2-Amino-2-methyl-1-propanol

Industrial uses

Because 2-Amino-2-methyl-1-propanol has the advantages of excellent absorption and desorption capacity, high loading capacity, and low replenishment cost. AMP is one of the promising amines considered for usage in the industrial scale post-combustion CO2 capture technology[1]. At present, there are a large number of studies on the performance of 2-Amino-2-methyl-1-propanol for CO₂ adsorption. Using 2-amino-2-methyl-1-propanol (AMP) as the core adsorbent and silica as the shell, the AMP microcapsules prepared are expected to replace conventional adsorbents to achieve carbon dioxide capture in cold environments[2].

Uses

2-Amino-2-methyl-1-propanol is also used in ATR-FTIR spectroscopic investigation of the carbon monoxide absorption characteristics of a series of heterocyclic diamines.

General Description

A clear light colored liquid. Insoluble in water and about the same density as water. Flash point 172°F. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Amino-2-methyl-1-propanol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion.

Health Hazard

Causes severe irritation. Inhalation may be fatal as a result of spasm, inflammation, and edema of laryns and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Emits toxic fumes during fire conditions.

Safety Profile

On March 21, 2014, the Environmental Protection Agency (EPA) issued a direct final rule with a parallel proposal identifying 2-Amino-2-methyl-1-propanol (also known as AMP) as a chemical compound that it will no longer be regulated as a volatile organic compound (VOC) under the Clean Air Act. This will remove AMP from regulatory requirements related to controlling VOC emissions in order to meet the national ambient air quality standards (NAAQS) for ozone. EPA will add AMP to the list of negligibly reactive compounds in EPA’s regulatory definition of VOC.
AMP is used for pigment dispersion in water-based coatings such as house paints. Excluding this compound from the regulatory definition of VOC, facilitates access to AMP for manufacturers of water-based coatings in order to meet VOCs limits without impairing the performance of their products or using other more toxic chemicals.

Synthesis

The synthesis of 2-Amino-2-methyl-1-propanol is as follows:

In a 1L three-neck flask with mechanical stirring, first add 200ml of water, add a few drops of dilute sulfuric acid to make it slightly acidic (pH=3.5-4), then heat to 40-50, and start adding 99.0 at the same time. 2,2-Dimethylaziridine and 400ml dilute sulfuric acid aqueous solution, keep the temperature and slightly acidic condition, drop 2,2-dimethylaziridine, then continue to react at this temperature 1h, then under reduced pressure distillation to remove 80% of the water, add 500ml ethanol to the obtained system, neutralize with 30% sodium hydroxide to pH=9.5-10, filter and remove the salt, the obtained filtrate is distilled out of ethanol under normal pressure , And then distilled under reduced pressure to obtain crude 2-amino-2-methyl-1-propanol. This crude product is then rectified to obtain 112.9g 2-amino-2-methyl-1-propanol refined product with a yield of about 91.0%, chromatographic purity is about 99.4%.

Purification Methods

Purify it by distilling and fractional freezing. The hydrochloride has m 204o-206o. [Beilstein 4 III 783, 4 IV 1740.]

References

[1] Tan W, et al. Atmospheric Chemistry of 2-Amino-2-methyl-1-propanol: A Theoretical and Experimental Study of the OH-Initiated Degradation under Simulated Atmospheric Conditions. The Journal of Physical Chemistry A, 2021; 125: 7502–7519.[2] Rama ;S, et al. Encapsulation of 2-amino-2-methyl-1-propanol with tetraethyl orthosilicate for CO2 capture. Frontiers of Chemical Science and Engineering, 2019; 13: 672–683.