Bis(triethoxysilylpropyl) disulfide

Bis(triethoxysilylpropyl) disulfide Property

Melting point:

°C

Boiling point:

250

Density 

1.03

vapor pressure 

0-7910Pa at 20-25℃

refractive index 

1.457

Flash point:

75°C

storage temp. 

2-8°C

Specific Gravity

1.03

Appearance

Colorless to light yellow Liquid

Water Solubility 

14-1000000000μg/L at 20℃

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

InChI

InChI=1S/C18H42O6S2Si2/c1-7-19-27(20-8-2,21-9-3)17-13-15-25-26-16-14-18-28(22-10-4,23-11-5)24-12-6/h7-18H2,1-6H3

InChIKey

FBBATURSCRIBHN-UHFFFAOYSA-N

SMILES

CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC

LogP

-3-5.2 at 20℃

CAS DataBase Reference

56706-10-6(CAS DataBase Reference)

EPA Substance Registry System

3,14-Dioxa-8,9-dithia-4,13-disilahexadecane, 4,4,13,13-tetraethoxy- (56706-10-6)

Safety

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

TSCA 

Yes

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

Bis(triethoxysilylpropyl) disulfide Chemical Properties,Usage,Production

Application

Footwear
- Abrasion resistance
- Cutting and chunking resistance
- Flex life improvement
Rolls
- Abrasion resistance
- Aging resistance
- Processing- Set reduction (better load bearing)
- Reduced water swell
- Lower hysteresis
Mechanical Molded Goods
- Increased modulus
- Better heat aging
- Compression set reduction
- Dynamic property improvement
- Reduced swell to polar liquids
- Filler substitution (non-black for black)
Hose
- Improved abrasion on cover
- Better heat aging
- Increased modulus
- Lower compression set
- Improved adhesion to reinforcing elements
Solid Tires
- Improved abrasion
- Lower hysteresis
- Higher modulus
- Improved processing
- Possibly better adhesion
Tires
- Treads for abrasion, hot tear
- Carcass for adhesion and/or filler substitution
- Breaker (belt) stocks for adhesion
Belts
Flat Belts
- Increased abrasion
- Improved reversion resistance
- Reduced cost with clay substitution for black
- Improved cord adhesion
- Increased flex life and modulus
V Belts
- Increased modulus
- Improved abrasion
- Longer flex life
- Improved adhesion to reinforcing elements

Chemical Properties

Yellowish clear liquid

Flammability and Explosibility

Not classified

Synthesis

General procedure for the synthesis of (3-mercaptopropyl)triethoxysilane (MPTES), compounds (CAS:60764-86-5) and bis-[3-(triethoxysilyl)propyl]-disulfide (TESPD) from 3-chloropropyltriethoxysilane (CPTES): during the reaction, 50 wt.% NaHSO4 was added drop-wise to a NaHS solution solution. 325 g (2.69 mol) of NaHS solution with 8.2 g (0.0124 mol) of tetrabutylammonium bromide (TBAB) solution were added to a glass reactor, mixed well and heated to 75 °C. Subsequently, NaHSO4 solution was added slowly and dropwise just before the imminent addition. Next, CPTES was added. 497.8 g (2.07 moles) of CPTES was added to the reaction mixture within 8 min. the addition of NaHSO4 solution needed to be completed within 30 min. After 5 hours of reaction, the organic phase was separated and analyzed by gas chromatography (GC). The analysis showed that the product contained 2.0% wt. of CPTES, 87.6% wt. of MPTES, 2.7% wt. of TESPM, and 0.7% wt. of TESPD.Finally, the product was distilled under vacuum to yield MPTES with a purity of 95.4%, which is about 84% yield based on the amount of CPTES used.

References

[1] Patent: US6680398, 2004, B1. Location in patent: Page column 10-11
[2] Patent: US6680398, 2004, B1. Location in patent: Page column 8-9
[3] Patent: US6680398, 2004, B1. Location in patent: Page column 10
[4] Patent: US6680398, 2004, B1. Location in patent: Page column 9-10
[5] Patent: US6680398, 2004, B1. Location in patent: Page column 9