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Preferred IUPAC name [Tetrasulfanediyldi(propane-3,1-diyl)]bis(triethoxysilane) | |
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ChemSpider | |
ECHA InfoCard | 100.049.888 |
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Properties | |
C18H42O6S4Si2 | |
Molar mass | 538.95 |
Appearance | yellow syrup |
Density | 1.08 g/cm3 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Bis(triethoxysilylpropyl)tetrasulfide is an organosulfur compound with the formula S4[C3H6Si(OEt)3]2 (Et = C2H5). The molecule consists of two trialkoxysilyl propyl groups linked with a polysulfide. It is often sold as a mixture with the trisulfide. The compound is a colorless viscous liquid that is soluble in ordinary organic solvents such as toluene. Commercial samples often are yellowish. The compound is added to rubber compositions that contain silica filler. [1] [2] [3]
The compound was first prepared by the reaction of 3-(triethoxysilyl)propyl chloride with sodium tetrasulfide: [4]
Bis(triethoxysilylpropyl)tetrasulfide is a bifunctional molecule in that it contains two kinds of reactive functional groups. The tetrasulfide group is a polysulfide, which means that it consists of a chain of sulfur atoms. S-S bonds are susceptible to reduction (to thiols), attachment to metals (e.g., for protection against corrosion), and vulcanization. The triethoxysilyl groups are susceptible to hydrolysis, resulting in cross-linking via sol-gel condensation. In the usual application of this chemical, the hydrolyzed siloxy groups attach to silica particles and the polysulfide groups link to the organic polymer. [5]
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.
In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
In chemistry, catenation is the bonding of atoms of the same element into a series, called a chain. A chain or a ring shape may be open if its ends are not bonded to each other, or closed if they are bonded in a ring. The words to catenate and catenation reflect the Latin root catena, "chain".
In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.
Polysulfides are a class of chemical compounds derived from anionic chains of sulfur atoms. There are two main classes of polysulfides: inorganic and organic. The inorganic polysulfides have the general formula S2−
n. These anions are the conjugate bases of polysulfanes H2Sn. Organic polysulfides generally have the formulae R1SnR2, where R is an alkyl or aryl group.
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
Sulfur compounds are chemical compounds formed the element sulfur (S). Common oxidation states of sulfur range from −2 to +6. Sulfur forms stable compounds with all elements except the noble gases.
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.
Group 2 organometallic chemistry refers to the organic derivativess of any group 2 element. It is a subtheme to main group organometallic chemistry. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organometallic group 2 compounds are typically limited to academic interests.
Tetraethyl orthosilicate, formally named tetraethoxysilane (TEOS), ethyl silicate is the organic chemical compound with the formula Si(OC2H5)4. TEOS is a colorless liquid. It degrades in water. TEOS is the ethyl ester of orthosilicic acid, Si(OH)4. It is the most prevalent alkoxide of silicon.
Organozirconium chemistry is the science of exploring the properties, structure, and reactivity of organozirconium compounds, which are organometallic compounds containing chemical bonds between carbon and zirconium. Organozirconium compounds have been widely studied, in part because they are useful catalysts in Ziegler-Natta polymerization.
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes.
Organovanadium chemistry is the chemistry of organometallic compounds containing a carbon (C) to vanadium (V) chemical bond. Organovanadium compounds find only minor use as reagents in organic synthesis but are significant for polymer chemistry as catalysts.
Titanium ethoxide is a chemical compound with the formula Ti4(OCH2CH3)16. It is a commercially available colorless liquid that is soluble in organic solvents but hydrolyzes readily. Its structure is more complex than suggested by its empirical formula. Like other alkoxides of titanium(IV) and zirconium(IV), it finds used in organic synthesis and materials science.
Sodium polysulfide is a general term for salts with the formula Na2Sx, where x = 2 to 5. The species Sx2−, called polysulfide anions, include disulfide (S22−), trisulfide (S32−), tetrasulfide (S42−), and pentasulfide (S52−). In principle, but not in practice, the chain lengths could be longer. The salts are dark red solids that dissolve in water to give highly alkaline and corrosive solutions. In air, these salts oxidize, and they evolve hydrogen sulfide by hydrolysis.
Sodium tetrasulfide is an inorganic compound with the formula Na2S4. It is a yellow-orange solid that dissolves via hydrolysis in water. It is a precursor to some specialty polymers and intermediates in prototypes of the sodium-sulfur battery.
Siegfried Wolff is a now-retired Degussa chemist noted for first recognizing the potential of using silica in tire treads to reduce rolling resistance.
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Vinyltriethoxysilane is an organosilicon compound with the formula (C2H5O)3SiCH=CH2. It is a colorless liquid. The compound is bifunctional, featuring both a vinyl group and hydrolytically sensitive ethoxysilyl groups. As such it is a crosslinking agent.
Walter H. Waddell is a retired ExxonMobil Chemical senior research associate and consultant to the tire and rubber industry with expertise in silica technology, rubber compounding, butyl polymer applications and tire aging. Since 2015 he has served on the technical committee of the International Tire Exhibition & Conference (ITEC) for Tire Manufacturing.