Zielona chemia : zadania, cele, przykłady osiągnięć

• Autorzy: Burczyk B.

Warianty tytułu

EN

Green chemistry : principles, aims, and selected achievements

• Języki publikacji: PL

Abstrakty

EN

Green chemistry is the design, development, and implementation of chemical processes or products to reduce or eliminate the use and generation of substances hazardous to human health and the environment : Its aim is to combine technological and economic progress with the safeguarding of the environment, which is one of the challenges of the new millennium. To help to achieve this goal, a set of twelve principles of green chemistry was formulated by Anastas and Warner. These principles apply to a whole chemical process and to its main stages, which are: starting materials (or feedstock), reaction types and reagents, solvents and reaction conditions, and chemical products . This review only covers some of the important efforts and achievements of green chemistry. In Section 3.1 some saccharide- based syntheses are presented. Both simple sugars (glucose, lactose), and polymeric saccharides, as well as biomass have been successfully transformed into valuable chemicals. In Section 3.2, new reaction types fulfilling the atom economy principle formulated by Trost re described. The focus is on new oxidation reactions of olefins using clean oxidants: hydrogen peroxide and non-toxic, water-soluble iron catalysts, and oxygen. New possibilities of replacing toxic hydrogen cyanide and phosgene with safer reagents (e.g., dimethyl carbonate) were another topic of this Section. Section 3.3 deals with new reaction media. Water emerged as a non-toxic, environmentally benign and cheap solvent for many organic reactions, as it has several advantages: water soluble substrates (e.g., carbohydrates) can be used directly, the aqueous catalyst solution can be recycled easily, and no inert gas atmosphere is needed. The discovery of water soluble transition metal complexes made it possible to use aqueous/organic biphasic systems which have benefits in catalyst separation and recycling. Such a system has been used, for instance, in the industrial propylene hydroformylation process. Many other reactions performed in biphasic systems were reported. Water soluble rare earth trifluoromethane sulfonates have been shown to be strong Lewis acids . Supercritical fluids have been used as new reaction media; they posses a unique combination of gas- and liquid- like properties. Supercritical carbon dioxide (scCO2) and supercritical water (scH2O) were mostly exploited. New polymerization processes in scCO2 were proposed and new surfactants for scCO2 were discovered . Promising possibilities of performing oxidation reactions in scH2O were reported, as many organic compounds and oxygen are soluble in scH2O . Ionic liquids, which are characterized by a lack of measurable vapour pressure, constitute another group of neoteric solvents. They can serve both as powerful solvents (e.g., in extraction processes) and as reaction media with catalytic properties. The last Section (3.4) deals with chemical products safe for humans and for the environment. The focus is on polymers, pesticides and surfactants that are produced in a large volume. New "metallocene polyolefins" and water soluble, biodegradable polymers seem to fulfil this requirement. Selective pesticides, non-toxic to mammals, birds, and beneficial insects have been implemented, among them biopesticides. Biodegradable "sugar surfactants" and chemodegradable, acetal-type surfactants have been synthesized and some of them are already industrially produced. The review ends with some remarks on the perspectives of green chemistry in the near future (Section 4). In this context, the need for far-reaching educational initiative to promote the scientific principles of green chemistry, which were developed and implemented to the benefit of society, is stressed .

Słowa kluczowe

PL

zielona chemia; ochrona środowiska; surowce odnawialne; synteza amin aromatycznych; alternatywne reagenty; media reakcyjne

EN

green chemistry; environmental protection; alternative reactant

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2002
• Tom: [Z] 56, 9-10
• Strony: 709--770
• Opis fizyczny: tab., wykr., bibliogr. 244 poz.

Twórcy

autor

Burczyk B.

• Instytut Technologii Organicznej i Tworzyw Sztucznych Politechniki Wrocławskiej, Wybrzeże S.Wyspiańskiego 27, 50-370 Wrocław

Bibliografia

• [1] S.K. Ritter, Chem. Eng. News. 2001. 79 (29), 27.
• [2] P. Tundo. P.T. Anastas, D. StC. Black. J. Breen. T. Collins, S. Memoli, J. Miyamoto. M. Polyakoff, W. Tunias. Pure Appl. Chem.. 2000.72, 1207.
• [3] D.L. Hjeresen. P.T. Anastas. S. Wang, M. KirchhofT, Environ. Sci. Technol., 2001,35,114A.
• [4] www.epa.gov/greenchemistry/index.htm
• [5] www.lanl.gov/greenchemistry
• [6] S.K. Ritter. Chem. Eng. News, 2001, 79 (25). 10.
• [7] P.T. Anastas. J.C. Warner. Green Chemistry : Theory and Practice, Oxford University Press, Oxford, New York. 1998.
• [8] P.T. Anastas. T.C. Williamson. D.L. Hjeresen, J.J. Breen. Environ. Sci. Technol.. 1999,33. 116.
• [9] World Commission on Environment and Development, Our Common Future, Oxford University Press, Oxford, New York, 1987.
• [10] M. Taniewski. Przemysłowa synteza organiczna. Kierunki rozwoju. Wyd. 2 zmienione. Wydawnictwo Politechniki Śląskiej. Gliwice. 1999. s. 24.
• [11] B. Burczyk. Wiad. Chem.. 1998. 52. 175.
• [12] J. Marcinkiewicz. W. Zwierzykowski. ibid., 1989. 43, 159.
• [13] H. Bagmann. M. Buehler. H. Fochem. F. Hirsinger, H Zoebelein. J. Falbe. Angew. Chem. Int. Ed., 1988.27.41.
• [14] J.J. Lewis, [w:] Xonionic Surfactants : Organic Chemistry. N.M. van Os (red.), M. Dekker. Inc., New York-Basel-Hong Kong. 1998. s. 247.
• [15] M. Yalpani. D.E. Brooks. J. Polym. Sei. Polym. Chem. 1988. 23. 1395.
• [16] H. Kelkenberg. Tenside Surf. Det., 1988. 25, 8.
• [171 S & D News. Inform. 1997. 8.40
• [18] Y.-P. Zhu. MJ. Rosen, P.K. Vinson, W. Morrall. J. Surfact. Deterg., 1999. 2,357.
• [19] J E.K. Hildreth. Biochem. J.. 1982,207. 363.
• [20] M. Stalmans. E. Matthijs. E. Weeg. S. Morris. J., SÖFW - J., 1993.119.794.
• [21] T.J. Williams. N.R. Plessas. EJ. Goldstein. Arch. Biochem. Biophys., 1979. 195. 145.
• [22] L. Syper. K.A. Wilk. A. Sokołowski. B. Burczyk. Progr. Colloid Polym. Sei.. 1998. 110. 199.
• [23] B. Pfannemüller. W. Welte. Chem. Phys. Lipids. 1985.37. 227.
• [24] B. Burczyk. K.A. Wilk. A. Sokołowski. L. Syper, J. Colloid Interface Sei.. 2001. 240. 552.
• [25] I. Maliszewska. K.A. Wilk. B. Burczyk. L. Syper. Progr. Colloid Polym. Sei., 2001. 118. 172.
• [26] R. Garelli - Calvet. F. Brisset. I. Rico. A. Lattes. Synth. Commun.. 1993, 23. 35.
• [27] K.A. Wilk. L. Syper, B. Burczyk. A. Sokołowski. B. Domagalska. J. Surfact. Deterg.. 2000. 3, 185.
• [28] C.B.A. Briggs. LM. Newington. A.R. Pit, J. Chem. Soc., Chem. Commun., 1995. 379.
• [29] W. von Rybiński. K. Hill. Angew. Chem. Int. Ed.. 1998. 37. 1329.
• [30] E. Fischer. Chem. Ber.. 1895. 28. 1145.
• [31] M. Biermann, K. Schmid. P. Schulz. Starch/Stärke. 1993.45,281.
• [32] J. Steber. W. Guhl. N. Steher. F.R. Schroeder, Tenside Surf. Det., 1995.32.515.
• [33] P. Busch. H. Hensen. H. Tasmann, ibid.. 1993,30. 116.
• [34] K. Holmberg (red.). Novel Surfactants : Preparation, Applications, and Biodegradability. M. Dekker. Inc., New York-Basei-Hong Kong. 1998. s. iii.
• [35] L. Ember. Chem. Eng. News. 1989.67 (27). 23.
• [36] R. Dagani, ibid.. 1999. 77 (27). 30.
• [37] V.S. Chang. B. Burr, M. Holtzapple, Appl. Biochem. Biotechnol., 1997. 63-65, 3.
• [38] S.L. Wilkinson. Chem. Eng. News. 1997. 75 (31). 35.
• [39] H.G.W. Leuenberger. Pure Appl. Chem., 1990, 62. 753.
• [40] K. Faber (red.). Biotransformations. Advances in Biochemical Engineering Biotechnology. Vol. 63. Springer-Verlag. Berlin-Heidelberg-New York. 1999.
• [41] L.C. Webster. P.T. Anastas. T.C. Williamson, [w:] Green Chemistry : Designing Chemistry for the Environment. P.T. Anastas. T.C. Williamson (red.), ACS Syinp. Ser. 626. Washington. D. C., 1996. s. 198.: i piśmiennictwo tam cytowane.
• [42] C. Divne. J. Stahlberg. T. Reinikainen. L. Ruohonen. G. Pettersson. J.K.C. Knowles. T.T. Teeri, T.A. Jones. Nature, 1994. 265.524.
• [43] C.R. Waldron. C.A. Becker-Vallone. D.E. Eveleigh, Appl. Microbiol. Biotechnol.. 1986.24.477.
• 44] E.A. Johnson, M. Sakajoh, G. Halliwell. A. Madia, A.L. Demain, Appl. Environ. Microbiol., 1982,43, 1125.
• [45] K.M. Draths. J.W. Frost, J. Am. Chem. Soc., 1994. 116. 399.
• [46j B.M. Trost. Science. 1991.254. 1471.
• [47] (a) R.A. Sheldon. Pure Appl. Chem., 2000.72, 1233; (b) R.A. Sheldon. CHEMTECH. 1994,24 38.
• [48] M. Mąkosza, J. Winiarski. Acc. Chem. Res., 1987, 20,282; i piśmiennictwo tam cytowane.
• [49] M.K. Stem. F.D. Hileman. J.K. Bashkin. J. Am. Chem. Soc.. 1992. 114. 9237.
• [50] L.R. Raber. Chem. Eng. News. 1998. 76 (27). 25.
• [51] M.K. Stem. B.K. Cheng, J. Org. Chem.. 1993.58.6883.
• [52] E. Grzywa, J. Molenda, Technologia podstawowych syntez organicznych. Wyd. 3 zmienione, WNT Warszawa. 2000, t. II. s. 295.
• [53] E. Grzywa. J. Molenda, op. cit., s. 248
• [54] M.G. Clerici. P. Ingailina, [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas, T.C. Williamson (red.), ACS Symp. Ser. 626, Washington D.C., 1996. s.59.
• [55] M.C. White, A.G. Doyle. E.N. Jacobsen. J. Am. Chem. Soc., 2001. 123, 7194.
• [56] B.J. Walker. J.D. Lipscomb, Chem. Rev., 1996.96. 2625.
• [57] M. Costas. A.K. Tipton, K. Chen, D.-H. Jo. L. Que Jr., J. Am. Chem. Soc.. 2001. 123. 6722.
• [58] P. Wende. F.-H. Bernhardt, K. Pfleger, Eur. J. Biochem., 1989, 181, 189.
• [59] E.N. Jacobsen, [w:] Catalytic Asymmetric Synthesis, J. Oima (red.), Wiley-VCH, New York, 1993, s. 159.
• [60] C.P. Horwitz, D.R. Fooksman. L.D. Vuocolo, S.W. Gordon-Wyhe, N.J. Cox, T.J. Collins, J. Am. Chem. Soc.. 1998.120,4867.
• [61] A. Ghosh, S.S. Gupta. M.J. Bartos. Y. Hangun. L.D. Vuocolo. B.A. Steinhoff. C.A. Noser. D. Homer. S. Mayer, K. Inderhees, C.P. Horwitz, J. Spatz, A.D. Ryabov, S. Mondai. T.J. Collins, Pure Appl. Chem.. 2001, 73. 113.
• [62] M. Taniewski. op. cit., s. 55.
• [63] E. Grzywa, J. Molenda, op. cit., s.238.
• 1641 K. Sato. M. Aoki, R. Noyori, Science, 1998, 281, 1646.
• [65] G. Strukul, Angew. Chem. Int. Ed., 1998,37, 1198.
• [66] J. Fischer, W. F. Hölderich, Appl. Catal.A, 1999.180, 435.
• [67] A. Corma, L.T. Nemeth, M. Renz, S. Valence, Nature, 2001, 412,423.
• [68] J. Młochowski. L. Syper, Wiad. Chem.. 1990.44. 111.
• [69] J. Wasilewski. Przem. Chem.. 2001. 80.97.
• [70] G.-J. ten Brinks. J.W.C.E. Arends. G. Papadogianakis. R.A. Sheldon. Chem. Commun., 1998. 2359.
• [71] E. Grzywa, J. Molenda, op . cit., s. 227.
• [72] C. Döbler. G. Mehltretter. M. Beller. Angew. Chem. Int. Ed., 1999, 38, 3026.
• [73] K. Mori, K. Yamaguchi. T. Mizugaki, K. Ebitani, K. Kaneda, Chem. Commun., 2001,461.
• [74] K. Nakagawa, T. Tsuji. Chem., Pharm., Bull., 1963, 11,296.
• [75] (a) A. Strecker, Ann., 1850, 75,27; 1854.91,349. (b) T. Franczyk. Patent US A 5292936 (1994); (c) P.T. Anastas. J.C. Warner, op. cit., s. 98.
• [76] (a) T. Groth. W. Joentgen, P. Wagner. F. Dobert, E. Wenderoth, T. Roick, Patent USA 6107518 (2000); (b) S.K. Ritter, Chem. Eng. News. 2001.79(37), 24; (c) G. Boehmke, Patent USA 4839461 (1989).
• [77] W.D. McGhee, T.E. Waldman, Patent US A 5189205 (1993).
• [78] T.E. Waldman. W.D. McGhee, J. Chem. Soc.. Chem Commun., 1994, 957.
• [79] W.D. McGhee, M. Paster. D. Riley. K. Ruettimann, J. Solodar. T. Waldman, [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas, T.C. Williamson (red.), ACS Symp. Ser. 626, Washington, D. C., 1996, s. 49.
• [80] H.T. Clarke, E.E. Dreger, [w:] Org. Syn. Coll. Vol. I, Wiley and Sons. Inc., New York, 1941, s. 495.
• [81] Z. Wirpsza, [w:] Chemia Polimerów, Z. Florjańczyk, S. Penczek (red.). Oficyna Wydawnicza Politechniki Warszawskiej, Warszawa 1997, t. II, s. 265.
• [82] M. Taniewski, op. cit., s. 134.
• [83] T. Skwarski. [w:] Chemia Polimerów, Z. Florjańczyk, S. Penczek (red.), Oficyna Wydawnicza Politechniki Warszawskiej, Warszawa 1997, t. II, s. 247.
• [84] K. Komiya. S. Fukuoka. M. Aminaka. K. Hasegawa, H. Hachiya, H. Okamoto, T. Watanabe, H. Yoneda. I. Fukawa. T. Dozono. [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas. T.C. Williamson (red.), ACS Symp. Ser. 626, Washington, D. C., 1996, s. 20.
• [85] J. Wasilewski. B. Tkacz. A. Krueger. B. Krakówka. M. Dejnega. J. Poskrobko, Pol. J. Chem. Techn., 1999, 1.45.
• [86] P. Tundo. M. Selva. C.A. Marques, [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas. T.C. Williamson (red.), ACS Symp. Ser. 626. Washington D. C., 1996, s. 81.
• [87] Li. Romano. F. Rivetti, N. Di Muzio, Patent U S A 4318862 (1979).
• [88] M. MassiMauri. U. Romano, R. Terei, P. Rebora, Ind. Eng. Chem. Prod. Res. Dev., 1980. 19, 396.
• [89] P. Tundo. Pure Appl. Chem.. 2000, 72.1793.
• [90] M. Makosza, ibid., 2000. 72. 1399.
• [91] P. Tundo, F. Trotta, G. Moraglio. J. Chem. Soc., Perkin Trans. I, 1989. 1070.
• [92] P. Tundo, F. Trotta. G. Moraglio, J. Org. Chem., 1987. 52, 1300.
• [93] P. Tundo, F. Trotta, G. Moraglio, F. Ligorati, Ind. Eng. Chem. Res., 1988, 27, 1565.
• [94] D.C. Rideout, R. Breslow, J. Am. Chem. Soc.. 1980. 102,7816.
• [95] S. Otto. J.B.F.N. Engberts. Pure Appl. Chem., 2000, 72, 1365; i piśmiennictwo tam cytowane.
• [96] R. Breslow, Acc. Chem. Res., 1991, 24. 159.
• [97] C.-J. Li, Chem. Rev., 1993, 93, 2023.
• [98] A. Lubineau. J. Auge, Y. Queneau, Synthesis, 1994, 741.
• [99] C.-J. Li, Tetrahedron, 1996.52, 5643.
• [100] C.-J. Li, T.-H. Chan. Organic Reactions in Aqueous Media, Wiley, New York, 1997.
• [101] C.-J. Li, T.-H. Chan, Tetrahedron, 1999, 55, 11149.
• [102] P. Mastalerz, Chemia Organiczna, PWN, Warszawa. 1984, s. 340-344.
• [103] J. McMurry, Chemia Organiczna, Wydawnictwo Naukowe PWN. Warszawa, 2000, s. 736; 753.
• [104] P.B. Barbier, Compt. Rend., 1889, 128, 110.
• [105] V.G. Grignard, ibid., 1890, 130, 1322.
• [106] T. Huang, S. Venkatraman, Y. Meng, T.V. Nguyen, D. Kort, D. Wang, R. Ding, C.-J. Li, Pure Appl. Chem., 2001,73. 1315.
• [107] C. Petrier, C. Dupuy, J.L. Luche, Tetrahedron Lett., 1986, 27, 3149.
• [108] C. Petrier, J. Einhom, J.L. Luche, ibid., 1985,26, 1449.
• [109] C.-J. Li. T.-H. Chan. ibid.. 1991.32,701.
• [110] S. Araki, S. Jin, Y. Butsugan. Bull. Chem. Soc. Jpn. 1992,65. 1736.
• [111] S. Venkatraman.C.-J. Li. Tetrahedron Lett.. 2001, 42. 781.
• [112] M. Mąkosza. B. Serafinovva. Rocz. Chem.. 1965. 39, 1226.
• [113] M. Makosza, W. Wawrzyniewicz, Tetrahedron Lett.. 1969.4659.
• [114] M. Mąkosza. M. Fedoryński. Adv. Catal., 1987,35, 375.
• [115] E. V. Dehmlow, S. S. Dehmlow, Phase-Transfer Catalysis, 3rd Ed., Verlag Chemie. Weinheim. 1993.
• [116] C.M. Starks, C.L. Liotta, M. Halpem, Phase-Transfer Catalysis : Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall. New York, 1994.
• [117] K. Urata, N. Takaishi, J. Surfact. Deterg., 2001, 4, 191.
• [118] S.M. Reed, J.E. Hutchison, J. Chem. Educ., 2000, 77, 1627.
• [119] K. Urata, N. Takaishi, J. Am. Oil Chem. Soc., 1995, 73, 831.
• [120] (a) E. Kuntz, Patent Francuski 2349563 (1977); (b) E. Kuntz, Patent US A 4248802 (1981); (c) E. Kuntz. CHEMTECH. 1987, 17,570.
• [121] B. Comils, E. Wiebus, CHEMTECH, 1995,25, 33.
• [122] E. Grzywa, J. Molenda, op. cit., s. 124-140.
• [123] W.A. Herrmann, B. Comils, Angew. Chem. Int. Ed., 1997, 36, 1048.
• [124] A. Fukuoka. W. Kosugi, F. Morishita, M. Hirano, L. McCaffrey, W. Henderson, S. Komiya, Chem. Commun., 1999. 489.
• [125] M.S. Goedheijt. J.N.H. Reek, P.C.J. Kemer. P.W.N.M. van Leeuven, ibid ., 1998, 2431.
• [126] G. Papadogianakis. L. Maat, R.A. Sheldon. J. Mol. Catal. A: Chemical, 1997,116, 179.
• [127] J.M. Grosselin, C. Mercier, J. Mol. Catal., 1990. 63. L25.
• [128] J.M. Grosselin. C. Mercier, G. Allmang, F. Grass, Organometallics, 1991, 10,2126.
• [129] P. Genet. E. Blart, M. Savignac. S. Lemeune, J.-M. Paris, Tetrahedron Lett., 1993,34.4189.
• [130] VV.A. Herrmann. J.A. Kulpe. J. Kellner. H. Riepl, H. Bahrmann, W. Konkol, Angew. Chem. Int. Ed. Eng., 1990. 29.391.
• [131] Y. Uozumi. T. Watanabe. J. Org. Chem.. 1999, 64,6921.
• [132] (a) R.F. Heck. J. Am. Chem. Soc.. 1968.90.5518:5531; (b) R.F. Heck. Acc. Chem. Res.. 1979.12, 146.
• [133] A.J. Sandee. V.F. Slagt. J.N.H. Reek. P.C.J. Kamer. P.W.N.M. van Leeuwen. Chem. Commun., 1999,1633.
• [134] J.P. Arhancet. M.E. Davis. J.S. Merola. B.E. Hanson. Nature. 1989.339.454.
• [135] S. Kobayashi. K. Manabe. Pure Appl. Chem.. 2000. 72. 1373.
• [136] (a) T. Mukaiyama. K. Narasaka, K. Banno. Chem. Lett.. 1973.1011 : (b) T. Mukaiyama. K. Banno. K. Narasaka. J. Am. Chem. Soc., 1974.96. 7503.
• [137] S. Kobayashi. J. Hachiya. Tetrahedron Lett., 1992.33. 1625.
• [138] S. Kobayashi, T. Wakabayashi, S. Nagayama, H. Oyamada, ibid., 1997, 38, 4559.
• [139] R. Zieliński. Surfaktanty: towaroznawcze i ekologiczne aspekty ich stosowania, Wydawnictwo Akademii Ekonomicznej w Poznaniu, Poznań, 2000, rozdz. 3.
• [140] M. Gratzel. K. Kalyanasundaram, (red.). Kinetics and Catalysis in Microheterogeneous System s. M. Dekker. Inc.. New York, 1991.
• [141] K.A. Wilk, Wiad. Chem., 1989. 43.229.
• [142] M.-J. Schwuger. K. Stickdom. R. Schomacker, Chem. Rev., 1995, 95, 849.
• [143] C.A. Bunton, L. S. Romsted, [w:] Handbook of Microemulsion Science and Technology. P. Kumar, K.L. Mittal (red.), M. Dekker, Inc., New York-Basel, 1999, s. 457.
• [144] K. Holmberg, Adv. Colloid Interface Sci., 1994,51. 137.
• [145] I. Rico-Lattes. A. Lattes, E. Perez. F. Gonzaga. A. R. Schmitzer, [w:] Reactions and Synthesis in Surfactant Systems, J. Texter (red.), M. Dekker, Inc., New York-Basel, 2001, s. 337.
• [146] R. Schomacker, J. Chem. Res. (S), 1991, 92.
• [147] K. Pigoń, Z. Ruziewicz, Chemia Fizyczna, PWN, Warszawa. 1980, s. 91.
• [148] C.A. Eckert, B.L. Knutson. P.G. Debenedetti, Nature, 1996, 383, 313; i piśmiennictwo tam cytowane.
• [149] (a) K.Zosel, Patent USA 3806619 (1974); (b) K.Zosel, Angew. Chem. Int. Ed. Eng., 1978,17,702.
• [150] T. Wolski, A. Ludwiczuk, Przem. Chem., 2001, 80, 286.
• [151] B. Skowroński, Z. Mordecka, ib id ., 2001,80, 521.
• [152] P.G. Jessop, W. Leitner (red.). Chemical Synthesis using Supercritical Fluids, Wiley-VCH, Weinheim, 1999.
• [153] P.G. Jessop, T. Ikariya, R. Noyori, Chem. Rev., 1999, 99,475.
• [154] A. Baiker. ibid., 1999, 99, 453.
• [155] (a) J.L. Kendall, D.A. Canelas, J.L. Young, J.M. DeSimone, Chem. Rev., 1999, 99, 543; (b) J.L. Young, J.M. DeSimone. Pure Appl. Chem., 2000, 72, 1357; (c) J.A. Behles, J.M. DeSimone, Pure Appl Chem., 2001, 73. 1281; (d) S.L. Wells, J.M. DeSimone. Angew. Chem. Int Ed., 2001,40.518.
• [156] M. Poliakoff. S.M. Howdle. S.G. Kazarian, Angew. Chem. Int. Ed. 1995.34, 1275.
• [157] J.A. Banister, S.M. Howdle. M. Poliakoff, J. Chem. Soc. Chem. Commun., 1993, 1814
• [158] J.M. DeSimone. Z. Guan. C.S. Elsbemd, Science. 1992, 257, 945.
• [159] J.M. DeSimone. E.E. Maury. Y.Z. Menceloglu, J.B. McClain, T.J. Romack, J.R. Combes, ibid, 1994,265.356.
• [160] R. Arshady. Colloid Polym. Sei.. 1992. 270.717.
• [161] T. Carson. S.L. Wells, J.M. DeSimone, [w:] Reactions and Synthesis in Surfactant Systems, J. Texter (red.), M. Dekker, Inc., New York-Basel, 2001, s. 129.
• [162] Z. Guan. J.M. DeSimone, Macromolecules. 1994. 27, 5527.
• [163] X. Zhao. R. Watkins. S. Bartom J. Appl. Polym. Sei., 1995, 55, 733.
• [164] R. Mertsch. B. Wolf, Macromolecules, 1994.27,3289.
• [165] K.P. Johnston. K.L. Harrison, M.J. Clarke. S.M. Howdle, M.P. Heitz, F.K. Bright. C. Carlier, T.W. Randolph. Science. 1996,271, 624.
• [166] K. Harrison, J. Goveas, K.P. Johnston, E.A. O ’Rear, Langmuir, '994, 10, 3536.
• [167] W. Guo. Z. Li, B.M. Fung. E.A. O ’Rear, J. H. Harwell, J. Phys. Chem., 1992, 96,6738.
• [168] Z. Florjańczyk. [w:] Chemia polimerów, Z. Florjańczyk. S. Penczek (red.), Oficyna Wydawnicza Politechniki Warszawskiej, Warszawa, 1997,1.11. s. 145.
• [169] Anon., Chem. Eng. News. 2001, 79 (19). 63.
• [170] (a) P.G. Odell, Patent USA 5698665 (1997); (b) P.G. Odell. G.K. Hamer, Polym. Prepr., 1997,38. 470.
• [171] D.A. Morgenstern. R.M. LeLacheur, D.K. Morita, S.L. Borkowsky, S. Feng, G.H. Brown, L. Luan, M.F. Gross, M.J. Burk, W. Tumas, [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas. T.C. Williamson (red.), ACS Symp. Ser. 626, Washington D. C., 1996, s. 132.
• [172] P.B. Webb. P.C. Marr, A.J. Parsons, H.S. Gidda, S.M. Howdle, Pure Appl. Chem., 2000,72, 1347.
• [173] G.B. Jacobson. C.T. Lee, Jr., K.P. Johnston. J. Org. Chem., 1999,64, 1201.
• [174] G.B. Jacobson, C.T. Lee, Jr., S.R.P. daRocha, K. P. Johnston, ibid., 1999,64,1207.
• [175] B.H. Hutton, J.M. Perera, F. Grieser, G.W. Stevens, Colloids Surfaces A, 2001, 189, 177.
• [176] Y. Ikushima, Adv. Colloid Interface Sei., 1997, 71-72, 259.
• [177] K.P. Johnston, J.D. Holmes, G.B. Jacobson, C.T. Lee, G. Li, P. Psathas, M. Z. Yates, [w:] Reactions and Synthesis in Surfactant Systems, J. Texter (red.), M. Dekker, Inc., New York-Basel, 2001, s. 349.
• [178] P.E. Savage. Chem. Rev., 1999,99. 603.
• [179] D. Broil. C. Kaul. A. Krämer. P. Krasumer. T. Richter. M. Jung, H. Vogt, P. Zehner. Angevv. Chem. Int. Ed., 1999.38.2999.
• [180] E. Grzywa. J. Molenda, o p . c it .. s. 233.
• [181] H.P. Lesutis. R. Gläser, C.L. Liotta. C.A. Eckert, Chem. Commun.. 1999.2063.
• [182] P.A. Marrone. T.A. Arias, W.A. Peters, I.W. Tester, J. Phys. Chem. A. 1998,102, 7013.
• [183] C.M. Camana, Chem. Eng. Progr., 1995, 91, 10.
• [184] R.W. Shaw; T.B. Brill, A.A. Clifford, C.A. Eckert, E.M. Franck, Chem. Eng. News, 1991, 69(51), 26.
• [185] M.J. Earle, K.R. Seddon, Pure Appl. Chem., 2000, 72, 1391.
• [186] K.R. Seddon, J. Chem. Technol. Biotechnol., 1997, 68, 351.
• [187] T. Welton, Chem. Rev., 1999, 99,2071.
• [188] J. Pemak. Przem. Chem.. 2000,79, 150.
• [189] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed., 2000,39,3772.
• [190] J. Pemak, [w:] Czwartorzędowe sole amoniowe i obszary ich zastosowania w gospodarce, R. Zieliński (red.), Wydawnictwo Instytutu Technologii Drewna, Poznań, 2001, s. 188.
• [191] (a) J.D. Holbrey, K.R. Seddon, J. Chem. Soc., Dalton Trans. 1999, 2133; (b) C.M. Gordon, J.D. Holbrey. A.R. Kennedy, K.R. Seddon, J. Mater. Chem., 1998, 8, 2627.
• [192] J. Pemak, A. Czepukowicz, R. Poźniak, Ind. Eng. Chem. Res., 2001, 40,2379.
• [193] M. Freemantie. Chem. Eng. News. 1998. 76 (13), 32.
• [194] P.T. Anastas, J.C. Warner, op. cit., rozdz. 8.
• [195] United Nations Sustainable Development, http://www.un.org/esa/sustdev/agenda21.htm.
• [196] M. Eissen, J.O. Metzger, E. Schmidt. U. Schneidewind, Angew. Chem. Int. Ed.. 2002.41, 414.
• [197] J. Haber, [w:] Technologia chemiczna na przełomie wieków. Wydawnictwo Stałego Komitetu Kongresów Technologii Chemicznej, Gliwice. 2000. s. 69.
• [198] W. Kuran. [w:] Chemia polimerów. Z. Florjańczyk, S. Penczek (red.). Oficyna Wydawnicza Politechniki Warszawskiej. Warszawa. 1995,1.1, s. 246.
• [199] W. Kaminsky. Chemosphere. 2001. 43. 33.
• [200] W. Kaminsky, Mocromol. Chem. Phys., 1996. 196. 3907.
• [201] U. Romano. F. Garbassi. Pure Appl. Chem.. 2000. 72. 1383.
• [202] G. Swift. J. Macromol. Sei. Pure Appl. Chem.. 1995. A32.641.
• [203] L.P. Koskan. A.R.Y. Meah. Patent U S A 5219952 (1993)
• [204] L.P. Koskan. K.C. Low. Patent US A 5116513 (1992).
• [205] Report of the United Nations Conference on Environment and Development. Rio de Janeiro. June 1992; http://www.un.org/esa/sustdev.
• [206] M.B. Green, G.S. Hartley, T.F. West. Chemicals for Crop Improvement and Pest Management. Pergamon Press, Oxford-New York. 1987.
• [207] P. Mastalerz. Wiad. Chem., 2000. 54. 227.
• [208] http://www.epa.gov/greenchemistry/past.htm.
• [209] J.K. Moulton. D.A. Pepper, T.J. Denehy, Pest Manag. Sei., 2000, 56. 842.
• [210] L.G. Copping. J.J. Menn. ib id .. 2000, 56. 651.
• [211] J. Granados. Proc. CESIO 4th World Surfactants Congr., Barcelona, 03.-07. 06. 1996, A.E.P.S.A. T. Barcelona, 1996. Vol.1.s. 100.
• [212] R.D. Swisher. Surfactant Biodegradation. Second Ed., M. Dekker, Inc., New York-Basel, 1987.
• [213] P. Schoeberl, [w:] D ie Tenside. K. Kosswig, H. Stäche (red.), C. Hanser Verlag, Muenchen, 1993, s. 409.
• [214] B. Burczvk. [w:] Encyclopedia of Surface and Colloid Science, A. Hubbard (red.). M. Dekker, Inc., New York-Basel, 2002, s. 724-752.
• [215] W'. Von Rybiński. K.-H. Hill, [w:] Novel Surfactants : Preparation, Applications, and Biodegradability, K. Holmberg (red.), M. Dekker, Inc., New York-Basel-Hong Kong. 1998, s. 31.
• [216] A. Lif, M. Hellsten, [w:] Nonionic Surfactants : Organic Chemistry, N. M. van Os (red.), M. Dekker. Inc., New York-Basel-Hong Kong, 1998, s. 177.
• [217] B. Burczyk [w:] Technologia chemiczna na przełomie wieków . Wydawnictwo Stałego Komitetu Kongresów Technologii Chemicznej, Gliwice, 2000, s. 127.
• [218] B. Burczyk, VIIth Intern. Conf. Surface Active Substances, Bad Stuer (G.D.R.), April 22-30, 1988, Central Institute of Organic Chemistry of the Academy of Sciences of the G.D.R., Berlin, (G.D.R.), 1988, Preprints Abs.. s. 4.
• [219] G. Krüger. D. Boltersdorf, K. Overkempe. [w:] Novel Surfactants : Preparation, Applications, and Biodegradability, K. Holmberg (red.). M. Dekker. Inc.. New York-Basel-Hong Kong. 1998. s. 115.
• [220] P. Mastalerz. op. cit., s. 490.
• [221] H.G. Schlegel. Mikrobiologia ogólna. Wydawnictwo Naukowe PWN, Warszawa, 1996, s. 526.
• [222] D. Ono, S. Yamamura. N. Nakamura, T. Takeda, A. Masuyama, Y. Nakatsuji, J. Am. Oil Chem. Soc., 1995,72, 853.
• [223] D. Ono, A. Masuyama, T. Tanaka, M. Okahara, Tenside Surf. Det., 1992, 29,412.
• [224] (a) B. Burczyk. A. Sokołowski, Tenside Deterg., 1978,15,68; (b) A. Sokołowski, B. Burczyk, Pol. J. Chem., 1979, 53, 905; (c) A. Sokołowski, B. Burczyk, ibid ., 1979, 53, 412; (d) C. Yue, J.M. Harris, P.-E. Hellberg, K. Bergstroem, J. Am. Oil Chem. Soc., 1996, 73, 84
• [225] (a) R.C. Hoy, A.F. Joseph, Inform, 1996, 7,428; (b) A.F. Joseph, C.M. Wizda, S.W. Kaiser, Proc. CESIO 5th World Surfactants Congr., Firence, 29.05.-2.06.2000, Federchimica Assobase - P.I.T.I.O., Milano, 2000, Vol. 1. s. 272.
• [226] D.A. Jaeger, Supramol. Chem., 1995, 5, 27.
• [227] K. Holmberg, [w:] Novel Surfactants : Preparation, Applications, and Biodegradability, K. Holmberg (red.), M. Dekker. Inc.. New York-Basel-Hong Kong, 1998, s. 333.
• [228] A. Piasecki, [w:] Encyclopedia of Surface and Colloid Science, A. Hubbard (red.). M. Dekker, Inc., New York-Basel. 2002, s. 701-723.
• [229] J. Thornton, Pure Appl. Chem., 2001, 73, 1231.
• [230] MS. Simmons, [w:] Green Chemistry : Designing Chemistry for the Environment, P.T. Anastas. T.C. Williamson (red.). ACS Symp. Ser. 626, Washington. D. C., 1996. s. 116.
• [231] P.T. Anastas, M.K. Kirchhoff, T.C. Williamson, Appl. Catal. A: General, 2001, 221, 3.
• [232] J. Haber. Pure Appl. Chem., 1994, 66. 1597.
• [233] M. Misono. I. Ono. G. Koyano. A. Aoshima, ib id, 2000. 72. 1305.
• [234] I. Nowak. M. Ziółek, [w:] Uporządkowane materiały mezoporowate, Biblioteka Wiad. Chem., Wydawnictwo Uniwersytetu Wrocławskiego. Wrocław. 2001. s. 5
• [235] P.T. Anastas, J. C. Warner, op. cit., s. 115.
• [236] J.O. Metzger. Chemosphere. 2001.43. 83.
• [237] A. Albini, F. Fagnoni, M. Mella. Pure Appl. Chem., 2000. 72, 1321.
• [238] J. Marquie. C. Laporte. A. Laporterie. J. Dubac. J.-R. Desmurs, N. Roques, Ind. Eng. Chem. Res., 2000, 39, 1124; i piśmiennictwo tam cytowane.
• [239] D. Bogdał. Wiad. Chem., 1999, 53, 65.
• [240] A. Burghardt, [w:] Technologia chemiczna na przełomie wieków, Wydawnictwo Stałego Komitetu Kongresów Technologii Chemicznej, Gliwice, 2000, s. 33.
• [241] A. Dąbrowski, Adv. Colloid Interface Sci., 2001,93, 135.
• [242] A.S. Matlack, Introduction to Green Chemistry, M. Dekker, Inc., New York-Basel. 2001. s. iii.
• [243] (a) D.J. Hjeresen, D.L. Schutt, J.M. Boese, J. Chem. Educ., 2000, 77, 1543; (b) M.W. Warner, G. Succaw, J.E. Hutchison, Green Chemistry, 2001, 3, 267.
• [244] (a) S.A. Ware. Pure Appl. Chem., 2001, 73, 1247; (b) http://www.chemistry.org/education/greenchem.