2-(DODECYLSULFANYLTHIOCARBONYLSULFANYL)-2-METHYLPROPIONIC ACID Chemical Properties

Melting point:

62-64℃ (hexane )

Boiling point:

506.0±29.0 °C(Predicted)

Density 

1.082±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

2.89±0.10(Predicted)

color 

pale yellow

Sensitive 

light sensitive, store cold

InChI

InChI=1S/C17H32O2S3/c1-4-5-6-7-8-9-10-11-12-13-14-21-16(20)22-17(2,3)15(18)19/h4-14H2,1-3H3,(H,18,19)

InChIKey

DZFGVGDQHQHOKZ-UHFFFAOYSA-N

SMILES

C(O)(=O)C(SC(SCCCCCCCCCCCC)=S)(C)C

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2930.90.9250

2-(DODECYLSULFANYLTHIOCARBONYLSULFANYL)-2-METHYLPROPIONIC ACID Usage And Synthesis

Uses

A sulfur-based, chain-transfer agent providing a high degree of control for living radical polymerizations utilizing the RAFT (reversible addition-fragmentation chain-transfer polymerization) technique.

Uses

Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerization

General Description

Need help choosing the correct RAFT Agent? Please consult the RAFT Agent to Monomer compatibility table.

Industrial uses

The trithiocarbonates have a structure that contains three sulfur atoms.
All three sulfur atoms can participate in bonding to the mineral surfaces. Philips Petroleum Company did most of the development of this class of collectors. Monoalkyl trithiocarbonate (Orfom 800 series) is used as a collector in flotation of copper and copper–lead ores.

Synthesis

The general procedure for the synthesis of 2-[dodecylthio(thiocarbonyl)thio]-2-methylpropanoic acid from carbon disulfide, trichloromethane, acetone and n-dodecanethiol was as follows: n-dodecanethiol (0.1 mol) and Aliquot 336 (0.004 mol) were dissolved in 48 g of acetone. Subsequently, 50% sodium hydroxide solution (0.105 mol) was added, followed by slow dropwise addition of carbon disulfide (0.1 mol) to 10 g of acetone solution. The reaction mixture gradually changed from colorless to yellow. After 20 minutes of reaction, trichloromethane (0.15 mol) was added followed by dropwise addition of 50% NaOH solution (0.5 mol) and 5 g NaOH beads. The reaction mixture was stirred at 15-20 °C overnight, after which filtration was performed and the filtrate collected. The solid residue was washed with acetone. The acetone layer was concentrated to dryness. The resultant was dissolved in water and acidified with concentrated hydrochloric acid to precipitate out the product, followed by washing with water to collect the yellow solid. The solid was dissolved in 350 mL of hexane and the solution was dried with magnesium sulfate and filtered. The organic solution was cooled to allow the product to precipitate as yellow flakes. The final yield was 85%.

References

[1] Patent: US2004/73056, 2004, A1. Location in patent: Page 21
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 16, p. 3573 - 3586
[3] Chemical Communications, 2014, vol. 50, # 68, p. 9722 - 9724
[4] Soft Matter, 2011, vol. 7, # 22, p. 10763 - 10772
[5] Macromolecules, 2012, vol. 45, # 12, p. 4966 - 4977

2-(DODECYLSULFANYLTHIOCARBONYLSULFANYL)-2-METHYLPROPIONIC ACID(461642-78-4)Related Product Information

• Triphenyl phosphate
• sodium trithiocarbonate
• 2-(DODECYLSULFANYLTHIOCARBONYLSULFANYL)-2-METHYLPROPIONIC ACID
• diethyl trithiocarbonate