Chemistry:Tris(trifluoropropyl)trimethylcyclotrisiloxane

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Tris(trifluoropropyl)­trimethylcyclotrisiloxane
D3F structure.svg
Identifiers
3D model (JSmol)
EC Number
  • 219-154-7
Properties
C12H21F9O3Si3
Molar mass 468.538 g·mol−1
Hazards
GHS pictograms GHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H315, H319, H361, H372, H373
P203Script error: No such module "Preview warning".Category:GHS errors, P260, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P280, P302+352, P305+351+338, P318Script error: No such module "Preview warning".Category:GHS errors, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tris(trifluoropropyl)trimethylcyclotrisiloxane (D3F) is a chemical substance. It is a derivative of hexamethylcyclotrisiloxane (D3), but also belongs to the class of per- and polyfluoroalkyl substances (PFASs).

It occurs in two diastereomeric forms:[2]

D3F is used to produce polymethyltrifluoropropylsiloxane (PMTFPS). The starting material is dichloromethyl(3,3,3-trifluoropropyl)silane. Tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane (D4F) is produced as a reaction by-product.[3]

Reaction of dichloromethyl(3,3,3-trifluoropropyl)silane via D3F to form PMTFPS, with D4F as a reaction by-product

It has been detected in wastewater,[4] sewage sludge[5] as well as in biosolid-amended soils.[6]

References

  1. "Cyclotrisiloxane, 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/75410#section=Safety-and-Hazards. 
  2. Zhi, Liqin; Sun, Hongyu; Xu, Lin; Cai, Yaqi (2021-01-19). "Distribution and Elimination of Trifluoropropylmethylsiloxane Oligomers in Both Biosolid-Amended Soils and Earthworms" (in en). Environmental Science & Technology 55 (2): 985–993. doi:10.1021/acs.est.0c05443. ISSN 0013-936X. PMID 33356203. Bibcode2021EnST...55..985Z. https://pubs.acs.org/doi/10.1021/acs.est.0c05443. 
  3. OECD: Synthesis Report on Understanding Side-Chain Fluorinated Polymers and Their Life Cycle, Figure 5.1
  4. Huang, Zichun; Xiang, Xiaoling; Xu, Lin; Cai, Yaqi (2020-10-15). "Phenylmethylsiloxanes and trifluoropropylmethylsiloxanes in municipal sludges from wastewater treatment plants in China: Their distribution, degradation and risk assessment" (in en). Water Research 185: 116224. doi:10.1016/j.watres.2020.116224. ISSN 0043-1354. PMID 32758790. https://www.sciencedirect.com/science/article/pii/S0043135420307612. 
  5. Xiang, Xiaoling; Liu, Nannan; Xu, Lin; Cai, Yaqi (2021-11-01). "Review of recent findings on occurrence and fates of siloxanes in environmental compartments" (in en). Ecotoxicology and Environmental Safety 224: 112631. doi:10.1016/j.ecoenv.2021.112631. ISSN 0147-6513. PMID 34416634. 
  6. Zhi, Liqin; Sun, Hongyu; Xu, Lin; Cai, Yaqi (2021-01-19). "Distribution and Elimination of Trifluoropropylmethylsiloxane Oligomers in Both Biosolid-Amended Soils and Earthworms" (in en). Environmental Science & Technology 55 (2): 985–993. doi:10.1021/acs.est.0c05443. ISSN 0013-936X. PMID 33356203. Bibcode2021EnST...55..985Z. https://pubs.acs.org/doi/10.1021/acs.est.0c05443.