40372-72-3

Basic information

• Product Name: Bis[3-(triethoxysilyl)propyl]tetrasulfide
• Synonyms: TESPT;BIS(TRIETHOXYSILYLPROPYL)TETRASULPHANE;BIS(3-(TRIETHOXYSILYL)PROPYL)TETRASULFIDE;BIS [3-(TRIETHOXYSILYL )PROPYL ] TETRASULPHIDE;3,3'-TETRATHIOBIS(PROPYL-TRIETHOXYSILANE);16-Dioxa-8,9,10,11-tetrathia-4,15-disilaoctadecane,4,4’,15,15-tretraethoxy-3;9,10,11-tetrathia-4,15-disilaoctadecane,4,4,15,15-tetraethoxy-16-dioxa-8;CouplingagentG-407
• CAS NO: 40372-72-3
• Molecular Formula: C₁₈H₄₂O₆S₄Si₂
• Molecular Weight: 538.95
• EINECS: 254-896-5
• Product Categories: Industrial/Fine Chemicals;Sulfur;Adhesion Promoters;Coupling Agents;Dispersing Agents;Sulfur Silanes;Surface Modifiers;silane
• Mol File: 40372-72-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 250 °C
• Flash Point: 91°C
• Appearance: Yellowish clear liquid
• Density: 1.08 g/mL at 20 °C(lit.)
• Vapor Pressure: 5.34E-10mmHg at 25°C
• Refractive Index: n20/D 1.49
• Water Solubility: Miscible with toluene, primary alcohols, ketones, benzene, chlorinated hydrocarbons, acetonitrile, dimethylformaminde and dimeth
• BRN: 2062235
• CAS DataBase Reference: Bis[3-(triethoxysilyl)propyl]tetrasulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[3-(triethoxysilyl)propyl]tetrasulfide(40372-72-3)
• EPA Substance Registry System: Bis[3-(triethoxysilyl)propyl]tetrasulfide(40372-72-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 40372-72-3(Hazardous Substances Data)

Usage

Description

Bis[3-(triethoxysilyl)propyl]tetrasulfide is a silylating coupling agent and modifier that is used in the design of a new generation of sustainable self-healing styrene-butadiene compounds. It is a yellowish clear liquid with unique chemical properties that make it valuable in various applications.

Uses

Used in Rubber Industry:
Bis[3-(triethoxysilyl)propyl]tetrasulfide is used as a crosslinking agent, reinforcing filler, and curing agent in the manufacturing of rubber. It acts as a chemical intermediate and a coupling agent used to chemically modify the silica surface, enhancing the properties of rubber products.
Used in Footwear:
Bis[3-(triethoxysilyl)propyl]tetrasulfide is used as a coupling agent for non-black pigments, improving abrasion resistance, cutting and chunking resistance, and flex life.
Used in Rolls:
It is used to enhance abrasion resistance, aging resistance, processing, set reduction, reduced water swell, and lower hysteresis.
Used in Mechanical Molded Goods:
Bis[3-(triethoxysilyl)propyl]tetrasulfide is used as a curing agent for good heat aging, resulting in increased modulus, better heat aging, compression set reduction, dynamic property improvement, reduced swell to polar liquids, and filler substitution.
Used in Hose:
It is used to improve abrasion on the cover, better heat aging, increased modulus, lower compression set, and improved adhesion to reinforcing elements.
Used in Solid Tires:
Bis[3-(triethoxysilyl)propyl]tetrasulfide is used to improve abrasion, lower hysteresis, increase modulus, improve processing, and possibly better adhesion.
Used in Tires:
It is used in treads for abrasion and hot tear, carcass for adhesion and/or filler substitution, and breaker (belt) stocks for adhesion.
Used in Belts Flat Belts:
Bis[3-(triethoxysilyl)propyl]tetrasulfide is used to increase abrasion, improve reversion resistance, reduce cost with clay substitution for black, improve cord adhesion, and increase flex life and modulus.
Used in V Belts:
It is used to increase modulus, improve abrasion, extend flex life, and improve adhesion to reinforcing elements.
Additionally, Bis[3-(triethoxysilyl)propyl]tetrasulfide (TESPTS) is used as a crosslinking agent and reinforcing filler in the manufacturing of rubber, providing corrosion protection to metallic substrates. It is also used as a precursor in the synthesis of mesoporous organosilicas.

InChI:InChI=1/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

Synthetic route

(3-chloropropyl)triethoxysilane (5089-70-3) → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3)

Conditions	Yield
With sodium polysulfide In ethanol at 78℃; Product distribution / selectivity;	97.8%
With sodium sulfide; sodium hydrogencarbonate; sulfur In ethanol; water
With sodium sulfide; sulfur In ethanol; toluene for 4h; Reflux; Green chemistry;
With sodium sulfide; sodium borate; dodecyltrimethylammonium bromide; sulfur; potassium iodide In water at 40 - 55℃; for 1h; Temperature; Reagent/catalyst;

(3-chloropropyl)triethoxysilane (5089-70-3) → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7) + bis(triethoxysilylpropyl)penta-sulphane

Conditions	Yield
With sodium oligosulfide In 1,2-dimethoxyethane for 1h; Heating; Further byproducts given;

(3-chloropropyl)triethoxysilane (5089-70-3) → [(MeO)3Si(CH2)3]2S6 + [(EtO)3Si(CH2)3]2S7 + [(EtO)3Si(CH2)3]2S8 + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7) + bis(triethoxysilylpropyl)penta-sulphane

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sulfur at 80℃; Stage #2: With sodium trisulfide; tetrabutylammomium bromide In water at 80 - 90℃; for 3.66667h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With sulfur at 80℃; Stage #2: With sodium sulfide; tetrabutylammomium bromide In water at 80 - 90℃; for 3.66667h; Product distribution / selectivity;

...Expand

(3-chloropropyl)triethoxysilane (5089-70-3) → [(MeO)3Si(CH2)3]2S6 + [(EtO)3Si(CH2)3]2S7 + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7) + bis(triethoxysilylpropyl)penta-sulphane

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sulfur In toluene at 80℃; Stage #2: With tetrabutylammomium bromide; sulfur In water; toluene at 80 - 85℃; for 5.58333h; Product distribution / selectivity;
With sodium sulfide; tetrabutylammomium bromide; sulfur In water at 80 - 90℃; for 6.66667h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With sodium sulfide; tetrabutylammomium bromide; sulfur In water at 80 - 90℃; for 8.66667h; Stage #2: With tetrabutylammomium bromide; sulfur In water; toluene at 80 - 85℃; for 5.58333h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With sulfur In toluene at 80℃; Stage #2: With sodium sulfide; tetrabutylammomium bromide In water; toluene at 90 - 95℃; for 5.75h; Product distribution / selectivity;

(3-chloropropyl)triethoxysilane (5089-70-3) → [(MeO)3Si(CH2)3]2S6 + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7) + bis(triethoxysilylpropyl)penta-sulphane

Conditions	Yield
With sodium sulfide; tetrabutylammomium bromide; sulfur In water at 80 - 90℃; for 5.66667h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With tetrabutylammomium bromide; sulfur at 80℃; Stage #2: With sodium sulfide; tetrabutylammomium bromide In water at 70 - 80℃; for 5.83333h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With sulfur at 80℃; Stage #2: With sodium sulfide; tetrabutylammomium bromide In water at 80 - 90℃; for 5.58333h; Product distribution / selectivity;
Stage #1: (3-chloropropyl)triethoxysilane With tetrabutylammomium bromide In water at 80℃; Stage #2: With sodium sulfide; sulfur In water at 70 - 80℃; for 5.66667h; Product distribution / selectivity;

triethoxysilylpropyl chloride → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3)

Conditions	Yield
With disodium tetrasulfide In ethanol
With sodium sulfide; hydrogen sulfide In ethanol

(n-pr-1-Cl)SiCl3 (7787-88-4) + triethoxysilylpropyl chloride → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3)

Conditions	Yield
With disodium tetrasulfide In ethanol
With sodium sulfide; hydrogen sulfide In ethanol
With disodium tetrasulfide In ethanol
With disodium tetrasulfide In ethanol

sodium tetrasulfide + (3-chloropropyl)triethoxysilane (5089-70-3) → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3)

Conditions	Yield
With sodium sulfide nonahydrate; hydrogen sulfide; nitrogen In water; toluene

(3-chloropropyl)triethoxysilane (5089-70-3) → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
With sodium hydrogen sulfide monohydrate; sodium carbonate; sulfur; sodium hydroxide In ethanol; water at 65 - 75℃; Product distribution / selectivity;
With sodium hydrogen sulfide monohydrate; sodium carbonate; sulfur; sodium hydroxide In ethanol; water at 65 - 75℃; Product distribution / selectivity;

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + diethylene glycol (111-46-6) → bis[tri(hydroxydiethyleneoxy)silylpropyl] tetrasulfide (1036978-38-7)

Conditions	Yield
With sodium ethanolate In ethanol at 150℃; under 20 Torr; for 2h;	99%

triethanolamine (102-71-6) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → 1,1'-(tetrathiodi-3,1-propanediyl)bis-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane (68704-61-0)

Conditions	Yield
sodium ethanolate In ethanol at 150℃; under 200 Torr; for 2h;	98%

2-methyl-2,4-pentanediol (107-41-5) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → bis (3-(2-methyl-2,4-pentanedioxyethoxysilyl)-1-propyl) tetrasulfane

Conditions	Yield
sulfuric acid at 41 - 49℃; under 50 - 80 Torr; for 4h;	86.5%

1,1,1,3,5,5,5-heptamethyltrisiloxan (1873-88-7) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → C16H42O5SSi4

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene for 3h; Inert atmosphere;	59%

1-Tetradecanol (112-72-1) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → C90H186O6S4Si2

Conditions	Yield
toluene-4-sulfonic acid at 95 - 100℃; for 4h; Conversion of starting material;
tetrabutoxytitanium at 110 - 130℃; for 3h; Conversion of starting material;

1-dodecyl alcohol (112-53-8) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → C78H162O6S4Si2

Conditions	Yield
toluene-4-sulfonic acid at 110 - 120℃; for 4h; Conversion of starting material;

1-Hexadecanol (36653-82-4) + bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → C102H210O6S4Si2

Conditions	Yield
tetrabutoxytitanium at 120℃; under 15.0015 - 600.06 Torr; for 4.5h; Conversion of starting material;

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
Stage #1: bis(3-triethoxysilylpropyl) tetrasulfide With sodium In Solvent 140 at 110℃; for 0.75h; Stage #2: n-octanoic acid chloride In Solvent 140 at 45 - 104℃; for 1h; Stage #3: With water In toluene at 45℃; Product distribution / selectivity;

...Expand

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → bis[3-(trihydroxysilyl)propyl]-tetrasulfide (1186199-10-9)

Conditions	Yield
With acetic acid In ethanol; water for 24h; pH=4.5;

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) → allyltriethoxysilane (2550-04-1)

Conditions	Yield
at 590℃; for 0.00138889h; Pyrolysis;

Upstream product

• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 7787-88-4 (n-pr-1-Cl)SiCl₃ 

Downstream Products

• 220727-26-4 3-(octanoylsulfanyl)-1-propyltriethoxysilane 
• 106-32-1 octanoic acid ethyl ester 
• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 14814-09-6 3-Mercaptopropyltriethoxysilane 
• 60764-86-5 bis-[γ-(triethoxysilyl)propyl]sulfide 
• 56706-10-6 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 
• 56706-11-7 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane 
• 2550-04-1 allyltriethoxysilane 

Related news

Temperature dependent amphoteric behavior of Bis[3-(triethoxysilyl)propyl]tetrasulfide towards recycling of waste rubber: A triboelectric investigation07/11/2019

Here, we have examine the efficacy of bis[3-(triethoxysilyl)propyl]tetrasulfide (Si69) for physic-chemical recycling of waste rubber tyre (WRT) at two different operating temperatures (i.e., 170 °C and 190 °C). The reclaimed rubbers (RR) have been used to fabricate devices similar to the singl...detailed

Relevant articles and documents

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The invention relates to a method for preparing a silane coupling agent Si-69 in a water phase, and relates to a preparation method of a compound. The problems that a traditional method for preparingthe silane coupling agent Si-69 is long in reaction time, low in product purity, expensive in raw material price, not easy to store, high in production cost, severe in raw material and product hydrolysis phenomenon, high in operation requirement, and not easy to control a process flow are solved. The method comprises the following steps of (1) preparing a buffer solution; (2) preparing a sodium sulfide solution; (3) synthesizing a polysulfide inorganic phase solution; (4) preparing a catalyst solution; (5) synthesizing the silane coupling agent Si-69; (6) filtering, separating, decoloring, impurity-removing, drying, and purifying the silane coupling agent Si-69. The method provided by the invention has the advantages of short reaction period, high product purity, easiness in storing raw materials, low price of the raw materials, easiness in getting the raw materials, simple operation flow, easiness in controlling process conditions, high yield, easiness in controlling average Sulphur content, and low production cost. The product prepared through the method provided by the invention is high in purity (99 percent or more), not hydrolyzed or sulfur-separated, and long in preservationtime.

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