Nonylphenol: Properties, legislation, toxicity and determination

ARAUJO, FREDERICO G. DE; BAUERFELDT, GLAUCO F.; CID, YARA PELUSO

doi:10.1590/0001-3765201720170023

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Chemical Sciences • An. Acad. Bras. Ciênc. 90 (2 suppl 1) • Aug 2018 • https://doi.org/10.1590/0001-3765201720170023 linkcopy

Nonylphenol: Properties, legislation, toxicity and determination

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

This paper aims to gather and discuss important information about nonylphenol, such as physical chemistry properties, toxicity and analytical methods in various matrices. As a degradation product of ethoxylated alkylphenols, nonylphenol presents a higher degree of reactivity than its precursor. Due to its harmful effects on the environment, use and production of nonylphenol has been banned in European Union countries, alongside their precursors. The guide on quality of drinking water (USEPA) recommends a maximum concentration of 28 µg L^-1 for fresh water. In Brazil, there is no clear legislation containing values of maximum concentration of nonylphenol. Due to this lack of regulation, a continuous monitoring is necessary of this pollutant in environmental samples. This paper aims to encourage further studies on nonylphenol, seen as a critical environmental pollutant. For proper monitoring is necessary to have reliable analytical methods and easy to perform in routine analysis.

Key words:
nonylphenol; endocrine disrupter; pollutant; water analysis

Maximum concentration (µg L^-1 )
	Brazil		USA		WHO
Composto	1^a	2^b	1^c	2^d	1^e
Benzopyreno	0.7	0.018^c	0.2	n.m.^f	0.7
Nonylphenol	n.m.	n.m.	n.m.	28^g/7^h	n.m.
Pentachlorophenol	9	3	1	19^g/13^h	9
Dihexyl-phthalate	20	n.m	6	n.m.	8

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[TFN1] a: Portaria MS 2914/2011 (BRASIL 2011); b: Resolução CONAMA 357/2005 (BRASIL 2005); c: Safe Drinking Water Act, SDWA(USEPA 2004); d: National recommendation of water quality criteria (USEPA 2009); e: World Health Organization; f: not mentioned value; g: fresh water; h: salty water.

Sample	Extraction method	Steps			Recovery	Reference
Sample	Extraction method	Cartridgde	Clean-up^a	Eluition^b
Líquid	SPE	C18	H₂O / MeOH (9:1)	AcOEt	>80%	Liu et al. 2004
			X	MeOH / H₂O (1:9)	≈95%	Cai et al. 2003
			H₂O / MeOH (8:2) pH= 2.5	MeOH	Uninformed	Ciofi et al. 2014
			MeOH / H₂O (1:9)	AcOEt / MeOH (6:4)	≈80%	Souza 2011
			X	MeOH	≈70%	Fabregat-Cabello et al. 2013
			X	ACET; HOAc 0.1 % MS MeOH / DCM	50%	Petrie et al. 2013
			H₂O	DCM	> 90%	Martinez and Peñuela 2013
			HEX / DCM (1:4)	MeOH / DCM (9:1)	Uninformed	De Souza Leite et al. 2010
			H₂O	DCM / HEX (4:1)	35%	Gatidou et al. 2007
			X	MeOH	85%	Petrovic et al. 2003
			X	HEX / DCM (9:1) + MeOH / DCM (9:1)	92%	Jeannot et al. 2002
			X	DCM / MeOH c/ HOAc (9:1)	Uninformed	Díaz et al. 2002
			Na₂SO₄ + DCM	MeOH	65% - 84%	Fiedler et al. 2007
		C18 + Zr doped TiO₂	H₂O	DCM / MeOH (1:9)	93%	Su et al. 2012
		Polymeric	H₂O	HEX / DCM (1:1)	80%	Terzopoulou et al. 2014
			MeOH / H₂O (4:6) + H2O + MeOH / MH₄OH / H₂O (10:2:88)	MeOH / ETHER (1:9)	≈50%	Jeannot et al. 2002
			X	ACET + MeOH	89% - 92%	Kuch and Ballschmiter 2001
			H₂O	ACN / DCM (1:1)	73%	Azevedo et al. 2001
			X	MeOH (3 ciclos)	70%	Montagner and Jardim 2011
			X	MeOH	≈72%	Sodré et al. 2010a
			X	ACET + MeOH	70%	Sodré et al. 2010b
	Ultrasound + SPE	OSTRO^TM 96	Ultrasound: 3 cycles 120 s ACN/H₂O (3:1)	MeOH	80%	Huerta et al. 2015
	LLE	X	Column with Na₂SO₄ anhydrous	Solution aqueous / organic solvent (20:1) pH=3 / 20 min	81% - 87%	Cruceru et al. 2012
	LLE	X	Syringe with Silica gel + wool + Na₂SO₄	1) DCM + HEX 2) MeOH	86%	Oketola and Fagbemigun 2013
	DLLME	Disperser solvent: 0.5 mL MeOH Extractor solvent: 50 µL 1-hexyl-3-methylimidazolium hexafluorophosphate Separation: Centrifugation (3 minutes, 6000 rpm)			93.5%	Sun et al. 2013
	SPME	Sample + NaCl + magnetic stirring NaOH + internal standard + derivatization reagent (DMS + DES + MNNG) thermostated water bath 60 ºC + fiber (CW/DVB) + stirring (900 rpm) Desorption fiber (headspace) 250 ºC for 3 minutes			Uninformed	Díaz et al. 2002
	SPME	Sample + NaCl + magnetic stirring + fiber (CW/DVB) Desorption fiber (headspace) 250º C for 5 minutes			Uninformed	Hernández et al. 2007
Solid	Soxlet	4 hours ; 90 °C; HEX			54%	Bernacka et al. 2009
	Soxlet	4 hours; MeOH; Dilution of the methanolic extract in H₂O / MeOH (7:3) and extraction by cartridge C18			72%	Jeannot et al. 2002
	Ultrasound	30 minutes; 50 °C; MeOH / H₂O (2:1)			63%	Gatidou et al. 2007
		5 minutes; ACET			≈65%	Lara-Marín et al. 2012
		5 g dry sample + 25 mL DCM / HEX (2:1) 15 minutes Centrifugation: 1500 rpm 5 minutes Concentration and drying with Na₂SO₄			78%	Oketola and Fagbemigun 2013
	Ultrasound + SPE	3 cycles de 30 minutes; 50 °C; MeOH Cartridge: polymeric; Clean-up: H₂O; Elution: MeOH / DCM			≈98%	Ömeroğlu et al. 2015
	PLE	sample + Na₂SO₄ Extractor solvent: ACET / MeOH (1:1 Temperature: 75 ºC and pressure 1500 psi per 5 minutes Concentration of the extract by rotary evaporator Purification: cartridge C18			81%	Petrovic et al. 2003
	ASE	2 cycles de 12 minutes Solvent: MeOH (60% vol extraction cell) Argon purge cycles of 1 minute Purification: Na₂SO₄ + 15 mL MeOH			65% - 84%	Fiedler et al. 2007

Technique	LQ^a e LD^b	Analyhtical Conditions^c	Detection^d	Reference
HPLC	LD = 0.02 µg L^-1 LQ = 0.13 µg L^-1	Column: C18 (250 mm x 4.6 mm i.d , 13 Å) Mobile phase: H₂O/THF (1:1) Flow rate: 1 mL min^-1 Elution: Isocratic Time of analysis: 15 minutes	Fluorescence λexi = 225 nm λemi= 300 nm	Zgoła-Grześkowiak et al. 2009
	LD = 0.018 ng mL^-1	Column: C8 (150 mm x 4.6 mm i.d, 3 µm) Mobile phase: ACN/H₂O (75:25) Flow rate: 1 mL min^-1 Elution: Isocratic Time of analysis: 10 minutes	Fluorescence λexi = 220 nm λemi= 315 nm	Cai et al. 2003
	LD = 0.44 µg L^-1 LQ = 1.47 µg L^-1	Column: C18 Mobile phase: ACN/H₂O (70:30) Flow rate: 1 mL min^-1 Elution: Isocratic Time of analysis: 20 minutes	Fluorescence λexi = 233 nm λemi= 302 nm	Lou et al. 2012
	LQ < 4 µg L^-1	Column: C8 and aminossílica C8 - (250 mm x 4.6 mm i.d, 10 µm, with guard column 30 mm x 4 mm i.d Amino - 100 mm x 4 mm i.d, 3 µm Mobile phase: A/B (45:55) Phase A: isopOH/H₂O/ ACN Phase B: ACN:H₂O (45:55) Flow rate: 1.2 mL min^-1 Elution: gradient Time of analysis: 25 minutes	UV λreverse phase= 225 nm λnormal phase = 277 nm Fluorescence λexi = 230 nm λemi= 295 nm	Marcomini and Giger 1987
	Not available	Column: C18 (250 mm x 4.6 mm i.d, 10 µm) Mobile phase: HEX/THF (8:2) + isopOH/H₂O (9:1) Flow rate: 1.0 mL min^-1 Eluition: gradient	UV λ= 277 nm	Fytianos et al. 1997
	LD = 18 ng L^-1 LQ = 59 ng L^-1	Column: C18 (250 mm x 4.6 mm i.d) Mobile phase: ACN/H₂O (75:25) Flow rate: 0.8 mL min^-1 Elution: gradient Time of analysis: 40 minutes Injection volume: 40 µL	UV= 278 nm	Montagner and Jardim 2011
	LD = 0.03 µg L^-1 LQ = 0.08 µg L^-1	Column: C8 (125 mm x 3 mm i.d, 5 µm) Mobile phase: HEX/2-propOH (98,5:1,5) Flow rate: 0,4 mL min^-1 Elution: Isocratic Time of analysis: 10 minutes	Fluorescence λexi = 228 nm λemi= 305 nm	Ahel et al. 2000
	LD = 1 ng L^-1	Column: C18 (55 mm x 2 mm i.d, 3 µm) Mobile phase: MeOH / H₂O Flow rate: 0.4 mL min^-1 Elution: gradient Time of analysis: 24 minutes Injection volume: 10 µL	MS	Petrovic et al. 2003
	Not available	Column: C18 (250 mm x 4.6 mm i.d, 5 µm) Mobile phase: MeOH/H₂O (75:25) Flow rate: 0.8 mL min^-1 Eluition: Isocratic	UV = 225 nm	Cao et al. 2013
	LQ = 0.1 µg L^-1	Column: C18 (150 mm x 4.6 mm i.d, 5 µm) Mobile phase: MeOH + ACN (1:1) / H₂O Flow rate: 0.8 mL min^-1 Elution: gradient Injection volume: 20 µL Time of analysis: 15 minutes	MS	Jeannot et al. 2002
	Not available	Column: pentafluorfenil Mobile phase: H₂O c/ HCOOH + ACN/THF (1:9) Flow rate: 0.4 mL min^-1 Elution: Gradient Time of analysis: 25 minutes	MS	Ciofi et al. 2014
HPLC	LD = 0.76 µg L^-1	Column: C18 (150 mm x 2.1 mm i.d, 5 µm) Mobile phase: H₂O + MeOH (4:6) Flow rate: 0.3 mL min^-1 Elution: Isocratic Time of analysis: 10 minutes Injection volume: 10 µL	MS	Sun et al. 2013
HPLC	LD = 0.04 ng L^-1 LQ = 0.1 ng L^-1	Column: C18 (30 mm x 2.1 mm i.d, 3,5 µm) Mobile phase: H₂O c/ NH₄OH (1% v/v) + MeOH Flow rate: 0.3 mL min^-1 Elution: gradient Time of analysis: 10 minutes Injection volume: 10 µL	MS	Sodré et al. 2010a
GC	LD = 42 ng L^-1 LQ = 140 ng L^-1	Gas: He Column: ZB-5 Temperature: 100 °C - 320 °C Time of analysis: 20.4 minutes Derivatization: (MSTFA)	MS	Martinez and Peñuela 2013
	LD = 0.01 µg L^-1	Gas: He Column: HP-5MS Temperature: 60 °C - 300 °C Time of analysis: 24 minutes	MS	Azevedo et al. 2001
	LD = 0.8 ng L^-1 LQ = 2.6 ng L^-1	Gas: He Column: ZB-5 Temperature: 100 °C - 300 °C Time of analysis: 25 minutes Derivatization: pyridine + BSTFA	MS	Liu et al. 2004
	LQ = 2 ng L^-1	Gas: He Column: BPX-5 Temperature: 85 ºC - 300 ºC. Derivatization: BSTFA	MS	Jeannot et al. 2002
	LQ = 0.05 µg L^-1	Gas: He Column: HP-5MS Temperature: 90 °C - 300 °C Time of analysis: 35 minutes	MS	Hernández et al. 2007
	LD = 0.05 ng L^-1	Gas: He Column: DB-5MS Temperature: 80 °C - 300 °C Time of analysis: 75 minutes Derivatization: PFBCl	MS	Kuch and Ballschmiter 2001
GC	LD = 10.9 ng L^-1 LQ = 36 ng L^-1	Gas: He Column: TR-5MS Temperature: 60 °C - 320 °C Time of analysis: about 100 minutes	MS	Terzopoulou et al. 2014
	LD = 0.1 µg L^-1	Gas: He Column: DB-5MS Temperature: 70 °C - 285 °C Time of analysis: about 27 minutes Derivatization: DMS + DES + MNNG	MS	Díaz et al. 2002
	LD = 10 ng L^-1	Gas: He Column: DB-5 Temperature: 80 °C - 310 °C Time of analysis: about 50 minutes	MS	Planas et al. 2002
	LD = 2.0 ng L^-1 LQ = 7.0 ng L^-1	Gas: He Column: HP-5 Temperature: 50 °C - 300 °C Time of analysis: about 25 minutes Derivatization: 1) NaHCO3 + NaOH +stirring 2) HEX + HAc anhydrous +stirring	MS	Oketola, Fagbemigun 2013
	LD = 0.11 µg L^-1 LQ = 0.36 µg L^-1	Gas: He Column: DB-5MS Temperature: 80 °C - 300 °C Time of analysis: 38 minutes Derivatization: MTBSTFA + 1% TBDMCS	MS	Sodré et al. 2010b

Technique	LQ^a e LD^b	Analytical Conditions^c	Detection^d	Reference
HPLC	LD = 0.005 mg kg^-1 LQ = 0.01 mg kg^-1	Column: C18 (250 mm x 4.6 mm i.d , 5 µm) Mobile phase: ACN/H₂O Elution: gradient Time of analysis: 40 minutes	Fluorescence λexi = 275 nm λMSi= 300 nm	Bernacka et al. 2009
	Not available	Guard-column: C18 (4 mm x 3 mm i.d, 3.2 µm) Mobile phase: H₂O/MeOH Flow rate: 0.2 mL min^-1 Elution: gradient Time of analysis: 18 minutes	MS	De Sousa Leite et al. 2010
	LD = 30 µg kg^-1	Column: C18 (150 mm x 4,6 mm i.d, 5 µm) Mobile phase: ACN/H₂O Flow rate: 1 mL min^-1 Elution: gradient Time of analysis: 40 minutes	MS	Andreu et al. 2007
	LD = 0.5 µg kg^-1	Column: C18 (55 mm x 2 mm i.d, 3 µm) Mobile phase: MeOH / H₂O Flow rate: 0.4 mL min^-1 Elution: gradient Time of analysis: 24 minutes Injection volume: 10 µL	MS	Petrovic et al. 2003
	LQ = 1 ng g^-1	Column: C18 (150 mm x 4.6 mm i.d, 5 µm) Mobile phase: MeOH + ACN (1:1) / H₂O Flow rate: 0.8 mL min^-1 Elution: gradient Injection volume: 20 µL Time of analysis: 15 minutes	MS	Jeannot et al. 2002
UPLC	LD = 2.2 ng g^-1	Column: C18 (50 mm x 2 mm i.d, 1.8 µm) Mobile phase: ACN/(HCOOH/NH4HCO₂) Flow rate: 0.4 mL min^-1 Elution: gradient Time of analysis: 4 minutes	MS	Lara-Martín et al. 2012
GC	LD = 0.04 µg g^-1 LQ = 0.13 µg g^-1	Gas: He Column: DB5MS Temperature: 80 °C - 280 °C Time of analysis: 22 minutes Derivatization: pyridine + BSTFA	MS	Gatidou et al. 2007
	LQ = 0.1 µg kg^-1	Gas: He Column: HP-5MS Derivatization: anthracene deuterated Temperature: 50 °C - 290 °C Time of analysis: 23 minutes	MS	Fiedler et al. 2007
	LD = 0.3 ng g^-1 LQ = 0.3 ng g^-1	Gas: He Column: HP-5 Temperature: 50 °C - 300 °C Time of analysis: about. 25 minutes Derivatization: 1) NaHCO₃ + NaOH + stirring 2) HEX + HOAc anhydrous + stirring	MS	Oketola, Fagbemigun 2013