Novel solvents for sustainable production of specialty chemicals

Annual Review of Chemical and Biomolecular Engineering

Volumn 2, Issue , 2011, Pages 189-210

  Fadhel, Ali Z ^a,b   Pollet, Pamela ^b   Liotta, Charles L ^b   Eckert, Charles A ^a,b  

^a Georgia Institute of Technology   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

gas expanded liquids; near critical water; switchable; tunable

Indexed keywords

IONIC LIQUIDS; SUSTAINABLE DEVELOPMENT;

ALTERNATIVE SOLVENTS; GAS-EXPANDED LIQUIDS; HOMOGENEOUS REACTION; NEAR CRITICAL WATER; SPECIALTY CHEMICALS; SUSTAINABLE PRODUCTION; SWITCHABLE; TUNABLE;

SOLVENTS;

DRUG; IONIC LIQUID; MACROGOL DERIVATIVE; SOLVENT;

CHEMICAL INDUSTRY; CHEMICAL STRUCTURE; CHEMISTRY; LIQUID LIQUID EXTRACTION; METHODOLOGY; REVIEW; SYNTHESIS;

CHEMICAL INDUSTRY; IONIC LIQUIDS; LIQUID-LIQUID EXTRACTION; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; POLYETHYLENE GLYCOLS; SOLVENTS;

EID: 79959405288     PISSN: 19475438     EISSN: None     Source Type: Journal    
DOI: 10.1146/annurev-chembioeng-061010-114221     Document Type: Article

References (83)

1. Hines AL, Maddox RN. 1985. Mass Transfer Fundamentals and Applications. Englewood Cliffs,NJ: Prentice Hall
2. Bird RB, Stewart WE, Lightfoot EN. 2006. Transport Phenomena. New Delhi: Wiley India
3. Brunner G. 2010. Applications of supercritical fluids. Annu. Rev. Chem. Biomol. Eng. 1:321-42
4. Song I, Spuller M, Levitin G, Hess DW. 2006. Photoresist and residue removal using gas-expanded liquids. J. Electrochem. Soc. 153:G314-18 (Pubitemid 43352264)
5. Daintree LS, Kordikowski A, York P. 2008. Separation processes for organic molecules using SCF technologies. Adv. Drug Deliv. Rev. 60:351-72 (Pubitemid 351222676)
6. Dillow AK, Brown JS, Liotta CL, Eckert CA. 1998. Supercritical fluid tuning of reactions rates: The cis-trans isomerization of 4-4'-disubstituted azobenzenes. J. Phys. Chem. A 102:7609-17 (Pubitemid 128598808)
7. Eckert CA, Bush D, Brown JS, Liotta CL. 2000. Tuning solvents for sustainable technology. Ind. Eng. Chem. Res. 39:4615-21
8. Eckert CA, Chandler K. 1998. Tuning fluid solvents for chemical reactions. J. Supercrit. Fluids 13:187-95
9. Eckert CA, Knutson BL,Debenedetti PG. 1996. Supercritical fluids as solvents for chemical andmaterials processing. Nature 383:313-18
10. Eckert CA, Liotta CL, Bush D, Brown JS, Hallett JP. 2004. Sustainable reactions in tunable solvents. J. Phys. Chem. B 108:18108-18
11. Eckert CA, Van Alsten JG, Stoicos T. 1986. Supercritical fluid processing. Environ. Sci. ; Technol. 20:319-25
12. Jessop PG. 2006. Homogeneous catalysis using supercritical fluids: Recent trends and systems studied. J. Supercrit. Fluids 38:211-31 (Pubitemid 44441814)
13. Ramsey E, Sun QB, Zhang ZQ, Zhang CM, Gou W. 2009. Mini-review: Green sustainable processes using supercritical fluid carbon dioxide. J. Environ. Sci. China 21:720-26
14. Rayner CM. 2007. The potential of carbon dioxide in synthetic organic chemistry. Org. Process Res. Dev. 11:121-32
15. Rezaei K, Temelli F, Jenab E. 2007. Effects of pressure and temperature on enzymatic reactions in supercritical fluids. Biotechnol. Adv. 25:272-80 (Pubitemid 46498670)
16. Tang Z, Xie WH, Zong BN, Min EZ. 2004. Recent research progress of chemical reactions under supercritical conditions. Chin. J. Chem. Eng. 12:498-504 (Pubitemid 39496499)
17. BlasucciVM,Husain ZA,FadhelAZ, DonaldsonME, Vyhmeister E, et al. 2010. Combining homogeneous catalysis with heterogeneous separation using tunable solvent systems. J. Phys. Chem. A 114:3932-38
18. 2-expanded acetonitrile: A nucleophilic substitution reaction and solvatochromic probes. J. Org. Chem. 73:3364-68 (Pubitemid 351668638)
19. Lu J, Lazzaroni J, Hallett JP, Bommarius AS, Liotta CL, Eckert CA. 2004. Tunable solvents for homogeneous catalyst recycle. Ind. Eng. Chem. Res. 43:1586-90 (Pubitemid 38435837)
20. Lazzaroni MJ, Bush D, Jones R, Hallett JP, Liotta CL, Eckert CA. 2004. High-pressure phase equilibria of some carbon dioxide-organic-water systems. Fluid Phase Equilibria 224:143-54 (Pubitemid 39172140)
21. El Ali B, Tijani J, FettouhiM, El-Faer M, Al-Arfaj A. 2005. Rhodium(I) and rhodium(III)-heteropolyacids supported onMCM-41 for the catalytic hydroformylation of styrene derivatives. Appl. Catal. A283:185-96
22. Hallett JP, Ford JW, Jones RS, Pollet P, Thomas CA, et al. 2008. Hydroformylation catalyst recycle with gas-expanded liquids. Ind. Eng. Chem. Res. 47:2585-89 (Pubitemid 351666712)
23. Nair VS,Mathew SP, Chaudhari RV. 1999. Kinetics of hydroformylation of styrene using homogeneous rhodium complex catalyst. J. Mol. Catal. A 143:99-110
24. Hagen J. 2006. Industrial Catalysis: A Practical Approach.Weinheim, Ger.: Wiley-VCH
25. Herrmann WA, Kohlpaintner CW. 1993. Water-soluble ligands, metal complexes, and catalysts: Synergism of homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 32:1524-44
26. Herwig J, Fischer R. 2000. Aqueous biphasic hydroformylation. In Rhodium Catalyzed Hydroformylation, ed. PWNM van Leeuwen, C Claver, pp. 189-202. Oberhausen, Ger.: Kluwer Acad.
27. McAuliffe C. 1966. Solubility inwater of paraffin, cycloparaffin, olefin, acetylene, cycloolefin, and aromatic hydrocarbons. J. Phys. Chem. 70:1267-75
28. 9 hydrocarbons. Nature 200:1092-93
29. Pollet P, Hart RJ, Eckert CA, Liotta CL. 2010. Organic aqueous tunable solvent (OATS): A vehicle for coupling reaction and separation. Acc. Chem. Res. 43:1237-45
30. 3 on zeolite Y using phosphotungstic acid as tethering agent: A novel hydroformylation catalyst. J. Catal. 213:73-77
31. Neibecker D, Reau R, Lecolier S. 1989. Synthesis of 2- arylpropionaldehydes through hydroformylation. J. Org. Chem. 54:5208-10
32. Riley DP, Getman DP, Beck GR, Heintz RM. 1987. Selective metal-catalyzed autoxidation of 2- arylpropionaldehydes-an improved synthesis of ibuprofen. J. Org. Chem. 52:287-90 (Pubitemid 17005557)
33. Hamza K, Blum J. 2007. Highly selective hydroformylation of vinylarenes to branched aldehydes by [Rh(cod)Cl]2 entrapped in ionic liquid modified silica sol-gel. Eur. J. Org. Chem. 2007:4706-10
34. 2-induced organic-aqueous tunable solvents. Angew. Chem. Int. Ed. 45:4670-73 (Pubitemid 44106093)
35. Hill EM, Broering JM, Hallett JP, Bommarius AS, Liotta CL, Eckert CA. 2007. Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation. Green Chem. 9:888-93
36. U.S. Food Drug Admin. 2010. Sect. 172.820. Polyethylene glycol (mean molecular weight 200-9,500). Code of Federal Regulations, Title 21, Vol. 3. (CITE: 21CFR172.820)
37. Uematsu M, Franck EU. 1980. Static dielectric constant of water and steam. J. Phys. Chem. Ref. Data 9:1291-306
38. Hoffmann MM, Conradi MS. 1997. Are there hydrogen bonds in supercritical water? J. Am. Chem. Soc. 119:3811-17 (Pubitemid 27234386)
39. Hoffmann MM, Conradi MS. 1998. Are there hydrogen bonds in supercritical methanol and ethanol? J. Phys. Chem. B 102:263-71 (Pubitemid 128576559)
40. Liotta CL, Hallett JP, Pollet P, Eckert CA. 2007. Reactions in nearcritical water. In Organic Reactions in Water: Principles, Strategies and Applications, ed. UM Lindstr öm, pp. 256-97. Oxford, UK: Blackwell
41. Marshall WL, Franck EU. 1981. Ion product of water substance, 0-1000°C, 1-10,000 bars: New international formulation and its background. J. Phys. Chem. Ref. Data 10:295-304
42. Anderson FE, Prausnitz JM. 1986. Mutual solubilities and vapor pressures for binary and ternary aqueous systems containing benzene, toluene, m-xylene, thiophene and pyridine in the region 100-200°C. Fluid Phase Equilibria 32:63-76
43. Brown JS, Hallett JP, Bush D, Eckert CA. 2000. Liquid-liquid equilibria for binary mixtures of water plus acetophenone, plus 1-octanol, plus anisole, and plus toluene from 370 K to 550 K. J. Chem. Eng. Data 45:846-50
44. Chandler K, Eason B, Liotta CL, Eckert CA. 1998. Phase equilibria for binary aqueous systems from a near-critical water reaction apparatus. Ind. Eng. Chem. Res. 37:3515-18 (Pubitemid 128718116)
45. Connolly JF. 1966. Solubility of hydrocarbons in water near the critical solution temperatures. J. Chem. Eng. Data 11:13-16
46. HooperHH, Michel S, Prausnitz JM. 1988. Correlation of liquid-liquid equilibria for some water-organic liquid systems in the region 20-250°C. Ind. Eng. Chem. Res. 27:2182-87
47. Miller DJ, Hawthorne SB. 1998. Method for determining the solubilities of hydrophobic organics in subcritical water. Anal. Chem. 70:1618-21
48. Miller DJ, Hawthorne SB. 2000. Solubility of liquid organics of environmental interest in subcritical (hot/liquid) water from 298 K to 473 K. J. Chem. Eng. Data 45:78-81 (Pubitemid 32212668)
49. Rebert CJ, Kay WB. 1959. The phase behavior and solubility relations of the benzene-water system. AIChE J. 5:285-89
50. Sherman SR, Trampe DB, Bush DM, SchillerM, Eckert CA, et al. 1996. Compilation and correlation of limiting activity coefficients of nonelectrolytes in water. Ind. Eng. Chem. Res. 35:1044-58 (Pubitemid 126460252)
51. Stephenson RM. 1992. Mutual solubilities-water ketones, water ethers, and water gasoline alcohols. J. Chem. Eng. Data 37:80-95
52. Stevenson RL, LaBracio DS, Beaton TA, ThiesMC. 1994. Fluid phase equilibria and critical phenomena for the dodecane-water and squalane-water systems at elevated temperatures and pressures. Fluid Phase Equilibria 93:317-36
53. Tsonopoulos C, Wilson GM. 1983. High-temperature mutual solubilities of hydrocarbons and water. 1. Benzene, cyclohexane and normal-hexane. AIChE J. 29:990-99 (Pubitemid 14488627)
54. Hallett JP. 2002. Enhanced recovery of homogeneous catalysts through manipulation of phase behavior. PhD thesis. Atlanta: Ga. Inst. Technol.
55. Sørenson JM, Arlt W. 1979. Liquid-Liquid Equilibrium Data Collection. Frankfurt am Main: Deutsche Gesellschaft f ür Chemisches Apparatewesen
56. Akiya N, Savage PE. 2002. Roles of water for chemical reactions in high-temperature water. Chem. Rev. 102:2725-50 (Pubitemid 35381647)
57. An JY, Bagnell L,Cablewski T, StraussCR, Trainor RW. 1997. Applications of high-temperature aqueous media for synthetic organic reactions. J. Org. Chem. 62:2505-11 (Pubitemid 127492254)
58. Katritzky AR, Allin SM, Siskin M. 1996. Aquathermolysis: Reactions of organic compounds with superheated water. Acc. Chem. Res. 29:399-406 (Pubitemid 126453222)
59. Katritzky AR, Nichols DA, Siskin M, Murugan R, Balasubramanian M. 2001. Reactions in hightemperature aqueous media. Chem. Rev. 101:837-92
60. Li CJ. 2005. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update. Chem. Rev. 105:3095-165
61. Savage PE. 1999. Organic chemical reactions in supercritical water. Chem. Rev. 99:603-21 (Pubitemid 129606087)
62. Savage PE, Gopalan S, Mizan TI, Martino CJ, Brock EE. 1995. Reactions at supercritical conditions- applications and fundamentals. AIChE J. 41:1723-78
63. Siskin M, Katritzky AR. 2000. A review of the reactivity of organic compounds with oxygen-containing functionality in superheated water. J. Anal. Appl. Pyrolysis 54:193-214 (Pubitemid 30557635)
64. Siskin M, Katritzky AR. 2001. Reactivity of organic compounds in superheatedwater: General background. Chem. Rev. 101:825-35 (Pubitemid 35377387)
65. Chandler K, Deng FH, Dillow AK, Liotta CL, Eckert CA. 1997. Alkylation reactions in near-critical water in the absence of acid catalysts. Ind. Eng. Chem. Res. 36:5175-79 (Pubitemid 127481720)
66. Sears CA. 1948. Alkylation of phenol with tert-butyl alcohol in the presence of perchloric acid. J. Org. Chem. 13:120-22
67. Chandler K, Liotta CL, Eckert CA, Schiraldi D. 1998. Tuning alkylation reactions with temperature in near-critical water. AIChE J. 44:2080-87 (Pubitemid 29025360)
68. Brown JS, Glaser R, Liotta CL, Eckert CA. 2000. Acylation of activated aromatics without added acid catalyst. Chem. Commun. 2000:1295-96 (Pubitemid 30484222)
69. Lu J, Brown JS, Boughner EC, Liotta CL, Eckert CA. 2002. Solvatochromic characterization of nearcritical water as a benign reaction medium. Ind. Eng. Chem. Res. 41:2835-41 (Pubitemid 34625733)
70. Lu XY, Li Z, Gao F. 2006. Base-catalyzed reactions in NH3-enriched near-critical water. Ind. Eng. Chem. Res. 45:4145-49 (Pubitemid 43966387)
71. Hunter SE, Savage PE. 2004. Recent advances in acid- and base-catalyzed organic synthesis in hightemperature liquid water. Chem. Eng. Sci. 59:4903-9 (Pubitemid 39605730)
72. Hunter SE, Savage PE. 2004. Kinetics andmechanism of p-isopropenylphenol synthesis via hydrothermal cleavage of bisphenol A. J. Org. Chem. 69:4724-31 (Pubitemid 38890638)
73. Vinci D, DonaldsonM,Hallett JP, JohnEA, Pollet P, et al. 2007. Piperylene sulfone: A labile and recyclable DMSO substitute. Chem. Commun. 2007:1427-29 (Pubitemid 46496518)
74. Jiang N, Vinci D, Liotta CL, Eckert CA, Ragauskas AJ. 2008. Piperylene sulfone: A recyclable dimethyl sulfoxide substitute for copper-catalyzed aerobic alcohol oxidation. Ind. Eng. Chem. Res. 47:627-31 (Pubitemid 351269504)
75. Donaldson ME, Mestre VL, Vinci D, Liotta CL, Eckert CA. 2009. Switchable solvents for in-situ acidcatalyzed hydrolysis of β-pinene. Ind. Eng. Chem. Res. 48:2542-47
76. Jessop PG, Heldebrant DJ, Li XW, Eckert CA, Liotta CL. 2005. Green chemistry: Reversible nonpolarto- polar solvent. Nature 436:1102 (Pubitemid 41232279)
77. Phan L, Chiu D, Heldebrant DJ, Huttenhower H, John E, et al. 2008. Switchable solvents consisting of amidine/alcohol or guanidine/alcohol mixtures. Ind. Eng. Chem. Res. 47:539-45 (Pubitemid 351269493)
78. Blasucci V, Hart R, Mestre VL, Hahne DJ, Burlager M, et al. 2010. Single component, reversible ionic liquids for energy applications. Fuel 89:1315-19
79. Blasucci V, Dilek C, Huttenhower H, John E, Llopis-Mestre V, et al. 2009. One-component, switchable ionic liquids derived from siloxylated amines. Chem. Commun. 2009:116-18
80. Hart R, Pollet P, Hahne DJ, John E, Llopis-Mestre V, et al. 2010. Benign coupling of reactions and separations with reversible ionic liquids. Tetrahedron 66:1082-90
81. Blasucci VM, Hart R, Pollet P, Liotta CL, Eckert CA. 2010. Reversible ionic liquids designed for facile separations. Fluid Phase Equilibria 294:1-6
82. Jessop PG, Phan L, Carrier A, Robinson S, Durr CJ, Harjani JR. 2010. A solvent having switchable hydrophilicity. Green Chem. 12:809-14
83. Desset SL, Cole-Hamilton DJ. 2009. Carbon dioxide induced phase switching for homogeneous-catalyst recycling. Angew. Chem. Int. Ed. 48:1472-74