453:. In the petrochemical industry, NA's refer to alkyl carboxylic acids found in petroleum. The term naphthenic acid has roots in the somewhat archaic term "naphthene" (cycloaliphatic but non-aromatic) used to classify hydrocarbons. It was originally used to describe the complex mixture of petroleum-based acids when the analytical methods available in the early 1900s could identify only a few naphthene-type components with accuracy. Today "naphthenic" acid is used in a more generic sense to refer to all of the carboxylic acids present in petroleum, whether cyclic, acyclic, or aromatic compounds, and carboxylic acids containing heteroatoms such as N and S. Although commercial naphthenic acids often contain a majority of cycloaliphatic acids, multiple studies have shown they also contain straight chain and branched aliphatic acids and aromatic acids; some naphthenic acids contain >50% combined aliphatic and aromatic acids.
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about 1.0 mg KOH/g oil usually qualify as a high acid crude or oil. At the 1.0 mg/g TAN level, acidic crude oils begin to be heavily discounted in value and so are referred to as opportunity crudes. Commercial grades of naphthenic acid are most often recovered from kerosene/jet fuel and diesel fractions, where their corrosivity and negative impact on burning qualities require their removal. Naphthenic acids are also a major contaminant in water produced during the extraction of oil from
241:
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The complex mixture and hydrophobic nature of naphthenic acid allows metal naphthenates to be highly soluble in organic media such as petroleum-based hydrocarbons, oftentimes much more so than single isomer carboxylates such as metal acetates and stearates. Their industrial applications exploits this
492:
is equal to 0 for saturated, acyclic acids and increases to 2 in monocyclic naphthenic acids, to 4 in bicyclic naphthenic acids, to 6 in tricyclic acids, and to 8 in tetracyclic acids. Crude oils with total acid number (TAN) as little as 0.5 mg KOH/g acid or petroleum fractions greater than
666:
It has been stated that "naphthenic acids are the most significant environmental contaminants resulting from petroleum extraction from oil sands deposits." Nonetheless, the same authors suggest that "under worst-case exposure conditions, acute toxicity is unlikely in wild mammals exposed to
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used in painting and wood surface treatment. Industrially useful naphthenates include those of aluminium, magnesium, calcium, barium, cobalt, copper, lead, manganese, nickel, vanadium, and zinc. Illustrative is the use of cobalt naphthenate for the oxidation of tetrahydronaphthalene to the
440:
are carboxylic acids with a carbon backbone of 9 to 20 carbons. McKee et al. claim that "naphthenic acids (NAs) are primarily cycloaliphatic carboxylic acids with 10 to 16 carbons", although acids containing up to 50 carbons have been identified in heavy petroleum.
764:
Qian, K. and W.K. Robbins (2001). Resolution and identification of elemental compositions for more than 3000 crude acids in heavy petroleum by negative-ion microelectrospray high-field
Fourier Transform ion cyclotron resonance mass spectrometry.
513:
returns the acids free from hydrocarbons. Naphthenic acid is removed from petroleum fractions not only to minimize corrosion but also to recover commercially useful products. Some crude oils are high in acidic compounds (up to 4%).
566:
for basic oxides. Metal naphthenates are not well defined in conventional chemical sense because they are a complex mixture rather than a specific single component, structure or formula. They have diverse applications.
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782:
Barros, Eliane V.; Filgueiras, Paulo R.; Lacerda, Valdemar; Rodgers, Ryan P.; Romão, Wanderson (2022). "Characterization of
Naphthenic Acids in Crude Oil Samples – A literature review".
651:. Industrially useful metal naphthenates include those of aluminum, barium, calcium, cobalt, copper, iron, lead, magnesium manganese, nickel, potassium, vanadium, zinc, and zirconium.
675:
522:
The composition varies with the crude oil composition and the conditions during refining and oxidation.. Fractions that are rich in naphthenic acids can cause corrosion damage to
1289:
Vincent V. Rogers; Karsten Liber & Michael D. MacKinnon (August 2002). "Isolation and characterization of naphthenic acids from
Athabasca oil sands tailings pond water".
1196:
Vincent V. Rogers; Karsten Liber & Michael D. MacKinnon (August 2002). "Isolation and characterization of naphthenic acids from
Athabasca oil sands tailings pond water".
943:
Vincent V. Rogers, Karsten Liber, and
Michael D. MacKinnon (August 2002). "Isolation and characterization of naphthenic acids from Athabasca oil sands tailings pond water".
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naphthenic acids in AOS tailings pond water, but repeated exposure may have adverse health effects." Naphthenic acids are present in
Athabasca oil sands and
1043:
Walter E. Rudzinski; Leon
Oehlers & Yi Zhang (2002). "Tandem Mass Spectrometric Characterization of Commercial Naphthenic Acids and a Maya Crude Oil".
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332:
546:. Metal naphthenates are referred often to as "salts" of naphthenic acids, but metal naphthenates are not ionic. They are covalent, hydrophobic
909:
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to mammals. Damage, however, induced by NAs while transient in acute or discontinuous exposure, may be cumulative in repeated exposure.
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966:
Allen, E. W. (2008). "Process water treatment in Canada’s oil sands industry: I. Target pollutants and treatment objectives" (PDF).
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Clemente, J. S.; Fedorak, P. M. (2005). "A review of the occurrence, analyses, toxicity, and biodegradation of naphthenic acids".
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Article abstract regarding molecular origins of heavy crude oil interfacial activity mainly caused by
Naphthenic acids
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1318:"Process water treatment in Canada's oil sands industry: I. Target pollutants and treatment objectives"
1163:"Process water treatment in Canada's oil sands industry: I. Target pollutants and treatment objectives"
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Slavcheva E.; Shone B.; Turnbull A. (1999). "Review of naphthenic acid corrosion in oil refining".
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Richard H. McKee; Colin M. North; Paula
Podhasky; Jeffrey H. Charlap; Adam Kuhl (February 2014).
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Richard H. McKee; Colin M. North; Paula
Podhasky; Jeffrey H. Charlap; Adam Kuhl (February 2014).
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Naphthenic acids are the major contaminant in water produced from the extraction of oil from
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530:(NAC). Crude oils with a high content of naphthenic acids are often referred to as high
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James Brient, Peter Wessner, Mary Doyle (1995). "Naphthenic Acid" in Kirk-Othmer, ed.
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1258:"Acute and Subchronic Mammalian Toxicity of Naphthenic Acids from Oil Sands Tailings"
1226:"Acute and Subchronic Mammalian Toxicity of Naphthenic Acids from Oil Sands Tailings"
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734:"Acute and Subchronic Mammalian Toxicity of Naphthenic Acids from Oil Sands Tailings"
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Presentation by ChevronTexaco on crude oils with a high content of naphthenic acids
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Naphthenic acids have both acute and chronic toxicity to fish and other organisms.
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As the greatest current and historical usage, naphthenic acid are used to produce
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Vincent V. Rogers; Mark Wickstrom; Karsten Liber; Michael D. MacKinnon (2001).
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Article concerning refining crude oil with a high content of naphthenic acids
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Article about stabilisation of water-in-oil emulsions by naphthenic acids
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Conrad Environmental Aquatics Technical Advisory Group (CEATAG ) (1998).
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Spectrometric Identification of Naphthenic Acids Isolated from Crude Oil
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Crude oils with a high content of naphthenic acids in China's refineries
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M. Landau. 1993. "Driers and metallic soaps", in J. Kroschwitz, ed.,
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Details regarding Kuwaitian heavy crudes and naphthenic acid corrosion
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647:(driers) used in oil-based paint and wood surface treatment including
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J. A. Brient; P. J. Wessner; M. N. Doyle (1995). "Naphthenic Acids".
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Except where otherwise noted, data are given for materials in their
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Crude oils containing naphthenic acids in the Grangemouth refinery
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The naphthenates have industrial applications including synthetic
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carboxylic acids with molecular weights of 120 to well over 700
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Knight, H. B.; Swern, Daniel (1954). "Tetralin Hydroperoxide".
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Information by Seth Laboratories on Naphthenic acid corrosion
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Naphthenic acids are extracted from petroleum distillates by
1389:
Presentation by Baker Petrolite on naphthenic acid corrosion
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protocols for testing toxicity, refined NAs are not acutely
623:, corrosion inhibitors, fuel and lubricating oil additives,
578:, corrosion inhibitors, fuel and lubricating oil additives,
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1117:. New York: John Wiley & Sons. Vol. 8, pp. 432-445.
1098:"Article with details concerning naphthenic acid corrosion"
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Naphthenic Acids Background Information Discussion Report
892:
Nora, Angelo; Koenen, Gunther (2010). "Metallic Soaps".
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Naphthenic acid can refer to derivatives and isomers of
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Naphthenic acids are represented by a general formula C
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Organisation for Economic Co-operation and Development
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water at an estimated concentration of 81 mg/L
1424:Article about processes to remove Naphthenic acids
1384:Presentation by Nalco on naphthenic acid corrosion
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509:with aqueous base. Acidification of this extract
1325:Journal of Environmental Engineering and Science
1170:Journal of Environmental Engineering and Science
968:Journal of Environmental Engineering and Science
534:(TAN) crude oils or high acid crude oil (HAC).
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1115:Kirk-Othmer Encyclopedia of Chemical Technology
999:Kirk-Othmer Encyclopedia of Chemical Technology
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1374:Literature survey of naphthenic acid corrosion
894:Ullmann's Encyclopedia of Industrial Chemistry
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1379:Removing naphthenic acids from the crude oil
1439:Hydrogen flux and naphthenic acid corrosion
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1409:Article regarding naphthenic acid removal
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1369:Overview of naphthenic acid corrosion
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1262:International Journal of Toxicology
927:"Processing high TAN crude: Part 1"
866:Encyclopedia of Chemical Technology
738:International Journal of Toxicology
488:specifies a homologous series. The
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456:Salts of naphthenic acids, called
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839:10.1016/j.chemosphere.2005.02.065
484:indicates the carbon number and
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554:with the formula M(naphthenate)
402:(at 25 °C , 100 kPa).
550:. More specifically they are
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1210:10.1016/S0045-6535(02)00133-9
956:10.1016/S0045-6535(02)00133-9
902:10.1002/14356007.a16_361.pub2
526:equipment; the phenomenon of
451:naphthalene carboxylic acids
552:metal carboxylate complexes
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1084:10.1179/000705999101500761
796:10.1016/j.fuel.2022.123775
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518:Naphthenic acid corrosion
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299:Precautionary statements
1243:10.1093/toxsci/66.2.347
1001:. Weinheim: Wiley-VCH.
1231:Toxicological Sciences
548:coordination complexes
501:Sources and occurrence
211:Variable
1316:Allen, E. W. (2008).
1161:Allen, E. W. (2008).
511:acidic neutralization
655:Environmental impact
831:2005Chmsp..60..585C
767:Energy & Fuels.
661:Athabasca oil sands
495:Athabasca oil sands
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1454:Petroleum products
625:wood preservatives
580:wood preservatives
544:metal naphthenates
538:Metal naphthenates
406:Infobox references
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1136:Organic Syntheses
1057:10.1021/ef020013t
925:Qing, W. (2010).
911:978-3-527-30385-4
645:oil drying agents
608:oil drying agents
532:total acid number
434:atomic mass units
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1045:Energy Fuels
1044:
1038:
1030:
1025:
998:
994:
970:
967:
962:
947:
944:
939:
930:
920:
893:
873:
869:
865:
822:
818:
812:
787:
783:
766:
760:
741:
737:
700:Organic acid
684:
673:
665:
658:
629:insecticides
613:
584:insecticides
569:
543:
541:
527:
524:oil refinery
521:
504:
489:
485:
481:
467:
458:naphthenates
457:
455:
448:
445:Nomenclature
421:
417:
416:
260:
222:
46:Identifiers
1291:Chemosphere
1198:Chemosphere
945:Chemosphere
872:: 1017-1029
819:Chemosphere
436:. The main
426:cyclopentyl
388:Flash point
255:Signal word
189:Properties
81:100.014.239
18:Naphthenate
1448:Categories
716:References
710:Paraffinic
705:Resin acid
637:acaricides
633:fungicides
621:lubricants
617:detergents
592:acaricides
588:fungicides
576:lubricants
572:detergents
507:extraction
430:cyclohexyl
234:Pictograms
207:Molar mass
145:YNM5U6B7A4
53:CAS Number
804:247340497
680:genotoxic
438:fractions
373:P403+P233
357:P337+P313
353:P333+P313
349:P332+P313
333:P304+P340
329:P302+P352
225:labelling
102:215-662-8
94:EC Number
63:1338-24-5
1033:, 65 pp.
868:4th ed.
847:15963797
689:See also
480:, where
216:Hazards
125:20849290
827:Bibcode
663:(AOS).
649:varnish
261:Warning
112:PubChem
1142:: 90.
1013:
908:
845:
802:
674:Using
604:napalm
558:, or M
1321:(PDF)
1166:(PDF)
1101:(PDF)
800:S2CID
1011:ISBN
906:ISBN
843:PMID
784:Fuel
606:and
474:2n-z
428:and
381:P501
377:P405
369:P391
365:P363
361:P362
345:P321
341:P312
325:P280
321:P273
317:P272
313:P271
309:P264
305:P261
291:H411
287:H335
283:H319
279:H317
275:H315
136:UNII
1333:doi
1299:doi
1270:doi
1239:doi
1206:doi
1178:doi
1144:doi
1119:doi
1080:doi
1053:doi
1003:doi
975:doi
952:doi
898:doi
835:doi
792:doi
788:319
746:doi
602:of
422:NAs
223:GHS
162:EPA
115:CID
1450::
1327:.
1323:.
1295:48
1293:.
1266:33
1264:.
1260:.
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1009:.
997:.
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904:.
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798:.
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774:^
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635:,
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627:,
619:,
598:,
594:,
590:,
586:,
582:,
574:,
497:.
379:,
375:,
371:,
367:,
363:,
359:,
355:,
351:,
347:,
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227::
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564:6
560:3
556:2
490:z
486:z
482:n
478:2
476:O
472:H
470:n
420:(
164:)
160:(
20:)
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