335-95-5

Usage

Uses

Used in Pharmaceutical Industry:
SODIUM PERFLUOROOCTANOATE is used as an excipient for enhancing the bioavailability of drugs. Its ability to modify the gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine vesicle membranes allows for improved drug delivery and absorption.
Used in Medical Applications:
In the medical field, SODIUM PERFLUOROOCTANOATE is used as a component in various diagnostic and therapeutic procedures. Its unique properties enable it to act as a contrast agent in imaging techniques, such as ultrasound and magnetic resonance imaging (MRI), providing better visualization of internal structures.
Used in Industrial Applications:
SODIUM PERFLUOROOCTANOATE is utilized in the manufacturing of high-performance fluids, lubricants, and surfactants due to its exceptional chemical and thermal stability. Its resistance to degradation and low surface tension make it an ideal additive for various industrial processes.
Used in Environmental Applications:
Due to its non-stick and water-repellent properties, SODIUM PERFLUOROOCTANOATE is employed in environmental applications, such as soil remediation and water treatment. It can help in the removal of contaminants and improve the efficiency of these processes.

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

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Process for removing fluorinated anionic surfactants from gaseous mixtures

An elimination process of fluorinated anionic sufactants from exhausted gaseous streams, wherein the gaseous stream is put into contact with aqueous solutions having pH in the range from 3.5 to 13.8, the aqueous solution density being lower than 1.05 g/cm3, wherein the concentration in the aqueous solution of the fluorinated anionic surfactant removed by the gaseous stream is lower than or equal to 70 ppm.

Chlorotrifluoroethylene-derived fluids. I. Model compound synthesis

A series of chlorofluoroalkanes having chlorines on adjacent carbon atoms has been prepared, i.e. n-C5F11CFClCCl3, n-C6F13CFClCCl3, n-C5F11CFClCFCl2, n-C6F13CFClCFCl2, n-C5F11CFClCF2Cl, n-C2F5CFClCFClC3F7 and n-CF3CFClCFClC4F9, by a combination of halogen exchange, dehalogenation and chlorine addition reactions.An attempt to synthesize n-C6F13CFClCF2CFCl2 by the coupling of n-C6F13CFClI with an excess of ICF2CFCl2 under UV radiation in the presence of Hg gave only n-C6F13CFClCFClC6F13 together with CFCl2CF2CF2CFCl2.Under parallel conditions from n-C6F13CFClI and CF2ClCFClI, n-C6F13CFClCFClCF2Cl was obtained in 48percent yield.

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.