Choline peroxydisulfate: Environmentally friendly biodegradable oxidizing TSIL for selective and rapid oxidation of alcohols

Industrial and Engineering Chemistry Research

Volumn 53, Issue 49, 2014, Pages 19010-19018

  Gadilohar, Balu L ^a   Kumbhar, Haribhau S ^a   Shankarling, Ganapati S ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADABILITY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; IONIC LIQUIDS; OXIDATION; PHYSICOCHEMICAL PROPERTIES;

ANTI-MICROBIAL ACTIVITY; ENERGY CALCULATION; ENVIRONMENTALLY BENIGN; MILD REACTION CONDITIONS; OXIDIZING AGENTS; SELECTIVE OXIDATION; SHORT REACTION TIME; TASK-SPECIFIC IONIC LIQUIDS;

CYCLIC VOLTAMMETRY;

EID: 84916606230     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie5032919     Document Type: Article

References (51)

1. Rogers, R. D.; Seddon, K. R. Ionic Liquids-Solvents of the Future? Science 2003, 302, 792-793
2. Ranke, J.; Stolte, S.; Stormann, R.; Arning, J.; Jastorff, B. Design of Sustainable Chemical Products-The Example of Ionic Liquids Chem. Rev. 2007, 107, 2183-2206
3. Jastorff, B.; Stormann, R.; Ranke, J.; Molter, K.; Stock, F.; Oberheitmann, B.; Hoffmann, W.; Hoffmann, J.; Nuhter, M.; Ondruschka, B.; Filser, J. How hazardous are ionic liquids? Structure-activity relationships and biological testing as important elements for sustainability evaluation Green Chem. 2003, 5, 136
4. Ranke, J.; Moulter, K.; Stock, F.; Bottin-Weber, U.; Hoffmann, J.; Ondruschka, B.; Filser, J.; Jastorff, B. Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays Ecotoxicol. Environ. Safety. 2004, 58, 396
5. Stolte, S.; Arning, J.; Weber, U.; Matzke, M.; Stock, F.; Thiele, K.; Uerdingen, M.; WelzBiermann, U.; Jastorffand, B.; Ranke, J. Anion effects on the cytotoxicity of ionic liquids Green Chem. 2006, 8, 621-629
6. Jadhav, A. H.; Chinnappan, A.; Patil, R. H.; Kostjuk, S.; Kima, H. Short oligo ethylene glycolic tailor-made ionic liquids as highly efficient and reusable catalyst for one-pot synthesis of 1,5-benzodiazepine derivatives under solvent free condition Chem. Eng. J. 2014, 240, 228-234
7. Zhao, D.; Liu, M.; Zhang, J.; Li, J.; Ren, P. Synthesis, characterization, and properties of imidazole dicationic ionic liquids and their application in esterification Chem. Eng. J. 2013, 221, 99-104
8. Davis, J. H., Jr. Task-Specific Ionic Liquids Chem. Lett. 2004, 9 (33) 1072-1077
9. Backvall, J. E. Modern Oxidation Methods; Wiley-VCH: Weinheim, Germany, 2004.
10. Trost, B. M. Comprehensive Organic Synthesis: Oxidation; Pergamon Press: New York, 1991; Vol. 7.
11. Dubcek, A.; Kirsch, S. F. 2-Iodoxybenzoic Acid-A Simple Oxidant with a Dazzling Array of Potential Applications Angew. Chem., Int. Ed. 2011, 50, 1524-1552
12. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. A Mild, Chemoselective Oxidation of Sulfides to Sulfoxides Using o -Iodoxybenzoic Acid and Tetraethylammonium Bromide as Catalyst J. Org. Chem. 2003, 68, 5422
13. Huang, K. C.; Zhao, Z.; Hoag, G. E.; Dahmani, A.; Block, P. A. Degradation of volatile organic compounds with thermally activated persulfate oxidation Chemosphere 2005, 61, 51-560
14. Kolthoff, I. M.; Miller, I. K. The Chemistry of Persulfate. I. The Kinetics and Mechanism of the Decomposition of the Persulfate Ion in Aqueous Medium J. Am. Chem. Soc. 1951, 73, 3055-3059
15. Kolthoff, I. M.; Medalia, A. I.; Raaen, H. P. The reaction between ferrous iron and peroxides. IV. Reaction with potassium persulfate J. Am. Chem. Soc. 1951, 73, 1733-1739
16. Chaskar, A. C.; Bhandari, S. R.; Patil, A. B.; Sharma, O. P.; Mayeker, S. Solvent-Free Oxidation of Alcohols with Potassium Persulphate in the Presence of Brönsted Acidic Ionic Liquids Synth. Commun. 2009, 39, 366-370
17. Zhu, C.; Ji, L.; Wei, Y. Catalytic hypervalent iodine oxidation of alcohols to corresponding aldehydes or ketones using 2,2,6,6-tetramethylpiperidinyl-1-oxy and potassium peroxodisulfate Monatsh. Chem. 2010, 141, 327-331
18. 8: A Mild and Inexpensive Reagent for Efficient Oxidation of Organic Compounds under Nonaqueous and Aprotic Conditions Bull. Chem. Soc. Jpn. 1998, 71, 1649
19. Minghu, W.; Guichun, Y.; Zuxing, C. Polymer supported peroxodisulfate: A mild and clean oxidation of organic compounds under nonaqueous and aprotic conditions React. Funct. Polym. 2000, 44, 97-100
20. Park, M. Y.; Jadhav, A.; Kim, H. A Simple and Selective Oxidation of Sulfides to Sulfoxides Using Tetrabutylammonium Peroxydisulfate: A Rebuttal Synth. Commun. 2004, 34 (18) 3367-3372
21. Shi, S.; Kong, A.; Zhao, X.; Zhang, Q.; Shan, Y. Synthesis and Characterization of Task-Specific Ionic Liquids Based on Peroxydisulfate and Their Application in Oxidation Reactions Eur. J. Inorg. Chem. 2010, 2283-2289
22. Johnathan, T. G.; Friedrich, S.; Kazlauskas, R. J. Hydrolase-catalyzed biotransformation in deep eutectic solvents Chem. Commun. 2008, 1235-1237
23. Coleman, D.; Gathergood, N. Biodegradation studies of ionic liquids Chem. Soc. Rev. 2010, 39, 600-637
24. Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Ionic liquids: A pathway to environmental acceptability Chem. Soc. Rev. 2011, 40, 1383-1403
25. Abbott, A. P.; Capper, G.; Davies, L.; Munro, H. L.; Rasheed, R. K.; Tambyrajah, V. Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains Chem. Commun. 2001, 19, 2010-2011
26. Qinghua, Z.; Karine, De O. V.; Sébastien, R.; François, J. Deep eutectic solvents: Syntheses, properties and applications Chem. Soc. Rev. 2012, 41, 7108-7146
27. Mara, F.; Adriaan van den, B.; Maaike, C. K. Low-Transition-Temperature Mixtures (LTTMs): A New Generation of Designer Solvents Angew. Chem., Int. Ed. 2013, 52, 3074-3085
28. Ping, W.; Fei-Ping, M.; Zhan-Hui, Z. l -(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N -substituted pyrroles via Clauson-Kaas reaction J. Mol. Liq. 2014, 198, 259-262
29. Yadav, U. N.; Shankarling, G. S. Synergistic effect of ultrasound and deep eutectic solvent choline chloride-urea as versatile catalyst for rapid synthesis of β-functionalized ketonic derivatives J. Mol. Liq. 2014, 195, 188-193
30. Dariush, S.; Jafar, A.; Samaneh, M.; Akbar, H. Reductive amination of aldehydes and ketones catalyzed by deep eutectic solvent using sodium borohydride as a reducing agent J. Mol. Liq. 2014, 196, 208-210
31. Sanap, A. K.; Shankarling, G. S. Choline chloride based eutectic solvents: Direct C-3 alkenylation/alkylation of indoles with 1,3-dicarbonyl compounds RSC Adv. 2014, 4, 34938-34943
32. Phadtare, S. B.; Shankarling, G. S. Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9,10-quinone in deep eutectic solvent (choline chloride: urea) Green Chem. 2010, 12, 458-465
33. Sonawane, Y. A.; Phadtare, S. B.; Borse, B. N.; Jagtap, A. R.; Shankarling, G. S. Synthesis of Diphenylamine-Based Novel Fluorescent Styryl Colorants by Knoevenagel Condensation Using a Conventional Method, Biocatalyst, and Deep Eutectic Solvent Org. Lett. 2010, 12, 1456-1459
34. Gathergood, N.; Garcia, M.; Scammells, P. Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation Green Chem. 2004, 6, 166-175
35. Garcia, M.; Gathergood, N.; Scammells, P. Biodegradable ionic liquids: Part II. Effect of the anion and toxicology Green Chem. 2005, 7, 9-14
36. Manuela, P.; Worth, A. P. Review of Estimation Models for Biodegradation QSAR Comb. Sci. 2008, 27 (1) 32-40
37. Boethling, R. S.; Lynch, D. G.; Jaworska, J. S.; Tunkel, J. L.; Thom, G. C.; Webb, L. S. Using Biowin, Bayes, and batteries to predict ready biodegradability Environ. Toxicol. Chem. 2004, 23 (4) 911-920
38. Boethling, R. S.; Howard, P. H.; Meylan, W.; Stiteler, W.; Beauman, J.; Tirado, N. Group contribution method for predicting probability and rate of aerobic biodegradation Environ. Sci. Technol. 1994, 28, 459-465
39. Exposure Assessment Tools and Models. U.S. Environmental Protection Agency, Washington, DC, 2013; available at http://www.epa.gov/oppt/exposure/docs/episuitedl.htm. Accessed July 2013.
40. SRC, Inc. Home Page. Syracuse Research Corporation, Syracuse, NY, 2014; available at http://www.syrres.com/esc/biodeg.htm. Accessed July 2013.
41. Rücker, C.; Kümmerer, K. Modeling and predicting aquatic aerobic biodegradation-A review from a user's perspective Green Chem. 2012, 14, 875
42. WEF: Standard Methods for the Examination of Water and Wastewater; American Public Health Association, American Water Works Association, and Water Environment Federation: Washington, DC, 2005.
43. OECD SIDS Initial Assessment Report for Persulfates; U.S. Environmental Protection Agency: Washington, DC, 2005.
44. OECD SIDS Initial Assessment Report for Choline Chloride; National Centre for Ecotoxicology & Hazardous Substances: Wallingford, U.K., 2004.
45. Performance Standards for Antimicrobial Disk and Dilution Susceptibility Tests for Bacteria Isolated from Animals; National Committee for Clinical Laboratory Standards: Wayne, PA, 2002.
46. Arning, J.; Stolte, S.; Böschen, A.; Stock, F.; Pitner, W. R. Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalized side chains and anions of ionic liquids on acetyl cholinesterase Green Chem. 2008, 10, 47-58
47. Romero, A.; Santos, A.; Tojo, J.; Rodriguez, A. Toxicity and biodegradability of imidazolium ionic liquids J. Hazard Mater. 2008, 151, 268-273
48. Fukaya, Y.; Iizuka, Y.; Sekikawa, K.; Ohno, H. Bio ionic liquids: Room temperature ionic liquids composed wholly of biomaterials Green Chem. 2007, 9, 1155-1157
49. Hapiot, P.; Lagrost, C. Electrochemical reactivity in room-temperature ionic liquids Chem. Rev. 2008, 108, 2238-2264
50. 2] in dependence on temperature at atmospheric pressure J. Phys. Chem. B 2008, 112, 12420-12430
51. Jarag, K. J.; Pinjari, D. V.; Pandit, A. B.; Shankarling, G. S. Synthesis of chalcone (3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one): Advantage of sonochemical method over conventional method Ultrason. Sonochem. 2011, 18, 617-623