Synthesis of technically useful perfluorocarboxylic acids

Wróblewska, Agnieszka; Meissner, Egbert; Milchert, Eugeniusz

doi:10.1016/j.jfluchem.2005.12.026

Cited by 3 publications

(5 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of iso -perfluoroalkyl telomer iodides and fluorotelomer olefins with 5, 7, 9, and 11 perfluorinated carbons was described by Wroblewska et al Also a Daikin patent described the production and use of isopropyl branched C 5 –C 16 PFCAs, synthesized from the corresponding isopropyl telogens . Isopropyl branched perfluorinated acids were better at reducing surface tension of the aqueous medium than its respective linear isomer .…”

Section: Resultsmentioning

confidence: 99%

Isomer Profiles of Perfluoroalkyl Substances in Water and Soil Surrounding a Chinese Fluorochemical Manufacturing Park

Jin

Zhang

Zhu

et al. 2015

Environ. Sci. Technol.

125

View full text Add to dashboard Cite

Despite that China is the largest global manufacturer of perfluoroalkyl substances (PFASs), the manufacturing methods and isomer purity of these chemicals are generally unknown. Here, sampling was conducted around a major fluorochemical manufacturing park in China in 2012, including soil and water collection inside the park, including from a wastewater treatment plant (WWTP), as well as in surrounding rivers and soil (∼15 km radius). Perfluoroalkyl sulfonates (PFSAs) were lower than perfluoroalkyl carboxylates (PFCAs) in all samples, and short-chain (C4-C6) PFCAs were predominant. Perfluoroalkyl phosphonates and phosphate diesters were occasionally detected, but at low detection frequency. Branched isomers of perfluorobutanesulfonate (PFBS) are reported for the first time, accounting for 15-27% of total PFBS in water. An enrichment of isopropyl-PFOA (28%) was found in WWTP influent, suggesting its manufacturing primarily by isopropyl telomerization. More numerous branched isomers were observed for the longer C9-C13 PFCAs (e.g., C12 PFCA had 16 branched isomers), including high proportions of one major branched isomer (likely isopropyl), possibly as impurities from isopropyl-PFOA manufacturing. Overall, short-chain perfluorinated acids were the predominant PFASs being released, but PFOA was still a major chemical in use at this site, primarily from isopropyl telomerization.

show abstract

Section: Resultsmentioning

confidence: 99%

Isomer Profiles of Perfluoroalkyl Substances in Water and Soil Surrounding a Chinese Fluorochemical Manufacturing Park

Jin

Zhang

Zhu

et al. 2015

Environ. Sci. Technol.

125

View full text Add to dashboard Cite

show abstract

“…Perfluorooctanoate appeared to bioaccumulate in dolphins from Charleston in a study by Houde et al [46] in which n ‐PFCAs were measured in water, sediment, and fish of that area. In that study, effluent from wastewater treatment plants in Charleston contained high concentrations of PFCAs and were postulated to be a significant source [47]. This may account for the similarity in PFOA and PFNA isomer profiles in humans and dolphins.…”

Section: Discussionmentioning

confidence: 99%

“…Perfluoroalkyl iodides are unstable and considered intermediates for further syntheses. Preparation of iso ‐perfluoroalkyl telomer iodides and fluorotelomer olefins with 5, 7, 9, and 11 perfluorinated carbons was recently described by Wroblewska et al [47]. According to patent literature, these compounds may be further reacted to form isopropyl fluoro‐acrylate monomers for polymer synthesis used as antisoiling in textile treatments, batteries, optical recording disks, and so on and, in one case, in perfluorinated acids in firefighting formulas (references in Supporting Information; ).…”

Section: Discussionmentioning

confidence: 99%

Distribution of perfluorocarboxylate isomers in select samples from the north american environment

Silva

Muir

Mabury

2009

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

Perfluorinated acids are anthropogenic pollutants with primarily two industrial synthetic routes: electrochemical fluorination (ECF) and telomerization. A mixture of structural isomers is produced by ECF, while telomerization conserves the geometry of its starting materials, which are typically linear. To contribute to a discussion on sources of perfluorinated acid pollution, isomer profiles of perfluorinated carboxylates (PFCAs) were determined in a diverse set of environmental and biotic samples from remote to urban locations. Analysis was conducted on the derivatized extracts using gas chromatography/mass spectrometry. The perfluorooctanoate (PFOA) isomer profile in most samples contained linear and branched isomers congruent with an ECF input, but linear PFOA (n-PFOA) predominated (>90%) greater than in the ECF technical product (78%). The perfluorononanoate (PFNA) isomer pattern varied from only n-PFNA, n- and iso-PFNA (isopropyl isomer), or n-PFNA and multiple branched isomers. At midlatitudes, PFNA isomer profiles containing multiple branched isomers are attributed to ECF sources such as impurities in ECF PFOA. In surface water from Lake Ontario (Canada) and an Arctic lake, only n- and iso-PFNA were observed. Human and dolphin blood contained multiple branched PFNA, consistent with an ECF signature albeit n-isomer enriched. Both n- and isopropyl isomers of longer-chain PFCAs were observed with a distinct pattern for dolphin and Arctic samples compared to those from the Lake Ontario ecosystem. These results support the hypothesis that long-range atmospheric transport of linear volatile precursors, subsequent degradation, and deposition contribute to the presence of n-PFCAs in the Arctic freshwater environment. The presence of longer-chain isopropyl isomers may be preliminary evidence of isopropyl fluorinated organic precursors.

show abstract

“…Catalytic hydroxylation of phenol is an industrially important reaction as the products catechol and hydroquinone have several important applications such as medicines (contraceptives, urinary tract medicinal preparation, acne treating prepara-tions, antidepressants, and anorexia medicinal preparation), cosmetics, pesticides, perfumes and polymer industry (bearings, heat-resistant cable insulations, films and plates for electrical circuit boards) [21,22] . Industrial scale phenol hydroxylation process is carried out at 373 K in presence of large amounts of methanol (30 wt.%) using TS-1 catalyst.…”

Section: Introductionmentioning

confidence: 99%

“…Industrial scale phenol hydroxylation process is carried out at 373 K in presence of large amounts of methanol (30 wt.%) using TS-1 catalyst. The molar ratio of hydroquinone and catechol products is 1 : 1 with a phenol conversion of 25-30 mol % [21,23,24] . The major disadvantage with TS-1 catalyst is leaching of titanium from the framework during hydroxylation and the same is also reported with other catalysts such as TS-2, Ti-MCM-41 [25,26] .…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid Templated Ordered Hexagonal Mesoporous Iron Phosphate Molecular Sieves: A Highly Effective Heterogeneous Catalysts with Remarkable Selectivity for Phenol Hydroxylation Reaction

Kumar

Selvam

2023

Chemistry An Asian Journal

View full text Add to dashboard Cite

A highly organized hexagonal mesoporous iron phosphate framework structure with the designation HMI-41 was successfully synthesized for the first-time in a reproducible way using imidazolium-based ionic liquid as structure directing agent. The unique templating properties of ionic liquid generated a highly ordered well-crystallized mesoporous matrix having high surface area (445 m 2 g À 1 ), thicker pore wall (2.1 nm) and narrow pore size distribution (3.1 nm).The presence of active sites within a tetrahedral framework structure made the novel HMI-41 catalyst highly effective for phenol hydroxylation in an acidic medium with hydrogen peroxide as the oxidant. The catalyst exhibited outstanding performance, achieving an impressive 80% hydroquinone selectivity and 21% phenol conversion with a hydroquinoneto-catechol ratio of seven, which is the highest value ever reported.

show abstract

Synthesis of technically useful perfluorocarboxylic acids

Cited by 3 publications

References 9 publications

Isomer Profiles of Perfluoroalkyl Substances in Water and Soil Surrounding a Chinese Fluorochemical Manufacturing Park

Isomer Profiles of Perfluoroalkyl Substances in Water and Soil Surrounding a Chinese Fluorochemical Manufacturing Park

Distribution of perfluorocarboxylate isomers in select samples from the north american environment

Ionic Liquid Templated Ordered Hexagonal Mesoporous Iron Phosphate Molecular Sieves: A Highly Effective Heterogeneous Catalysts with Remarkable Selectivity for Phenol Hydroxylation Reaction

Contact Info

Product

Resources

About