Tris(trifluoropropyl)trimethylcyclotrisiloxane

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).

Tris(trifluoropropyl)­trimethylcyclotrisiloxane
Identifiers
3D model (JSmol)
ECHA InfoCard 100.017.414 Edit this at Wikidata
EC Number
  • 219-154-7
  • InChI=1S/C12H21F9O3Si3/c1-25(7-4-10(13,14)15)22-26(2,8-5-11(16,17)18)24-27(3,23-25)9-6-12(19,20)21/h4-9H2,1-3H3
    Key: URZHQOCYXDNFGN-UHFFFAOYSA-N
  • C[Si]1(O[Si](O[Si](O1)(C)CCC(F)(F)F)(C)CCC(F)(F)F)CCC(F)(F)F
Properties
C12H21F9O3Si3
Molar mass 468.538 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazard
Danger
H315, H319, H361, H372, H373
P203, P260, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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  1. ^ "Cyclotrisiloxane, 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-". pubchem.ncbi.nlm.nih.gov.
  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". Environmental Science & Technology. 55 (2): 985–993. Bibcode:2021EnST...55..985Z. doi:10.1021/acs.est.0c05443. ISSN 0013-936X. PMID 33356203. S2CID 229687934.
  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". Water Research. 185: 116224. Bibcode:2020WatRe.18516224H. doi:10.1016/j.watres.2020.116224. ISSN 0043-1354. PMID 32758790. S2CID 221037569.
  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". Ecotoxicology and Environmental Safety. 224: 112631. Bibcode:2021EcoES.22412631X. 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". Environmental Science & Technology. 55 (2): 985–993. Bibcode:2021EnST...55..985Z. doi:10.1021/acs.est.0c05443. ISSN 0013-936X. PMID 33356203. S2CID 229687934.