Bis(triethoxysilylpropyl)tetrasulfide: Difference between revisions

Bis(triethoxysilylpropyl)tetrasulfide
Names
	Preferred IUPAC name [Tetrasulfanediyldi(propane-3,1-diyl)]bis(triethoxysilane)
	Other names Bis[3-(triethoxysilyl)propyl]tetrasulfide; Bis(3-triethoxysilylpropyl)tetrasulfane; Si-69; TESPT;
Identifiers
CAS Number	40372-72-3;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3188179;
ChemSpider	142291;
ECHA InfoCard	100.049.888
EC Number	254-896-5;
PubChem CID	162012;
UNII	J98V193ZRY;
CompTox Dashboard (EPA)	DTXSID3029362 ;
	InChI InChI=1S/C18H42O6S4Si2/c1-7-19-29(20-8-2,21-9-3)17-13-15-25-27-28-26-16-14-18-30(22-10-4,23-11-5)24-12-6/h7-18H2,1-6H3 Key: VTHOKNTVYKTUPI-UHFFFAOYSA-N;
	SMILES CCO[Si](CCCSSSSCCC[Si](OCC)(OCC)OCC)(OCC)OCC;
Properties
Chemical formula	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). Infobox references

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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]

Synthesis and reactivity

Reaction

The compound was first prepared by the reaction of 3-(triethoxysilyl)propyl chloride with sodium tetrasulfide:^[4]

Na₂S₄ + 2 ClC₃H₆Si(OEt)₃ → S₄[C₃H₆Si(OEt)₃]₂ + 2 NaCl

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]

References

^ Kohjiya, Shinzo; Ikeda, Yuko (2000). "Reinforcement of general-purpose grade rubbers by silica generated in situ". Rubber Chemistry and Technology. 73 (3): 534–550. doi:10.5254/1.3547604.
^ Wolff, Siegfried (1996). "Chemical aspects of rubber reinforcement by fillers". Rubber Chemistry and Technology. 69 (3): 325–346. doi:10.5254/1.3538376.
^ Vilmin, F.; Bottero, I.; Travert, A.; Malicki, N.; Gaboriaud, F.; Trivella, A.; Thibault-Starzyk, F. (2014). "Reactivity of Bis[3-(triethoxysilyl)propyl] Tetrasulfide (TESPT) Silane Coupling Agent over Hydrated Silica: Operando IR Spectroscopy and Chemometrics Study". The Journal of Physical Chemistry C. 118 (8): 4056–4071. doi:10.1021/jp408600h.
^ Thurn, Friedrich; Meyer-Simon, Eugen; Michel, Rudolf "Verfahren zur Herstellung von Organosiliziumverbindungen (Continuous manufacture of bis[3-(triethoxysilyl)propyl] tetrasulfide)" Ger. Offen. (1973), DE 2212239 A1 19731004.
^ Choi, S.-S.; Kim, I.-S.; Woo, C.-S. (2007). "Influence of TESPT Content on Crosslink Types and Rheological Behaviors of Natural rubber compounds reinforced with Silica". Journal of Applied Polymer Science. 106 (4): 2753–2758. doi:10.1002/app.25744.

[1] Kohjiya, Shinzo; Ikeda, Yuko (2000). "Reinforcement of general-purpose grade rubbers by silica generated in situ". Rubber Chemistry and Technology. 73 (3): 534–550. doi:10.5254/1.3547604.

[2] Wolff, Siegfried (1996). "Chemical aspects of rubber reinforcement by fillers". Rubber Chemistry and Technology. 69 (3): 325–346. doi:10.5254/1.3538376.

[3] Vilmin, F.; Bottero, I.; Travert, A.; Malicki, N.; Gaboriaud, F.; Trivella, A.; Thibault-Starzyk, F. (2014). "Reactivity of Bis[3-(triethoxysilyl)propyl] Tetrasulfide (TESPT) Silane Coupling Agent over Hydrated Silica: Operando IR Spectroscopy and Chemometrics Study". The Journal of Physical Chemistry C. 118 (8): 4056–4071. doi:10.1021/jp408600h.

[4] Thurn, Friedrich; Meyer-Simon, Eugen; Michel, Rudolf "Verfahren zur Herstellung von Organosiliziumverbindungen (Continuous manufacture of bis[3-(triethoxysilyl)propyl] tetrasulfide)" Ger. Offen. (1973), DE 2212239 A1 19731004.

[5] Choi, S.-S.; Kim, I.-S.; Woo, C.-S. (2007). "Influence of TESPT Content on Crosslink Types and Rheological Behaviors of Natural rubber compounds reinforced with Silica". Journal of Applied Polymer Science. 106 (4): 2753–2758. doi:10.1002/app.25744.

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[2]

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[5]

@@ Line 1: / Line 1: @@
 {{Chembox
 | ImageFile = Si69.svg
+| Name=Bis(triethoxysilylpropyl){{shy}}tetrasulfide
 | ImageSize =
 | ImageAlt =
+| PIN = [Tetrasulfanediyldi(propane-3,1-diyl)]bis(triethoxysilane)
-| IUPACName =
-| OtherNames = bis[3-(triethoxysilyl)propyl]tetrasulfide, bis(3-triethoxysilylpropyl)tetrasulfane, Si-69
+| OtherNames = {{ubl|Bis[3-(triethoxysilyl)propyl]tetrasulfide|Bis(3-triethoxysilylpropyl)tetrasulfane|Si-69|TESPT}}
 |Section1={{Chembox Identifiers
 | CASNo = 40372-72-3
-| PubChem =
+| PubChem = 162012
-| SMILES = }}
+| EC_number = 254-896-5
+| UNII = J98V193ZRY
+| ChEMBL = 3188179
+| ChemSpiderID = 142291
+| StdInChI = 1S/C18H42O6S4Si2/c1-7-19-29(20-8-2,21-9-3)17-13-15-25-27-28-26-16-14-18-30(22-10-4,23-11-5)24-12-6/h7-18H2,1-6H3
+| StdInChIKey = VTHOKNTVYKTUPI-UHFFFAOYSA-N
+| SMILES = CCO[Si](CCCSSSSCCC[Si](OCC)(OCC)OCC)(OCC)OCC
+ }}
 |Section2={{Chembox Properties
 | Formula = C<sub>18</sub>H<sub>42</sub>O<sub>6</sub>S<sub>4</sub>Si<sub>2</sub>
 | MolarMass = 538.95
-| Appearance = colorless or yellow syrupy liquid
+| Appearance =yellow syrup
 | Density = 1.08 g/cm<sup>3</sup>
 | MeltingPt =
@@ Line 23: / Line 31: @@
 }}
-'''Bis(triethoxysilylpropyl)tetrasulfide''' is an [[organosulfur compound]] with the formula S<sub>4</sub>[C<sub>3</sub>H<sub>6</sub>Si(OEt)<sub>3</sub>]<sub>2</sub> ([[Ethyl group|Et]] = C<sub>2</sub>H<sub>5</sub>).  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.<ref>Kohjiya, Shinzo; Ikeda, Yuko "Reinforcement of general-purpose grade rubbers by silica generated in situ" Rubber Chemistry and Technology 2000, volume 73, pages 534-550. http://dx.doi.org.proxy2.library.illinois.edu/10.5254/1.3547604</ref><ref>Wolff, Siegfried "Chemical aspects of rubber reinforcement by fillers" Rubber Chemistry and Technology 1996, volume 69, pages 325-346.http://dx.doi.org.proxy2.library.illinois.edu/10.5254/1.3538376</ref>
+'''Bis(triethoxysilylpropyl)tetrasulfide''' is an [[organosulfur compound]] with the formula S<sub>4</sub>[C<sub>3</sub>H<sub>6</sub>Si(OEt)<sub>3</sub>]<sub>2</sub> ([[Ethyl group|Et]] = C<sub>2</sub>H<sub>5</sub>).  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.<ref>{{cite journal | last1 = Kohjiya | first1 = Shinzo | last2 = Ikeda | first2 = Yuko | year = 2000 | title = Reinforcement of general-purpose grade rubbers by silica generated in situ | journal = Rubber Chemistry and Technology | volume = 73 | issue = 3 | pages = 534–550 | doi=10.5254/1.3547604}}</ref><ref>{{cite journal | last1 = Wolff | first1 = Siegfried | year = 1996 | title = Chemical aspects of rubber reinforcement by fillers | journal = Rubber Chemistry and Technology | volume = 69 | issue = 3 | pages = 325–346 | doi=10.5254/1.3538376}}</ref><ref>{{cite journal|author=Vilmin, F.|author2= Bottero, I.|author3=  Travert, A.|author4=   Malicki, N.|author5=    Gaboriaud, F.|author6=     Trivella, A.|author7=     Thibault-Starzyk, F.|title=Reactivity of Bis[3-(triethoxysilyl)propyl] Tetrasulfide (TESPT) Silane Coupling Agent over Hydrated Silica: Operando IR Spectroscopy and Chemometrics Study|journal=The Journal of Physical Chemistry C|year=2014|volume=118|issue= 8|page=4056–4071|doi=10.1021/jp408600h}}</ref>
 ==Synthesis and reactivity==
+[[file:Synthesis Bis(triethoxysilylpropyl)tetrasulfide.svg|thumb|left|Reaction]]
-The compound was first prepared by the reaction of the 3-chloropropylalkoxysilane with [[sodium tetrasulfide]]:<ref>Thurn, Friedrich; Meyer-Simon, Eugen; Michel, Rudolf "Verfahren zur Herstellung von Organosiliziumverbindungen (Continuous manufacture of bis[3-(triethoxysilyl)propyl] tetrasulfide)" Ger. Offen. (1973), DE 2212239 A1 19731004.</ref>
+The compound was first prepared by the reaction of 3-(triethoxysilyl)propyl chloride with [[sodium tetrasulfide]]:<ref>Thurn, Friedrich; Meyer-Simon, Eugen; Michel, Rudolf "Verfahren zur Herstellung von Organosiliziumverbindungen (Continuous manufacture of bis[3-(triethoxysilyl)propyl] tetrasulfide)" Ger. Offen. (1973), DE 2212239 A1 19731004.</ref>
 :Na<sub>2</sub>S<sub>4</sub>  +  2 ClC<sub>3</sub>H<sub>6</sub>Si(OEt)<sub>3</sub>  →   S<sub>4</sub>[C<sub>3</sub>H<sub>6</sub>Si(OEt)<sub>3</sub>]<sub>2</sub>  +  2 NaCl
-Bis(triethoxysilylpropyl)tetrasulfide is a bifunctional molecule in that it contains two kinds of reactive [[functional group]]s.  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-link]]ing via [[sol-gel#polymerization|sol-gel condensation]].  In the usual application of Si-69, the hydrolyzed siloxy groups attach to silica particles and the polysufide groups link to the organic polymer.
+Bis(triethoxysilylpropyl)tetrasulfide is a bifunctional molecule in that it contains two kinds of reactive [[functional group]]s.  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-link]]ing via [[sol-gel#polymerization|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.<ref>{{cite journal|author=Choi, S.-S.|author2= Kim, I.-S.|author3= Woo, C.-S.|title=Influence of TESPT Content on Crosslink Types and Rheological Behaviors of Natural rubber compounds reinforced with Silica|journal=Journal of Applied Polymer Science|year=2007|volume=106|issue= 4|page=2753–2758|doi=10.1002/app.25744}}</ref>
 ==References==
+{{Reflist}}
-<references />
 [[Category:Sulfur compounds]]
-[[Category:Corrosion]]
+[[Category:Corrosion inhibitors]]
 [[Category:Ethoxides]]
-[[Category:Silicate esters]]
+[[Category:Organosilicon compounds]]
-[[Category:Orthoesters]]