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Ammonium perfluorononanoate
Names
	IUPAC name Heptadecafluorononanoic acid ammoniate (1:1)
Identifiers
CAS Number	4149-60-4;
3D model (JSmol)	Interactive image;
ChemSpider	69647;
ECHA InfoCard	100.242.185
PubChem CID	160734;
CompTox Dashboard (EPA)	DTXSID20880205 ;
	InChI InChI=1S/C9HF17O2.H3N/c10-2(11,1(27)28)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)9(24,25)26;/h(H,27,28);1H3 Key: ORBBVPFDROYXQS-UHFFFAOYSA-N; InChI=1/C9HF17O2.H3N/c10-2(11,1(27)28)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)9(24,25)26;/h(H,27,28);1H3 Key: ORBBVPFDROYXQS-UHFFFAOYAU;
	SMILES FC(F)(C(F)(F)C(=O)O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.N;
Properties
Chemical formula	C9H4F17NO2
Molar mass	481.106
Density	1.753 g/mL
Boiling point	196 °C (385 °F; 469 K)
	Surface tension:
CMC	~8.0 mmol/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ammonium perfluorononanoate (APFN) is an anionic surfactant that in water forms liquid crystalline phases (Lyotropic liquid crystal). It is the ammonium salt of perfluorononanoic acid.

The phase diagram of APFN/H₂O system is delineated by the presence of a lamellar phase and a nematic phase with awide isotropic solution. The nematic phase is of the type I, and the aggregates have a positive and diamagnetic anisotropy. In the presence of a magnetic field, the aggregates align parallel to the field direction. The change of phase at the lamellar-nematic temperature has been ascribed to order-disorder transitions.

MLV Formation

It has recently been shown that the lamellar phase of the APFN/2H₂O system form multilamellar vesicles under shear rate.^[2]

Restrictions

In 2020, a California bill was passed banning APFN as an intentionally added ingredient from cosmetics.^[3]

References

^ Ivanchev, S. S.; Likhomanov, V. S.; Primachenko, O. N.; Khaikin, S. Ya.; Barabanov, V. G.; Kornilov, V. V.; Odinokov, A. S.; Kulvelis, Yu. V.; Lebedev, V. T.; Trunov, V. A. (2012). "Scientific principles of a new process for manufacturing perfluorinated polymer electrolytes for fuel cells". Petroleum Chemistry. 52 (7): 453–461. doi:10.1134/S0965544112070067. ISSN 0965-5441. S2CID 95976747.
^ Coppola, Luigi; Gentile, Luigi; Nicotera, Isabella; Rossi, Cesare Oliviero; Ranieri, Giuseppe Antonio (2010). "Evidence of Formation of Ammonium Perfluorononanoate/²H₂O Multilamellar Vesicles: Morphological Analysis by Rheology and Rheo-²H NMR Experiments". Langmuir. 26 (24): 19060–5. doi:10.1021/la102887e. PMID 21073179.
^ "Assembly Bill No. 2762". State of California. September 30, 2020. Retrieved 10 October 2020.

[IvanchevLikhomanov2012-1] Ivanchev, S. S.; Likhomanov, V. S.; Primachenko, O. N.; Khaikin, S. Ya.; Barabanov, V. G.; Kornilov, V. V.; Odinokov, A. S.; Kulvelis, Yu. V.; Lebedev, V. T.; Trunov, V. A. (2012). "Scientific principles of a new process for manufacturing perfluorinated polymer electrolytes for fuel cells". Petroleum Chemistry. 52 (7): 453–461. doi:10.1134/S0965544112070067. ISSN 0965-5441. S2CID 95976747.

[2] Coppola, Luigi; Gentile, Luigi; Nicotera, Isabella; Rossi, Cesare Oliviero; Ranieri, Giuseppe Antonio (2010). "Evidence of Formation of Ammonium Perfluorononanoate/²H₂O Multilamellar Vesicles: Morphological Analysis by Rheology and Rheo-²H NMR Experiments". Langmuir. 26 (24): 19060–5. doi:10.1021/la102887e. PMID 21073179.

[3] "Assembly Bill No. 2762". State of California. September 30, 2020. Retrieved 10 October 2020.

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