Fatty Alcohols

1.	Introduction
2.	Saturated Fatty Alcohols
2.1.	Physical Properties
2.2.	Chemical Properties
2.3.	Production from Natural Sources
2.3.1.	Hydrolysis of Wax Esters
2.3.2.	Reduction of Wax Esters with Sodium
2.3.3.	Hydrogenation of Natural Raw Materials
2.3.3.1.	Raw Materials and Pretreatment
2.3.3.2.	Hydrogenation Processes
2.4.	Synthesis from Petrochemical Feedstocks
2.4.1.	Ziegler Alcohol Processes
2.4.2.	Oxo Process
2.4.3.	Hydrogenation of Fatty Acids produced by Oxidation of Paraffinic Hydrocarbons
2.4.4.	Bashkirov Oxidation
2.4.5.	Other Processes
2.5.	Uses
3.	Unsaturated Fatty Alcohols
4.	Guerbet Alcohols
5.	Bifunctional Fatty Alcohols
6.	Quality Specifications
7.	Storage and Transportation
8.	Economic Aspects
9.	Ecotoxicology and Toxicology
9.1.	Ecotoxicology and Environmental Aspects
9.2.	Toxicology

General References

Specific References

7 H. Adkins, K. Folkers, J. Am. Chem. Soc. 53 (1931) 1095 – 1097.
10.1021/ja01354a042
CAS Google Scholar
8 W. Normann, Angew. Chem. 44 (1931) 714 – 717. DE 617 542, 1930 (W. Normann, H. Prückner);
Google Scholar
Böhme Fettchemie GmbH, DE 639 527, 1930 (W. Normann).
Google Scholar
9 W. Schrauth, O. Schenk, K. Stickdorn, Ber. Dtsch. Chem. Ges. 64 (1931) 1314 – 1318.
10.1002/cber.19310640616
Web of Science® Google Scholar
10 O. Schmidt, Ber. Dtsch. Chem. Ges. 64 (1931) 2051 – 2053.
10.1002/cber.19310640827
Web of Science® Google Scholar
11 D. Precht, Fette, Seifen, Anstrichm. 78 (1976) no. 4, 145.
10.1002/lipi.19760780402
CAS Web of Science® Google Scholar
12 Alfol-Alkohole, Typische Analysendaten, Condea Chemie, Brunsbüttel.
Google Scholar
13 VDI-Wärmeatlas, Düsseldorf 1984.
Google Scholar
14 D'Ans Lax – Taschenbuch für Chemiker und Physiker, vol. II, Springer Verlag, Berlin 1964.
Google Scholar
15 CRC Handbook, 55th ed., Cleveland 1974 /75.
Google Scholar
16 Houben-Weyl, E3, 265 – 300.
Google Scholar
17 Houben-Weyl, E5/1, 202 – 212.
Google Scholar
18 K. Heyns, L. Blasejewicz, Tetrahedron 9 (1960) 67.
10.1016/0040-4020(60)80054-3
CAS Web of Science® Google Scholar
19 E. S. Gore, Platinum Met. Rev. 27 (1983) no. 3, 111.
CAS Google Scholar
20 Atlantic Richfield Co., US 3 997 578, 1976 (Ming Nan Sheng).
Google Scholar
21 Kirk-Othmer, 9, 795 ff.
Google Scholar
22 U. R. Kreutzer, J. Am. Oil Chem. Soc. 61 (1984) no. 2, 343.
10.1007/BF02678792
CAS Web of Science® Google Scholar
23 H.-D. Komp, M. P. Kubersky in: Fettalkohole, 2nd ed., Henkel, Düsseldorf 1982, p. 51 ff.
Google Scholar
24 E. F. Hill, G. R. Wilson, E. C. Steinle, Jr., Ind. Eng. Chem. 46 (1954) 1917.
10.1021/ie50537a042
CAS Web of Science® Google Scholar
25 M. L. Karstens, H. Peddicord, Ind. Eng. Chem. 41 (1949) 438.
10.1021/ie50471a002
Web of Science® Google Scholar
26 H. Igo, CEER Chem. Econ. Eng. Rev. 8 (1976) no. 3, 31.
CAS Google Scholar
27 WO 90/08121, 1990.
Google Scholar
28 DE 4343320 A1, 1993.
Google Scholar
29 Oleofina, DE 3425758 C2, 1984/94.
Google Scholar
30 DE 3425758 A1, 1984.
Google Scholar
31 H. Buchold, Chem. Eng. (N.Y.) 90 (1983) no. 4, 42.
CAS Web of Science® Google Scholar
32 Th. Voeste, H. Buchold, J. Am. Oil Chem. Soc. 61 (1984) no. 2, 350.
10.1007/BF02678794
CAS Web of Science® Google Scholar
33 Chem. Ind. (Düsseldorf) 32 (1980) 739.
Google Scholar
34 Metallgesellschaft AG, DE 2 853 990, 1978 (Th. Voeste, H.-J. Schmidt, F. Marschner).
Google Scholar
35 Dehydag GmbH, DE 1 005 497, 1954 (W. Rittmeister).
Google Scholar
36 Dehydag GmbH, US 3 193 586, 1965 (W. Rittmeister).
Google Scholar
37 Henkel KGaA, DE-AS 2 613 226, 1976 (G. Demmering)
Google Scholar
38 VEB Deutsches Hydrierwerk Rodleben, DD 213 430, 1983 (H. Aring, K. Busch, P. Franke, G. Konetzke et al.)
Google Scholar
39 Institut Français du Pétrole, DE-OS 3 217 429, 1982 (R. Snappe, J.-P. Bournonville).
Google Scholar
40 B. C. Triverdi, D. Grote, Th. O. Mason, J. Am. Oil Chem. Soc. 58 (1981) no. 1, 17.
10.1007/BF02666046
Web of Science® Google Scholar
41 Ashland Oil, Inc. US 4 104 478, 1978 (B. C. Triverdi).
Google Scholar
42 Houben-Weyl, 13/4, 1 ff.
Google Scholar
43 T. Mole, E. A. Jeffery: Organoaluminium Compounds, Elsevier, Amsterdam 1972.
Google Scholar
44 A. Lundeen, R. Poe: Alpha-Alcohols, in J. J. Mc Ketta, W. A. Cunningham (eds.): Encyclopedia of Chemical Processing and Design, vol. 2, Marcel Dekker, New York 1977, p. 465.
Google Scholar
45 K. Ziegler, H.-G. Gellert, K. Zosel, E. Holzkamp et al., Justus Liebigs Ann. Chem. 629 (1960) 121.
10.1002/jlac.19606290111
CAS Web of Science® Google Scholar
46 H. Wesslau, Justus Liebigs Ann. Chem. 629 (1960) 198.
10.1002/jlac.19606290114
CAS Web of Science® Google Scholar
47 P. H. Washecheck, ACS Symp. Ser. 159 (1981) 87.
10.1021/bk-1981-0159.ch007
CAS Google Scholar
48 K. L. Lindsay: “Alpha-Olefins,” in J. J. Mc Ketta, W. A. Cunningham (eds.): Encyclopedia of Chemical Processing and Design, vol. 2, Marcel Dekker, New York 1977, p. 482.
Google Scholar
49 Produkte aus der Oxosynthese, Ruhrchemie AG, Frankfurt 1969.
Google Scholar
50 J. Falbe: Synthesen mit Kohlenmonoxid, Berlin 1967.
10.1007/978-3-642-95008-7
Google Scholar
51 R. E. Vincent, ACS Symp. Ser. 159 (1981) 159.
10.1021/bk-1981-0159.ch010
CAS Google Scholar
52 B. Cornils, Compend. Dtsch. Ges. Mineralölwiss. Kohlechem. 78/79 (1978) no. 1, 463.
Google Scholar
53 B. Cornils, “New Syntheses with Carbon Monoxide,” React. Struct. Concepts Org. Chem. 11 (1980) .
CAS Google Scholar
54 H. Lemke, Hydrocarbon Process. 45 (1966) no. 2, 148.
CAS Web of Science® Google Scholar
55 C. E. O'Rourke, P. R. Kavasmaneck, R. E. Uhl, ACS Symp. Ser. 159 (1981) 71.
10.1021/bk-1981-0159.ch006
CAS Google Scholar
56 B. A. Murrer, J. H. Russel, Catalysis 6 (1983) 169.
10.1039/9781847553188-00169
CAS Google Scholar
57 A. H. Turner, J. Am. Oil Chem. Soc. 60 (1983) no. 3, 623.
10.1007/BF02679801
CAS Web of Science® Google Scholar
58 R. L. Banks, Appl. Ind. Catal. 1984, no. 3, 215.
Google Scholar
59 E. R. Freitas, C. R. Gum, Chem. Eng. Prog. 75 (1979) 73.
CAS Web of Science® Google Scholar
60 E. L. T. M. Spitzer, Seifen, Oele, Fette, Wachse 107 (1981) no. 6, 141.
CAS Google Scholar
61 H. Stage, Seifen, Oele, Fette, Wachse 99 (1973) no. 6/7, 143; no. 8, 185; no. 9, 217; no. 11, 299.
Google Scholar
62 N. Kurata, K. Koshida, Hydrocarbon Process. 57 (1978) 145.
CAS Web of Science® Google Scholar
63 N. J. Stevens, J. R. Livingstone, Jr., Chem. Eng. Prog. 64 (1968) no. 7, 61.
CAS Web of Science® Google Scholar
64 N. Kurata, K. Koshida, H. Yokoyama, T. Goto, ACS Symp. Ser. 159 (1981) 113.
10.1021/bk-1981-0159.ch009
CAS Google Scholar
65 L. Marko, J. Organomet. Chem. 283 (1985) 221.
10.1016/0022-328X(85)80002-4
CAS Web of Science® Google Scholar
66 B. N. Bobylev, M. J. Farberov, S. A. Kesarev, Khim. Promst. (Moscow) 1979 no. 3, 138.
CAS Web of Science® Google Scholar
67 Unilin Alcohols, Petrolite Corp., St. Louis 1985.
Google Scholar
68 Petrolite Corp., US 4 426 329, 1984 (J. H. Woods, C. E. Laughlin, T. R. Graves).
Google Scholar
69 S. K. Ries, V. Wert, C. S. Sweely, R. A. Leavitt, Science 195 (1977) 1339.
10.1126/science.195.4284.1339
CAS ADS PubMed Web of Science® Google Scholar
70 J. Penninger, M. Biermann, H.-J. Krause, Fette, Seifen, Anstrichm. 85 (1983) no. 6, 239.
10.1002/lipi.19830850608
CAS Web of Science® Google Scholar
71 T. Gibson, L. Tulich, J. Org. Chem. 46 (1981) no. 9, 1821.
10.1021/jo00322a015
CAS Web of Science® Google Scholar
72 A. V. Rama Rao, J. S. Yadav, G. S. Annapurna, Synth. Commun. 13 (1983) no. 4, 331.
10.1080/00397918308066984
Web of Science® Google Scholar
73 S. M. Kulkarni, V. R. Mamdapur, M. S. Chadha, Indian J. Chem., Sect. B 22 (1983) no. 7, 683.
Web of Science® Google Scholar
74 U. T. Bhalerao, S. J. Rao, B. D. Tilak, Tetrahedron Lett. 25 (1984) no. 47, 5439.
10.1016/S0040-4039(01)91306-1
CAS Web of Science® Google Scholar
75 G. Kirchner, H. Weidmann, Liebigs Ann. Chem. 1985, no. 1, 214.
10.1002/jlac.198519850123
CAS Web of Science® Google Scholar
76 H. J. Richtler, J. Knaut, J. Am. Oil Chem. Soc. 61 (1984) no. 2, 160 – 175.
10.1007/BF02678762
Web of Science® Google Scholar
77 J. Knaut, H. J. Richtler, J. Am. Oil Chem. Soc. 62 (1985) no. 2, 317.
10.1007/BF02541398
CAS Web of Science® Google Scholar
78 H. Bertsch, H. Reinheckel, K. Haage, Fette, Seifen, Anstrichm. 66 (1964) 763.
10.1002/lipi.19640661005
CAS Google Scholar
79 H. Bertsch, H. Reinheckel, K. Haage, Fette, Seifen, Anstrichm. 71 (1969) 357, 785.
10.1002/lipi.19690710908
CAS Web of Science® Google Scholar
80 H. Bertsch, K. Haage, H. Reinheckel, Fette, Seifen, Anstrichm. 71 (1969) 851.
10.1002/lipi.19690711008
CAS Web of Science® Google Scholar
81 K. Lindner: Tenside, Textilhilfsmittel, Waschrohstoffe, vol. I, 2nd ed., Wissenschaftl. Verlags GmbH, Stuttgart 1964, p. 144.
Google Scholar
82 J. Richter: Dissertation, TH Delft, 1968.
Google Scholar
83 J. W. E. Coenen, Fette, Seifen, Anstrichm. 77 (1975) 431.
Google Scholar
84 Dehydag, US 3 193 586, 1965 (W. Rittmeister).
Google Scholar
85 Henkel, US 3 729 520, 1973 (H. Rutzen, W. Rittmeister).
Google Scholar
86 Henkel, DE-AS 2 513 377, 1975 (G. Demmering, H. Schütt, H. Rutzen).
Google Scholar
87 J. Cieslar, W. Bulanda, Przem. Chem. 63 (1984) 375;
CAS Web of Science® Google Scholar
Chem. Abstr. 101 (1984) 153 810 t.
Google Scholar
88 Institute Blachownia and Nitrogen Works Kedzierzyn, PL 118 880, 1978 (E. Fabisz, K. Chmielewski, A. Jakubowicz, A. Mankowski et al.).
Google Scholar
89 Institute Blachownia and Nitrogen Works Kedzierzyn, PL 118 979, 1978 (E. Fabisz, K. Chmielewski, A. Jakubowicz, A. Mankowski et al.).
Google Scholar
90 New Japan Chemical Ltd., GB 1 335 173, 1972.
Google Scholar
91 VEB Deutsches Hydrierwerk Rodleben, DD 213 429, 1983 (H. Aring, K. Busch, P. Franke, G. Konetzke et al.).
Google Scholar
92 UOP Inc., US 4 340 546, 1982 (G. Qualeatti, D. Germanas).
Google Scholar
93 UOP Inc., US 4 446 073, 1984 (G. Qualeatti, D. Germanas).
Google Scholar
94 Kao Soap, JP 58 210 035, 1983 (K. Kokubo, K. Tsukada, Y. Miyabata, Y. Kazama).
Google Scholar
95 Kao Soap, JP 5 995 227, 1984 (K. Tsukada, Y. Miyabata).
Google Scholar
96 Kao Soap, JP 59 106 431, 1984 (K. Tsukada, Y. Miyabata, K. Fukuoka).
Google Scholar
97 H. Schütt in W. Foerst, H. Buchholz-Meisenheimer (eds.): Neue Verfahren, Neue Produkte, Wirtschaftliche Entwicklung, Urban und Schwarzenberg, München 1970.
Web of Science® Google Scholar
98 U. Ploog, Seifen, Oele, Fette, Wachse 109 (1983) no. 8, 225.
CAS Google Scholar
99 R. R. Egan, G. W. Earl, J. Ackermann, J. Am. Oil Chem. Soc 61 (1984) no. 2, 324.
10.1007/BF02678789
CAS Web of Science® Google Scholar
100 M. Guerbet, C. R. Hebd. Séances Acad. Sci. 128 (1898) 511;
Google Scholar
M. Guerbet, Bull. Soc. Chim. Fr. 21 (1899) no. 3, 487.
Google Scholar
101 J. Glasl in: Fettalkohole, 2nd ed., Henkel, Düsseldorf 1982, p. 169.
Google Scholar
102 Henkel & Cie GmbH, DE-OS 1 768 313, 1971 (H. Rutzen).
Google Scholar
103 PCT/WO96/19287;
Google Scholar
PCT/DE/95/01846,
Google Scholar
104 Henkel & Cie GmbH, DE 1 198 348, 1961 (W. Stein, M. Walther).
Google Scholar
105 Henkel & Cie GmbH, DE 1 207 371, 1963 (H. Hennig, W. Stein, M. Walther).
Google Scholar
106 Hüls AG, DE 38 43956,
Google Scholar
107 Mineral- und Brennstoffnormen, DIN-Taschenbuch, Beuth-Vertrieb, Berlin-Köln-Frankfurt 1984.
Google Scholar
108 Annual Book of ASTM Standards, Sections 5, 6, 15, 1985.
Google Scholar
109 Deutsche Einheitsmethoden zur Untersuchung von Fetten, Fettprodukten und verwandten Stoffen, Wissenschaftl. Verlags GmbH, Stuttgart 1950 – 1984.
Google Scholar
110 H. J. Richtler, J. Knaut, Chem. Ind. (Düsseldorf) 36 (1984) 131 – 134.
Google Scholar
111 H. J. Richtler, J. Knaut, Chem. Ind. (Düsseldorf) 36 (1984) 199 – 201.
Google Scholar
112 L. Marcou, Rev. Fr. Corps. Gras. 30 (1983) no. 1, 3 – 6.
CAS Web of Science® Google Scholar
113 J. Am. Oil Chem. Soc. 58 (1981) no. 11, 873 – 874A.
Web of Science® Google Scholar
114 A. L. de Jong, J. Am. Oil Chem. Soc. 60 (1983) no. 3, 634 – 639.
Google Scholar
115 E. C. Leonard, J. Am. Oil Chem. Soc. 60 (1983) no. 6, 1160 – 1161.
10.1007/BF02671350
CAS Web of Science® Google Scholar
116 C. A. Houston, J. Am. Oil Chem. Soc. 61 (1984) no. 2, 179 – 184.
10.1007/BF02678764
Web of Science® Google Scholar
117 J. Am. Oil Chem. Soc. 62 (1985) no. 4, 668.
Google Scholar
118 J. C. Dean, Chem. Week 1985, May 15, 3 – 34.
Google Scholar
119 P. Healey: “The Alcohol Market, A Decade of Change”, ICIS Lor Conference, Amsterdam, Oct. 2004.
Google Scholar
120 J. W. E. Coenen, J. Am. Oil Chem. Soc. 53 (1976) no. 6, 382 – 389.
10.1007/BF02605727
CAS Web of Science® Google Scholar
121 H. Klimmek, Chem. Ind. (Düsseldorf) 33 (1981) 136 – 141.
Google Scholar
122 H. Fochem, Fette, Seifen, Anstrichm. 87 (1985) no. 2, 47 – 52.
10.1002/lipi.19850870202
Web of Science® Google Scholar
123 Chem. Week 1982, April 28, 40 – 44.
Google Scholar
124 Chem. Ind. (Düsseldorf) 35 (1983) 251 – 255.
Google Scholar
125 J. Am. Oil Chem. Soc. 61 (1984) no. 8, 1298 – 1314.
Google Scholar
126 H. Lindemann, Chem. Ind. (Düsseldorf) 34 (1982) 713 – 716.
Google Scholar
127 S. Field, Hydrocarbon Process. 1984, Oct., 34 G – N.
Google Scholar
128 W. Stein, Fette, Seifen, Anstrichm. 84 (1982) no. 2, 45 – 54.
10.1002/lipi.19820840202
CAS Web of Science® Google Scholar
129 Public data on high volume chemicals: IUCLID CD-ROM, Year 2000 edition: European Commission, Joint Research Centre, Institute for Health and Consumer Protection, European Chemicals Bureau.
Google Scholar
130 D. L. J. Opdyke, Fd. Cosmet. Toxicol. 11 (1973) 95 – 115.
10.1016/0015-6264(73)90065-5
CAS PubMed Web of Science® Google Scholar
131 Food Cosmet. Toxicol. 13 (1975) 699 – 700.
10.1016/0015-6264(75)90182-0
Web of Science® Google Scholar
132 “Final Report on the Safety Assessment of Cetearyl Alcohol, Cetyl Alcohol, Isostearyl Alcohol, Myrsityl Alcohol, and Behenyl Alcohol”; J. Am. Coll. Toxicol. 7 (1988) no. 3, 359 – 411.
10.3109/10915818809023137
Google Scholar
133 D. L. J. Opdyke, Fragrance Raw Materials Monographs “Cetyl Alcohol”; Food Cosmet. Toxicol. 16 (1978) 683 – 686.
CAS Google Scholar
134 “Final Report on the Safety Assessment of Stearyl Alcohol, Oleyl Alcohol, and Octyl Dodecanol”, J. Am. Coll. Toxicol. 4 (1985) no. 5, 1 – 29.
10.3109/10915818509078685
Web of Science® Google Scholar

Citing Literature

Ullmann's Encyclopedia of Industrial Chemistry

Browse other articles of this reference work:

Fatty Alcohols

View previous versions

Fatty Alcohols

Abstract

General References

Specific References

Further Reading

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Fatty Alcohols

View previous versions

Fatty Alcohols

Abstract

General References

Specific References

Further Reading

Citing Literature

References

Related

Information