Decamethylcyclopentasiloxane

Last updated
Decamethylcyclopentasiloxane
Decamethylcyclopentasiloxane-2D.png
Decamethylcyclopentasiloxane-from-xtal-3D-bs-17-grey.png
Ball-and-stick model of the molecule as found in the crystal structure determined by single-crystal X-ray diffraction [1]
Dekametilsiklopentasiloksan.png
Sample of decamethylcyclopentasiloxane
Names
Preferred IUPAC name
Decamethyl-1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane
Other names
  • Cyclopentamethicone
  • Cyclic dimethylsiloxane pentamer
  • D5
  • D5
  • 2,2,4,4,6,6,8,8,10,10-Decamethylcyclopentasiloxane
Identifiers
3D model (JSmol)
1800166
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.969 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-764-9
MeSH Decamethylcyclopentasiloxane
PubChem CID
RTECS number
  • GY5945200
UNII
  • InChI=1S/C10H30O5Si5/c1-16(2)11-17(3,4)13-19(7,8)15-20(9,10)14-18(5,6)12-16/h1-10H3 Yes check.svgY
    Key: XMSXQFUHVRWGNA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H30O5Si5/c1-16(2)11-17(3,4)13-19(7,8)15-20(9,10)14-18(5,6)12-16/h1-10H3
    Key: XMSXQFUHVRWGNA-UHFFFAOYAC
  • C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1
  • O1[Si](O[Si](O[Si](O[Si](O[Si]1(C)C)(C)C)(C)C)(C)C)(C)C
Properties
[(CH3)2SiO]5
Molar mass 370.770 g·mol−1
AppearanceColourless liquid
Density 0.958 g/cm3
Melting point −47 °C; −53 °F; 226 K
Boiling point 210 °C (410 °F; 483 K)
17.03±0.72 ppb (23 °C) [2]
log P 8.07 [3]
Vapor pressure 20.4±1.1 Pa (25 °C) [4]
Viscosity 3.74 cP
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg
Warning
H226, H361, H412, H413
P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 73 °C (163 °F; 346 K)
Safety data sheet (SDS) External MSDS
Related compounds
Octamethylcyclotetrasiloxane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Decamethylcyclopentasiloxane, also known as D5 and D5, is an organosilicon compound with the formula [(CH3)2SiO]5. It is a colorless and odorless liquid that is slightly volatile. [5]

Contents

Use

The compound is classified as a cyclomethicone. Such fluids are commonly used in cosmetics, such as deodorants, sunblocks, hair sprays and skin care products. It is becoming more common in hair conditioners, as it makes the hair easier to brush without breakage. It is also used as part of silicone-based personal lubricants. D5 is considered an emollient. In Canada, among the volume used in consumer products approximately 70% were for antiperspirants and 20% for hair care products. [6] 10,000–100,000 tonnes per year of D5 is manufactured and/or imported in the European Economic Area. [7] Atmospheric emissions of D5 in the Northern Hemisphere were estimated to 30,000 tonnes per year. [8]

Decamethylcyclopentasiloxane has also been tried as a dry-cleaning solvent in the early 2000s. It was marketed as a more environmentally friendly solvent than tetrachloroethylene (the most common dry-cleaning solvent worldwide) despite being controlled in the EU for to its persistent, bioaccumulative and toxic characteristics. [9]

Production and polymerization

Commercially D5 is produced from dimethyldichlorosilane. Hydrolysis of the dichloride produces a mixture of cyclic dimethylsiloxanes and polydimethylsiloxane. From this mixture, the cyclic siloxanes including D5 can be removed by distillation. In the presence of a strong base such as KOH, the polymer/ring mixture is equilibrated, allowing complete conversion to the more volatile cyclic siloxanes: [10]

[(CH3)2SiO]5nn[(CH3)2SiO]5

where n is a positive integer. D4 and D5 are also precursors to the polymer. The catalyst is again KOH.

Safety and environmental considerations

D5 is nontoxic with an LD50 of >50 g/kg for rats. [10]

The environmental impacts of D5 and D4 have attracted attention because these compounds are pervasive. Cyclic siloxanes have been detected in some species of aquatic life. [11] A scientific review in Canada has determined that “Siloxane D5 does not pose a danger to the environment” [12] and a scientific assessment of D5 by the Australian government stated, "the direct risks to aquatic life from exposure to these chemicals at expected surface water concentrations are not likely to be significant." [13] However, in the European Union, D5 was characterized as a substance of very high concern (SVHC) due to its PBT and vPvB properties and was thus included in the candidate list for authorisation. [14] Since 31 January 2020, D5 cannot be placed on the market in the European Union in wash-off cosmetic products in a concentration equal to or greater than 0.1 % by weight. [15]

See also

Related Research Articles

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In organosilicon and polymer chemistry, a silicone or polysiloxane is a polymer composed of repeating units of siloxane. They are typically colorless oils or rubber-like substances. Silicones are used in sealants, adhesives, lubricants, medicine, cooking utensils, thermal insulation, and electrical insulation. Some common forms include silicone oil, grease, rubber, resin, and caulk.

<span class="mw-page-title-main">Dry cleaning</span> Cleaning of fabrics in non-aqueous solvents

Dry cleaning is any cleaning process for clothing and textiles using a solvent other than water.

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<span class="mw-page-title-main">Polydimethylsiloxane</span> Chemical compound

Polydimethylsiloxane (PDMS), also known as dimethylpolysiloxane or dimethicone, is a silicone polymer with a wide variety of uses, from cosmetics to industrial lubrication.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

<span class="mw-page-title-main">Siloxane</span> Organic functional group (Si–O–Si)

In organosilicon chemistry, a siloxane is an organic compound containing a functional group of two silicon atoms bound to an oxygen atom: Si−O−Si. The parent siloxanes include the oligomeric and polymeric hydrides with the formulae H[OSiH2]nOH and [OSiH2]n. Siloxanes also include branched compounds, the defining feature of which is that each pair of silicon centres is separated by one oxygen atom. The siloxane functional group forms the backbone of silicones [−R2Si−O−SiR2−]n, the premier example of which is polydimethylsiloxane (PDMS). The functional group R3SiO− is called siloxy. Siloxanes are manmade and have many commercial and industrial applications because of the compounds’ hydrophobicity, low thermal conductivity, and high flexibility.

<span class="mw-page-title-main">2-Butoxyethanol</span> Chemical compound

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Silicone rubber is an elastomer composed of silicone—itself a polymer—containing silicon together with carbon, hydrogen, and oxygen. Silicone rubbers are widely used in industry, and there are multiple formulations. Silicone rubbers are often one- or two-part polymers, and may contain fillers to improve properties or reduce cost. Silicone rubber is generally non-reactive, stable, and resistant to extreme environments and temperatures from −55 to 300 °C while still maintaining its useful properties. Due to these properties and its ease of manufacturing and shaping, silicone rubber can be found in a wide variety of products, including voltage line insulators; automotive applications; cooking, baking, and food storage products; apparel such as undergarments, sportswear, and footwear; electronics; medical devices and implants; and in home repair and hardware, in products such as silicone sealants.

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Hexamethyldisiloxane (HMDSO or MM) is an organosilicon compound with the formula O[Si(CH3)3]2. This volatile colourless liquid is used as a solvent and as a reagent in organic synthesis. It is prepared by the hydrolysis of trimethylsilyl chloride. The molecule is the protypical disiloxane and resembles a subunit of polydimethylsiloxane.

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<span class="mw-page-title-main">Octamethylcyclotetrasiloxane</span> Chemical compound

Octamethylcyclotetrasiloxane, also called D4, is an organosilicon compound with the formula [(CH3)2SiO]4. It is a colorless viscous liquid. It is a common cyclomethicone. It is widely used in cosmetics.

<span class="mw-page-title-main">Hexamethylcyclotrisiloxane</span> Chemical compound

Hexamethylcyclotrisiloxane, also known as D3 and D3, is the organosilicon compound with the formula [(CH3)2SiO]3. It is a colorless or white volatile solid. It finds limited use in organic chemistry. The larger tetrameric and pentameric siloxanes, respectively octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane, are of significant industrial interest, whereas 1,000–10,000 tonnes per year of the trimer is manufactured and/or imported in the European Economic Area.

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References

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  2. Sudarsanan Varaprath; Cecil L. Frye; Jerry Hamelink (1996). "Aqueous solubility of permethylsiloxanes (silicones)". Environmental Toxicology and Chemistry . 15 (8): 1263–1265. doi:10.1002/etc.5620150803.
  3. Shihe Xu, Bruce Kropscott (2012). "Method for Simultaneous Determination of Partition Coefficients for Cyclic Volatile Methylsiloxanes and Dimethylsilanediol". Analytical Chemistry. 84 (4): 1948–1955. doi:10.1021/ac202953t. PMID   22304371.
  4. Ying Duan Lei; Frank Wania; Dan Mathers (2010). "Temperature-Dependent Vapor Pressure of Selected Cyclic and Linear Polydimethylsiloxane Oligomers". Journal of Chemical & Engineering Data . 55 (12): 5868–5873. doi:10.1021/je100835n.
  5. Record of Decamethylcyclopentasiloxan in the GESTIS Substance Database of the Institute for Occupational Safety and Health , accessed on 25. September 2015.
  6. Donald Mackay, Christina E. Cowan-Ellsberry, David E. Powell, Kent B. Woodburn, Shihe Xu, Gary E. Kozerski, Jaeshin Kim (2015). "Decamethylcyclopentasiloxane (D5) environmental sources, fate, transport, and routes of exposure". Environmental Toxicology and Chemistry. 34 (12): 2689–2702. doi: 10.1002/etc.2941 . PMID   26213270.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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  9. Commission Regulation (EU) 2018/35 of 10 January 2018 amending Annex XVII to Regulation (EC) No 1907/2006 of the European Parliament and of the Council concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) as regards octamethylcyclotetrasiloxane (‘D4’) and decamethylcyclopentasiloxane (‘D5’) (Text with EEA relevance. ), 2018-01-10, retrieved 2023-08-10
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  12. Report of the Board of Review for Decamethylcyclopentasiloxane (Siloxane D5) established under Section 333(1) of the Canadian Environmental Protection Act of 1999, October 20, 2011
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