Acetic Acid
Carole Le Berre
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorPhilippe Serp
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorPhilippe Kalck
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorG. Paull Torrence
Celanese Corporation, Intermediate Chemistry, Clear Lake Technical Center, Pasadena, Texas, United States, 77507
Search for more papers by this authorCarole Le Berre
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorPhilippe Serp
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorPhilippe Kalck
Université de Toulouse, UPS-INP-LCC, Laboratoire de Chimie de Coordination (LCC), UPR CNRS 8241, ENSIACET, 4 allée Emile Monso, Toulouse, Cedex 4, France, BP 44362, 31030
Search for more papers by this authorG. Paull Torrence
Celanese Corporation, Intermediate Chemistry, Clear Lake Technical Center, Pasadena, Texas, United States, 77507
Search for more papers by this authorAbstract
The article contains sections titled:
1. | Introduction |
2. | Physical Properties |
3. | Chemical Properties |
4. | Production |
4.1. | Carbonylation of Methanol |
4.2. | Direct Oxidation of Saturated Hydrocarbons |
4.3. | Acetaldehyde Process |
4.4. | Other Processes |
4.5. | Concentration and Purification |
4.6. | Construction Materials |
5. | Wastewater Problems |
6. | Quality Specifications |
7. | Analysis |
8. | Storage, Transportation, and Customs Regulations |
9. | Uses |
10. | Derivatives |
10.1. | Salts |
10.1.1. | Aluminum Acetate |
10.1.2. | Ammonium Acetate |
10.1.3. | Alkali Metal Salts |
10.2. | Esters |
10.2.1. | Methyl Acetate |
10.2.2. | Ethyl Acetate |
10.2.3. | Butyl Acetate |
10.2.4. | 2-Ethylhexyl Acetate |
10.2.5. | Other Esters |
10.3. | Acetyl Chloride |
10.4. | Amides |
10.4.1. | Acetamide |
10.4.2. | N,N-Dimethylacetamide |
10.5. | Phenylacetic Acid |
11. | Economic Aspects |
12. | Toxicology and Occupational Health |
References
- 1 M.P. Malveda, C. Funada: “ Acetic Acid”, CEH Marketing Research Report, Chemical Economics Handbook-SRI Consulting, Englewood, Co July 2010, 602.5000A.
- 2 L.A. Paquette (ed.): Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, New York 1995, p. 11.
- 3 A.P. Kudchadker, G.H. Alani, B.J. Zwolinski, Chem. Rev. 68 (1968) no. 6, 659–735.
- 4 D.R. Lide, H.P.R. Frederikse (eds.): CRC Handbook of Chemistry and Physics, 77th ed., CRC Press, Boca Raton, Florida, No. 100. “Acetic acid”, Beilstein reference no. 4-02-00-000094; Merck Index, 10th ed., no. 47.
- 5 J.A. Ridduck, W.B. Bunger: Organic Solvents: Physical Properties and Methods of Purification, 3rd ed., Wiley-Interscience, New York 1970.
- 6 Kirk-Othmer, Encyclopedia of Chemical Technology, 4th ed., vol. 1, J. Wiley & Sons, New York 1991–1998, pp. 121–129.
- 7 D.D. Perrin, W.L.F. Armarego, D.R. Perrin: Purification of Laboratory Chemicals, Pergamon Press, New York 1966.
- 8 Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., vol. A1, VCH Verlagsgesellschaft, Weinheim 1985–1996, p. 45.
- 9 W.H. Seaton in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, p. 106.
- 10 W.H. Seaton, unpublished work for the Design Data Research Laboratory, Tennessee Eastman Co., Kingsport 1970–1974.
- 11 International Critical Tables, McGraw-Hill, New York 1926.
- 12 A. Ragni, G. Ferrari, P. Papoff, Ann. Chim. (Rome) 45 (1955) 960–969.
- 13 A.N. Campbell, E.M. Kartzmark, Can. J. Res. 28B (1950) 161–169.
- 14 J. Timmermans: Physico-chemical Constants of Pure Organic Compounds, Elsevier, New York 1950.
- 15 A.W. Francis, Chem. Eng. Sci. 10 (1959) 37.
- 16 I. Brown, A.H. Ewald, Austr. J. Sci. Res. Ser. A, 3 (1950) 306–323.
- 17 J.J. Jasper, J. Phys. Chem. Ref. Data 1 (1972) no. 4, 841–1009.
- 18 R. Barton, C.C. Hsu, J. Chem. Eng. Data 14 (1969) 184–187.
- 19 M.D. Taylor, J. Amer. Chem. Soc. 73 (1951) 315.
- 20 W.J. Weltner, J. Amer. Chem. Soc. 77 (1955) 3941–3950.
- 21 J.L. Derissen, J. Mol. Struct. 7 (1971) 67–80.
- 22 G. Arich, G. Tagliavini, Ric. Sci. 28 (1958) 2493.
- 23 S.D. Christian, H.E. Affsprung, C. Ling, J. Chem. Soc. 1965, 2378–2381.
- 24 R. Vilcu, E. Lecinescu, Rev. Roum. Chim. 14 (1969) 283–290.
- 25 C. Sandonnini, (Atti. Accad. Naz. Lincei CL. Sci.) Fis. Mat. Nat. Rend. 4 (1926) 63–68.
- 26 J.A. Dean (ed.): Lange's Handbook of Chemistry, 12th ed., McGraw-Hill, New York 1979, pp. 6–36.
- 27
G.S. Park,
K.K. Kelley,
J. Am. Chem. Soc.
47
(1925)
2089.
10.1021/ja01685a003 Google Scholar
- 28 J.J. Lagowski: The Chemistry of Nonaqueous Solvents, Academic Press, New York 1970, p. 244.
- 29 F.H. MacDougall, J. Am. Chem. Soc. 58 (1936) 2586.
- 30 I. Brown, A.H. Ewald, Aust. J. Sci. Res.-Series A-Phys. Sci. 3 (1950) 306–23.
- 31 S.P. Miskidzh'yan, H.A. Trifonof, Zh. Obshch. Khim. 17 (1947) 1033.
- 32 M. Usanovich, L.N. Vasil'eve, Zh. Obshch. Khim. 16 (1946) 1202.
- 33 K.T. Abtiev, Vestnik. Adad. Nauk Kazakh, S.S.R. 15 (1959) no. 12, 72–77.
- 34 R.D. Nelson, D.R. Lide, A.A. Maryott: Selected values of electric dipole moments in the gas phase, National Reference Data Sheet, National Bureau of Standards, Washington, D.C. 1967, p. 10.
- 35 D.D. Wagman et al., J. Phys. Chem. Ref., 11 (1982) S2.
- 36 N.I. Sax: Dangerous Properties of Industrial Materials, 5th ed., Van Nostrand Reinhold Co., New York 1979, p. 333.
- 37
E.K. Euranto in
S. Patai (ed.):
The Chemistry of Carboxylic Acids and Esters,
Interscience Publishers,
London
1969, pp.
505–588.
10.1002/9780470771099.ch11 Google Scholar
- 38 M. Gauß, A. Seidel, P. Torrence, P. Heymanns in B. Cornils, W.A. Herrmann (eds.): Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1, VCH Publishers, New York 1996, pp. 104–138.
- 39 P.M. Matlis, A. Haynes, G.J. Sunley, M.J. Howard, J. Chem. Soc., Dalton Trans. 1996, 2187–2196.
- 40 M.J. Howard, M.D. Jones, M.S. Roberts, S.A. Taylor, Catal. Today 18 (1994) 325–354.
- 41 Showa Denko K. K., WO94/22803, 1994 (T. Suzuki, H. Yoshikawa, K. Abe, K. Sano).
- 42 R.P. Lowry, A. Aguilo, Hydrocarbon Process. 53 (1974) no. 11, 103–113.
- 43 H. Hohenschutz et al., Hydrocarbon Process. 45 (1966) no. 11, 141–143.
- 44 J.W. Reppe: Acetylene Chemistry, Charles A. Meyer & Co., Boston 1949.
- 45 Hydrocarbon Process. 46 (1967) no. 11, 136.
- 46 Hydrocarbon Process. 52 (1973) no. 11, 92.
- 47 N.V. Kutepow, W. Himmele, H. Hohenschutz, Chem. Ing. Tech. 37 (1965) 383–388.
- 48 S.F. Dickson, J. Bakker, A. Kitai: “ Acetic Acid,” Chemical Economics Handbook, SRI International, Menlo Park 1982, rev. July 1982, 602.5020, 602.5021.
- 49 F.E. Paulik, J.F. Roth, Chem. Commun. 1968, 1578.
- 50 D. Forster in F.C.A. Stone, R. West (eds.): Advances in Organometallic Chemistry, Academic Press, New York 1979, pp. 255–267.
- 51 Chem. Eng. 5 (1978) 182.
- 52 Hoechst Celanese Corp., US5001259, 1991 (B.L. Smith, G.P. Torrence, A. Aguilo, S. Alder).
- 53 Chemical Market Reporter 1 (1997) 3.
- 54 Process Eng. 1996, 21.
- 55 D.J. Watson: “ The Cativa Process for the Production of Acetic Acid”, 15th Meeting of the North American Catalysis Society, Chicago 1997, pp. 18–22.
- 56 D. Forster, T.C. Singleton, J. Mol. Catal. 17 (1982) 299–314.
- 57 T. Dekleva, D. Forster, Adv. Catalysis 34 (1986) 81–130.
- 58 D.L. King, K.K. Ushiba, T.E. Whyte, Jr., Hydrocarbon Process. 61 (1982) no. 11, 131–136.
- 59 P. Ellwood, Chem. Eng. (N.Y.) 76 (1969) no. 11, 148–150.
- 60 J.J. McKetta, W.A. Cummingham (eds.): Encyclopedia of Chemical Processing Design, Marcel Dekker, New York 1976, pp. 216–246.
- 61 J. Hjortkjaer, V.W. Jenson, Ind. Eng. Chem., Prod. Res. Dev. 15 (1976) 46–49.
- 62 J. Hjortkjaer, O.R. Jenson, Ind. Eng. Chem., Prod. Res. Dev. 16 (1977) 281–285.
- 63 T. Matsumoto, K. Mori, T. Mizorki, A. Ozaki, Bull. Chem. Soc. Japan 50 (1977) no. 9, 2337–2340.
- 64 S.B. Dake, D.S. Kolhe, R.V. Chaudhari, Ind. Eng. Chem. Res. 28 (1989) 1107–1110.
- 65 Monsanto, US3769329, 1973 (F.E. Paulik, A. Hershman, W.R. Knox, J.F. Roth).
- 66 G.W. Adamson, J.J. Daly, D. Forster, J. Organomet. Chem. 71 (1974) C17–C18.
- 67 A.G. Kent, B.E. Mann, C.P. Manuel, J. Chem. Soc. Chem. Commun. 11 (1985) 728–729.
- 68 D. Forster, Ann. N.Y. Acad. Sci. 295 (1977) 79–82.
- 69 D. Forster, J. Am. Chem. Soc. 98 (1976) 846–848.
- 70 B.L. Smith, M.A. Murphy, G.T. Torrence, A. Aguilo, Inorg Chim Acta. 101 (1985) L47–L49.
- 71 M.A. Murphy, B.L. Smith, G.P. Torrence, A. Aguilo, J. Organomet. Chem. 303 (1986) 257–272.
- 72 M.A. Murphy, B.L. Smith, G.P. Torrence, A. Aguilo, J. Mol. Catal. 39 (1987) 115–136.
- 73 A. Haynes, B.E. Mann, D.J. Gulliver, G.E. Morris, P.M. Maitlis, J. Am. Chem. Soc. 113 (1991) 8567–8569.
- 74 A. Haynes, B.E. Mann, D.J. Gulliver, G.E. Morris, P.M. Maitlis, J. Am. Chem. Soc. 115 (1993) 4093–5000.
- 75 C.E. Hickey, P.M. Maitlis, J. Chem. Soc. Chem. Commun. 1984, 1609–1611.
- 76 A. Fulford, P.M. Maitlis, J. Organomet. Chem. 366 (1989) C20–C22.
- 77 A. Fulford, C.E. Hickey, P.M. Maitlis, J. Organomet. Chem. 398 (1990) 311–323.
- 78 P.M. Maitlis, A. Haynes, G.J. Sunley, M.J. Howard, J. Chem. Soc., Dalton Trans. 11 (1996) 2187–2196.
- 79 N. Lassauque, T. Davin, D.H. Nguyen, R.J. Adcock, Y. Coppel, C. Le Berre, P. Serp, L. Maron, P. Kalck, Inorg. Chem. 51 (2012) 4–6.
- 80 D.H. Nguyen, N. Lassauque, T. Davin, L. Vendier, S. Mallet-Ladeira, L. Maron, C. Le Berre, P. Serp, P. Kalck, in A.J.L. Pombeiro (ed.): Advances in Organometallic Chemistry and Catalysis, Wiley, Hoboken 2014.
- 81 E. Baker, D.E. Hendrickson, R. Eisenberg, J. Am. Chem. Soc. 102 (1980) 1020–1027.
- 82 B.R. James, G.L. Rempel, J. Chem. Soc. A 1969, 78–84.
- 83 T.C. Singleton, L.J. Park, D. Forster, Prepr. Am. Chem. Soc. Div. Pet. Chem. 24 (1979) 329–335.
- 84 D. Forster, The Chemist 1981, 7–10.
- 85 Monsanto, US4690912, 1987.
- 86 D.K. Dutta, P. Chutia, B.J. Sarmah, B.J. Borah, B. Deb, J.D. Woolins, J. Mol. Catal. A Chem. 300 (2009) 29, and their previous work quoted.
- 87 A. Haynes, Adv. Catal. 53 (2010) 1–45.
- 88 a) J. Rankin, A.C. Benyei, A.D. Poole, D.J. Cole-Hamilton, J. Chem. Soc., Dalton Trans. 1999, 3771–3837. b) C. Jimenez-Rodriguez, P.J. Pogorzelec, G.R. Eastham, A.M.Z. Slawin, D.J. Cole-Hamilton, Dalton Trans. 2007, 4160–4168.
- 89 A.E.C. McConnell, D.F. Forster, P. Pogorzelec, A.M.Z. Slawin, D.J. Law, D.J. Cole-Hamilton, Dalton Trans. 2003, 510–512
- 90 L. Gonsalvi, J.A. Gaunt, H. Adams, A. Castro, G.J. Sunley, A. Haynes, Organometallics 22 (2003) 1047–1054.
- 91 H.C. Martin, N.H. James, J. Aitken, J.A. Gaunt, H. Adams, A. Haynes, Organometallics 22 (2003) 4451–4458.
- 92 Celanese, WO2011/159268, 2011.
- 93 Rhône-Poulenc Chimie, US5625094, 1997.
- 94 Celanese International Corporation, US6211405, 2001.
- 95 BP Chemicals Limited, US6130355, 2000.
- 96 N. Yoneda, S. Kusano, M. Yasui, P. Pujado, S. Wilcher, Appl. Catal. A: Gen. 221 (2001) 253–265.
- 97 K. Omata, K. Fujimoto, T. Shikada, H. Tominaga, Ind. Eng. Chem. Res. 27 (1988) 2211–2213.
- 98 K. Fujimoto, T. Shikada, K. Omata, H. Tominaga, Ind. Eng. Chem. Prod. Res. Dev. 21 (1982) 429–432.
- 99 G.A. Flores-Escamilla, J.C. Fierro-Gonzalez, J. Mol. Catal. A: Chemical 359 (2012) 49–56.
- 100 R.W. Wegman, J. Chem. Soc. Chem. Commun. 1994, 947–948.
- 101 S. Yao, C. Yang, Y. Tan, Y. Han, Catal. Commun. 9 (2008) 2107–2111.
- 102 M.P. Kapoor, Y. Matsumura, Chem. Commun. 2000, 95–96.
- 103 N. De Blasio, M.R. Wright, E. Tempesti, C. Mazzocchia, D.J. Cole-Hamilton, J. Organomet. Chem. 551 (1998) 229–234.
- 104 Reilly Industries, Inc., US5155261, 1992.
- 105 Chiyoda, US5334755, 1994.
- 106 Chiyoda, US5364963, 1994.
- 107 Chiyoda, US5576458, 1996.
- 108 Eastman Chemical Company, US6916951, 2003.
- 109 Institut Français du Pétrole, US7115774, 2003.
- 110 G.C. Tustin, R.M. Moncier, J.R. Zoeller, ACS Symp. Ser. 975 (2007) 128.
- 111 Wacker Chemie AG, WO2006/122563, 2006.
- 112 A. Riisager, B. Jørgensen, P. Wasserscheid, R. Fehrmann, Chem. Commun. 2006, 994–996.
- 113 Eastman Chemical Company, US7582792, 2006.
- 114
J.R. Zoeller,
M.K. Moore,
A.J. Vetter,
A. Quillen,
T. Barnette:
Catalysis of Organic Reactions,
CRC Press,
Boca Raton
2008, pp.
329–338.
10.1201/9781420070774.ch37 Google Scholar
- 115 D. Brodzki, B. Denise, G. Pannetier, J. Mol. Catal. 2 (1977) 149–161.
- 116 D. Forster, J. Chem. Soc., Dalton Trans. 1979, 1639–1645.
- 117 M.J. Howard, M.D. Jones, M.S. Roberts, S.A. Taylor, Catal. Today 18 (1993) 325–354.
- 118 A. Haynes, P.M. Maitlis, G.E. Morris, G.J. Sunley, H. Adams, P.W. Badger, C.M. Bowers, D.B. Cook, P.I.P. Elliott, T. Ghaffar, H. Green, T.R. Griffin, M. Payne, J.M. Pearson, M.J. Taylor, P.W. Vickers, R.J. Watt, J. Am. Chem. Soc. 126 (2004) 2847–2861.
- 119 C.J.E. Vercauteren, K.E. Clode, D.J. Watson, EP616997, 1994.
- 120 P.R. Ellis et al., Organometallics 13 (1994) 3215–3226.
- 121 J.M. Pearson, A. Haynes, G.E. Morris, G.J. Sunley, P.M. Maitlis, J. Chem. Soc., Chem. Commun. 10 (1995) 1045–1046.
- 122 T. Ghaffar et al., Chem. Commun. 9 (1998) 1023–1024.
- 123 A. Haynes, J.M. Pearson, P.W. Vickers, J.P.H. Charmant, P.M. Maitlis, Inorg. Chim. Acta. 270 (1998) no. 1–2, 382–391.
- 124 Acetex Chimie, FR9813954, 1998.
- 125 Eastman Chemical Company, US2003/0054951 A1, 2003.
- 126 Eastman Chemical Company, US6137000, 2000.
- 127 Celanese International Coporation, US6458995 B1, 2002.
- 128 Eastman Chemical Company, US7582792 B2, 2009.
- 129 J. Gauthier-Lafaye, R. Perron: “ Methanol et Carbonylation,” Rhône-Poulenc Recherches, Courbevoie 1986 [English translation: Methanol Carbonylation, Editions Technip, Paris, and Rhône-Poulenc Recherches, Courbevoie 1987], pp. 117–148.
- 130 J.R. Zoeller in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, pp. 35–51.
- 131 W.R. Moser, B.J. Marshik-Guerts, S.J. Okrasinski, J. Mol. Catal. A: Chem. 143 (1999) 71–83.
- 132 Rhône-Poulenc, EP35458, 1981.
- 133 N. Rizkalla, ACS Symp. Ser. 328 (1987) 61.
- 134 A.A. Kelkar, R.S. Ubale, R.M. Deshpande, R.V. Chaudhari, J. Catal. 156 (1995) 290–294.
- 135 J. Yang, A. Haynes, P.M. Maitlis, Chem. Commun. 1999, 179.
- 136 S.S. Tonde, A.A. Kelkar, M.M. Bhadbhade, R.V. Chaudhari, J. Organomet. Chem. 690 (2005) 1677–1681.
- 137 A.A. Kelkar, D.S. Kolhe, R.V. Chaudhari, J. Organomet. Chem. 430 (1992) 111–116.
- 138 S. Shinoda, T. Yamakawa, J. Chem. Soc., Chem. Commun. 1990, 1511–1512.
- 139 a) T. Yamakawa, P. Tsai, S. Shinoda, Appl. Catal. 92 (1992) L1–L5. b) L.-C. Yang, T. Yamakawa, S. Shinoda, J. Mol. Catal. A: Chem. 130 (1998) 249–253.
- 140 T. Yamakawa, M. Hiroi, S. Shinoda, J. Chem. Soc., Dalton Trans. 1994, 2265–2269.
- 141 H. Einaga, T. Yamakawa, S. Shinoda, J. Mol. Catal. A: Chem. 97 (1995) 35–40.
- 142 T. Grewer, A. Schmidt, Chem. Ing. Tech. 35 (1973) 1063–1067.
- 143 R.T. Eby, T.C. Singleton, Appl. Ind. Catal. 1 (1983) 275–296.
- 144 BP Chemicals Limited, EP0728729, 1995 (S.J. Smith, R.J. Watt, B.L. Williams).
- 145 BP Chemicals Limited, US5750007, 1998 (K.E. Clode, D.J. Watson, C.J.E. Vercauteren).
- 146
C.C. Hobbs in
B. Cornils,
W.A. Herrmann (eds.):
Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1,
VCH Verlagsgesellschaft,
Weinheim
1996, p.
521.
10.1002/9783527619351.ch2h Google Scholar
- 147 Kirk-Othmer, Encyclopedia of Chemical Technology, 4th ed., vol. 13, J. Wiley & Sons, New York 1991–1998, pp. 682–717.
- 148 Ethylene and Derivatives, vol. 1, Wood Petrochemicals Program, SRI International, Menlo Park, CA, 1995, WORL-28.
- 149 G. Irick in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, p. 31.
- 150 S.W. Benson in R.R. Gould, F.R. Mayo (eds.): Advances in Chemistry Series 76, American Chemical Society, Washington D.C. 1968, pp. 143–153.
- 151 D.L. Llord, P.L. Eve, P.D. Gammer, Erdoel, Erdgas, Kohle 109 (1993) no. 6, 266.
- 152 R.A. Sheldon, J.K. Kochi: Metal-Catalyzed Oxidation of Organic Compounds, Academic Press, New York 1981, p. 143.
- 153 R.S. Drago, Coord. Chem. Rev. 117 (1992) 185.
- 154 C.C. Hobbs et al., Ind. Eng. Chem. Process Des. Der. 11 (1972) 59.
- 155 S.W. Benson, P.S. Nangia, Acc. Chem. Res. 12 (1979) no. 7, 223–228.
- 156 R.A. Sheldon, J.K. Kochi: Metal-Catalyzed Oxidation of Organic Compounds, Academic Press, New York 1981, p. 20.
- 157 A.T. Betts, H. Uri in R.R. Gould, F.R. Mayo (eds.): Advances in Chemistry Series 76, American Chemical Society, Washington D.C. 1968, pp. 161–181.
- 158 L. Sieg in W. Jost (ed.): Low Temperature Oxidation, Gordon and Breach, New York 1965, p. 222.
- 159 D. Swern (ed.): Organic Peroxides, John Wiley & Sons, New York 1970, p. 214.
- 160 J.F. Black, J. Amer. Chem. Soc. 100 (1978) 527.
- 161 J. Skriniarova, M. Hronec, J. Ilavsky, Oxid. Commun. 10 (1987) nos. 1–2, 51–68.
- 162 G.A. Russel, J. Amer. Chem. Soc. 79 (1957) 3871.
- 163 Q.J. Niu, G.D. Mendenhall, J. Amer. Chem. Soc. 114 (1992) no. 1, 165–172.
- 164 S.W. Benson, Oxid. Commun. 2 (1982) nos. 3–4, 169–172.
- 165 Ullmanns Encyclopädie der Technischen Chemie, 4th ed., vol. 11, Verlag Chemie, Weinheim 1972–1984, pp. 57–64.
- 166
H. Hofermann,
Chem. Ing. Tech.
36
(1964)
no. 5,
422–429.
10.1002/cite.330360503 Google Scholar
- 167 Acetic Acid, 37 A, SRI Internationals Process Economics Program, private report, Feb. 1968, March 1973.
- 168 T. Yamaguchi, Jpn. Chem. Q. IV-I (1968) 27–33.
- 169 J. Royer, M. Beugelmans-Verrier, C. R. Hebd. Seances Acad. Sci. Ser. C272 (1971) 1818.
- 170 N.A. Cliton, R.A. Kenley, T.G. Traylor, J. Am. Chem. Soc. 97 (1975) 3746–3752, 3757.
- 171 F. Colombo, Quad. Ing. Chim. Ital. 18 (1982) 68–84. Chem. Abstr. 98 142586.
- 172 A.T. Fanning in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, pp. 18–21.
- 173 W.J. DeKlein, E.C. Kooyman, J. Catal. 4 (1965) 626.
- 174
G.C. Allen,
A. Aguilo,
Adv. Chem. Ser.
76
(1968)
363.
10.1021/ba-1968-0076.ch053 Google Scholar
- 175 Celanese Corp., NL8004525, 1980.
- 176 D.R. Larkin, J. Org. Chem. 55 (1990) 1563.
- 177 R.A. Sheldon, J.K. Kochi: Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York 1981.
- 178 T.-C. Chou, F.-S. Lin, Can. J. Chem. 61 (1983) 1295–1300.
- 179 Standard Oil Co, US4408071, 1983 (S.E. Pedersen, H.F. Hardman, L.F. Wagner).
- 180 J.L. Seone, P. Boutry, R. Montarnal, J. Catal. 63 (1980) 182–190.
- 181 Showa Denko, JP11347412, 1999.
- 182 K-I. Sano, H. Uchida, S. Wakabayashi, Catalysis Survey Japan 3 (1999) no. 1, 55–60.
- 183 E.M. Thorstein, T.P. Wilson, F.G. Young, P.H. Kasai, J. Catal. 52 (1978) 116–132.
- 184 Union Carbide Corporation, EP0216264 A1, 1986 (R.M. Manyik, J.L. Brockwell, J.E. Kendall).
- 185 Union Carbide Chemicals and Plastics Technology Corporation, US5162578, 1992.
- 186 Union Carbide Corporation, EP0294845 A1, 1988 (J.H. McCain, S.W. Kaiser, G.L. O'Connor).
- 187 Rhône-Poulenc Chimie, EP0627401 A1, 1994 (F. Blaise, E. Bordes, M. Gubelman, L. Tessier).
- 188 Rhône-Poulenc Chimie, EP0479692 A1, 1991 (P. Barthe, G. Blanchard).
- 189 L. Tessier, E. Bordes, M. Gubelmann-Bonneau, Catal. Today 24 (1995) 335–340.
- 190 M. Roy, M. Gubelmann-Bonneau, H. Ponceblanc, J.-C. Volta, Catalysis Letters 42 (1996) 93–97.
- 191 Hoechst Research & Technology, WO9847851, 1998.
- 192 Hoechst Research & Technology, US6034270, 2000.
- 193 BP Chemicals Limited, EP0407091 A1, 1990 (M. Kitson).
- 194 BP Chemicals Limited, EP0480594 A2, 1991 (C. Hallet).
- 195 BP Chemicals Limited, US6333444 B1, 2001.
- 196 BP Chemicals Limited, US7491843 B2, 2009.
- 197 The Standard Oil Company, EP0518548 A2, 1992 (P.R. Blum, M.A. Pepera).
- 198 Hoechst AG, WO9805619 A1, 1998 (H. Borchert, U. Dingerdissen).
- 199 SABIC, US5907056, 1999.
- 200 SABIC, US6258992, 2001.
- 201 SABIC, US6030920, 2000.
- 202 SABIC, US6531631, 2003.
- 203 SABIC, US6638891, 2003.
- 204 SABIC, US6989342, 2006.
- 205 Celanese, USRE39074 E, 2006.
- 206 Mitsubishi Chemical Corporation, JP10017523, 1998.
- 207 L.R. Partin, W.H. Heise in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, pp. 3–13.
- 208
H. Ebner,
S. Sellmer,
H. Follmann in
H.J. Rehm,
G. Reed (eds.):
Biotechnology,
2nd ed.,
VCH Verlagsgesellschaft,
Weinheim
1996, pp.
381–401.
10.1002/9783527620883.ch12 Google Scholar
- 209 The Texas A&M University System, WO98/04729 A2, 1997 (M. Holtzapple, R. Davison, M. Loescher, C. Loeffler).
- 210 CPC International Inc., EP0120370, 1984 (F.A. Keller, J.S. Ganoung, S.J. Luenser).
- 211 T. Beppu, Antonie van Leeuwenhoek 64 (1993) 121–135.
- 212 K. Nanda, M. Taniguchi, S. Ujike, N. Ishihara, H. Mori, H. Ono, Y. Murooka, Appl. Environ. Microbiol. 67 (2001) no. 2, 986–990.
- 213 B.K. Babu, H.K. Atiyeh, M.R. Wilkins, R.L. Huhnke, Biol. Eng. 3 (2010) no. 1, 19–35.
- 214 Haldor Topsoe, EP5286900, 1994.
- 215 Haldor Topsoe, US5728871, 1998.
- 216 Acetex Limited, US6846951 B1, 2005.
- 217 Acetex Limited, US7732499 B2, 2010.
- 218 BP Chemicals Limited, US5763654, 1998.
- 219 BP Chemicals Limited, US7465822 B2, 2008.
- 220 S. Wu, G. Li, S-X. Zhou, H-J. Tong, Changzhou Daxue Xuebao, Ziran Kexueban 23 (2011) no. 3, 17–22.
- 221 A.A. Vedyagin, P.G. Tsyrul'nikov, N.O. Struikhina, T.A. Dashuk, A.V. Bubnov, Kataliz v Promyshlennosti 3 (2006) 29–33.
- 222 H-Y. Li, J-M. Zhou, G-D. Lin, H-B. Zhang, Gaodeng Xuexiao Huaxue Xuebao 18 (1997) no. 8, 1364–1366.
- 223 Kokai Tokkyo Koho, JP07291892 A, 1995.
- 224 G. Bub, H-U. Hog, J. Mol. Cat.A Chem. 95 (1995) 45–52.
- 225 M. Cheong, H-J. Kang, Korean J. Chem. Eng. 12 (1995) no. 3, 396–398.
- 226 J. Wang, X. Yang, J. Zhang, Z. Liu, Thianranqi Huagong 24 (1999) no. 2, 8–12.
- 227 Rhône Poulenc Chimie, WO9735829 A1, 1997.
- 228 Kookaï Tokkyo Koho, JP10114701, 1998.
- 229 M. Kurioka, K. Nakata, T. Jintoku, Y. Taniguchi, K. Takaki, Y. Fujiwara, Chem. Let. 1995, 244.
- 230 M. Lin, T.E. Hogan, A. Sen, J. Am. Chem. Soc. 118 (1996) no. 19, 4574–4580.
- 231 E.G. Chepaikin, A.P. Bezruchenko, A.A. Leshcheva, G.N. Boyko, I.V. Kuzmenkov, E.H. Grigoryan, A.E. Shilov, J. Mol. Cat. A Chem. 169 (2001) nos. 1–2, 89–98.
- 232 E.G. Chepaikin, G.N. Boyko, A.P. Bezruchenk, A.A. Leshcheva, E.H. Grigoryan, J. Mol. Cat. A Chem. 129 (1998) no. 1, 15–18.
- 233 A. Pombiero, J. Frausto Da Silva, Y. Fujiwara, J.A. Silva, P.M. Reis, A.F. Palavra, Instituto Superior Technico, WO2004037416, 2004.
- 234 M. Kirillova, M.L. Kutsnetsov, P.M. Reis, J.A.L. da Silva, J.J.R. Frausto da Silva, A.J.L. Pombeiro, J. A. C. S. 129 (2007) no. 34, 10531–10545.
- 235 R.A. Periana, O. Mironov, D. Taube, C. Jones, G. Bhalla, Topics in Catalysis 32 (2005) nos. 3–4, 169–174.
- 236 R.A. Periana, US2006167314, 2006.
- 237 A.T. Bell, S. Mukhopadhyay, M. Zerrella, J.G. Sunley, S. Gaemers, US2005020856, 2005.
- 238 M. Zerella, A. Kahros, A. Bell, J. Cat. 237 (2006) no. 1, 111–117.
- 239 A. Bell, M. Zerella, A. Kahros, US 20070078280, 2007.
- 240 A.T. Bell, S. Mukhopadhyay, M. Zerrella, J.G. Sunley, S. Gaemers, US20050065364, 2005.
- 241 K.X. Wang, H.F. Xu, W.S. Li, X.P. Zhou, J. Mol. Cat. A Chem. 225 (2005) 65–69.
- 242 K.X. Wang, H.F. Xu, W.S. Li, C.T. Au, X.P. Zhou, Appl. Cat. 304 (2006) 168–177.
- 243 S.V. Volkov, G.R. Kosmenbetova, L.B. Kharkova, O.V. Shvets, O.G. Yanko, V.I. Gritsenko, P.E. Strizhak, J. Natural Gas Chem. 18 (2009) no. 4, 399–406.
- 244 A. Phan, A.U. Czaja, F. Gandara, C.B. Knobler, O.M. Yaghi, Inorg. Chem. 50 (2011) no. 16, 7388–7390.
- 245 M. Soofholtz, R.J. White, T. Zimmermann, M-M. Titirici, M. Antonietti, R. Palkovits, F. Schuth, Chem. Commun. 49 (2013) 240–242.
- 246 P.N. Lodal in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, pp. 65–69.
- 247 N.L. Ricker, J.N. Micheals, C.J. King, J. Separ. Tech. 1 (1979) 36–41.
- 248 F. Chen, H. Tanaka, Y. Naka, E. Oshima, J. Chem. Eng. Japan 22 (1989) 6–11.
- 249 A.M. Eyal, R. Canari, Ind. Eng. Chem. Res. 34 (1995) 1789–1798.
- 250 J.M. Wardell, C.J. King, J. Chem. Eng. Data 23 (1974) 144.
- 251 Dow Chemical Co., US3980701, 1975 (R.R. Ginstead).
- 252 M. Sittig (ed.): Handbook of Toxic and Hazardous Chemicals and Carcinogens, 3rd ed., vol. 1, Noyes Publications, Park Ridge, NJ, 1991, p. 22.
- 253 J.J. McKetta, W.A. Cunningham (eds.): Encyclopedia of Chemical Process Design, Marcel Dekker, New York 1976, pp. 216–246.
- 254 K.A. Roberts: private communication, Celanese Limited, Chemical Division, Dallas, TX, June 16, 1998.
- 255 Material Safety Data Sheet for Glacial Acetic Acid, Eastman Chemical Products, Inc., Kingsport, Tennessee, 1990.
- 256 American Conferences of Governmental Industrial Hygienists (ACGIH) (ed): Threshold Limits Values, Cincinnati, Ohio, 1982; cf. Deutsche Forschungsgemeinschaft, Maximale Arbeitsplatzkonzentrationen, Verlag Chemie, Weinheim 1983, p. 15.
- 257 Celanese Ltd., Celanese Chemicals Division, http://www.celanese.com (accessed 9 Oct 2013).
- 258 R.E. Langa, K.L. Votoupal (eds.): The Sigma-Aldrich Library of regulatory and Safety Data, vol. 1, Sigma-Aldrich Chemical Company, Milwaukee, WI, 1993, pp. 533–534.
- 259 New York Department of Health (ed.): Hazardous Substances Fact Sheet, Trenton, NJ, Sept. 1985.
- 260 A.I. Grigor'ev, E.G. Pogudilova, A.V. Novoselova, Zh. Neorg. Khim. 10 (1965) 772.
- 261 Stickstoffdunger AG, US2141477, 1937 (J. Losch).
- 262 J.C. Bailar, H.J. Emeleus, R. Nyholm, A.F. Trotman-Dickenson: Comprehensive Inorganic Chemistry, vol. 1, Pergamon Press, Oxford 1973, pp. 462–464.
- 263 H. Stephen, T. Stephen: Solubilities of Inorganic and Organic Compounds, vol. 1, part 1, Macmillan Publishing, New York 1963, pp. 107–212.
- 264 J.S. Witzeman, V.H. Agreda in V.H. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Marcel Dekker, New York 1993, pp. 257–284.
- 265
S. Patai (ed.):
The Chemistry of Carboxylic Acids and Esters,
Wiley-Interscience,
New York
1969.
10.1002/9780470771099 Google Scholar
- 266 R.W. Johnson, E. Fritz (eds.): Fatty Acids in Industry, Marcel Dekker, New York 1989.
- 267 Z. Gomzi, S. Zrncevic: Croat. Chem. Acta 53 (1980) no. 1, 25–32. Chem. Abstr. 13 (1993) 131701x.
- 268 H.P. Thahar, S.A. Puranik, M.G. Kher, Fluid. Ses. Appl., C. R. Congr. Int. 1972, 615–627. Chem. Abstr. 3 (1987), 22303z.
- 269 Eur. Chem. News 1986, March 17, 6.
- 270 Org. Synth. 4 (1963) 261, 417.
- 271 Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd ed., vol. 9, J. Wiley & Sons, New York 1978–1984, p. 328.
- 272 Albemarle Corporation, US5672749, 1997 (W.B. Wautes, R.E. Young, P.R. DeVrou).
- 273 Kokoku, JP274567, 1952.
- 274
S. Patai (ed.):
The Chemistry of Acyl Halides,
Interscience,
New York
1972.
10.1002/9780470771273 Google Scholar
- 275 A. Parkins, WO96/30379, 1996.
- 276 Nitrokemia Ipartelepek, EP0418646 A2, 1990 (J. Paal et al.).
- 277 Sumitomo, EP0568072 A2, 1993 (Y. Takashima, K. Kumagai, S. Mitsuda).
- 278 M.B. Neduv et al., US4139557, 1976.
- 279 Japan Gas-Chemical Co., JP46015082, 1971 (M. Kuraguchi, S. Asano, N. Isogai); CAN 75: 98190.
- 280 Japan Gas-Chemical Co., JP46015083, 1971 (Y. Kuraishi, S. Asano, T. Oota); CAN 75: 63169.
- 281 Armstrong World Industries, US4956121, 1989 (T.M. Tymon, A.F. Turbak).
- 282 Y. Yamazaki, A. Masuda, Yuki Gosei Kagaku Kyokaishi, 1982, 40, 218–226; CAN 96: 199175.
- 283 Y.N. Pozdnyakovich, E.S. Nazarenko, S.M. Shein, Khim. Prom-st. 1 (1985) 5–8; CAN 102: 115486.
- 284 D.L. Opdyke, Food Cosmet. Toxicol. 13 (1975) 901–902.
- 285 American Conferences of Governmental Industrial Hygienists (ACGIH) (ed): Threshold Limits Values (TLV), Biological exposure indices (BEI), Cincinnati, Ohio, 1997.
- 286 H.J. Nicholas, B.E. Thomas, Brain 84 (1961) 320–328.
- 287 P.N. Lodal in V. Agreda, J.R. Zoeller (eds.): Acetic Acid and Its Derivatives, Dekker, New York 1993, p. 361.
- 288 I.G. Scott: Tennesse Eastman Company Technical Report TEAD-R-DC-706–2254, Kingport, TN, April 24, 1986.
- 289 United States Department of Health and Human Services (ed.): Registry of Toxic Effects of Chemical Substances, vol. 1–4, U.S. Government Printing Office, Washington D.C. 1988.
- 290 A.J. Weiss, Science 136 (1962) 151.