to carboxylic acids—a guide to current common practice. Springer, Berlin Tojo G, Fernandez M (2007) Oxidation of primary alcohols to carboxylic acids—a guide to current common practice. Springer, Berlin
go back to reference Vaghari H, Jafarizadeh-Malmiri H, Berenjian A, Anarjan N (2013) Recent advances in application of chitosan in fuel cells. Sustain Chem Process 1:16–28CrossRef Vaghari H, Jafarizadeh-Malmiri H, Berenjian A, Anarjan N (2013) Recent advances in application of chitosan in fuel cells. Sustain Chem Process 1:16–28CrossRef
go back to reference Varma RS (2012) Greener approach to nanomaterials and their sustainable applications. Curr Opin Chem Eng 1:123–128CrossRef Varma RS (2012) Greener approach to nanomaterials and their sustainable applications. Curr Opin Chem Eng 1:123–128CrossRef
go back to reference Ventura-Espinosa D, Vicent C, Bayac M, Mata JA (2016) Ruthenium molecular complexes immobilized on graphene as active catalysts for the synthesis of carboxylic acids from alcohol dehydrogenation. Catal Sci Technol. doi:10.1039/C6CY01455K) Ventura-Espinosa D, Vicent C, Bayac M, Mata JA (2016) Ruthenium molecular complexes immobilized on graphene as active catalysts for the synthesis of carboxylic acids from alcohol dehydrogenation. Catal Sci Technol. doi:10.​1039/​C6CY01455K)
go back to reference Verendel JJ, Church TL, Andersson PG (2011) Catalytic one-pot production of small organics from polysaccharides. Synthesis 11:1649–1677 Verendel JJ, Church TL, Andersson PG (2011) Catalytic one-pot production of small organics from polysaccharides. Synthesis 11:1649–1677
go back to reference Zhou J, Dong Z, Yang H, Shi Z, Zhou X, Li R (2013) Pd immobilized on magnetic chitosan as a heterogeneous catalyst for acetalization and hydrogenation reactions. Appl Surf Sci 279:360–366CrossRef Zhou J, Dong Z, Yang H, Shi Z, Zhou X, Li R (2013) Pd immobilized on magnetic chitosan as a heterogeneous catalyst for acetalization and hydrogenation reactions. Appl Surf Sci 279:360–366CrossRef
Metadata
Title
Chitosan-modified Pd(II)-d-penicillamine: preparation, characterization, and catalyst application
Authors
Sajjad Keshipour
Farivar Ahmadi
Behnam Seyyedi
Publication date
01-02-2017
Publisher
Springer Netherlands
Published in
Cellulose / Issue 3/2017
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-017-1206-0

Other articles of this Issue 3/2017

Cellulose 3/2017 Go to the issue