Diethyl dibutylmalonate Chemical Properties

Boiling point:

150 °C12 mm Hg(lit.)

Density 

0.945 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.433(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Almost colorless

BRN 

518421

Stability:

Stable. Incompatible with bases, strong oxidizing agents. Combustible.

InChI

InChI=1S/C15H28O4/c1-5-9-11-15(12-10-6-2,13(16)18-7-3)14(17)19-8-4/h5-12H2,1-4H3

InChIKey

WHKKUUPZLWUOIW-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(CCCC)(CCCC)C(OCC)=O

CAS DataBase Reference

596-75-8(CAS DataBase Reference)

NIST Chemistry Reference

Propanedioic acid, dibutyl-, diethyl ester(596-75-8)

EPA Substance Registry System

Propanedioic acid, dibutyl-, diethyl ester (596-75-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

TSCA 

Yes

HS Code 

29153900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diethyl dibutylmalonate Usage And Synthesis

Chemical Properties

colourless liquid

Application

Diethyl dibutylmalonate can be used to prepare Guerbet acid. Guerbet acid is a fatty acid with a long branched alkane at the α position of the carboxylic acid. Compared with straight-chain fatty acids with the same carbon number, it has the characteristics of being colorless and odorless, having almost no adverse effects on the human body, having a low freezing point, and having low irritation. It is widely used in industrial lubricants, metalworking fluids, cosmetics, surfactants and additives.

Synthesis

Under nitrogen protection, 100 g of diethyl malonate and 300 ml of anhydrous ethanol were added to a 1000 ml three-necked round bottom flask. 40.5 g of sodium methanol was slowly added at room temperature followed by dropwise addition of 102.8 g of n-bromobutane. The reaction mixture was heated to reflux for 3 hours. Upon completion of the reaction, the reaction was cooled to room temperature, 40.5 g of sodium methanol was added again and 102.8 g of n-bromobutane was added slowly dropwise and the reaction was continued to be heated and refluxed for 3 hours. At the end of the reaction, cooled to room temperature and removed the solvent under reduced pressure. The pH of the reaction system was adjusted to 7 with 1 mol/L aqueous sulfuric acid, and the organic phase was separated and washed with appropriate amount of water. Finally, diethyl di-n-butylmalonate was purified by distillation under reduced pressure to yield 154 g (90.6% yield).

References

[1] Patent: CN106748724, 2017, A. Location in patent: Paragraph 0024
[2] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6379 - 6388
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1992, # 18, p. 2679 - 2684

Diethyl dibutylmalonate(596-75-8)Related Product Information

• Malonic acid
• Diethyl phenylmalonate
• Diethyl ethylmalonate
• Diethyl butylmalonate
• Methyl acrylate
• DIETHYL DIMETHYLMALONATE
• Diethyl ketomalonate
• Dimethyl malonate
• Diethyl isopropylmalonate
• Diethyl bis(hydroxymethyl)malonate
• Tris(trimethylsilyl)phosphate
• Diethyl dipropylmalonate
• Diethyl malonate
• DIETHYL DIETHYLMALONATE
• BUTYL OLEATE
• Diethyl methylmalonate
• Diethyl allylmalonate
• Diethyl ether