4-methylmorpholine
N-Methylmorpholine
CAS: 109-02-4
Molecular Formula: C5H11NO
4-methylmorpholine - Names and Identifiers
| Name | N-Methylmorpholine |
| Synonyms | NMM AKOS 89985 LUPRAGEN(R) N 105 methyl morpholine 1-Methylmorpholine 4-METHYLMORPHOLINE N-METHYLMORPHOLINE 4-methylmorpholine N-Methylmorpholine N-methyl morpholine N-Methyl morphofine 4-methylmorpholin-4-ium 4-Methyl-1-oxa-4-azacyclohexane 4-METHYL-1-OXA-4-AZACYCLOHEXANE 4-methylmorpholine hydrochloride |
| CAS | 109-02-4 |
| EINECS | 203-640-0 |
| InChI | InChI=1/C5H11NO/c1-6-2-4-7-5-3-6/h2-5H2,1H3/p+1 |
| InChIKey | SJRJJKPEHAURKC-UHFFFAOYSA-N |
4-methylmorpholine - Physico-chemical Properties
| Molecular Formula | C5H11NO |
| Molar Mass | 101.15 |
| Density | 0.92g/mLat 25°C(lit.) |
| Melting Point | −66°C(lit.) |
| Boling Point | 115-116°C750mm Hg(lit.) |
| Flash Point | 75°F |
| Water Solubility | >500 g/L (20 ºC) |
| Vapor Presure | 18 mm Hg ( 20 °C) |
| Vapor Density | >1 (vs air) |
| Appearance | Liquid |
| Specific Gravity | 0.920 (20/4℃) |
| Color | Clear |
| Merck | 14,6277 |
| BRN | 102719 |
| pKa | 7.38(at 25℃) |
| PH | 10.6 (50g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 2.1%(V) |
| Refractive Index | n20/D 1.435(lit.) |
| Physical and Chemical Properties | Liquid with corrosive properties, slight toxicity and pungent odor, colorless transparent liquid viscosity (23 ℃) 2.3mPa · s boiling range 111~117 ℃ freezing point -65 ~-66 ℃ refractive index (20 ℃) 1.4328~1.4337 vapor pressure (20 ℃) 2200Pa solubility in water, pKa = 7.5. Explosion limit of 2.2% ~ 11.8% in air, soluble in organic solvents, miscible with water and ethanol |
| Use | This product is soluble in water, alcohol, ether, can be used as a solvent for rayon, corrosion inhibitors, but also for the synthesis of rubber accelerators and other fine chemicals, also used as a polyurethane catalyst, catalysts for the synthesis of aminobenzylpenicillin and hydroxypenicillin. N-methylmorpholine oxide can be produced by double oxidation. |
4-methylmorpholine - Risk and Safety
| Risk Codes | R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R34 - Causes burns R10 - Flammable R22 - Harmful if swallowed |
| Safety Description | S16 - Keep away from sources of ignition. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S25 - Avoid contact with eyes. |
| UN IDs | UN 2535 3/PG 2 |
| WGK Germany | 1 |
| RTECS | QE5775000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29349990 |
| Hazard Class | 3 |
| Packing Group | II |
| Toxicity | LD50 orally in Rabbit: 1960 mg/kg LD50 dermal Rabbit 1240 mg/kg |
4-methylmorpholine - Nature
Open Data Verified Data
colorless transparent liquid. Has a special odor. Melting Point -65 °c. Boiling point 114 °c. The relative density was 0.919. Viscosity 0.90mPa.s(20 degrees C). Vapor pressure (20 °c) 2.213kPa. Soluble in organic solvents, miscible with water and ethanol.
Last Update：2025-06-10 22:55:16
4-methylmorpholine - Preparation Method
Open Data Verified Data
formaldehyde and then formic acid were slowly added dropwise to morpholine, and during the reaction, reflux was performed automatically, and CO2 was released. Formic acid is added, heated and refluxed for 4-5 hours, then cooled, and immediately distilled by adding NaOH to collect all fractions before boiling point 99 °c, and then NaOH is added to the distillate until saturation, cooling, separation of the oil layer, drying, fractionation, collection of boiling point 114.5~117 C fraction is the finished product.
Last Update：2022-01-01 10:53:25
4-methylmorpholine - Application
Open Data Verified Data
This product is mainly used as a solvent, Catalyst, corrosion inhibitor; Also used for rubber vulcanization accelerator and other fine chemicals synthesis, also used as polyurethane plastic foaming catalyst, catalysts for the synthesis of aminobenzylpenicillin and carboxy benzylpenicillin.
can be produced by oxidation with hydrogen peroxide
N-methyl morpholine oxide. Recently, with N-methyl morpholine oxide as solvent, a "new technology for preparing synthetic fiber by solvent" has been developed abroad, which will open up broad prospects for the application of N-methyl Morpholine.
Last Update：2025-08-19 16:24:40
4-methylmorpholine - Safety
Open Data Verified Data
- when the drug is administered to an animal by any route, short-term excitation occurs, and then changes to inhibition and atrophy. Inhalation of this product vapor, there are stimulation of the mucosa, so that animals appear spasm. This product poisoning caused by the organization to change the liver, kidney malnutrition phenomenon. Mice inhaled 2 hours, its LC50 a 25.2 mg/L. Rats were fed with LD50 1.97mg/kg. According to the change of the sum capacity of the central nervous system, the threshold concentration of the primary effect was 0. 09~0.1 mg/L. The threshold concentration of stimulation in humans was 0.2 mg/L. Irritation of the skin as
- used as 1.5/2 of Morpholine. The maximum allowable concentration in air is 5 mg/m3.
- This product is toxic and has a stimulating effect on human skin and mucous membranes. The production workshop should be well ventilated and the equipment should be closed. The operator should wear protective gear. See morpholine (D 059).
- tightly sealed in glass bottles or ceramic cans, jacket barrel packaging. Store in a cool, dry and ventilated place. Sunscreen, moisture, away from fire, heat source. Light loading and light unloading should be carried out to avoid package breakage. According to the provisions of the storage and transportation of toxic chemicals.
Last Update：2022-01-01 10:53:26
4-methylmorpholine - Reference Information
| LogP | -0.32 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | N-methylmorpholine 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 surfactants, lubricating oil coolants, metal rust inhibitors and fiber treatment agents. N-methyl morpholine is an important organic chemical intermediate. It is an excellent solvent, emulsifier, corrosion inhibitor, polyurethane foam catalyst, and can also be used as pesticide intermediate. The synthesis method mainly includes N-methylation method using morpholine as raw material, ring method using diethanolamine as raw material, the ring method using diethanolamine as raw material and the synthesis method using dichloroethane as raw material, etc. |
| Application | N-methyl morpholine, as an organic chemical intermediate, has the dual properties of tertiary amine and ether, can be used as surfactants, extractants, corrosion inhibitors, but also widely used in the field of pesticides and pharmaceuticals. N-methyl morpholine is a heterocyclic tertiary amine, with the properties of ether and Amine, widely used in the synthesis of pesticides, fungicides, plant growth regulators and other pesticide compounds, but also for surfactants, lubricating oil coolant, synthesis of fine chemical products such as metal rust inhibitors and fiber treatment agents. NMM is a kind of heterocyclic tertiary amine, which is an important fine chemical raw material. It can be used as a catalyst for polyurethane foam production, pharmaceutical synthesis and organic synthesis, can also be used for the synthesis of pharmaceuticals, pesticides, surfactants, emulsifiers, corrosion inhibitors and other fine chemical products, can also be used as solvents, extractants and polyurethane coating curing agents. |
| preparation | when 87g of morpholine is added to a ML three-head bottle with a reflux condenser tube and an electric stirrer, while stirring, a mixture of 57.7g of sodium dihydrogen phosphite and 36g of polyoxymethylene is added, and reflux occurs when the temperature reaches 115 ° C. The reaction is maintained at the temperature for 20min, and then cooled, the solid was separated by filtration to give a filtrate as a product, which was directly distilled without drying, and a fraction at 114-117 ° C. Was collected to obtain 95g of N-methylmorpholine, which was 98% pure by gas chromatography. 1) synthesis: in a 1.1 ml Four-necked flask, 110g of concentrated sulfuric acid (98% mol,) was slowly added dropwise (the temperature was controlled not to exceed 60 ℃, at the end of the dropwise addition in about 30 minutes) to 119.16G of N-methyldiethanolamine (1mol), heated to 160~170 ° C. Reflux reaction for 7 hours, Water was distilled off during the reaction. After completion of the reaction, the reaction mixture was cooled to room temperature to obtain a synthesis reaction solution. 2), ammonium salt transfer: under the condition of stirring at room temperature, 119.16gN-methyl diethanolamine (1mol) Dropwise into (dropping time is about 30 minutes) synthesis reaction liquid, then, 1.19g of PEG-8000 (about 1% of the mass of N-methyldiethanolamine) was added, followed by heating to 60-70 ° C. And stirring for 30 minutes. 3) distillation: the ammonium salt transfer reaction solution obtained in step 2) is subjected to vacuum distillation, and the fraction at 55~60 ° C. Is collected at a pressure of -0.95MPA, 98.72g of N-methylmorpholine was obtained. The purity of the product was 99.9%; The yield was 97.5% based on the consumption of N-methyldiethanolamine. |
| Application | used as solvent, Catalyst, emulsifier, organic synthesis intermediate, etc. Used in organic synthesis and pharmaceutical industry, N-methylmorpholine (NMM) is also used as a gas chromatographic stationary liquid. for the production of extraction solvents, stabilizers of chlorinated hydrocarbons, corrosion inhibitors, catalysts and drugs. pharmaceutical and chemical synthesis Media organic synthesis raw materials, Analytical reagents, extraction solvents, stabilizers of chlorinated hydrocarbons, corrosion inhibitors, catalysts, drug production, etc. NMM is soluble in water, alcohol and ether, and can be used as a solvent and corrosion inhibitor for rayon, as well as for the synthesis of rubber accelerators and other fine chemicals, and as a polyurethane catalyst, catalysts for the synthesis of aminobenzylpenicillin and hydroxypenicillin. N-methylmorpholine oxide can be produced by double oxidation. N-methyl morpholine (NMM) is used as a catalyst, an extractant, a stabilizer for chlorinated hydrocarbons, a corrosion inhibitor, an analytical reagent and a pharmaceutical product. extraction solvents, catalysts, corrosion inhibitors, Analytical reagents and pharmaceutical manufacturing, etc. |
| production method | from the reaction of morpholine with formaldehyde, formic acid. Formaldehyde was slowly added to morpholine, and formic acid was added dropwise with stirring. The reaction was automatically refluxed and carbon dioxide was evolved. After completion of the addition of formic acid, it was heated to reflux for 4-5H. After cooling, sodium hydroxide is added and immediately distilled to collect all fractions below 99 ° C., sodium hydroxide is added to saturation, the oil layer is separated by cooling, dried and fractionated, and the 114.5-117 ° C. Fraction is collected as the finished product. The other method uses dichloroethyl ether, methylamine aqueous solution, liquid alkali and other raw materials for one-step synthesis, with short process, simple equipment, mild process conditions, less dosage, high product yield and good quality. The preparation method is to slowly add formaldehyde Dropwise to morpholine, add formic acid Dropwise under stirring to react, automatically reflux, and release carbon dioxide. After formic acid is added, the mixture is heated and refluxed for 4-5H. After cooling, sodium hydroxide is added for immediate distillation to collect all fractions before the boiling point of 99 ℃, drying and fractionation gave the product. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 1960 mg/kg; Oral-mouse LD50: 1970 mg/kg |
| stimulation data | eyes-rabbits 920 MCG severe; Skin-rabbits 460 mg mild |
| flammability hazard characteristics | in case of fire, high temperature, oxidant flammable; toxic NOx smoke from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; Stored separately from oxidants and acids |
| extinguishing agent | dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent |
| Occupational Standard | TWA 20 mg/m3; Tel 40 mg/m3 |
| autoignition temperature | 165°C DIN 51794 |
Last Update：2024-04-09 20:49:11
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