Identification

Product Name:    4-Methylmorpholine

Synonyms:    NMM;N-Methyl morphofine;N-METHYLMORPHOLINE;4-METHYL-1-OXA-4-AZACYCLOHEXANE;4-METHYLMORPHOLINE;AKOS 89985;LUPRAGEN(R) N 105;1-Methylmorpholine    

CAS:    109-02-4    

MF:    C5H11NO    

MW:    101.15    

EINECS:    203-640-0   

Properties

Melting point     ?66 °C(lit.)   

Boiling point     115-116 °C750 mm Hg(lit.)   

Density     0.92 g/mL at 25 °C(lit.)   

Vapor density     >1 (vs air)   

Vapor pressure     18 mm Hg ( 20 °C)   

Refractive index     n20/D 1.435(lit.)   

Fp   75 °F   

Storage temp.     Store at RT.    

Pka  7.38(at 25℃)    

Form  Liquid    

Specific Gravity    0.920 (20/4℃)    

Color  Clear    

PH 10.6 (50g/l, H2O, 20℃)    

Explosive limit    2.1%(V)    

Water Solubility     >500 g/L (20 oC)    

N-methyl morpholine is an important fine chemical product. It is an excellent solvent, emulsifier, corrosion inhibitor, polyurethane foam catalyst, can also be used as pesticide intermediates. It is also used in the synthesis of fine chemical products such as surface active agent, lubricating oil coolant, metal rust inhibitor, fiber treatment agent and so on.

Application

As an organic chemical intermediate, N-methylmorpholine has the dual properties of tertiary amine and ether. It can be used as surfactant, extractant and corrosion inhibitor, and is also widely used in the fields of pesticide and medicine. N-methylmorpholine is a heterocyclic tertiary amine with the properties of ether and amine. It is widely used in the synthesis of pesticide compounds such as insecticides, fungicides and plant growth regulators, as well as in the synthesis of fine chemical products such as surfactants, lubricating oil coolant, metal rust inhibitor and fiber treatment agent.

NMM is a heterocyclic tertiary amine, is an important fine chemical raw material, it can be used as a catalyst for polyurethane foam production, pharmaceutical synthesis and organic synthesis catalyst, can also be used in the synthesis of pharmaceutical, pesticide, surfactants, emulsifiers, corrosion inhibitors and other fine chemical products. It can also be used as solvent, extractant and curing agent for polyurethane coatings.

Preparation

1) Synthesis: in a four-mouth flask of 500ml, add 110g of concentrated sulfuric acid (1.1mol, 98%) slowly (control temperature does not exceed 60℃, the end of the drip within 30 minutes) to 119.16g of N-methyldiethanolamine (1mol), heat up to 160-170 ℃ for reflux reaction for 7 hours, and water is steamed out in the reaction process. After the reaction, it was cooled to room temperature to obtain the synthetic reaction solution. 

2) Ammonium salt transfer: 119.16Gn-methyldiethanolamine (1mol) was dropped into the synthetic reaction solution (the dripping time was about 30 minutes) under the stirring condition of room temperature, and then 1.19g PEG-8000(about 1% of the mass of N-methyldiethanolamine) is added, and then the temperature was raised to 60 ~ 70℃ and stirred for 30 minutes. 

3) Distillation: the ammonium salt transfer reaction solution obtained in Step 2 was distilled under reduced pressure, and the fraction was collected at 55 ~ 60℃ under -0.95MPa pressure to obtain 98.72g of N-methyl morpholine. The purity of the product is 99.9%; The yield of N-methyldiethanolamine was 97.5% based on the consumed N-ethyldiethanolamine.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Run off from fire control or dilution water may cause pollution.