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Home > Encyclopedia > 4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane structure

4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 

structure
  • CAS No:

    56706-10-6

  • Formula:

    C18H42O6S2Si2

  • Chemical Name:

    4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

  • Synonyms:

    3,14-Dioxa-8,9-dithia-4,13-disilahexadecane,4,4,13,13-tetraethoxy-;4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane;Bis[3-(triethoxysilyl)propyl] disulfide;3,3′-Bis(triethoxysilylpropyl) disulfide;Si 266;Si 75 (sulfide);Si 75;Silquest A 1589;A 1589;Degussa Si 75;SCA 985;KBE 886B;Cabrus 2A;Si 266/2;SIB 1824.6;Bis[γ-(triethoxysilyl)propyl] disulfide;Struktol 985;Irusil S 175;Z 6820;CF 4289;Bis-(triethoxysilylpropyl)disulfane;Struktol SCA 985;SG-Si 996;X 75S;HP 1589;OFS 6920;Xiameter OFS 6920;Luvomaxx TESPD;264889-67-0;928390-99-2

  • Categories:

    Chemical Reagents  >  Silane Reagent

Description

Yellowish clear liquid


Liquid; WetSolid, Liquid

4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane Basic Attributes

474.82

474.82

260-350-7

DTXSID5069122

Characteristics

106

5.24480

Liquid; WetSolid, Liquid

1.025 g/cm3

°C

250

75°C

1.457

Safety Information

20/21/22-36/37/38

26-36/37/39

P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

H302

Not Classified

4,4,13,13-Tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane Use and Manufacturing

Methods of Manufacturing

A 50 percent by weight solution of NaHSOThe purpose of this example is to show that while the addition of sulfur reduced the formation of TESPM, the formation of TESPD increased. Thus, in a similar reaction to the one in Example 1, the ratio of sulfur to NaHS was increased to 0.05 to convert the TESPM into TESPD. NaHS flakes (146.3 g., 1.83 mole), sulfur (2.92 g, 0.092 mole), and 100 g DI water, were mixed in a glass-jacketed reactor and heated to 70° C. TBAB solution (14.4 g, 0.011 mole) was added and mixed. Instantly, an oily omega phase was formed at the surface. CPTES (400 g, 1.66 mole) was added at a rate of about 30 ml/min. The reaction temperature increased to 94° C. due to the exotherm, and some gel was observed in the organic phase. 380.1 g (95 percent by weight of CPTES) organic phase was collected after a three hour reaction. The gas chromatography analysis showed 1.5 percent CPTES, 66.7 percent MPTES, 3.37 percent TESPM, and 27.9 percent TESPD.The purpose of this example is to further minimize the TESPM formation and to increase the MPTES yield. Accordingly, an HCl solution was added dropwise to an NaHS solution during its reaction with CPTES at atmospheric pressure. Hydrogen sulfide gas formed in the reaction was neutralized in a caustic scrubber. 150.1 g (1.2 mole) of a 45 percent by weight NaHS solution, and 9.63 g (0.015 mole) of a 50 percent by weight TBAB catalyst solution, was added to the reactor, mixed, and heated to 65° C. 100 g (0.15 mole) of a 1.3 molar HCl solution, and 240.0 g (1.0 mole) of CPTES, were added simultaneously from two addition funnels, at a rate such that the addition of CPTES was completed in 15 minutes, and the addition of HCl was complete in about an hour. The reaction was continued at 70° C. for 5 hours. GC data showed 11.4 weight percent of unreacted CPTES remaining, and therefore 12.48 g (0.1002 mole) of an NaHS solution was again added and reacted for 5 hours. The organic phase was separated after cooling and filtered through a 0.45 micron filter disc. Gas chromatographic (GC) analysis of the organic phase showed that the product contained 2.6 weight percent of CPTES, 91.0 weight percent of MPTES, 1.99 weight percent of TESPM, and 2.34 weight percent of TESPDThis example shows the benefits obtained by using a solution of NaHS instead of NaHS flakes. In this example, the yield of MPTES was increased while the amount of the TESPM and TESPD byproducts decreased, by using the NaHS solution. Thus, NaHS flakes were replaced with a solution containing 45 weight percent of NaHS. No additional water was used in the aqueous phase as the NaHS solution contained water. Thus, a solution containing 45 weight percent NaHS (143 g., 1.15 mole) and 50 weight percent of a TBAB solution (99.6 g, 0.015 mole) were added into a glass reactor, mixed, and heated to 70° C. CPTES (240.8 g., 1.0 mole) was slowly added to maintain the reaction temperature below 80° C. After 5 hours, the reaction mixture was cooled to room temperature, and water was added to dissolve the NaCl salt in the aqueous phase. 229 g. of a light yellow organic phase was collected (95 weight percent based on CPTES), and analyzed. The GC analysis showed that it contained 1.6 weight percent CPTES, 84 weight percent MPTES, 6.9 weight percent TESPM, and 1.4 weight percent TESPD. No gel was found in the product. Color in the product was removed by treating it with 1-2 weight percent activated carbon black and clay.; Example 6 [00056] The NaHS/CPTES ratio in this example was changed from 1.15 to 1.30. All other conditions were similar to An increase in rate of reaction was observed with an increase in NaHS concentration in the reaction mixture. No significant change was observed in the product composition. The reaction was completed in 3 hours. The GC analysis results showed 0.8 weight percent CPTES, 82.3 weight percent MPTES, 6.6 weight percent TESPM, and 0.8 weight percent TESPD; Example 7Using 45 Weight Percent NaHS Solution, Reverse Addition [00057] Example 6 was repeated, except the order of addition of the reactants was reversed. Thus, CPTES (240.8 g., 1.0 mole) and solid TBAB (4.82 g., 0.015 mole) were added into a glass reactor, mixed, and heated to 70° C. A solution containing 45 weight percent NaHS (160.4 g., 1.30 mole) was added using an addition funnel in about 20 minutes. A slight exotherm was observed during the initial addition of NaHS. The reaction was stopped after 4 hours, and the byproduct NaCl was dissolved in water. The organic phase recovered after the phase separation was 225.5 g. (93.6 weight percent based on CPTES). The product composition by GC analysis showed that it contained 0.83 weight percent CPTES, 84.2 weight percent MPTES, 6.79 weight percent TESPM, and 0.7 weight percent TESPD. There was a slight improvement in MPTES yield by changing the order of addition of the sodium hydrosulfide. The GC analysis also showed a lower content of hydrolyzed oligomers than the GC analysis in Example 6.This example is the same as Example 3 except that a salt was added so that no gelation would occur in the organic phase. However, while the formation of TESPM was reduced, the formation of TESPD increased. Accordingly, an excess amount of NaHS flakes were used, and NaCl salt was added to saturate the aqueous phase before the addition of CPTES. The sulfur/NaHS ratio was 0.05. The catalyst solution was also added after the CPTES addition was completed. Thus, NaHS flakes (100 g., 1.248 mole), NaCl 87.7 g, sulfur (2.0 g, 0.063 mole), and 161.5 g of water, were mixed and heated to 60° C. CPTES (161.5 g., 0.671 mole) was added slowly and mixed at 300 rpm. A 25 weight percent solution of TBAB catalyst was added to the reaction mixture at 65° C. A slight exotherm was observed, and the reaction was completed in about 5 hours. The GC analysis of the organic phase showed that it contained 0.35 weight percent CPTES, 62.2 weight percent MPTES, 1.1 weight percent TESPM, and 34.1 weight percent TESPD. The product was stable. The MPTES yield was less due to side reactions when sodium hydrosulfide flakes were used.Boric acid was used in this example to lower the pH of the reaction mixture. The order of addition of CPTES and NaHS as compared to Example 10 was also reversed to minimize any potential formation of a gel. Thus, 206.3 g (0.86 mole) of CPTES, 4.13 g (0.013 mole) of solid TBAB, and 51.4 g (0.83 mole) of HA pressure reactor containing NaHS solution was pressurized with HA pressure reactor containing an NaHS solution was pressurized with COSodium di-hydrogen phosphate monohydrate was used as a pH adjusting agent in this example to reduce the formation of TESPM in the product. Thus, 27.6 g (0.2 mole) of NaHThe purpose of this example is to show no reduction in TESPM formation when none of the pH adjusting agents of the invention are employed. Thus, in a three neck round bottom flask equipped with an addition funnel, condenser, stirrer and thermometer, was added with 100 g (1.26 moles) of NaHS flakes containing 61.7 percent by weight NaHS and 6.07 weight percent NaExample 3 2580 g of ClPTES (3-chloropropyltriethoxysilane) are reacted with 304 g of NPS (sodium polysulphide, Na2Sz where z is on average 4, water content 0.1percent by weight) and 298 g of NST (dry sodium sulphide, Na

Uses

It is a multifunctional silicone coupling agent that has been successfully applied in the rubber industry. Its role is to improve the elastic modulus and tensile strength of the rubber, significantly improve the wear resistance and compression performance of the rubber, and at the same time reduce the rubber viscosity and save processing energy consumption. It is most suitable for rubber formulations containing hydroxyl-containing fillers in polymers containing double bonds or their blends. Suitable fillers include white carbon smoke, silicate, chalk, etc.; suitable rubbers include natural rubber (NR), styrene-butadiene rubber (SBR), isoprene rubber (IR), butadiene rubber (BR), butyronitrile Rubber (NBR) and EPDM (EPDM) etc. Compared with 40372-72-3, this product has a less active disulfane functional group, so it can provide more reliable scorch safety.


Crosslinker


Plastic and rubber products not covered elsewhere

Production

1,000,000 - 10,000,000 lb

All other chemical product and preparation manufacturing|3,14-Dioxa-8,9-dithia-4,13-disilahexadecane, 4,4,13,13-tetraethoxy-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Computed Properties

Molecular Weight:474.8
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:21
Exact Mass:474.19613447
Monoisotopic Mass:474.19613447
Topological Polar Surface Area:106
Heavy Atom Count:28
Complexity:290
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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