Propionic Acid and Derivatives

1.	Introduction
2.	Physical Properties
3.	Chemical Properties
4.	Production
4.1.	Carbonylation of Ethylene (BASF Process)
4.2.	Oxidation of Propanal
4.3.	Direct Oxidation of Hydrocarbons
4.4.	Construction Materials
5.	Storage and Transportation
6.	Quality Specifications
7.	Environmental Protection
8.	Uses
8.1.	Use as Food and Feed Preservative
8.2.	Other Uses
9.	Economic Aspects
10.	Toxicology
11.	Derivatives
11.1.	Salts
11.2.	Propionic Anhydride and Propionyl Chloride
11.3.	Esters
11.4.	Chloropropionic Acid and Derivatives
11.4.1.	Properties and Production
11.4.1.1.	2-Chloropropionic Acid and Derivatives
11.4.1.2.	3-Chloropropionic Acid and Derivatives
11.4.1.3.	2,2-Dichloropropionic Acid
11.4.2.	Uses
11.4.2.1.	2-Chloropropionic Acid and Derivatives
11.4.2.2.	3-Chloropropionic Acid
11.4.2.3.	2,2-Dichloropropionic Acid
11.4.3.	Toxicology

References

1 H. Sackmann, F. Sauerwald, Z. Phys. Chemie (Leipzig) 195 (1950) 295 – 312.
10.1515/zpch-1950-19528
CAS Google Scholar
2 C. H. D. Calis-van Ginkel et al., J. Chem. Thermodyn. 10 (1978) 1083 – 1088.
10.1016/0021-9614(78)90082-4
CAS Web of Science® Google Scholar
3 A. Apelblat, E. Manzurola, Fluid-Phase Equilib. 32 (1987) 163 – 193.
10.1016/0378-3812(87)85035-5
CAS Web of Science® Google Scholar
4 M. Blinc, R. Blinc, J. Polym. Sci. 32 (1958) 506 – 508.
10.1002/pol.1958.1203212518
CAS ADS Web of Science® Google Scholar
5 K. Tyuzyo, Bl. Chem. Soc. Jpn. 30 (1957) 782 – 789, 851 – 856.
10.1246/bcsj.30.851
Web of Science® Google Scholar
6 J. J. Christensen, R. W. Hanks, R. M. Izatt: Handbook of Heats and Mixing, Wiley & Sons, New York 1982, pp. 1173 – 1175, 1449.
Google Scholar
7 (6) Supplementary vol. 1988, pp. 858 – 860.
Google Scholar
8 J. Timmermans: The Physico-Chemical Constants of Binary Systems in Concentrated Solution, Interscience, vol. 2, New York 1959, p. 941.
Google Scholar
9 D. R. Linde: Handbook of Chemistry and Physics, 70th ed., CRC Press, Boca Raton 1989, D – 15.
Google Scholar
10 G. Glaxton: Physical and Azeotropic Data, National Benzol and Allied Product Association, W. Heffer & Sons, Cambridge 1958.
Google Scholar
11 L. H. Horsley: “Azeotropic Data III,” Adv. Chem. Ser. 116 (1973) p. 4 ff.
Google Scholar
12 T. Ito, F. Yoshida, J. Chem. Eng. Data 8 (1963) 315 – 320.
10.1021/je60018a012
CAS Google Scholar
13 J. Gmehling, U. Onken, J. R. Rarey-Nies: Vapor – Liquid – Equilibrium Data Collection, Chemistry Data Series, vol. I, part 1 (1977), 1 a (1981), 1 b (1981), 2 d (1982), 3 + 4 (1979), 5 (1982).
Google Scholar
14 H. Stephen, T. Stephen: Solubilities of Inorganic and Organic Compounds, vol. 1, part 2, Pergamon Press, London 1963.
Google Scholar
15 (14) vol. 2, part 2 (1964).
Google Scholar
16 VDI-Wärmeatlas, 5th ed., Düsseldorf 1988.
Google Scholar
17 The Texas A & M University System, Table 23–2-1-(1.1210)-d, p. 1, College Station 1984.
Google Scholar
18 R. R. Dreisbach, R. A. Martin, Ind. Eng. Chem. 41 (1949) 2875.
10.1021/ie50480a053
CAS Web of Science® Google Scholar
19 J. J. Jasper, J. Phys. Chem. Ref. Data 1 (1972) 851.
10.1063/1.3253106
ADS Google Scholar
20 W. Jobst, Int. J. Heat Mass Transfer 7 (1964) 725.
10.1016/0017-9310(64)90003-1
CAS Google Scholar
21 G. Kortüm, W. Vogel, K. Andrussow, Pure Appl. Chem. 1 (1961) 243.
Google Scholar
22 D. D. Perrin, J. Chem. Soc. 1959, 1710, 1714.
Google Scholar
23 W. J. Canady, H. M. Papée, K. J. Laidler, Trans. Faraday. Soc. 54 (1958) 502.
10.1039/tf9585400502
CAS Web of Science® Google Scholar
24 Landolt – Börnstein, 6th. ed., vol. IV/4 a.
Google Scholar
25 Ullmann, 4th ed., 19, 454 ff.
Google Scholar
26 M. A. Goodman, S. L. Whittenburg, J. Chem. Eng. Data 28 (1983) 350 – 351.
10.1021/je00034a002
CAS Web of Science® Google Scholar
27 BASF AG Ludwigshafen, Result of Techn. Lab., Ludwigshafen 1969.
Google Scholar
28 T. Ackermann, F. Schreiner, Z. Elektrochem. 62 (1958) 1143 – 1151.
10.1002/bbpc.19580621016
CAS Web of Science® Google Scholar
29 R. W. Gallant, Hydrocarbon Process 47 (1968) no. 6, 139 – 148.
CAS Web of Science® Google Scholar
30 E. Przewalski, J. Prakt. Chem. 88 (1913) 500.
Google Scholar
31 Kirk-Othmer, 2nd ed., 16, 554.
Google Scholar
32 Ullmann, 3rd ed., 14, 383.
Google Scholar
33 Ullmann, 3rd ed., 8, 744.
Google Scholar
34 Celanese, BP 771 583, 1957.
Google Scholar
35 SRI-Process Economics Program, no. 42, A 1, Menlo Park 1975, pp. 18.
Google Scholar
36 Dow Chemical, US 1 926 068, 1933 (C. J. Strosacker, C. C. Kennedy, E. L. Pelton).
Google Scholar
37 Ullmann, 4th ed., 9, 161 ff.
Google Scholar
38 Texaco Dev., DE 3 124 720, 1981 (J. F. Knifton).
Google Scholar
39 M. Sittig, Chem. Proc. Monogr. no. 8 (1965) p. 76.
Google Scholar
40 (39) no. 23 (1966) pp. 105.
Google Scholar
41 Monsanto, BE 793 203, 1971 (M. D. Forster, D. E. Morris).
Google Scholar
42 Monsanto, US 3 989 748, 1968 (F. E. Paulik, A. Hershman, J. F. Roth).
Google Scholar
43 Monsanto, US 3 989 747, 1968 (J. H. Craddock, J. F. Roth, A. Hershman, F. E. Paulik).
Google Scholar
44 BP Chemicals, DE-OS 2 101 909, 1970 (G. E. Foster, J. R. Bethell).
Google Scholar
45 Monsanto, BE 796 294, 1972 (D. E. Morris).
Google Scholar
46 BP Chemicals, GB 1 363 961, 1972 (M. J. Wriglesworth, D. J. Westlake).
Google Scholar
47 Monsanto, US 3 944 603, 1972 (D. E. Morris).
Google Scholar
48 Monsanto, DE-AS 2 263 442, 1972 (D. Forster, D. E. Morris).
Google Scholar
49 BASF, DE-AS 2 604 545, 1976 (K. Schwirten, W. Disteldorf, W. Eisfeld, R. Kummer).
Google Scholar
50 E. Drent, ACS Symp. Ser. 328 (1987) 154 – 175.
10.1021/bk-1987-0328.ch011
CAS Web of Science® Google Scholar
51 Texaco, US 4 362 822, 1981 (J. F. Knifton).
Google Scholar
52 P. Blanc, G. Goma, Biotechnol. Lett. 11 (1989) 189 –194.
10.1007/BF01026057
Web of Science® Google Scholar
53 M. J. T. Carrondo, J. P. S. G. Crespo, M. J. Moura, Appl. Biochem. Biotechnol. 17 (1988) 295 – 312.
10.1007/BF02779164
CAS Web of Science® Google Scholar
54 H. Dellweg: Biotechnology, vol. 3, Verlag Chemie, Weinheim, Germany 1983, p. 472.
Google Scholar
55 Dow Chemical, US 3 151 155, 1964 (J. W. McKoy, N. Swanson).
Google Scholar
56 Ullmann, 4th ed., 7, 123 ff.
Google Scholar
57 D. Powergas, J. Matthey, Chem. Eng. (N.Y.) 84 (1977) Dec. 5, 110 – 115.
Google Scholar
58 D. Forster, A. Hershman, D. E. Morris, Catal. Rev. Sci. Eng. 23 (1981) 89 – 105.
10.1080/03602458108068070
CAS Web of Science® Google Scholar
59 B. Cornils, R. Payer, K. C. Traenckner, Hydrocarbon Process. 54 (1975) no. 6, 83 – 91.
CAS Web of Science® Google Scholar
60 Hydrocarbon Process 54 (1975) no. 11, 87.
Google Scholar
61 SRI-Process Economic Program no. 37, 1968, pp. 83 ff pp. 83 ff.
Google Scholar
62 SRI-Process Economic Program no. 37 a, 1973, pp. 33 ff pp. 33 ff.
Google Scholar
63 Distillers, GB 771 991, 1957 (A. Elce, I. K. M. Robson, D. P. Young).
Google Scholar
64 BP Oil, GB 743 989, 1956 (J. Habeshaw et al.).
Google Scholar
65 Distillers, GB 743 991, 1956 (A. Elce, I. K. Miles, D. P. Young).
Google Scholar
66 Distillers, FR 1 091 333, 1954 (A. Elce, I. K. Miles, D. P. Young).
Google Scholar
67 Hydrocarbon Process 54 (1975) no. 11, 102.
Google Scholar
68 G. B. Elder in B. J. Monitz, W. I. Pollock (eds.): Process Ind. Corros., NACE Houston Tex., 1986, pp. 287 – 296.
Web of Science® Google Scholar
69 Food and Chemical Codex, 3rd ed., National Academy Press, Washington, DC 1981.
Google Scholar
70 BASF, data sheet D 030 d, e, Ludwigshafen, Aug. 1988.
Google Scholar
71 OECD Guidelines for Testing of Chemicals, 302 B, Paris 1981.
Google Scholar
72 K. Verschueren: Handbook of Environmental Data of Organic Chemicals, 2nd ed., 1983, p. 1023.
Google Scholar
73 BASF, Entwurf zum Sicherheitsdatenblatt der BASF, Ludwigshafen 1988.
Google Scholar
74 Data sheet no. 140, Katalog wassergefährdender Stoffe, Gemeinsames Ministerialblatt, Bonn 1985.
Google Scholar
75 BASF AG, unpublished results.
Google Scholar
76 T. A. Luft, Gemeinsames Ministerialblatt, ed. A, no. 7, Bonn, Feb. 1986.
Google Scholar
77 BASF, Periodical Animal Nutrition in Research and Practice, vol. 2, no. 4 (1973), no. 5 (1974), no. 7 (1975), no. 11 (1979).
Google Scholar
78 I. Brglez, Prax. Vet. Br. 1977 no. 1, 17 – 22.
Google Scholar
79 V. Haßling: Rekontaminationsprobleme von Tiermehlen gegen Salmonellen durch Propionsäure, Propionate und Ameisensäure, Dissertation, Universität Gießen 1985.
Google Scholar
80 I. Wekerle, Tierärztl. Umsch. 43 (1988) 646 – 654.
Web of Science® Google Scholar
81 K.-H. Bässler, Z. Lebensm. Unters. Forsch. 110 (1959) 28 – 42.
10.1007/BF01001966
CAS Google Scholar
82 H. Giessler, S. Dammert, Landwirtsch. Forsch. Sonderh. 38 (1981) 484 – 489.
Google Scholar
83 G. Bolduan et al., J. Anim. Physiol. 59 (1988) 72 – 78.
10.1111/j.1439-0396.1988.tb00049.x
CAS Web of Science® Google Scholar
84 G. Gaus: BASF Documentation MEA 3310 AD, Oct. 89, Technical Symposium Aug. 9, 1989, Whitestone, S.C., USA.
Google Scholar
85 K. H. Bässler, Z. Lebensm. Unters. Forsch. 110 (1959) 28 – 42.
10.1007/BF01001966
CAS Google Scholar
86 P. Karlson: Kurzes Lehrbuch der Biochemie, Thieme Verlag, Stuttgart 1987.
Google Scholar
87 WHO Food Additives Series no. 5, Genf 1974, pp. 110 – 118.
Google Scholar
88 BASF AG, Department of Toxicology, unpublished results.
Google Scholar
89 H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 23 (1962) 95 – 107.
10.1080/00028896209343211
CAS PubMed Google Scholar
90 Patty's 2nd, pp. 1779 – 1780 and 3rd ed., pp. 4911 –4913.
Google Scholar
91 NIOSH, Registry of Toxic Effects of Chemicals, CD-Rom Version, update 9001.
Google Scholar
92 K. Mori, GANN 44 (1953) 421 – 427.
CAS PubMed Google Scholar
93 S. Imai et al., Nara Igaku Zasshi 32 (1981) 715 – 722.
CAS Google Scholar
94 W. D. Graham et al., J. Pharm. Pharmacol. 6 (1954) 534 – 545.
10.1111/j.2042-7158.1954.tb10983.x
CAS PubMed Web of Science® Google Scholar
95 H.-J. Altmann, W. Grunow, unpublished report BGA (1988).
Google Scholar
96 W. Griem, Bundesgesundheitsbl. 28 (1985) 322 – 327.
Google Scholar
97 Bundesgesundheitsbl. no. 30, Bonn 1987, 370 – 371.
Google Scholar
98 BP International, unpublished results.
Google Scholar
99 C. Rodriguez et al., Toxicology 38 (1986) 103 – 117.
10.1016/0300-483X(86)90176-9
PubMed Web of Science® Google Scholar
100 Report of Litton Bionetics for FDA, Nat. Tech. Inf. Serv. USA PB-266 897 (1976).
Google Scholar
101 A. Basler et al., Food Chem. Toxic. 25 (1987) 287 –290.
10.1016/0278-6915(87)90124-4
CAS PubMed Web of Science® Google Scholar
102 W. v.d. Hude et al., Mutat. Res. 203 (1988) 81 – 94.
10.1016/0165-1161(88)90023-4
PubMed Web of Science® Google Scholar
103 W. Szybalski, Ann. N.Y. Acad. Sci. 76 (1958) 475 –489.
10.1111/j.1749-6632.1958.tb57106.x
CAS ADS PubMed Web of Science® Google Scholar
104 M. Ishidate et al., Food Chem. Toxic. 22 (1984) 623 –636.
10.1016/0278-6915(84)90271-0
CAS PubMed Web of Science® Google Scholar
105 T. Kawachi et al. in R. Montesano et al. (eds.): IARC Sci. Publ. 27 (1980) 323 – 330.
Google Scholar
106 W. W. Heseltine, J. Pharm. Pharmacol. 4 (1952) 120 –122.
10.1111/j.2042-7158.1952.tb13123.x
CAS PubMed Web of Science® Google Scholar
107 S. Zuffanti, J. Am. Chem. Soc. 63 (1941) 3124.
10.1021/ja01856a068
Google Scholar
108 R. Escales, H. Koepke, J. Prakt. Chem. 87 (1913) 264.
Google Scholar
109 G. E. Symons, A. M. Buswell, Ind. Eng. Chem. 24 (1932) 460.
10.1021/ie50268a024
CAS Google Scholar
110 A. Renard, C. R. 104 (1887) 914.
Google Scholar
111 B. Behrens, J. Wajzer, Biochem. Z. 264 (1933) 124.
Google Scholar
112 Index Merck, 9th ed., Verlag Chemie, Weinheim, Germany 1961, p. 633.
Google Scholar
113 The Merck Index, 10th ed., Merck & Co Inc., Rahway 1983, p. 1127.
Google Scholar
114 NIOSH, Registry of Toxic Effect of Chemical Substances, 1980.
Google Scholar
115 Knapsack AG, DE 951 809, 1954 (W. Vogt).
Google Scholar
116 G. Leiderer, DE-AS 1 932 303, 1969.
Google Scholar
117 W. Reppe, H. Kröper, Ann. 582 (1953) 47, 61.
Google Scholar
118 R. E. Brooks, W. F. Gresham, J. v. Hardy, J. M. Lupton, Ind. Eng. Chem. 49 (1957) 2004.
10.1021/ie50576a034
CAS Web of Science® Google Scholar
119 BASF, DE 848 355, 1943 (W. Reppe, H. Kröper).
Google Scholar
120 BASF, DE 863 194, 1943 (W. Reppe, H. Kröper).
Google Scholar
121 Monsanto, US 3 989 751, 1974 (D. Forster, A. Hershman).
Google Scholar
122 J. D. Roberts, J. Am. Chem. Soc. 72 (1950) 4237.
10.1021/ja01165a114
CAS Web of Science® Google Scholar
123 IG Farben, DE 765 969, 1940 (W. Reppe, H. Kröper).
Google Scholar
124 BASF, DE 915 567, 1953 (W. Reppe, H. Kröper).
Google Scholar
125 Rohm & Haas, US 1 898 687, 1931 (F. O. Rice).
Google Scholar
126 Kirk-Othmer, 3rd ed., 10, 456 ff.
Google Scholar
127 BASF AG, Company data from Aug. 15, 1991.
Google Scholar
128 Dow Chem., US 2 010 685, 1932.
Google Scholar
129 Dow Chem., US 1 993 713, 1935.
Google Scholar
130 BASF AG, Company data from Aug. 15, 1991.
Google Scholar
131 3 M, US 2 682 504, 1954.
Google Scholar
132 BASF, DE 1 140 185, 1963.
Google Scholar
133 Goodrich, US 2 548 161, 1951.
Google Scholar
134 Dow Chem., US 2 809 992, 1957.
Google Scholar
135 Brit. Celanese, GB 892 564, 1962.
Google Scholar
136 BASF, DE 1 133 710, 1963.
Google Scholar
137 R. Wegler: Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, vol. V, Springer Verlag, Berlin 1977, p. 188 ff.
10.1007/978-3-642-66592-9
Google Scholar
138 Hoechst, DE-OS 2 223 894, 1973.
Google Scholar
139 Stauffer Chem., GB 1 066 606, 1967.
Google Scholar
140 Shell Int., GB 1 164 160, 1969.
Google Scholar
141 A. Kleemann, I. Engel: Pharmazeutische Wirkstoffe, Thieme Verlag, Stuttgart 1978.
Google Scholar
142 J. L. O'Donoghue, Neurotoxicity of Industrial and Commercial Chemicals, vol. II, CRC Press, Inc., Boca Raton, Florida 1985, pp. 115 – 116.
Google Scholar
143 BASF AG, Department of Toxicology, unpublished results, Ludwigshafen 1960, 1988, 1990, 1992.
Google Scholar
144 RTECS, update 8910.
Google Scholar
145 J. L. Morrison, J. Pharmacol. Exp. Pharmaceut. 86 (1946) 336 – 338.
CAS Web of Science® Google Scholar
146 E. Yount et al., J. Pharmacol. Exp. Therap. 222 (1982) 501 – 508.
CAS PubMed Web of Science® Google Scholar
147 Japan Chemical Industry Ecology — Toxicology & Information Center (JETOC), Newsletter 4 (1985) 15 (14 – 20).
Google Scholar

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