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).
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.006.420 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C₁₆H₂₈F₁₂O₄Si₄ | |
| Molar mass | 624.71 |
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| GHS labelling:[1] | |
 
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| Warning | |
| H302, H312, H315, H319, H332, H335, H410, H413 | |
| 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 [77 °F], 100 kPa).
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It occurs in four diastereomeric forms:[2]
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cis-D4F -
trans-D4F (2R,4r,6S,8s) -
trans-D4F (2R,4R,6S,8S) -
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.[3]
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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
edit- ^ "Cyclotetrasiloxane, 2,4,6,8-tetramethyl-2,4,6,8-tetrakis(3,3,3-trifluoropropyl)-". pubchem.ncbi.nlm.nih.gov.
- ^ 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.
- ^ OECD: Synthesis Report on Understanding Side-Chain Fluorinated Polymers and Their Life Cycle, Figure 5.1
- ^ 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.
- ^ 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.
- ^ 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.