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Detergents pp 1–88Cite as

Anionic Surfactants

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Part of the book series: Anthropogenic Compounds ((HEC3,volume 3 / 3F))

Summary

The various types of anionic surfactants are listed and the five most used types are dealt with in detail. More attention is given to linear alkyl benzene sulfonates (LAS), since they are used more than any other surfactant and more data have been reported on them. The structure, methods of production and application of each type are presented and relevant analytical methods are summarized. The legislation regulating their use is explained and their routes to and fate in the various environmental sectors are discussed. Their impact on the aquatic and soil environment has been assessed by comparing evidence of their concentrations in the various environmental sectors with those concentrations which produce observed effects on appropriate aquatic organisms. It is concluded that no environmental problems arise from the use of present-day anionic surfactants.

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Abbreviations

ABS:

alkyl benzene sulfonate

AE:

alcohol ethoxylate

AES:

alcohol ethoxylate sulfate

AOS:

a-olefine sulfonate

APES:

alkyl phenol ethoxylate sulfate

AS:

alkyl sulfate

BODn :

biochemical oxygen demand after n days

COD:

chemical oxygen demand

DOC:

dissolved organic carbon

ECn :

concentration of chemical giving effect of n%

EC (EEC):

European (Economic) Community

EO:

ethylene oxide

FAB:

fast atom bombardment

g:

gram

GC:

gas chromatography

GC/MS:

gas chromatography-mass spectroscopy

h:

hour

IR:

infra-red

ISO:

International Organisation for Standardisation

k:

first order reaction constant

kg:

kilogram

L:

litre

LAB:

linear alkyl benzene

LAS:

linear (secondary) alkyl benzene sulfonate

LCn :

concentration giving n% death of the population

LPAS:

linear primary alkyl sulfate

M:

molar

mM:

milli-molar

MB:

methylene blue

MBAS:

methylene blue active substances

mg:

milligram

MITI:

Ministry of International Trade and Industry (Japan)

mL:

millilitre

MW:

molecular weight

n :

normal, linear

ng:

nanogram

nm:

nanometre

NMR:

nuclear magnetic resonance

NOEC:

no observed effect concentration

OECD:

Organisation for Economic Co-operation and Development

PAS:

primary alkyl sulfate

R:

alkyl or other group

SAS:

secondary alkane sulfonate

SDA:

Soap and Detergent Association

sec:

secondary

TLC:

thin layer chromatography

ThCO2 :

theoretical yield of carbon dioxide

ThOD:

theoretical oxygen demand

TPBS:

tetrapropylene benzene sulfonate

UV:

ultra-violet

µ :

specific growth rate

μg:

microgram

φ :

benzene ring

References

  1. Davidsohn AS, Milwidsky B (1987) Synthetic detergents. Longman, London

    Google Scholar 

  2. Swisher RD (1987) Surfactant biodegradation, Marcel Dekker, New York

    Google Scholar 

  3. Gerike P (1987) In: Falbe J (ed) Surfactants in consumer products, Springer, Berlin Heidelberg New York, p 450

    Book  Google Scholar 

  4. Schöberl P, Bock KJ, Huber L (1988) Tenside Surfactants Detergents 25:2

    Google Scholar 

  5. Little AD (1977) Human safety and environmental aspects of major surfactants. Prepared for Soap and Detergent Association New York. AD Little, Cambridge MA

    Google Scholar 

  6. Little AD (1981) As 5

    Google Scholar 

  7. Sisley PJ (1964) Encyclopaedia of surface-active agents. Chemical Publishing Co., New York

    Google Scholar 

  8. Cain RB (pers. comm.)

    Google Scholar 

  9. Berth P, Jeschke P (1989) Tenside Surfactants Detergents 26:75

    CAS  Google Scholar 

  10. FRG Bundesgetzblatt Pt 1 Nr 128 (1976) pp 3017–3032

    Google Scholar 

  11. Control of Pollution Act (1974) Part 2 Pollution of Water HMSO, London

    Google Scholar 

  12. FRG Bundesgesetzblatt Part 1. No. 49 Dec. 12 1962. 698–706

    Google Scholar 

  13. Soap and detergent association (1965) JAOCS 42:986

    Google Scholar 

  14. Organisation for economic co-operation and development Pollution by detergents: Determination of the biodegradability of anionic synthetic surface active agents, OECD, Paris, 1971

    Google Scholar 

  15. OECD proposed method for the determination of the biodegradability of surfactants used in synthetic detergents, Paris, 1976

    Google Scholar 

  16. Council directives 73/404 and 73/405 Off J European Comm L347/53 7th December 1973

    Google Scholar 

  17. Council directive, amending 73/405 Off J European Comm C.112/4 14th May 1981

    Google Scholar 

  18. Council directive, amending 73/404 Off J European Comm L109/1 22nd April 1982

    Google Scholar 

  19. Council directive, 67/548, 6th amendment Off J European Comm L259/10 15th October 1979

    Google Scholar 

  20. Sweeney WA, Foote JK (1964) JWPCF 36:14

    CAS  Google Scholar 

  21. Sweeney WA (1966) JWPCF 38:1023

    CAS  Google Scholar 

  22. Berna JL, Ferrer J, Moreno A, Prats D, Ruiz Bevia F (1989) Tenside Surfactants Deterg 26:101

    CAS  Google Scholar 

  23. Giger W, Brunner PH, Ahel M, McEvoy J, Marcomini A, Schaffner C (1987) Gas Wass-Abwass 67:3

    Google Scholar 

  24. Matthijs E, De Henau H (1985) Tenside Deterg 22:299

    CAS  Google Scholar 

  25. Urano K, Saito M, Murata C (1984) Chemosphere 13:293

    Article  CAS  Google Scholar 

  26. Swanwick JD, Shurben DG, Jackson S (1969) Wat Pollut Control 68:639

    CAS  Google Scholar 

  27. Janicke W, Niemitz W (1973) Vom Wasser 40:369

    CAS  Google Scholar 

  28. Urano K, Saito M (1984) Chemosphere 13:285

    Article  CAS  Google Scholar 

  29. Games LM (1982) In: Dickson KL, Maki AW, Cairns J (eds) 4th meeting Modelling the fate of chemicals in the aquatic environment. Ann Arbor Sci Ann Arbor Michigan U.S.A. 1981

    Google Scholar 

  30. Hand VC, Williams GK (1987) Env Sci Technol 21:370

    Article  CAS  Google Scholar 

  31. Llenado RA, Neubecker TA (1983) Anal Chem 55:93R

    Article  Google Scholar 

  32. Llenado RA, Jamieson RA (1981) Anal Chem 53:174R

    Article  Google Scholar 

  33. International organisation for standardization (1984) ISO 7875–1. Determination of anionic surfactants by the methylene blue spectrometric method

    Google Scholar 

  34. Abbott DC (1962) Analyst 87:266

    Article  Google Scholar 

  35. Longwell J, Maniece WD (1955) Analyst 80:167

    Article  CAS  Google Scholar 

  36. Standing committee of analysts (1982) Analysis of surfactants in waters, waste waters and sludges. Methods for the examination of waters and associated materials, HMSO, London

    Google Scholar 

  37. Uchijama M, Takamura M (1980) Jap J Wat Pollut Res 3:133

    Article  Google Scholar 

  38. Waters J, Garrigan JT (1983) Wat Res 17:1549

    Article  CAS  Google Scholar 

  39. Osburn QW (1986) JAOCS 63:257

    Article  CAS  Google Scholar 

  40. Hon-Nami H, Hanya T (1978) J Chromatog 161:205

    Article  CAS  Google Scholar 

  41. Hon-Nami H, Hanya T (1980) Wat Res 14:1251

    Article  CAS  Google Scholar 

  42. McEvoy J, Giger W (1986) Env Sci Technol 20:376

    Article  CAS  Google Scholar 

  43. Tsukioka T, Murakami T (1983) Bunseki Kagaku 32:723

    Article  CAS  Google Scholar 

  44. Matsutani S, Shige T, Nagai T (1979) Yukagaku 28:847

    CAS  Google Scholar 

  45. Eganhouse RP, Ruth EC, Kaplan IR (1983) Anal Chem 55:2120

    Article  CAS  Google Scholar 

  46. Tanaka Y, Ikebe K, Yoshida M, Tanaka R, Kanita N (1976) Ken Kyusho Kenku Hokuku, Shokunin Eisei Hen 7:21

    CAS  Google Scholar 

  47. Gloor R, Johnson EL (1977) J Chrom Sci 15:413

    Article  CAS  Google Scholar 

  48. Jandera P, Churacek J (1980) J Chromatog 197:181

    Article  CAS  Google Scholar 

  49. Linder DE, Allen MC (1982) JAOCS 59:152

    Article  CAS  Google Scholar 

  50. Nakae A, Tsuji K, Yamanaka N (1980) Anal Chem 52:2275

    Article  CAS  Google Scholar 

  51. Nakae A, Tsuki K, Yamanaka M (1981) Anal Chem 53:1818

    Article  CAS  Google Scholar 

  52. De Henau H, Matthijs E, Hopping WD (1986) Int J Environ Anal Chem 26:279

    Article  Google Scholar 

  53. Matthijs E, De Henau H (1987) Tenside Deterg 24:193

    CAS  Google Scholar 

  54. Castles MA, Ward SR (1987) Analysis of LAS in environmental matrices by reverse phase HPLC with fluorescence detection. Presented at 8th annual meeting. Soc Env Tox Chem Nov 9–12, Pensacola, Florida, U.S.A.

    Google Scholar 

  55. Kikuchi M, Tokai A, Yoshida T (1986) Wat Res 20:643

    Article  CAS  Google Scholar 

  56. Hellmann H (1982) Zf Wass-u Abwass-Forsch 15:15

    CAS  Google Scholar 

  57. Swisher RD (1981) J Environ Qual 10:243

    Article  CAS  Google Scholar 

  58. Schaumberg GD, Le Vesque-Madore CS, Sposito G, Lund LJ (1981) J Environ Qual 10:244

    Article  CAS  Google Scholar 

  59. Uchiyama M (1977) Wat Res 11:205

    Article  CAS  Google Scholar 

  60. Mizuno M, Kawasaki T, Kojima I (1984) Mizu Shori Gijutsu 25:207

    CAS  Google Scholar 

  61. Sedlak RI, Booman KA (1986) Soap Cosmet Chem Spec 62:44

    CAS  Google Scholar 

  62. Rapaport RA, Hopping WD, Eckhoff WS (1987) Monitoring LAS in the environment. Presented at 8th annual meeting. Soc Env Tox Chem Nov 9–12, Pensacola, Florida, U.S.A.

    Google Scholar 

  63. Wagner R (1978) Gas v. Wasserfach (Wasser Abwasser) 119:235

    CAS  Google Scholar 

  64. Painter HA, King EF (1979) Water Research Centre, Rep. 709-S Stevenage U.K.

    Google Scholar 

  65. Painter HA, King EF, Moorhouse P (1980) Water Research Centre, Rep. 4-M Stevenage U.K.

    Google Scholar 

  66. Stiff MJ (1987) (pers. comm.)

    Google Scholar 

  67. 18th Annual Report, Standing Technical Committee on Synthetic Detergents, HMSO, London 1978.

    Google Scholar 

  68. Nara T, Oyamada K, Toanaka M, Hayakari T, Noda M, Yamasaki Y, Imis T, Ishida H (1983) Aomori-ken Kogai Senta Shoho 6:39

    CAS  Google Scholar 

  69. Kondoh H, Aoi T (1982) Hokkaido Kogai Boshi Kenkyushoho 9:69

    Google Scholar 

  70. Painter HA (1977) Water Research Centre Report 626-S Stevenage U.K.

    Google Scholar 

  71. Gilbert PA, Pettigrew R (1984) Int J Cosmet Sci 6:149

    Article  CAS  Google Scholar 

  72. Bruce AM, Swanwick JD, Ownsworth RA (1966) J Proc Inst Sew Purif Pt 5:427

    Google Scholar 

  73. McEvoy J, Giger W (1985) Naturwiss 72:429

    Article  CAS  Google Scholar 

  74. Yoshimura K (1984) XV Jornados Com Espanol Deterg p 103

    Google Scholar 

  75. Waters J, Holt MS, Matthijs E (1989) Tenside Surfactants Deterg 26:129

    CAS  Google Scholar 

  76. Kobuke Y (1985) Rikusuigaku Zasshi 46:279

    Article  CAS  Google Scholar 

  77. Hennes EC, Rapaport RA (1989) Tenside Surfactants Deterg 26:141

    CAS  Google Scholar 

  78. Fischer WK (1980) Tenside Deterg 17:250

    CAS  Google Scholar 

  79. Gerike P, Winkler K, Schneider W, Jakob W (1989) Tenside Deterg 26:136

    CAS  Google Scholar 

  80. Morena Danvila A (1987) Private presentation, Petroquiaicu Espanola SA, Madrid, Spain

    Google Scholar 

  81. Institut d’Hygiene et d’Epidemiologie (1985) Reseau de mesure de la qualité’ des eaux superficielles Belges en 1985. 14 rue Juliette Wytsman, Bruxelles

    Google Scholar 

  82. Motoyama S, Mukai H (1981) Niigata Rikagaku 7:21

    CAS  Google Scholar 

  83. Okamoto T, Shirane Y (1982) Hiroshima-Ken Kankyo Senta Kenkyu Hokoku 3:60

    CAS  Google Scholar 

  84. Takada H, Ishiwatari R (1987) Env Sci Tech 21:875

    Article  CAS  Google Scholar 

  85. Katsuno T, Tsukuoka T, Kono Y (1983) Nagano-Ken Eisei Kogai Kenkyusho Kenkyu Hokoku 6:23

    CAS  Google Scholar 

  86. De Henau H, Matthijs E, Hopping WD (1986) Int J Environ Anal Chem 26:279

    Article  Google Scholar 

  87. Uchiyama M (1979) Wat Res 13:847

    Article  CAS  Google Scholar 

  88. Siron R, Giusti G (1985) CR Acad Sci Ser 3 :301 313

    Google Scholar 

  89. Mochalov OS, Autonova NM, Nesterova MP (1984) Geol Istov Geokhim Balt Morja p 165

    Google Scholar 

  90. Utsunomiya A, Ito S, Setsuda S, Naato S, Shimozata T (1980) Eisei Kaguku 26:159

    Article  CAS  Google Scholar 

  91. Waters J (1976) Vom Wasser 47:131

    CAS  Google Scholar 

  92. Anon (1978) Yushi 31:30

    Google Scholar 

  93. Imaida M, Sumimoto T, Miyano K, Yoshida A (1979) Osaka-furitsa Koshu Eisei Kenkyusho Kenkyu Hokoku, Shokuhin Esei Hen 10:63

    CAS  Google Scholar 

  94. Mancini P, Bellandi S, Lan Conca P, Pantani F (1984) Riv Mercoed 23:143

    CAS  Google Scholar 

  95. Yoshimura K, Hayashi K, Kawase J, Tsuji K (1984) Jap J Limnol 45:51

    Article  CAS  Google Scholar 

  96. Painter HA, Zabel TF (1988) Review of the environmental safety of LAS Con 1652 Water Research Centre, August 1988, Medmenham, U.K.

    Google Scholar 

  97. Cain RB, (1987) Biochem Soc Trans 15 (Suppl):7S

    Google Scholar 

  98. Schöberl P (1989) Tenside Surfactants Deterg 26:86

    Google Scholar 

  99. Willetts AJ (1973) Envir and Change 2:110

    Google Scholar 

  100. Divo C, Cardini G (1980) Tenside Deterg 17:30

    CAS  Google Scholar 

  101. Phillips WK (1978) Symbiotic degradation of linear alkyl benzene sulfonate. Thesis. In: Diss Abstr Int B 39:3158

    Google Scholar 

  102. Huddleston RL, Allred RC (1963) Dev Ind Microbiol 4:24

    Google Scholar 

  103. Bock KJ, Wickbold R (1966) Vom Wasser 33:242

    CAS  Google Scholar 

  104. Swisher RD (1972) Yukagaku 21:130

    CAS  Google Scholar 

  105. Gledhill WE (1975) Appl Microbiol 30:922

    CAS  Google Scholar 

  106. Simko JP, Emery EM, Blank EW (1965) JAOCS 42:627

    Article  CAS  Google Scholar 

  107. Abe S, Seno M (1985) Nippon Kagaku Kaishi 5:814

    Article  Google Scholar 

  108. Utsunomiya A, Naito S, Tomita I (1986) Eisei Kagaku 32:258

    Article  CAS  Google Scholar 

  109. Larson RJ, De Henau H (1988) In: Proceedings of 2nd World surfactants congress, Paris, France 24–27 May

    Google Scholar 

  110. Ward TE (1986) In: 7th ann meeting of Soc Environ Toxicol Chem. November, Arlington, VA, U.S.A.

    Google Scholar 

  111. OECD (1981) Chemicals Group. Guidelines for testing chemicals ISBN 92–64-1222–4, Paris

    Google Scholar 

  112. International Organization for Standardization (1984) ISO 7827 Evaluation of the ultimate biodegradability of organic compounds—Method by analysis of dissolved organic carbon

    Google Scholar 

  113. Painter HA, King EF (1985) In: Hutzinger O (ed) The handbook of environmental chemistry, vol 2, Part C, Springer, Berlin Heidelberg New York

    Google Scholar 

  114. Gerike P, Fischer WK (1979) Ecotoxicol Env Safety 3:159

    Article  CAS  Google Scholar 

  115. Gerike P, Fischer WK (1981) Ecotoxicol Env Safety 5:45

    Article  CAS  Google Scholar 

  116. Painter HA, King EF (1983) Reg Toxicol Pharmacol 3:144

    Article  CAS  Google Scholar 

  117. Leidner H, Gloor R, Wuhrmann K (1976) Tenside Deterg 13:122

    CAS  Google Scholar 

  118. Painter HA (1978) Water Research Centre, Rep 663-S Stevenage, U.K.

    Google Scholar 

  119. Larson RJ (1979) Appl Env Microbiol 38:1153

    CAS  Google Scholar 

  120. Gilbert PA, Kleiser HA (1986) Presentation at 32nd Referate-Tagung Waschereiforschung, Krefeld, FRG 23 April 1986

    Google Scholar 

  121. Lotzsch K, Neufahrt A, Tauber G (1979) Tenside Deterg 16:150

    Google Scholar 

  122. Urano K, Saito M (1985) Chemosphere 14:1333

    Article  CAS  Google Scholar 

  123. Larson RJ, Wentler GE (1982) Soap Cosmet Chem Spec (May):33

    Google Scholar 

  124. Painter HA, Durrant K (1976) Water Research Centre, Tech Rep TR19, Stevenage, U.K.

    Google Scholar 

  125. De Oude NT (1977) Tenside Deterg 14:189

    Google Scholar 

  126. Yoshimura K, Ara K, Hayashi K, Kawase J, Tsuji K (1984) Jap J Limnol 45:204

    Article  Google Scholar 

  127. Swisher RD (1967) JAOCS 44:717

    Article  CAS  Google Scholar 

  128. Nielsen AM, Huddleston RL (1981) Dev Ind Microbiol 22:415

    CAS  Google Scholar 

  129. Commission Directive of 18th November 1987 adapting Council Directive 67/548/EEC (1988) Off J European Comm L133 10th May 1988

    Google Scholar 

  130. Brown D (1976) 7th Int Surfactant Congress, 4 vols U.S.S.R. Nat Comm on Surface Active Substances. Moscow 4:44

    Google Scholar 

  131. Hrsak D, Bosnjak M, Johanides V (1981) Tenside Deterg 18:137

    CAS  Google Scholar 

  132. Painter HA (1979) Water Research Centre, Rep 699-S, Stevenage, U.K.

    Google Scholar 

  133. Brown VM, King EF, Painter HA (1981) Water Research Centre. Rep 68-M. Stevenage, U.K.

    Google Scholar 

  134. Brown VM, King EF, Painter HA (1981) Water Research Centre. Rep 222-M. Stevenage, U.K.

    Google Scholar 

  135. Petresa (1987) Private Comm

    Google Scholar 

  136. Gerike P, Jasiak W (1985) Tenside Deterg 22:305

    CAS  Google Scholar 

  137. Gerike P, Fischer WK, Holtmann W (1980) Wat Res 14:753

    Article  Google Scholar 

  138. Painter HA, King EF (1978) Wat Res 12:909

    Article  CAS  Google Scholar 

  139. Steber J (1979) Tenside Deterg 16:140

    CAS  Google Scholar 

  140. Nielsen AM, Meyers JD, Bleckmann CA, Huddleston RL (1980) Soap Cosmet Chem Spec 56:48

    CAS  Google Scholar 

  141. Shimp RJ, Procter and Gamble Co (to be published)

    Google Scholar 

  142. Stiff MJ, Rootham RC (1973) Wat Res 7:1407

    Article  CAS  Google Scholar 

  143. Gledhill WE (1974) Adv Appl Microbiol 17:265

    Article  CAS  Google Scholar 

  144. Larson RJ, Perry RL (1981) Wat Res 15:697

    Article  CAS  Google Scholar 

  145. Larson RJ, Payne AG (1981) Appl Env Microbiol 41:621

    CAS  Google Scholar 

  146. Larson RJ (1983) Residue Rev 85:159

    Article  CAS  Google Scholar 

  147. Ventullo RM, Larson RJ, Procter and Gamble Co (to be published)

    Google Scholar 

  148. Ventullo RM, Ward TE, Larson RJ, Procter and Gamble Co (to be published)

    Google Scholar 

  149. Larson RJ, Federle TW, Shimp RJ, Ventullo RM (1989) Tenside Surfactants Deterg 26:116

    CAS  Google Scholar 

  150. Ward TE, Larson RJ (1988) Ecotoxicol Environ Saf 17:119

    Article  Google Scholar 

  151. Larson RJ, Bishop WE (1988) Soap Cosmet Chem Spec

    Google Scholar 

  152. Giger W, Brunner PH, Ahel M, McEvoy J, Marcomini A, Schaffner C (1987) Gas-Wasser-Abwasser 67:111

    CAS  Google Scholar 

  153. Haberl R, Konig M, Pollhammer P (1980) Osterreichische Abwasser-Rundschau 25:53

    CAS  Google Scholar 

  154. Pitter P, Veselský J, Ciperova M (1971) Sb Vvys SK, Chem-Technol Praze, Technol Vody 16:37

    CAS  Google Scholar 

  155. Larson RJ, Ventullo RM (to be published)

    Google Scholar 

  156. Vandoni MV, Goldberg-Federico L (1973) Riv Ital Sostanze Grasse 50:185

    CAS  Google Scholar 

  157. Litz N, Doering HW, Thiele M, Blume H-P (1987) Ecotoxicol Environ Saf 14:103

    Article  CAS  Google Scholar 

  158. Kimerle RA (1989) Tenside Surfactant Deterg 26:169

    CAS  Google Scholar 

  159. Lewis MA (1986) Environ Toxicol Chem 5:319

    Article  CAS  Google Scholar 

  160. Bishop WE, Perry RL (1981) In: Branson DR, Dickson KL (eds) Aquatic toxicology and hazard assessment. 4th Conf ASTM STP 737 pp 421–35

    Chapter  Google Scholar 

  161. Hitchcock WS, Martin DF (1977) Bull Environ Contam Toxicol 18:291

    Article  CAS  Google Scholar 

  162. Lal H, Misra V, Viswanathan PN, Krishna Murti CR (1983) Ecotoxicol Environ Saf 7:538

    Article  CAS  Google Scholar 

  163. Lal H, Misra V, Viswanathan PN, Krishna Murti CR (1984) Ecotoxicol Environ Saf 8:447

    Article  CAS  Google Scholar 

  164. Lewis MA, Perry RL (1981) In: Branson DR, Dickson KL (eds) 4th Conf Aquatic Toxicity and Hazard Assessment. ASTM STP 737 pp 402–418

    Chapter  Google Scholar 

  165. Moreno-Danvila A (1983) 14th Jorn Com Espanol Deterg pp 23–36

    Google Scholar 

  166. Proctor and Gamble Co (unpublished)

    Google Scholar 

  167. Kimerle RA, Swisher RD (1977) Wat Res 11:31

    Article  CAS  Google Scholar 

  168. Monsanto Co (unpublished)

    Google Scholar 

  169. Lewis MA, Supprenant D (1983) Ecotoxicol Environ Saf 7:313

    Article  CAS  Google Scholar 

  170. Calabrese DM, Davis HC (1967) Proc Nat Shellfisheries Assoc 57:11

    Google Scholar 

  171. Ladle M, House WA, Armitage PD, Farr IS (1989) Tenside Surfactant Deterg 26:159

    CAS  Google Scholar 

  172. Gafa S (1974) Riv Ital Sostanze Grasse 51:183

    CAS  Google Scholar 

  173. Macek KJ, Sleight BH (1977) In: Mayer FL, Hamelink GL (eds) Aquatic toxicity and hazard assessment, ASTM STP 634 pp 137–146

    Google Scholar 

  174. Swisher RD, Gledhill WE, Kimerle RA, Taulli TA (1976) 7th Surf Cong U.S.S.R. Nat Comm Surface active substances, Moscow, 1978, 4:218

    Google Scholar 

  175. Pickering QH, Thatcher TO (1970) JWPCF 42:243

    CAS  Google Scholar 

  176. Vailati G, Calamari D, Marchetti R (1975) Naovi Ann Ig Microbiol 26:69

    CAS  Google Scholar 

  177. Pittager CA, Woltering DM, Masters JA, Procter and Gamble (to be published)

    Google Scholar 

  178. Bressan M, Brunetti R, Casellato S, Fara GC, Giro P, Marin M, Negrisolo P, Tallandini L, Thomann S, Tosoni L, Turchetto M (1989) Tenside Surfactants Deterg 26:148

    CAS  Google Scholar 

  179. Windeatt AJ (1987) Unpublished study (Brixham Study No Q334/A) Unilever Research Laboratories, 1987

    Google Scholar 

  180. Mieure JP Unpublished study, Monsanto Co St Louis, MO

    Google Scholar 

  181. Gloxhuber C (ed) (1980) Anionic surfactants. Biochemistry toxicology, dermatology. Marcel Dekker Inc New York

    Google Scholar 

  182. Hill JT In: 181 pp 405–410

    Google Scholar 

  183. Swisher RD (1968) Arch Environ Health 17:232

    Article  CAS  Google Scholar 

  184. Oba K (1980) In: Ref 181. “Carcinogenic, mutagenic and teratogenic properties” pp 327–404

    Google Scholar 

  185. Krienke EG, Ritter S, v Muhlendahl KE (1980) In: Ref 181 “Observations on tolerance in cases of ingestion” pp 127–138

    Google Scholar 

  186. Matson TP (1978) JAOCS 55:66

    Article  CAS  Google Scholar 

  187. Longman GF (1975) The analysis of detergents and detergent products. J Wiley and Sons, London, New York

    Google Scholar 

  188. Oba K, Miura K, Sekiguchi R, Yagi R, Mori A (1976) Wat Res 10:149

    Article  CAS  Google Scholar 

  189. Arisue J, Inoue T, Konishi K (1985) Hokkaido Kogai Boshi Kenkyushko 12:52

    Google Scholar 

  190. Smedes F, Kraak JC, Werkhoven-Goewie CF, Brinkman UAT, Rei RW (1982) J Chromatogr 247:123

    Article  CAS  Google Scholar 

  191. Nakamura K, Morikawa Y, Matsumoto I (1981) JAOCS 58:72

    Article  CAS  Google Scholar 

  192. Nakamura K, Morikawa Y (1982) JAOCS 59:64

    Article  CAS  Google Scholar 

  193. Irgolic KJ, Hobill JE (1987) Spectrochim Acta 42B:269

    Article  Google Scholar 

  194. Lyon PA, Stebbings WL, Crow FW, Tomer KB, Lippstreu DL, Gross ML (1984) Anal Chem 56:8

    Article  CAS  Google Scholar 

  195. Righton MJG, Watts CD (1986) Water Research Centre, Rep ER1194-M, Medmenham, U.K.

    Google Scholar 

  196. Rivera J, Fraisse D, Ventura F, Caixach J, Figueras A (1987) Fresenius Z Anal Chem 328:577

    Article  CAS  Google Scholar 

  197. Maurer EW, Cordon TC, Stirton AJ (1971) JAOCS 48:163

    Article  CAS  Google Scholar 

  198. Borstlap C, Kooijman PL (1963) JAOCS 40:78

    Article  CAS  Google Scholar 

  199. Miura K, Yamanaka K, Sangai T, Yoshimura K, Hayashi N (1979) Yukagaku 28:351

    CAS  Google Scholar 

  200. Itoh S, Setsuda S, Utsunomiya A, Naito S (1976) Eisei Kagaku 22:254

    Article  CAS  Google Scholar 

  201. De Fulvio S, Marconi A, Pierini N (1980) Inquinamento 22:31

    Google Scholar 

  202. Lundahl P, Cabridenc R, Xuereff R (1972) 6th Surf Cong Zurich, Chemie and Anwendungstechnik der Grenzflachenacktiven Stoffe, Carl Hauser, Munich 1973, 3:689

    Google Scholar 

  203. Fischer WK (1981) In: Fettalkohole—Rohstoffe, Verfahren und Verwendung, Henkel, Dussedlorf, English edn pp 181–222

    Google Scholar 

  204. Sales Marquez D, Galan Vallejo M, Munoz Cueto MJ, Flores Luque V (1981) Comun Journ Com Esp Deterg 12th 193–225 Asoc Invest Détergentes, Tensioactivos, Afines: Barcelona, Spain

    Google Scholar 

  205. Degens PN, Vander Zee H, Commer JD, Kamphuis HA (1950) J Proc Inst Sew Purif pp 63–68

    Google Scholar 

  206. Hammerton C (1955) J Appl Chem 5:517

    Article  CAS  Google Scholar 

  207. Crauland M, Courtier A, Bolle J (1964) 4th Surf Cong Brussels, Chemistry physics and application of surface active substances 1:93 Gordon and Breach, London 1967

    Google Scholar 

  208. Hammerton C (1956) Proc Soc Water Treat Exam 5:145

    CAS  Google Scholar 

  209. Bosari GB, Buosi F, Fuochi EP (1974) Riv Ital Sost Grasse 51:193

    Google Scholar 

  210. Kawaski T, Mizuno M, Sato M, Kojima I (1983) Jap J Water Waste 25:1251

    Google Scholar 

  211. Sekiguchi H, Miura K, Oba K (1975) Yakagaku 24:451

    CAS  Google Scholar 

  212. Steber J, Gode P, Guhl W (1988) Fett Wiss Technol 90:32

    CAS  Google Scholar 

  213. Livingston JR, Drogin R, Kelly RJ (1965) Ind Eng Chem Prod Res Dev 4:28

    Article  CAS  Google Scholar 

  214. Winter W (1962) Wasserwirtsch-Wassertech 12:265

    CAS  Google Scholar 

  215. Gebril BA, Abou-Zeid H (1966) Tenside 3:150

    Google Scholar 

  216. Flores Luque V, Sales Marquez D, Torregrosa RE (1980) Inq Quim (Madrid) 12:123

    CAS  Google Scholar 

  217. Cook TM, Goldman CK (1974) Chesapeake Sci 15:52

    Article  CAS  Google Scholar 

  218. Sales D, Quiroga JM, Gomez-Parra A (1987) Bull Environ Contam Toxicol 39:385

    Article  CAS  Google Scholar 

  219. Vives-Rego J, Vaque MD, Leal JS, Parra J (1987) Tenside, Surfactants, Deterg 24:20

    CAS  Google Scholar 

  220. Abe S (1984) Nippon Kagaku Kaishi 9:1465

    Article  Google Scholar 

  221. Janicke W (1971) Wat Res 5:917

    Article  CAS  Google Scholar 

  222. Fischer WK, Gerike P (1975) Wat Res 9:1131

    Article  CAS  Google Scholar 

  223. Gerike P, Jasiak W (1984) Welt-Tensid-Kongress, Munich, Kongressberichte, Kürle Druck Geinhausen, 1:195

    Google Scholar 

  224. Moreno Danvila A (1979) X Jörn Com Esp Deterg pp 59–80

    Google Scholar 

  225. Berger B (1964) Ind Chim (Paris) 51:421

    CAS  Google Scholar 

  226. Mann AH, Reid VW (1971) JAOCS 48:798

    Article  CAS  Google Scholar 

  227. Pitter P (1964) 4th Surf Cong Brussels, Chemistry, physics and application of surface active substances, Gordon and Breach, London (1967) 3:861

    Google Scholar 

  228. Maurer EW, Cordon TC, Weil JK, Nunez-Ponzoa MV, Ault WC, Stirton AJ (1965) JAOCS 42:189

    Article  CAS  Google Scholar 

  229. Oba K, Yoshida Y, Tomiyama S (1967) Yukagaku 16:517

    CAS  Google Scholar 

  230. Itoh S, Naito S, Unemoto T (1986) Eisei Kagaku 32:101

    Article  CAS  Google Scholar 

  231. Itoh S, Naito S, Unemoto T (1987) Eisei Kagaku 33:415

    Article  CAS  Google Scholar 

  232. Wagener S, Schink B (1987) Wat Res 21:615

    Article  CAS  Google Scholar 

  233. Steber J, Wierich P (1987) Wat Res 21:661

    Article  CAS  Google Scholar 

  234. Birch RR, Biver C, Campagna R, Gledhill WE, Pagga U, Steber J, Reust H, Bentinck WJ (1989) Chemosphere 19:1527

    Article  CAS  Google Scholar 

  235. Dodgson KS, White GF, Massey JA, Shapleigh J, Payne WJ (1984) FEMS Microbiol Lett 24:53

    Article  CAS  Google Scholar 

  236. White GF, Dodgson KS, Davies I, Matts PJ, Shapleigh JP, Payne WJ (1987) FEMS Microbiol Lett 40:173

    Article  CAS  Google Scholar 

  237. Cain RB (1987) Biochem Soc Trans 15 (Suppl):7S

    Google Scholar 

  238. Elnabarawy MT, Robideau RR, Beach SA (1988) Tox Assess 3:361

    Article  CAS  Google Scholar 

  239. Dutka BJ, Nyholm N, Petersen J (1983) Wat Res 17:1363

    Article  CAS  Google Scholar 

  240. King EF (1984) In: Toxicity screening procedures using bacterial systems. Liu D, Dutka B J (eds) Marcel Dekker, Inc. New York, Basel, 175–194

    Google Scholar 

  241. Xu H, Dutka BJ (1987) Tox Assess 2:149

    Article  CAS  Google Scholar 

  242. Vives-Rego J, Vaque D, Martinez J (1986) Wat Res 20:1411

    Article  CAS  Google Scholar 

  243. Beaubien A, Bouchard A, Jolicoeur C (1986) Tox Assess 1:187

    Article  CAS  Google Scholar 

  244. Nyberg H (1988) Wat Res 22:217

    Article  CAS  Google Scholar 

  245. Lenova LI, Stavskaya SS, Ratushnaya MY (1980) Gidrobiol ZH 16:83

    CAS  Google Scholar 

  246. Roderer G (1987) Arch Environ Contam Toxicol 16:291

    Article  CAS  Google Scholar 

  247. Ukeles R (1965) J Phycol 1:102

    Article  Google Scholar 

  248. Roberts MH, Warrinner JE, Tsai CF, Wright D, Cronin LE (1982) Arch Environ Contam Toxicol 11:681

    Article  CAS  Google Scholar 

  249. Lundahl P, Cabridenc R (1978) Wat Res 12:25

    Article  CAS  Google Scholar 

  250. LeBlanc GA (1982) Environ Pollut (Ser A) 27:309

    Article  CAS  Google Scholar 

  251. Moore SB, Diehl RA, Barnhardt JM, Avery GB (1987) World Textile Abstracts 19:290

    Google Scholar 

  252. Lundahl P, Cabridenc R (1976) J Fran Hydrol 7:143

    Article  CAS  Google Scholar 

  253. Bode H, Ernst R, Arditti J (1978) Environ Pollut 17:175

    Article  CAS  Google Scholar 

  254. Patzner AM, Adam H (1979) Zool Anz Jena 202:199

    Google Scholar 

  255. Conti E (1987) Aquatic Toxicol 10:325

    Article  CAS  Google Scholar 

  256. Price KS, Waggy GT, Conway RA (1974) JWPCF 46:63

    CAS  Google Scholar 

  257. Tatem HE, Anderson JW, Neff JM (1976) Bull Environ Contam Toxicol 16:368

    Article  CAS  Google Scholar 

  258. Piper WD, Maxwell KE (1971) J Econ Entomol 64:601

    CAS  Google Scholar 

  259. Graney RL, Giesy JP (1988) Environ Toxicol Chem 7:301

    CAS  Google Scholar 

  260. Cardwell RD, Woelke CE, Carr MI, Sanborn E (1978) Bull Environ Contam Toxicol 20:128

    Article  CAS  Google Scholar 

  261. Hidu H (1965) JWPCF 37:262

    CAS  Google Scholar 

  262. Verna SR, Mohan D, Dalela RC (1978) Acta Hydrochim Hydrobiol 6:121

    Article  Google Scholar 

  263. Van Embden HM, Kroon CCM, Schoeman EN, Van Seventer HA (1974) Environ Pollut 6:297

    Article  Google Scholar 

  264. Kikuchi K, Wakabayashi M, Nakamura T, Inoue W, Takahashi K, Kawana T, Kawahara H, Koido Y (1976) Ann Rep Tokyo Metrop Res Inst Environ Prot 57–69

    Google Scholar 

  265. Tovell PWA, Newsome CS, Howes D (1974) Wat Res 8:291

    Article  CAS  Google Scholar 

  266. Fogels A, Sprague JB (1977) Wat Res 11:811

    Article  CAS  Google Scholar 

  267. Hara TJ, Thompson BE (1978) Wat Res 12:893

    Article  CAS  Google Scholar 

  268. Dalela RC, Tyagi AK, Pal N, Verna SR (1981) Wat Air Soil Pollut 15:3

    CAS  Google Scholar 

  269. Wakabayashi M, Kikuchi M, Kojima H, Yoshida T (1978) Chemosphere 11:917

    Article  Google Scholar 

  270. Kikuchi M, Wakabayashi M (1979) Seitai Kagaku 1:195

    CAS  Google Scholar 

  271. Nadasy M, Dobozy OK, Bartha B, Pafli D, Kolesei M (1972) 6th Int Cong Surface Activity. Zurich 1972, Chemie, physikalische Chemie und Anwendungstechnik der grenzflachenaktiven Stoffe, 4 vols, Carl Hanser, Munich 1973

    Google Scholar 

  272. Antonielli M, Lapattelli M (1977) Agrochimica 21:15

    CAS  Google Scholar 

  273. Taniyana T, Nomura T (1978) Mie Daigaku Kankyo Kagaku Kenkyo Kiyo 3:93

    Google Scholar 

  274. Muramoto S, Oki Y (1988) J Environ Sci Health A23:603

    Article  Google Scholar 

  275. Yagami K, Yokota Y, Iwashita S, Nakayama M (1984) Yukagaku 33:284

    CAS  Google Scholar 

  276. Neubecker TA, Brag JP (1983) ACS Env Chem Div Ext Abstr 23:112

    Google Scholar 

  277. Goodnow RA, Harrison AP (1972) Appl Microbiol 24:555

    CAS  Google Scholar 

  278. Hales SG, Dodgson KS, White GF, Jones N, Watson GK (1982) Appl Env Microbiol 44:790

    CAS  Google Scholar 

  279. Yoshimura K, Masuda F (1982) JAOCS 59:328

    Article  CAS  Google Scholar 

  280. Griffiths ET, Hales SG, Russell NJ, White GF (1987) Biotechnol Appl Biochem 9:217

    CAS  Google Scholar 

  281. Steinie EC, Myerly RC, Vath CA (1984) JAOCS 41:804

    Google Scholar 

  282. Stead JB, Pugh AT, Koduji II, Morland RA (1972) 6th Int Surf Cong Zurich Chemie, physikalische Chemie und Anwendungstechnik der grenzflachenaktiven Stoffe, Carl Hanser, Munich, 1973,3:721

    Google Scholar 

  283. Vashon RD, Schwab BS (1982) Env Sci Technol 16:433

    Article  CAS  Google Scholar 

  284. Oba K (1971) Nippon Eiseigaku Zasshi 25:494

    Article  CAS  Google Scholar 

  285. Hales SG, Watson GK, Dodgson KS, White GF (1986) J gen Microbiol 132:953

    CAS  Google Scholar 

  286. Yamane AN, Okada M, Sudo R (1984) Wat Res 18:1101

    Article  CAS  Google Scholar 

  287. Kutt EC, Martin DF (1974) Marine Biology 28:253

    Article  CAS  Google Scholar 

  288. Maki AW (1979) J Fish Res Bd Can 36:411

    Article  CAS  Google Scholar 

  289. Shell Chemical Company, unpublished

    Google Scholar 

  290. Reiff B, Lloyd R, How MJ, Brown D, Alabaster JS (1979) Wat Res 13:20

    Article  Google Scholar 

  291. Maki AW (1979) Spec Tech Publ 667, Am Soc Testing Materials pp 77–95

    Google Scholar 

  292. Farone WA (1979) U.S. Pat App 4171968 23 Oct 1979, pp 7

    Google Scholar 

  293. Scailteur V, Maurer JK, Walker AP, Calvin G (1986) Fd Chem Toxic 24:175

    Article  CAS  Google Scholar 

  294. Takeshita R, Jinnai N, Yoshida H (1976) J Chromatog 123:301

    Article  CAS  Google Scholar 

  295. Matsutani S, Shige T, Nagai T (1980) Yukagaku 29:189

    CAS  Google Scholar 

  296. Matsutani S, Shige T, Nagai T (1980) Yukagaku 29:926

    CAS  Google Scholar 

  297. Kroner M, Schneider G (1968) Fette-Seifen-Anstrichmittel 70:753

    Article  Google Scholar 

  298. Sekiguchi H, Miura K, Oba K, Mori A (1975) Yukagaku 24:145

    CAS  Google Scholar 

  299. McAteer JH, Kinnard LM (1964) 4th Int Surf Cong Burssels, Chemistry, physics and application of surface active substances Gordon and Breach, London, 1967 (3 vols) 1:127

    Google Scholar 

  300. Eden GE, Truesdale GA, Stennett GV (1968) Wat Pollut Control 67:107

    CAS  Google Scholar 

  301. Walther H, Knaack D (1970) Wasserwirt-Wassertech 20:306

    CAS  Google Scholar 

  302. Thysse GJE, Wanders TH (1974) A van Leeuwenhoek 40:25

    Article  CAS  Google Scholar 

  303. Stavskaya SS, Taranova LA, Grigor’eva TY, Degtyarev VA, Pisarev VT, Rotmistrov MN (1984) Mikrobiologiya 53:218

    CAS  Google Scholar 

  304. Rotmistrov MN, Taranova LA, Radchenko OS, Stavskaya SS, Dumanskii AV (1986) Dokl Akad Nouk SSSR 288:246

    CAS  Google Scholar 

  305. Guhl W, Gode P (1989) Tenside Surfactants Detergents 26:383

    Google Scholar 

  306. Knauf W (1973) Tenside 10:251

    CAS  Google Scholar 

  307. Oba K, Mori A, Tomiyama S (1968) Yukagaku 17:517

    CAS  Google Scholar 

  308. Wolf T, McPherson BP (1976) JAOCS 54:347

    Google Scholar 

  309. Allen MC, Martin TT (1971) JAOCS 48:790

    Article  CAS  Google Scholar 

  310. Nagai T, Hashimoto S, Yamane I, Mori A (1970) JAOCS 47:505

    Article  CAS  Google Scholar 

  311. Johannessen RO, DeWitt WJ, Smith RS, Tuvell ME (1983) JAOCS 60:858

    Article  CAS  Google Scholar 

  312. Kravetz L, Chung H, Guin KF, Shebs WT (1979) Presented at AOCS Am Oil Chemists Society 70th Ann Meeting, San Francisco, May 1979

    Google Scholar 

  313. Itoh S, Setsuda S, Utsunomiya A, Naito S (1979) Yukagaku 28:199

    CAS  Google Scholar 

  314. Kravetz L, Chung H, Rapean LC (1982) JAOCS 59:206

    Article  CAS  Google Scholar 

  315. Miura K, Nishizawa H (1982) Yukagaku 31:367

    CAS  Google Scholar 

  316. Pitter P, Horakova M, Fuka T, Struharik L (1980) Chem Prum 30:188

    CAS  Google Scholar 

  317. Tuvell ME, Kuehnhanss GO, Heidebrecht GD, Hu PC, Zielinski AD (1978) JAOCS 55:70

    Article  CAS  Google Scholar 

  318. Tomiyama S, Takao M, Mori A, Sekiguchi H, Oba K (1968) Ann Meeting Am Oil Chemists Society, New York, October 1968

    Google Scholar 

  319. Continental Oil Company, unpublished

    Google Scholar 

  320. Colgate Palmolive Company, unpublished

    Google Scholar 

  321. Monsanto Company, unpublished

    Google Scholar 

  322. Lopez-Zavala A, de Alujz AS, Elias BL, Manjarrez L, Buchmann A, Mercado L, Caltenco S (1975) Prog Water Tech 7:73

    CAS  Google Scholar 

  323. Takita Y (1982) Yukagaku 31:507

    CAS  Google Scholar 

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  1. Water Research Centre Medmenham UK, Freshfield Analysis Ltd., Caxton Villa, Park Lane, Knebworth, SG3 6PF, UK

    H. A. Painter

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Painter, H.A. (1992). Anionic Surfactants. In: de Oude, N.T. (eds) Detergents. Anthropogenic Compounds, vol 3 / 3F. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-47108-0_1

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