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Tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane

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Tetrakis(trifluoropropyl)­tetramethylcyclotetrasiloxane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.420 Edit this at Wikidata
EC Number
  • 207-060-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H28F12O4Si4/c1-33(9-5-13(17,18)19)29-34(2,10-6-14(20,21)22)31-36(4,12-8-16(26,27)28)32-35(3,30-33)11-7-15(23,24)25/h5-12H2,1-4H3Key: XOVNCWWRDSAYNE-UHFFFAOYSA-N
SMILES
  • C1(O(O(O(O1)(C)CCC(F)(F)F)(C)CCC(F)(F)F)(C)CCC(F)(F)F)CCC(F)(F)F
Properties
Chemical formula C₁₆H₂₈F₁₂O₄Si₄
Molar mass 624.71
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H312, H315, H319, H332, H335, H410, H413
Precautionary statements P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane (D4F) is a chemical substance. It is a derivative of octamethylcyclotetrasiloxane (D4), but also belongs to the class of per- and polyfluoroalkyl substances (PFASs).

It occurs in four diastereomeric forms:

  • cis-D4F cis-D4F
  • trans-D4F (2R,4r,6S,8s) trans-D4F (2R,4r,6S,8s)
  • trans-D4F (2R,4R,6S,8S) trans-D4F (2R,4R,6S,8S)
  • trans-D4F (2r,4r,6r,8r) trans-D4F (2r,4r,6r,8r)

D4F is formed as a reaction by-product in the synthesis of polymethyltrifluoropropylsiloxane (PMTFPS). The starting material is dichloromethyl(3,3,3-trifluoropropyl)silane and tris(trifluoropropyl)trimethylcyclotrisiloxane (D3F) is an intermediate.

  • Reaction of dichloromethyl(3,3,3-trifluoropropyl)silane via D3F to form PMTFPS, with D4F as a reaction by-product 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, sewage sludge as well as in biosolid-amended soils.

References

  1. "Cyclotetrasiloxane, 2,4,6,8-tetramethyl-2,4,6,8-tetrakis(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. 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. 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. doi:10.1016/j.ecoenv.2021.112631. 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. PMID 33356203. S2CID 229687934.
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