3-Methylamino-1,2-propanediol Chemical Properties

Melting point:

69°C (estimate)

Boiling point:

247 °C

Density 

1.095 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.476

Flash point:

152 °C

storage temp. 

Inert atmosphere,Room Temperature

pka

14.09±0.20(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.0921

PH

11.5 (100g/l, H2O, 20℃)

Water Solubility 

miscible

BRN 

1733341

InChI

InChI=1S/C4H11NO2/c1-5-2-4(7)3-6/h4-7H,2-3H2,1H3

InChIKey

WOMTYMDHLQTCHY-UHFFFAOYSA-N

SMILES

C(O)C(O)CNC

CAS DataBase Reference

40137-22-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

2735

WGK Germany 

3

F 

3-10-34

HazardClass 

8

PackingGroup 

II

HS Code 

29221980

Toxicity

LD50 orally in Rabbit: > 2000 mg/kg

MSDS

• Language:English Provider:3-Methylamino-1,2-propanediol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Methylamino-1,2-propanediol Usage And Synthesis

Description

3-Methylamino-1,2-propanediol (MAPD) is a clear liquid with the chemical formula C₄H₁₁NO₂. It can be synthesized from allylamine and alkanolamine via a thermal process. It reacts with chloride to form methyl chloroacetate, which can then be converted into 3-methylamino-1,2-propanediol by reaction with methanol. The production process for this substance has been shown to generate low levels of hazardous substances such as polycyclic aromatic hydrocarbons (PAHs) and dioxins.

Chemical Properties

clear colorless to pale yellow viscous liquid

Uses

3-Methylamino-1,2-propanediol is a reactive compound that is used in the synthesis of organic acids. It is also used as an intermediate in the manufacture of polyethylene glycols and particle coatings.

Definition

ChEBI: 3-methylamino-1,2-propanediol is a secondary amine.

Preparation

3-Methylamino-1,2-propanediol (MAPD) is synthesized by reacting 3-chloro-1,2-propanediol (CPD) with monomethyl amine in alkaline environment by adding sodium hydroxide. Afterwards, the product undergoes a series of purification steps.  

N-Methyl-1-amino-2,3-propandiol (45A) Methylamine (172ml of a 40% solution in water, 2 mol) was cooled to 0 °C and 2,3-epoxy-1-propanol (25g, 0.34mol) was added at a rate to maintain the temperature at or below 10 °C. The mixture was stirred for 3 hours at 0 °C. Excess methylamine and water was evaporated in vacuo and the product was purified by distillation at 103-105 °C, at 0.5 mm Hg, to give the compound 3-Methylamino-1,2-propanediol.

Hazard

3-Methylamino-1,2-propanediol is danger.
H314 (32.76%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H315 (67.24%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (65.52%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Synthesis

II, Synthesis of 3-methylamino-1,2-propanediol (1) Pressure test: the reactor is subjected to pressure test to ensure that all test indexes are qualified before use. (2) feeding: start the hydraulic vacuum pump, vacuum the autoclave to 0.03MPa, then add the raw material into the high-pressure reactor according to the ratio of glycerol and liquid monomethylamine molar ratio of 1:10. (3) Reaction conditions: the temperature of the amination reactor was raised to 50℃±5℃, the pressure was maintained at 4.1-4.2MPa, and the reaction lasted 40 minutes. (4) Monomethylamine recovery: After the reaction is completed, monomethylamine is recovered by vacuum at 0.080 MPa, and the monomethylamine recovery device is utilized to recover the monomethylamine to the storage tank for reuse. (5) Distillation and purification: (1) Primary distillation: cool the autoclave to below 30℃, transfer the reaction mixture to the distillation kettle. Start the water jet vacuum pump, pass steam heating to the jacket of the distillation kettle, control the vacuum in the kettle to 0.06~0.07MPa. When the condensate starts to flow out, switch to the high-vacuum root-water ring unit, adjust the vacuum of the receiving tank to 0.0990~0.0998MPa, and monitor the temperature of the gas phase to 98.0℃ in order to remove the pre-fraction. (2) Main fraction collection: when the distillation temperature exceeds 98.1°C, switch to the finished product condensate tank, keep the vacuum degree to 0.0990~0.0998MPa, collect the fraction with condensing vapor temperature of 98.1-101.0°C, which is the target product of 3-methylamino-1,2-propanediol. The product was a colorless transparent viscous liquid with 98.99% yield, 99.96% purity, 0.04% impurity content and 0.35% moisture content.

References

[1] Patent: CN104844463, 2016, B. Location in patent: Paragraph 0186-0200
[2] Patent: EP1201644, 2002, A2. Location in patent: Page 17-20
[3] Chemische Berichte, 1899, vol. 32, p. 752

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