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Ammonium perfluorononanoate

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^[1]
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.

Ammonium salts

Inorganic salts

monatomic anions	NH₄F (NH₄)₂S NH₄Cl (NH₄)₂Se NH₄Br NH₄I
oxyanions	NH₄NO₂ NH₄NO₃ (NH₄)₂CO₃ (NH₄)₄UO₂(CO₃)₂ (NH₄)HCO₃ NH₄H₂AsO₄ NH₄OCN (NH₄)₃PO₄ (NH₄)₂HPO₄ (NH₄)H₂PO₄ (NH₄PO₄)_n(OH)₂ NH₄NaHPO₄ (NH₄)₂SO₃ (NH₄)₂SO₄ (NH₄)Al(SO₄)₂·12H₂O (NH₄)₂Fe(SO₄)₂·6H₂O NH₄Fe(SO₄)₂·12H₂O NH₄SO₃NH₂ (NH₄)HSO₄ (NH₄)₂S₂O₈ (NH₄)₂S₂O₃ NH₄ClO₃ NH₄ClO₄ NH₄VO₃ (NH₄)₂CrO₄ (NH₄)₂Cr₂O₇ NH₄MnO₄ (NH₄)₃AsO₄ NH₄BrO₄ (NH₄)₂MoO₄ (NH₄)₆Mo₇O₂₄ (NH₄)₃Mo₁₂PO₄₀ NH₄IO₃ (NH₄)₂Ce(NO₃)₆ (NH₄)₈Ce₂(SO₄)₈·4H₂O (NH₄)₁₀H₂W₁₂O₄₂·4H₂O NH₄ReO₄
other anions	NH₄BF₄ NH₄N₃ NH₄CN (NH₄)HF₂ (NH₄)₂SeBr₆ (NH₄)₃AlF₆ NH₄SbF₆ NH₄AsF₆ (NH₄)₃CrF₆ (NH₄)₃FeF₆ (NH₄)₃GaF₆ (NH₄)₂GeF₆ (NH₄)₃InF₆ NH₄NbF₆ (NH₄)₂PtF₆ (NH₄)₂ReF₆ (NH₄)₂SnF₆ NH₄TaF₆ (NH₄)₂UF₆ (NH₄)₃VF₆ (NH₄)SiF₆ (NH₄)HS NH₄SCN (NH₄)₂ZnCl₄ (NH₄)₂MoS₄ NH₄I₃ (NH₄)₂PtBr₆ (NH₄)₂SnBr₆ (NH₄)₂TeCl₆ (NH₄)₂IrCl₆ (NH₄)₂OsCl₆ (NH₄)₂PtCl₆ (NH₄)₂ReCl₆ (NH₄)₂PdCl₆ (NH₄)₂PbCl₆ (NH₄)₃RhCl₆ (NH₄)₂SeCl₆ (NH₄)₂SnCl₆ (NH₄)₄[Fe(CN)₆]

Organic salts

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