335-95-5

Basic information

• Product Name: SODIUM PERFLUOROOCTANOATE
• Synonyms: Octanoicacid,pentadecafluoro-,sodiumsalt;Pentadecafluorooctanoicacid,sodiumsalt;pentadecafluoro-octanoicacisodiumsalt;SODIUM PERFLUORO-N-OCTANOATE;SODIUM PERFLUOROOCTANOATE;SODIUM PENTADECAFLUORO OCTANOATE;PERFLUOROOCTANOIC ACID, SODIUM SALT;Sodium perfluoro-n-octanoate 98%
• CAS NO: 335-95-5
• Molecular Formula: C₈F₁₅O₂*Na
• Molecular Weight: 436.05
• EINECS: 206-404-5
• Product Categories: organofluorine compounds
• Mol File: 335-95-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 277-280°C (dec.)
• Boiling Point: 188 °C at 760 mmHg
• Flash Point: 62.1 °C
• Appearance: off-white/Powder
• Density: 1.745 g/cm3
• Water Solubility: Soluble in water.
• CAS DataBase Reference: SODIUM PERFLUOROOCTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: SODIUM PERFLUOROOCTANOATE(335-95-5)
• EPA Substance Registry System: SODIUM PERFLUOROOCTANOATE(335-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: RH0783500
• TSCA: Yes
• Hazardous Substances Data: 335-95-5(Hazardous Substances Data)

Usage

Uses

Sodium perfluorooctanoate on gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine vesicle membrane.

InChI:InChI=1/C8HF15O2.Na/c9-2(10,1(24)25)3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)23;/h(H,24,25);/q;+1/p-1

Synthetic route

Perfluorooctanoic acid (335-67-1) → sodium perfluorooctanoate (335-95-5)

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 66℃; for 10h;	95%
With sodium hydroxide Yield given;
With sodium hydroxide In water pH=6.91 - 10; Purification / work up;

1-perfluorooctyl bromide (423-55-2) → hydroperfluorooctane (335-65-9) + sodium perfluorooctanoate (335-95-5)

Conditions	Yield
With rongalite; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 85℃; for 20h;	A n/a B 86%

1-iodoheptadecafluorooctane (507-63-1) → hydroperfluorooctane (335-65-9) + sodium perfluorooctanoate (335-95-5)

Conditions	Yield
With rongalite; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 85℃; for 31h;	A n/a B 70%

bis(pentadecafluoro-octanoyl) peroxide (34434-27-0) + sodium 2-nitropropane (24163-39-1) → sodium perfluorooctanoate (335-95-5) + C10H6F15N2O3 + C14F30NO + acetone (67-64-1)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;

bis(pentadecafluoro-octanoyl) peroxide (34434-27-0) + 2-nitro-butane; sodium salt → sodium perfluorooctanoate (335-95-5) + C11H8F15N2O3 + C14F30NO + butanone (78-93-3)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;

bis(pentadecafluoro-octanoyl) peroxide (34434-27-0) + C5H8NO2(1-)*Na(1+) → sodium perfluorooctanoate (335-95-5) + cyclopentanone (120-92-3) + C12H8F15N2O3 + C14F30NO

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;

bis(pentadecafluoro-octanoyl) peroxide (34434-27-0) + C6H10NO4(1-)*Na(1+) → levulinic acid methyl ester (624-45-3) + sodium perfluorooctanoate (335-95-5) + C13H10F15N2O5 + C14F30NO

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;

bis(pentadecafluoro-octanoyl) peroxide (34434-27-0) → sodium perfluorooctanoate (335-95-5) + C10H6F15N2O3 + C14F30NO

Conditions	Yield
With lithium 2-nitropropane In 1,1,2-Trichloro-1,2,2-trifluoroethane at 20℃;

1-iodoheptadecafluorooctane (507-63-1) → sodium perfluorooctanoate (335-95-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 1.) 145 - 150 deg C, 20 h, 2.) reflux, 4 h 2: 10percent NaOH / 1.) rt, 2.) 40 deg C, 3 - 4 h 3: 2N NaOH View Scheme

methyl perfluorooctanoate (376-27-2) → sodium perfluorooctanoate (335-95-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 10percent NaOH / 1.) rt, 2.) 40 deg C, 3 - 4 h 2: 2N NaOH View Scheme

ammonium salt of perfluorooctanoic acid (3825-26-1) → sodium perfluorooctanoate (335-95-5)

Conditions	Yield
Stage #1: ammonium salt of perfluorooctanoic acid In water at 23 - 28℃; for 24h; Stage #2: With sodium hydroxide In water at 80 - 85℃; for 0.5h; Product distribution / selectivity;

sodium perfluorooctanoate (335-95-5) → Perfluorooctanoic acid (335-67-1)

Conditions	Yield
With sulfuric acid In water at 60 - 70℃; for 0.0333333 - 0.0833333h;	99.9%
With sulfuric acid at 120℃;	84%

sodium perfluorooctanoate (335-95-5) → perfluoro-1-heptene (355-63-5)

Conditions	Yield
Heating;	95%
at 300℃;	81.3%
at 280 - 320℃; under 0.01 Torr;

sodium perfluorooctanoate (335-95-5) + octyltrimethylammonium bromide (2083-68-3) → octyltrimethylammonium perfluorooctanoate

Conditions	Yield
In dichloromethane; water at 20℃; for 2h;	91%

2,2-dimethyl-1,1,3,3-tetraallylguanidin-2-ium chloride (1008430-60-1) + sodium perfluorooctanoate (335-95-5) → C8F15O2(1-)*C15H26N3(1+) (1257408-67-5)

Conditions	Yield
In methanol at 20℃; for 56h;	88%

dichlorodimethoxysilane (18544-45-1) + sodium perfluorooctanoate (335-95-5) → dimethoxysilanediyl bis(pentadecafluorooctanoate) (137348-81-3)

Conditions	Yield
In various solvent(s)	82.8%

sodium perfluorooctanoate (335-95-5) → 1-Chloroperfluoroheptane (375-89-3) + 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl fluoride (375-84-8)

Conditions	Yield
With ClSO3F for 48h; Ambient temperature;	A 78% B 18%

titanium butoxide trichloride (3112-68-3) + sodium perfluorooctanoate (335-95-5) → titanium butoxide tris(perfluorooctanoate)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane byproducts: NaCl; mixt. refluxed with stirring for 100 h at room temp., under N2; filtered, evapd. under vac.; elem. anal.;	59.7%

sodium perfluorooctanoate (335-95-5) → perfluorooctanoyl fluoride (335-66-0)

Conditions	Yield
With sulfur tetrafluoride In diethylene glycol dimethyl ether for 1h; Heating;	55%

sodium perfluorooctanoate (335-95-5) → pentadecafluorooctanoyl chloride (335-64-8)

Conditions	Yield
With Phthaloyl dichloride

sodium perfluorooctanoate (335-95-5) + mono-4-methoxytrityl chloride (14470-28-1) → 4-methoxytriphenylmethyl pentadecafluorooctanoate

Conditions	Yield
In tetrachloromethane for 576h;

sodium perfluorooctanoate (335-95-5) → CO2, H2O

Conditions	Yield
With cerium(IV) oxide; copper at 1000℃; Product distribution;

sodium perfluorooctanoate (335-95-5) → 3β-(perfluoro-trans-1-heptenyl-1-oxy)-5α-cholestan

Conditions	Yield
Multi-step reaction with 2 steps 1: 81.3 percent / 300 °C 2: 1) n-BuLi / 1) THF, hexane, 0 deg C, 20 min; RT, 3 h; 2) THF, hexane, RT, 12 h View Scheme

sodium perfluorooctanoate (335-95-5) → 3β-(perfluoro-trans-1-heptenyl-1-oxy)-pregn-5-ene-20-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 81.3 percent / 300 °C 2: 1) n-BuLi / 1) THF, hexane, 0 deg C, 30 min; RT, 45 min; 2) THF, hexane, RT, 1 h View Scheme

sodium perfluorooctanoate (335-95-5) → N-(2-cyanophenyl)F-octanamide

Conditions	Yield
Multi-step reaction with 2 steps 1: phthaloyl chloride 2: 68 percent / pyridine View Scheme

sodium perfluorooctanoate (335-95-5) → 2-Pentadecafluoroheptyl-3H-quinazolin-4-one

Conditions	Yield
Multi-step reaction with 3 steps 1: phthaloyl chloride 2: 68 percent / pyridine 3: 30.6 percent / NaOH, H2O2 / H2O; dioxane; ethyl acetate / 16 h / 100 °C View Scheme

sodium perfluorooctanoate (335-95-5) → carbamoyl-2' pentadecafluorooctananilide

Conditions	Yield
Multi-step reaction with 2 steps 1: phthaloyl chloride 2: 75 percent / pyridine / 1 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: phthaloyl chloride 2: 68 percent / pyridine 3: 22 percent / NaOH, H2O2 / H2O; dioxane; ethyl acetate / 16 h / 100 °C View Scheme

sodium perfluorooctanoate (335-95-5) → perfluoro-2-heptene, trans isomer (24010-46-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / Heating 2: 22 percent Spectr. / CsF / dimethylformamide / 18 h / Ambient temperature View Scheme

Upstream product

• 3825-26-1 ammonium salt of perfluorooctanoic acid 
• 376-27-2 methyl perfluorooctanoate 
• 507-63-1 1-iodoheptadecafluorooctane 
• 34434-27-0 bis(pentadecafluoro-octanoyl) peroxide 
• 91113-96-1 2-nitro-butane; sodium salt 
• 24163-39-1 sodium 2-nitropropane 
• 423-55-2 1-perfluorooctyl bromide 
• 335-67-1 Perfluorooctanoic acid 

Downstream Products

• 134948-34-8 Sodium perfluorooctanoxyacetate 
• 134918-66-4 Potassium perfluorooctanoxyacetate 
• 335-66-0 perfluorooctanoyl fluoride 
• 335-67-1 Perfluorooctanoic acid 
• 335-64-8 pentadecafluorooctanoyl chloride 
• 355-63-5 perfluoro-1-heptene 
• 375-89-3 1-Chloroperfluoroheptane 
• 375-84-8 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl fluoride 

Relevant articles and documents

Method for regenerating basic anion-exchange resin

A simple and efficient method for regenerating a basic anion-exchange resin, whereby at the time of removing a fluorinated emulsifier from a basic anion-exchange resin having the fluorinated emulsifier adsorbed thereon, it is unnecessary to provide a safety device/recovery technique necessary for handling an organic solvent by the use of a combustible organic solvent represented by an alcohol, and a burden imposed by e.g. treatment against COD load, is eliminated. A basic anion-exchange resin having a fluorinated emulsifier adsorbed thereon is contacted with an aqueous alkaline solution having a temperature of from 60 to 105° C. to elute the fluorinated emulsifier thereby to regenerate the basic anion-exchange resin.

Synthesis of Anionic Surfactants Having Two Polyfluoroalkyl Chains and Their Flocculation Ability for Dispersed Magnetite Particles in Water

Four anionic surfactants having two polyfluoroalkyl chains in a molecule, sodium salt of bis(1H,1H,2H,2H-heptadecafluorodecyl) 2-sulfosuccinate, CF3(CF2)7(CH2)2OCOCH2CH(SO3Na)COO(CH2)2(CF2)7CF3, sodium salt of bis(1H,1H,9H-hexadecafluorononyl) 2-sulfosuccinate, H(CF2)8CH2OCOCH2CH(SO3Na)COOCH2(CF2)8H, sodium salt of bis(1H,1H,7H-dodecafluoroheptyl) 2-sulfosuccinate, H(CF2)6CH2OCOCH2CH(SO3Na)COOCH2(CF2)6H and sodium salt of bis(1H,1H,5H-octafluoropentyl) 2-sulfosuccinate, H(CF2)4CH2OCOCH2CH(SO3Na)COOCH2(CF2)4H, were prepared from maleic anhydride, the corresponding alcohols having a polyfluoroalkyl chain and sodium hydrogensulfite.The flocculation and redispersion abilities of these surfactants against dispersed magnetite particles in water have been examined in comparison with other four anionic surfactants having a single polyfluoroalkyl chain in a molecule; sodium pentadecafluorooctanoate, CF3(CF2)6COONa, sodium 9H-hexadecafluorononanoate, H(CF2)8COONa, sodium 7H-dodecafluoroheptanoate, H(CF2)6COONa, and sodium 5H-octafluoropentanoate, H(CF2)4COONa.These abilities were estimated by measurement of the contact angle against water using pelleted surface-modified magnetite.The abilities of the surfactants having two polyfluoroalkyl chains against flocculation-redispersion were superior to those of the surfactants having one polyfluoroalkyl chain.Especially, sodium salt of bis(1H,1H,2H,2H-heptadecafluorodecyl) 2-sulfosuccinate was the most effective surface active agent for these abilities.

A NEW METHOD FOR THE PREPARATION OF PERFLUOROCARBOXYLIC ACIDS

The reaction of both primary perfluoroalkyl iodides and bromides containing 3-12 carbon atoms with a rongalite-NaHCO3 reagent in aqueous dipolar aprotic solvents, such as DMF or DMSO, has been investigated.The reaction gave sodium perfluorocarboxylates in 51-86percent yields, and these were transformed to the respective perfluorocarboxylic acids by treatment with sulfuric acid.This provides a new method for the synthesis of perfluorocarboxylic acids.