Tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane

Tetrakis(trifluoropropyl)tetramethylcyclotetrasiloxane
Identifiers
CAS Number	429-67-4;
3D model (JSmol)	Interactive image;
ChemSpider	61251;
ECHA InfoCard	100.006.420
EC Number	207-060-9;
PubChem CID	67934;
UNII	6UZH4CP48X;
CompTox Dashboard (EPA)	DTXSID7059985 ;
	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/h5-12H2,1-4H3 Key: XOVNCWWRDSAYNE-UHFFFAOYSA-N;
	SMILES C[Si]1(O[Si](O[Si](O[Si](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
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 [77 °F], 100 kPa). Infobox references

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:^[2]

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]

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

^ "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.

[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.

[1]

[2]

[3]

[4]

[5]

[6]