Cited by 251Ionic liquids properties and applicationsChemical and Physical Properties in Aqueous SolutionsPhase Equilibria and Thermodynamics

Design and evaluation of switchable-hydrophilicity solvents

Open access
Vanderveen, Jesse R., Durelle, Jeremy, Jessop, Philip G.·2014·Green Chem.

Abstract

Switchable-hydrophilicity solvents (SHS) can switch reversibly between one form that is miscible with water and another that forms a biphasic mixture with water. New examples are reported and compared in terms of safety and environmental impact.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1039/c3gc42164c

Cites

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • Some SHSs, especially those formed from secondary amines, are expected to be safer than traditional solvents in terms such as flammability or smog formation.

    “Second, about their safety, some SHSs (especially, those formed from secondary amines) are expected to be safer than traditional solvents in some terms like flammability or smog formation [19].”

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

The citation lists haven’t been fetched yet

References 70 · Cited by 251

Research works printed but not linked: 67

  1. N-H), 2964, 2934, 2878, 1731 (CvO), 1463, 1377, 1356, 1259, 1186, 1099, 1063, 1002, 736; m/z (EI) 187 (1), 186 (1), 172 (8), 158 (100), 144 (1), 130 (8), 128 (6), 116 (9), 112 (8), 98 (65), 86 (60), 84 (8), 72 (15), 70 (36), 56 (98);
  2. N-H), 2960, 2873, 1731 (CvO), 1467, 1379, 1337, 1262, 1173, 1148, 1064, 1021, 840, 739; m/z (EI) 187 (2), 186 (2), 172 (70), 144 (14), 130 (4), 116 (13), 114 (17), 98 (64), 88 (10), 72 (100), 70 (22), 56 (89);
  3. Anal. Calcd for C 10 H 21 NO 2 : C 64.12, H 11.31, N 7.48; found C 64.08, H 11.45, N 7.49. Propyl 3-(diethylamino)propanoate. Using the same pro- cedure as for ethyl 3-(diethylamino)propanoate, 1.2 g (0.011 mol) propyl acrylate and 1.4 g (0.019 mol) of diethyl- amine yielded 1.6 g of product (85% yield); bp 67 °C (4 torr): 1 H NMR (500 MHz, CDCl 3 ) δ 0.94 (t, J = 7.4 Hz, 3H), 1.02 (t, J = 7.2 Hz, 6H), 1.64 (apparent sextet, J = 7.1 Hz, 2H), 2.44 (t, J = 7.5 Hz, 2H), 2.51 (q, J = 7.2 Hz, 4H), 2.79 (t, J = 7.5 Hz, 2H), 4.03 (t, J = 6.7 Hz, 2H); 13 C NMR (500 MHz, CDCl 3 ) δ 10.36, 11.85, 21.96, 32.30, 46.80, 48.12, 65.94, 172.96; ν max (ATR) cm -1 2968, 2937, 2878, 2805, 1735 (CvO), 1465, 1382, 1266, 1198, 1178, 1062, 996, 909; m/z (EI) 187 (6), 172 (17), 158 (2), 144 (1), 130 (6), 128 (3), 100 (1), 99 (1), 98 (1), 86 (100), 73 (17), 70 (2), 58 (17), 55 (2);
  4. P. G. Jessop, L. Phan, A. Carrier, S. Robinson, C. J. Dürr and J. R. Harjani, Green Chem., 2010, 12, 809-814.
  5. P. G. Jessop, L. Kozycz, Z. G. Rahami, D. Scheonmakers, A. R. Boyd, D. Wechsler and A. M. Holland, Green Chem., 2011, 13, 619-623.
  6. A. R. Boyd, P. Champagne, P. J. McGinn, K. M. MacDougall, J. E. Melanson and P. G. Jessop, Bioresour. Technol., 2012, 118, 628-632.
  7. C. Samori, D. L. Barreiro, R. Vet, L. Pezzolesi, D. W. F. Brilman, P. Galletti and E. Tagliavini, Green Chem., 2013, 15, 353-356.
  8. A. Holland, D. Wechsler, A. Patel, B. M. Molloy, A. R. Boyd and P. G. Jessop, Can. J. Chem., 2012, 90, 805-810.
  9. N. F. Hall and M. R. Sprinkle, J. Am. Chem. Soc., 1932, 54, 3469-3485.
  10. U. Oesch, Z. Brzozka, A. Xu, B. Rusterholz, G. Suter, H. V. Pham, D. H. Welti, D. Ammann, E. Pretsch and W. Simon, Anal. Chem., 1986, 58, 2285-2289.
  11. C. Wiles and P. Watts, Beilstein J. Org. Chem., 2011, 7, 1360- 1371.
  12. H. K. Hall, J. Phys. Chem., 1956, 60, 63-70.
  13. V. Frenna, N. Vivona, G. Consiglio and D. Spinelli, J. Chem. Soc., Perkin Trans. 2, 1985, 1865-1868.
  14. M. M. Kreevoy and S.-W. Oh, J. Am. Chem. Soc., 1973, 95, 4805-4810.
  15. R. E. McMahon and N. R. Easton, J. Med. Pharm. Chem., 1961, 4, 423-586.
  16. L. C. Craig and R. M. Hixon, J. Am. Chem. Soc., 1931, 53, 4367-4372.
  17. S. Jarmelo, N. Maiti, V. Anderson, P. R. Carey and R. Fausto, J. Phys. Chem. A, 2005, 109, 2069-2077.
  18. I. V. Tetko and V. Y. Tanchuk, J. Chem. Inf. Comput. Sci., 2002, 42, 1136-1145.
  19. I. V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V. A. Palyulin, E. V. Radchenkco, N. S. Zefirov, A. S. Makarenko, V. Y. Tanchuk and V. V. Prokopenko, J. Comput.-Aided Mol. Des., 2005, 19, 453- 463.
  20. J. Hine and M. N. Khan, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 1992, 31, 427-435.
  21. G. M. Steinberg and J. Bolger, J. Am. Pharm. Assoc., 1957, 46, 188-191.
  22. R. J. Littel, M. Bos and G. J. Knoop, J. Chem. Eng. Data, 1990, 35, 276-277.
  23. F. Wang and L. M. Sayre, J. Am. Chem. Soc., 1992, 114, 248- 255.
  24. A. Gero, J. Med. Chem., 1963, 6, 457-458.
  25. F. Bougie and M. C. Iliuta, J. Chem. Eng. Data, 2012, 57, 635-669.
  26. J. Zhang, R. Misch, Y. Tan and D. W. Agar, Chem. Eng. Technol., 2011, 34, 1481-1489.
  27. C. W. Hoerr, M. R. McCorkle and A. W. Ralston, J. Am. Chem. Soc., 1943, 65, 328-329.
  28. Y. Takeuchi, Environ. Res., 1993, 62, 76-80.
  29. O. F. Sendur, Y. Turan, S. Bal and A. Gurgan, Inhalation Toxicol., 2009, 21, 210-214.
  30. G. D. Ritchie, K. R. Still, W. K. Alexander, A. F. Nordholm, C. L. Wilsom, J. Rossi III and D. R. Mattie, J. Toxicol. Environ. Health, Part B, 2001, 4, 223-312.
  31. E. J. Gallegos, Anal. Chem., 1981, 53, 187-189.
  32. W. B. Wright Jr., J. Org. Chem., 1962, 27, 1042-1045.
  33. H. Yoshikawa and K. Kawai, Ind. Health, 1966, 4, 63.
  34. T. Caronna, A. Citterio, T. Crolla, M. Ghirardini and F. Minisci, J. Heterocycl. Chem., 1976, 13, 955-960.
  35. A. R. Lepley and W. A. Khan, J. Org. Chem., 1966, 31, 2061- 2064.
  36. N. C. Deno and R. E. Fruit, J. Am. Chem. Soc., 1968, 90, 3502-3506.
  37. R. E. Watson, A. M. Hafez, J. N. Kremsky and G. O. Bizzigotti, Int. J. Toxicol., 2007, 26, 503-512.
  38. P. A. A. Klusener, L. Tip and L. Brandsma, Tetrahedron, 1991, 47, 2041-2064.
  39. W. B. Burnett, R. L. Jenkins, C. H. Peet, E. E. Dreger and R. Adams, J. Am. Chem. Soc., 1937, 59, 2248-2252.
  40. P. G. Stone and S. G. Cohen, J. Am. Chem. Soc., 1982, 104, 3435-3440.
  41. F. Franks and B. Watson, Trans. Faraday Soc., 1967, 63, 329-334.
  42. D. G. Norton, V. E. Haury, F. C. Davis, L. J. Mitchell and S. A. Ballard, J. Org. Chem., 1954, 19, 1054-1066.
  43. D. Redmore, J. Org. Chem., 1978, 43, 992-996.
  44. V. A. Benignus, Neurotoxicology, 1981, 2, 567-588.
  45. E. T. Kimura, D. M. Ebert and P. W. Dodge, Toxicol. Appl. Pharmacol., 1971, 19, 699-704.
  46. G. W. Kabalka and S. T. Summers, J. Org. Chem., 1981, 46, 1218-1221.
  47. N. Chang, Z.-Y. Gu and X.-P. Yan, J. Am. Chem. Soc., 2010, 132, 13645-13647.
  48. Documentation of the Threshold Limit Values of Biological Exposure Indices, American Conference of Governmental Industrial Hygienists, Cincinnati, Ohio, 6th edn, 1991.
  49. Ethel Browning's Toxicity and Metabolism of Industrial Sol- vents, ed. R. Snyder, Elsevier, New York, 2nd edn, 1987.
  50. A. N. Campbell, Can. J. Chem., 1981, 59, 127-131.
  51. L. M. Besley and G. A. Bottomley, J. Chem. Thermodyn., 1974, 6, 577-580.
  52. S. A. Wieczorek and J. Stecki, J. Chem. Thermodyn., 1978, 10, 177-186.
  53. J. R. Baker, M. W. Milke and J. R. Mihelcic, Water Res., 1999, 33, 327-334.
  54. W. P. L. Carter, J. Air Waste Manage. Assoc., 1994, 44, 881- 899.
  55. R. S. Boethling, E. Sommer and D. DiForge, Chem. Rev., 2007, 107, 2207-2227.
  56. P. H. Howard, R. S. Boethling, W. M. Stiteler, W. M. Meylan, A. E. Hueber, J. A. Beauman and M. E. Larosche, Environ. Toxicol. Chem., 1992, 11, 593-603.
  57. I. Eide-Haugmo, O. G. Brakstad, K. A. Hoff, K. R. Sorheim, E. F. da Silva and H. F. Svendsen, Energy Procedia, 2009, 1, 1297-1304.
  58. I. Eide-Haugmo, H. Lepaumier, A. Einbu, K. Vernstad, E. F. da Silva and H. F. Svendsen, Energy Procedia, 2011, 4, 1631-1636.
  59. I. Eide-Haugmo, O. G. Brakstad, K. A. Hoff, E. F. da Silva and H. F. Svendsen, Int. J. Greenhouse Gas Control, 2012, 9, 184-192.
  60. D. Calamari, R. Da Gasso, S. Galassi, A. Provini and M. Vighi, Chemosphere, 1980, 9, 753-762.
  61. M. Kawasaki, Ecotoxicol. Environ. Saf., 1980, 4, 444-454.
  62. K. Kawahara, Y. Yakabe, T. Ohide and K. Kida, Chemo- sphere, 1999, 39, 2007-2018.
  63. E. M. Davis, H. E. Murray, J. G. Liehr and E. L. Powers, Water Res., 1981, 15, 1125-1127.
  64. G. Pasteris, D. Werner, K. Kaufmann and P. Höhener, Environ. Sci. Technol., 2002, 36, 30-39.
  65. J. A. Gowland and G. H. Schmid, Can. J. Chem., 1969, 47, 2953-2958.
  66. B. Zou and H.-F. Jiang, Chin. J. Chem., 2008, 26, 1309- 1314.
  67. S. R. Cheruku, S. Maiti, A. Dorn, B. Scorneaux, A. K. Bhattacharjee, W. Y. Ellis and J. L. Vennerstrom, J. Med. Chem., 2003, 46, 3166-3169.

Authors
Vanderveen, J. R., Durelle, J., & Jessop, P. G.
Affiliations
Queen's University (CA)
Corresponding author
Jessop, Philip G.
Venue
Green Chem.
Published
2014
Volume
16
Issue
3
Pages
1187-1197
ISSN
  • 1463-9262 (ISSN-L)
  • 1463-9270
OpenAlex
W2122740875
Cited by
251
References
70
Citations by year
2026: 10 · 2025: 13 · 2024: 22 · 2023: 25 · 2022: 18 · 2021: 29 · 2020: 30 · 2019: 25 · 2018: 27 · 2017: 18 · 2016: 14 · 2015: 13 · 2014: 7
FWCI
4.49
Type
journal article
Language
en
Open access
Licence
cc-by
Locations
Green Chemistry (publishedVersion, cc-by)
Funders
Canada Research Chairs
Topics
  • Physical Sciences › Chemical Engineering › Catalysis › Ionic liquids properties and applications
  • Physical Sciences › Chemical Engineering › Filtration and Separation › Chemical and Physical Properties in Aqueous Solutions
  • Physical Sciences › Engineering › Biomedical Engineering › Phase Equilibria and Thermodynamics
Keywords
switchable hydrophilicity solvents, biphasic solvent system, water miscibility, solvent design, solvent safety, environmental impact, phase separation

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review