Pentadecafluorooctanoic acid

Base Information

• Chemical Name: Pentadecafluorooctanoic acid
• CAS No.: 335-67-1
• Deprecated CAS: 65618-66-8,71244-15-0,71244-15-0
• Molecular Formula: C8HF15O2
• Molecular Weight: 414.071
• Hs Code.: 29159080
• European Community (EC) Number: 206-397-9
• ICSC Number: 1613
• NSC Number: 95114
• UN Number: 3261
• UNII: 947VD76D3L
• DSSTox Substance ID: DTXSID8031865
• Nikkaji Number: J65.650J
• Wikipedia: Fluorosurfactant,Perfluorooctanoic_acid
• Wikidata: Q418348
• Metabolomics Workbench ID: 74805
• ChEMBL ID: CHEMBL172988
• Mol file: 335-67-1.mol

Synonyms:Hexanoyl fluoride, 3,3,4,4,5,5,6,6,6-nonafluoro-2-oxo-;Pentadecafluoro-1-octanoic acid;Perfluorocaprylic acid;

Chemical Property of Pentadecafluorooctanoic acid

Chemical Property:

• Appearance/Colour: white or off-white powder
• Vapor Pressure: 0.155mmHg at 25°C
• Melting Point: 55-56 °C(lit.)
• Refractive Index: 1.387
• Boiling Point: 188 °C at 760 mmHg
• PKA: 0.50±0.10(Predicted)
• Flash Point: 62.1 °C
• PSA: 37.30000
• Density: 1.745 g/cm³
• LogP: 4.44510
• Storage Temp.: 2-8°C
• Solubility.: 3.4g/l
• Water Solubility.: 3.4 g/L
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 6
• Exact Mass: 413.9737017
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

99% ^*data from raw suppliers

PerfluorooctanoicAcid(50μg/mLinMethanol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi, F, T
• Hazard Codes: C,Xi,T,F
• Statements: 22-34-52/53-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: PFAS,Other Classes -> Perfluoroalkyl Acids
• Canonical SMILES: C(=O)(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the liver and immune system. This substance is possibly carcinogenic to humans. May cause toxicity to human reproduction or development.
• Description: Concerns about the potential environmental and toxicological impacts of long-chain perfluoroalkyl sulfonates and carboxylic acids have led to: (1) the phaseout of production of perfluorooctane sulfonate (PFOS) and related compounds and perfluorooctanoic acid (PFOA) by their major global manufacturer in 2000–02; (2) the conclusion of a stewardship agreement between the United States Environmental Protection Agency (US EPA) and eight leading global companies to reduce emissions and product content of PFOA and related chemicals by 95% by 2010 and to work toward their elimination by 2015; (3) a similar agreement between the Canadian environmental and health authorities and five companies to restrict perfluorinated carboxylic acids in products; (4) a European Union Marketing and Use Directive restricting the use of ‘PFOSs’ in the European Union; and (5) the inclusion of PFOS in the Stockholm Convention on Persistent Organic Pollutants as an Annex B substance, i.e., restricted in its use; and other regulatory and voluntary initiatives intended to reduce environmental emissions of this family of compounds.
• Uses: Perfluorooctanoic acid (PFOA) is fluorinated surfactant used, primarily as its ammonium salt (APFO), as an aid in the chemical synthesis of fluoropolymers and fluoroelastomers. As such, it may be found in nonstick cookware and utensils, stain-repellant fabric treatments, and water-proofing treatments for garments. Although an effort is underway by the U.S. EPA to reduce use of and replace perfluoroalkyls with other substances, PFOA is still used in United States industry. Perfluorooctanoic acid (PFOA, C8, pentadecafluorooctanoic acid, perfluoro caprylic acid) is an eightcarbon compound in the perfluoroalkyl family of chemicals. Perfluorooctane sulfonate is used in a variety of applications, including nonstick cookware, waterproof clothing, leather products, cleaning products, and pesticides. Its main use was as a stain repellent on carpet, furniture, and other consumer products. In 2006, the U.S. Protection Agency along with eight major companies that utilized PFOA embarked on a program to reduce emissions and use of the chemical by 2015 (USEPA, 2012). PFOA is a completely fluorinated organic acid that is produced synthetically as its salts. The typical structure has a nonbranched chain of eight carbon atoms. The industrial production of perfluoroalkyl carboxylates started in the late 1940s. Two principal production processes are used to manufacture PFOA, viz. electrochemical fluorination and telomerization. PFOA can also appear as a result of degradation of some precursors, e.g., fluorotelomer alcohols. The ammonium salt of PFOA is primarily used as an emulsifier or ‘processing aid’ in industrial applications, for example, in the production of fluoropolymers such as polytetrafluoroethylene, but also produced for fluorosurfactant use. Typical uses include fluoropolymers in electronics, textiles, and nonstick cookware, and fluorosurfactants in aqueous filmforming foams used for fire fighting. Pentadecafluorooctanoic acid solution may be used as an ion-pairing reagent in the development of a chromatographic method for the separation and determination of underivatized proteinic amino acids using liquid chromatography with evaporative light scattering detection (LC-ELSD) and atmospheric pressure ionization-mass spectrometry (LC-API-MS), respectively.

Technology Process of Pentadecafluorooctanoic acid

There total 42 articles about Pentadecafluorooctanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

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

Guidance literature:

With sulfuric acid; In water; at 60 - 70 ℃; for 0.0333333 - 0.0833333h;

Reference yield: 99.6%

pentadecafluorooctanoyl chloride (335-64-8) → Perfluorooctanoic acid (335-67-1)

Guidance literature:

With water;

Reference yield: 81.0%

1-iodoheptadecafluorooctane (507-63-1) + allyl bromide (106-95-6) → hydroperfluorooctane (335-65-9) + Perfluorooctanoic acid (335-67-1) + 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundec-1-ene (61589-64-8)

Guidance literature:

With potassium hydroxide; 2,2'-azobis(isobutyronitrile); at 80 ℃; for 15h;

DOI:10.1016/S0022-1139(99)00137-2

upstream raw materials:

Octanoic acid

octanoic acid anhydride

perfluoroheptyl iodide

carbon dioxide

Downstream raw materials:

pentadecafluoro-octanoic acid butyl ester

perfluoro-1-heptene

perfluorooctanoyl fluoride

3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononan-2-one

Refernces

• 1、 Xiao, Yelan,Chun, Yuen-Kiu,Cheng, Shun-Cheung,Ng, Chi-On,Tse, Man-Kit,Lei, Ngai-Yu,Liu, Ruoyang,Ko, Chi-Chiu. "Photocatalytic amidation and esterification with perfluoroalkyl iodide". . p. 556 - 562. Retrieved 2021/02/09.
• 2、 -. "Synthetic method of medicine raw material namely 3-methyl perfluorooctanoic acid". Paragraph 0006. . Retrieved 2017/01/19.