Names | |
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Preferred IUPAC name Octamethyl-1,3,5,7,2,4,6,8-tetroxatetrasilocane | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.008.307 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
[(CH3)2SiO]4 | |
Molar mass | 296.616 g·mol−1 |
Density | 0.956 g/mL |
Melting point | 17–18 °C (63–64 °F; 290–291 K) |
Boiling point | 175–176 °C (347–349 °F; 448–449 K) |
56.2±2.5 ppb (23 °C) [1] | |
log P | 6.98±0.13 [2] |
Vapor pressure | 124.5±6.2 Pa (25 °C) [3] |
Hazards | |
GHS labelling: | |
[4] | |
Warning | |
H361f, H410 M=10 [4] | |
Related compounds | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [5]
Commercially D4 is produced from dimethyldichlorosilane. Hydrolysis of the dichloride produces a mixture of cyclic dimethylsiloxanes and polydimethylsiloxane. From this mixture, the cyclic siloxanes including D4 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: [5]
D4 and D5 are also precursors to the polymer. The catalyst is again KOH.
It is among the most important of all the cyclic siloxanes, with a global production volume of 136 million kilograms in 1993. [6] 100,000–1,000,000 tonnes per year of D4 is manufactured and/or imported in the European Economic Area. [7]
This article may be too technical for most readers to understand.(September 2022) |
D4 is of low acute toxicity. The LC50 for a single four hour inhalation exposure in rats is 36 mg/L. The oral LD50 in rats is above 4800 mg/kg and the dermal LD50in rats is above 2400 mg/kg. [8]
As the smallest cyclic dimethylsiloxane that does not experience considerable ring strain, [9] D4 is one of the most abundant siloxanes in the environment, e.g. in landfill gases. [10] D4 and D5 have attracted attention because they are pervasive. Cyclic siloxanes can be detected in some species of aquatic life. [11] An independent, peer-reviewed study in the US found "negligible risk from D4 to organisms" [12] while a scientific assessment 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]
In the European Union, D4 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] [ clarification needed ] D4 shall not be placed on the market in wash-off cosmetic products in a concentration equal to or greater than 0.1% by weight of either substance, after 31 January 2020. [15] Conversely, a detailed review and analysis of the science by the State of Washington in 2017 led to the removal of D4 from their CHCC listing. [16] [ clarification needed ] That decision prompted the State of Oregon to follow suit in 2018. [17]
Silly Putty is a toy containing silicone polymers that have unusual physical properties. It bounces, but it breaks when given a sharp blow, and it can also flow like a liquid. It contains viscoelastic liquid silicones, a type of non-Newtonian fluid, which makes it act as a viscous liquid over a long time period but as an elastic solid over a short time period. It was originally created during research into potential rubber substitutes for use by the United States in World War II.
A silicone or polysiloxane is a polymer made up of siloxane (−R2Si−O−SiR2−, where R = organic group). 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, silicone grease, silicone rubber, silicone resin, and silicone caulk.
Phthalates, or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably.
Polydimethylsiloxane (PDMS), also known as dimethylpolysiloxane or dimethicone, is a silicone polymer with a wide variety of uses, from cosmetics to industrial lubrication.
Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) is a European Union regulation dating from 18 December 2006. REACH addresses the production and use of chemical substances, and their potential impacts on both human health and the environment. Its 849 pages took seven years to pass, and it has been described as the most complex legislation in the Union's history and the most important in 20 years. It is the strictest law to date regulating chemical substances and will affect industries throughout the world. REACH entered into force on 1 June 2007, with a phased implementation over the next decade. The regulation also established the European Chemicals Agency, which manages the technical, scientific and administrative aspects of REACH.
A siloxane is a functional group in organosilicon chemistry with the Si−O−Si linkage. 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 (O) atom. The siloxane functional group forms the backbone of silicones, the premier example of which is polydimethylsiloxane (PDMS). The functional group R3SiO− (where the three Rs may be different) is called siloxy. Siloxanes are manmade and have many commercial and industrial applications because of the compounds’ hydrophobicity, low thermal conductivity, and high flexibility.
Brominated flame retardants (BFRs) are organobromine compounds that have an inhibitory effect on combustion chemistry and tend to reduce the flammability of products containing them. The brominated variety of commercialized chemical flame retardants comprise approximately 19.7% of the market. They are effective in plastics and textile applications like electronics, clothes and furniture.
2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH (Bu = CH3CH2CH2CH2). This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritant and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen. A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased child BMI.
Chlorosilanes are a group of reactive, chlorine-containing chemical compounds, related to silane and used in many chemical processes. Each such chemical has at least one silicon-chlorine bond. Trichlorosilane is produced on the largest scale. The parent chlorosilane is silicon tetrachloride.
The European Chemicals Agency is an agency of the European Union which manages the technical and administrative aspects of the implementation of the European Union regulation called Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH). ECHA is the driving force among regulatory authorities in implementing the EU's chemicals legislation. ECHA has to ascertain that companies comply with the legislation, advances the safe use of chemicals, provides information on chemicals and addresses chemicals of concern. It is located in Helsinki, Finland. ECHA is an independent and mature regulatory agency established by REACH. It is not a subsidiary entity of the European Commission.
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.
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.
Diisobutyl phthalate (DIBP) is a phthalate ester having the structural formula C6H4(COOCH2CH 2)2. It is formed by the esterification of isobutanol and phthalic anhydride. This and other phthalates are used as plasticizers due to their flexibility and durability. They are found in many industrial and personal products, such as lacquers, nail polish and cosmetics. DIBP can be absorbed via oral ingestion and dermal exposition. When it comes to excretion, DIBP is first converted into the hydrolytic monoester monoisobutyl phthalate (MIBP). The primary excretory route is urine, with biliary excretion being noted in minor amounts. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP).
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.
Decabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). It was commercialised in the 1970s and was initially thought to be safe, but is now recognised as a hazardous and persistent pollutant. It was added to Annex A of the Stockholm Convention on Persistent Organic Pollutants in 2017, which means that treaty members must take measures to eliminate its production and use. The plastics industry started switching to decabromodiphenyl ethane as an alternative in the 1990s, but this is now also coming under regulatory pressure due to concerns over human health.
The European Chemicals Bureau (ECB) was the focal point for the data and assessment procedure on dangerous chemicals within the European Union (EU). The ECB was located in Ispra, Italy, within the Joint Research Centre (JRC) of the European Commission. In 2008 the ECB completed its mandate. Some of its activities were taken over by the European Chemicals Agency (ECHA); others remained within the Joint Research Centre. The history of the ECB has been published as a JRC technical report.
Galaxolide is a synthetic musk with a clean sweet musky floral woody odor used in fragrances. It is one of the musk components that perfume and cologne manufacturers use to add a musk odor to their products. Galaxolide was first synthesized in 1965, and used in the late 1960s in some fabric softeners and detergents. High concentrations were also incorporated in fine fragrances.
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.
A solvent is a substance that is liquid at the temperature at which it is used. It has the ability to dissolve, dilute or extract other substances without changing them chemically and without changing itself. The traditional organic solvents, although very effective, raise today many problems as they are associated with adverse effects, both on the health and safety of workers (burns, cancer, eczema, brain disorder, fetotoxicity, and inflammations of several peripheral nerves at the same time, as well as on the environment and health of the general population. Solvents represent a major part of the chemical use in various domains and in consequence define a lot of the environmental performance of the chemical industry.
Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).
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