basf238
Morpholine
CAS: 110-91-8;138048-80-3
Molecular Formula: C4H9NO
basf238 - Names and Identifiers
| Name | Morpholine |
| Synonyms | basf238 BASF 238 Morpholine 1,4-Oxazinan morpholin-4-ium diethylenimideoxide Diethylenimide oxide morpholine sigmaultra tetrahydro-1,4-oxazine 1,4-oxazine,tetrahydro- Tetrahydro-2H-1,4-oxazine 2H-1,4-Oxazine, tetrahydro- 4H-1,4-Oxazine, tetrahydro- Morpholine-2,2,3,3,5,5,6,6-d8 |
| CAS | 110-91-8 138048-80-3 |
| EINECS | 203-815-1 |
| InChI | InChI=1/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2/p+1 |
| InChIKey | YNAVUWVOSKDBBP-UHFFFAOYSA-N |
basf238 - Physico-chemical Properties
| Molecular Formula | C4H9NO |
| Molar Mass | 87.12 |
| Density | 0.996 g/mL at 25 °C (lit.) |
| Melting Point | -7--5 °C (lit.) |
| Boling Point | 126.0-130.0 °C129 °C (lit.) |
| Flash Point | 96°F |
| Water Solubility | MISCIBLE |
| Solubility | water: miscible |
| Vapor Presure | 31 mm Hg ( 38 °C) |
| Vapor Density | 3 (vs air) |
| Appearance | Liquid |
| Specific Gravity | 0.996 |
| Color | APHA: ≤15 |
| Exposure Limit | TLV-TWA 20 ppm (～70 mg/m3) (ACGIH,MSHA, and OSHA); STEL skin 30 ppm(ACGIH); IDLH 8000 ppm. |
| Merck | 14,6277 |
| BRN | 102549 |
| pKa | 8.33(at 25℃) |
| PH | 11.2 (H2O)(undiluted) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides. Hygroscopic. |
| Sensitive | Hygroscopic |
| Explosive Limit | 1.4-15.2%(V) |
| Refractive Index | n20/D 1.454(lit.) |
| Physical and Chemical Properties | Appearance and properties of colorless oily liquid, ammonia flavor melting point -4.6 ℃ Boiling Point: 128.4 ℃ density relative density (water = 1)1.00; Relative density (Air = 1)3.0 vapor pressure 0.93kPa/20 ℃ Flash point: 35 ℃ refractive index 1.4545 solubility miscible with water, miscible with most organic solvents |
| Use | The main raw materials of accelerator NOBS are used as analytical reagents and resins, waxes, shellac and other solvents for the production of sodium sulfate, water glass and ultramarine. It is also used in the manufacture of glass, paper, detergent, soap, dye, synthetic fiber, leather, pharmaceutical and ceramic industries. Analytical reagents, such as nitrogen determination, dehydrating agents. |
basf238 - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R10 - Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R34 - Causes burns |
| Safety Description | S23 - Do not breathe vapour. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2054 8/PG 1 |
| WGK Germany | 3 |
| RTECS | QD6475000 |
| TSCA | Yes |
| HS Code | 2934 99 90 |
| Hazard Class | 8 |
| Packing Group | I |
| Toxicity | LD50 orally in female rats: 1.05 g/kg (Smyth) |
basf238 - Nature
Open Data Verified Data
colorless oily liquid with ammonia odor. Strong alkaline, soluble in general organic solvents (acetone, ethylene glycol, ether, oil, etc.), can be evaporated with water vapor, and form an azeotropic mixture with water, after high heat can be decomposed into N2O. In case of open flame, high heat or contact with oxidant, there is a risk of combustion explosion. Corrosion of aluminum, copper, lead, tin and its alloys, corrosion of certain plastics, rubber and coatings.
Last Update：2024-01-02 23:10:35
basf238 - Preparation Method
Open Data Verified Data
obtained by reacting diethylene glycol with ammonia in the presence of hydrogen and a nickel catalyst at an atmospheric pressure of 30 to 40MPa and a temperature of 150 to 400 °c. Alternatively, it is prepared by the reaction of diethanolamine with an excess of concentrated hydrochloric acid (or concentrated sulfuric acid).
Last Update：2022-01-01 09:30:25
basf238 - Safety
Open Data Verified Data
female rat LD50:1.05g/kg. Ingestion or inhalation can cause poisoning. Inhalation of this product vapor or fog strong corrosion of respiratory mucosa, can cause bronchitis, Pneumonia, pulmonary edema. The allowable concentration in air is 70mg/m3 in the United States. Work clothes should be worn during operation. If contact with eyes or skin, rinse with water immediately. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Keep the container sealed. Should not be large or long-lived. Should be stored separately from the oxidant.
Last Update：2022-01-01 09:30:26
basf238 - Uses and synthesis methods
Solubility
can be miscible with water in any proportion, easily soluble in aromatic hydrocarbons, alcohols, ketones, ethers and organic solvents, slightly soluble in mineral oil and aliphatic hydrocarbons, with slight toxicity.
application
Morpholine occupies an important position in chemical production and is an intermediate for manufacturing many fine chemical products, it can be used to prepare NOBS(N-oxodiethylene-2-benzothiazolimesulfonamide), OTOS(N-oxodiethylenethiocarbamoyl-N-oxodiethylenesulfothionamide) and other rubber vulcanization accelerators and rust inhibitors, preservatives, cleaners, descaling agents, analgesics, local anesthetics, fruit preservatives, textile printing and dyeing auxiliaries, etc, it is widely used in rubber, medicine, pesticide, dye, coating and other fields. Morpholine contains secondary amine groups and has all the typical reaction characteristics of secondary amine groups. Reacts with inorganic acids to form salts, and reacts with organic acids to form salts or amides. It can carry out alkylation reaction, reaction with ethylene oxide, ketone or Wiiigerodt reaction. Due to its chemical properties, morpholine has become one of the fine petrochemical products with important commercial applications. In addition, morpholine is also an important organic solvent.
Last Update：2024-04-09 15:16:18
basf238 - Reference Information
| freezing point | -4.9 ℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 47, 71) 1999 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Product characteristics | morpholine, also known as 1, 4-oxazane, diethylene imine oxide, colorless alkaline oily liquid, ammonia odor and hygroscopicity, with water vapor evaporation, miscible with water, soluble in acetone, benzene, ether, pentane, methanol, ethanol, carbon tetrachloride, propylene glycol and other organic solvents. The vapor and air form an explosive mixture, and the explosion limit is 1.8% ~ 15.2% (volume fraction). Morpholine is a secondary amine, but also has the properties of inorganic acid and organic acid, can produce salts and amides. Morpholine contains a secondary amine group with all the typical reaction characteristics of the secondary amine group. The reaction with an inorganic acid to form a salt and the reaction with an organic acid to form a salt or amide can be carried out by alkylation, by reaction with ethylene oxide, a ketone, or by wilgerodt. Due to its unique chemical properties, morpholine has become one of the fine petrochemical products with important commercial uses, which can be used to prepare NOBS, DTOS, MDS and other rubber vulcanization accelerators, rust inhibitors, corrosion inhibitors, detergents, detergents, detergents, analgesics, local anesthetics, sedatives, respiratory and vascular stimulants, surfactants, optical bleaching agents, fruit preservatives, textile printing and dyeing auxiliaries, in rubber, medicine, pesticides, dyes, coatings and other industries have a wide range of uses, medicine for the production of moroxydine, Virazole, ibuprofen, cough must, naproxen, dichloroaniline, sodium phenylacetate and other important drugs. Foreign polymer in recent years, the rapid development of new monomer acrylic acid morpholine is also worth noting. Acrylic Acid morpholine is obtained by the reaction of acrylic acid ester and morpholine, the product is a water-soluble monomer, which is also water-soluble after polymerization, so it is used for the modification of water-based polymers; in addition, a large number of reactive diluents for ultraviolet curing resin; With the deepening of the application research, Many new specific applications have been developed as a very rapidly evolving polymer monomer. Figure 1 is the structural formula of morpholine |
| metal corrosion inhibitor | as a metal corrosion inhibitor, morpholine is mainly used for corrosion prevention of iron, copper, zinc, lead and other metals, china is currently in its infancy, a considerable proportion of foreign metal gas rust inhibitor, to prevent metal corrosion by the atmosphere, and has been widely used in mechanical instruments, automobiles, medical equipment and other fields, the early use of metal atmospheric rust inhibitors dicyclohexylamine nitrite and cyclohexylamine carbonate is toxic to human body and the environment, and morpholine as a metal gas-liquid corrosion inhibitor has the advantage of low toxicity and good development prospects. |
| Rubber vulcanization accelerator | before the 90 s of the 20th century, the consumption of rubber vulcanization accelerators in developed regions such as Europe, America and Japan accounted for more than 50% of the total demand for Morpholine, at present, more than 30% of China's consumption is used for NOBS. In recent years, more and more attention has been paid to the toxicity of accelerators that are easy to produce harmful nitrosamines in the process of rubber processing. Many restrictive regulations have been introduced in the world. For example, Germany promulgated regulations to control the content of nitrosamines as early as 1982, japan, France, and the United Kingdom are actively developing new vulcanization accelerators that do not produce nitrosamines, and have successively stopped using vulcanization accelerators that produce nitrosamines. Therefore, the consumption of morpholine in foreign countries decreased year by year with the disabling of NOBS. Although China does not have the corresponding regulations to disable the accelerator NOBS, but China has joined the WTO, due to the large number of foreign tires to enter, the required additives localization, but also requires China's rubber vulcanization accelerator environmental protection, the use of non-toxic accelerators in place of NOBS has become a general trend. In recent years, the demand for NOBS in China is significantly reduced. At present, China will not use the secondary amine accelerator which can decompose nitrosamines. As the main substitute for NOBS, NS (n-tert-butyl-2-benzothiazole sulfenamide), which does not produce nitrosamines, has formed a large production capacity of 14,000 t in 2005years, it accounts for 10.1% of the total accelerator, and the development trend is good. |
| preparation | morpholine is industrially prepared by dehydrating diethanolamine with sulfuric acid. |
| content analysis | 4 parts of methanol solution of 0.1% bromocresol green and 1 part of aqueous solution of 0.1% methyl red sodium salt were mixed, as a mixed indicator. A 0.4ml flask was filled with 50 ml of water, 0.1 ml of the above mixed indicator was added, and moI/L hydrochloric acid was added dropwise to neutralize to a green color. Accurately weigh 1.4-1.6g of sample, add to the flask, and mix. Titrated to green with 0.5mol/L hydrochloric acid. Per ml,0.5mol/L hydrochloric acid is equivalent to 43.56mg of C4H9NO. |
| toxicity | LD501050mg/kg (rat, oral). |
| purpose | , raw materials of rubber accelerator and fluorescent brightener morpholine is an intermediate of the bactericide dimethomorph, flumorph and organophosphate insecticide. It is mainly used in the production of rubber vulcanization accelerators, and also used in the synthesis of surfactants, Textile Auxiliaries, pharmaceuticals and pesticides. Morpholine is also used as a catalyst for the polymerization of butadiene, corrosion inhibitor, optical bleach, this product is also a dye, resin, wax, early glue, casein and other solvents. At present, the world production of morpholine is 3-40,000 t/a. Morpholine salts are also widely used, morpholine hydrochloride (10024-89-2) is the intermediate of organic synthesis; Morpholine fatty acid salt can be used as fruit or melon fruit vegetable skin coating agent, can properly inhibit the respiratory function, prevent the evaporation of water and atrophy of the epidermis. The main raw materials of accelerator NOBS are used as analytical reagents and solvents for resins, waxes, shellac, etc., for the production of sodium sulfate, water glass and ultramarine. It is also used in the manufacture of glass, paper, detergent, soap, dye, synthetic fiber, leather, pharmaceutical and ceramic industries. Analytical reagents, such as nitrogen determination, dehydrating agents. Solvents used as analytical reagents and resins, waxes, casein, shellac and various dyes morpholine reacts with inorganic acid to form salt, and reacts with organic acid to form salt or amide. The alkylation reaction may be performed, and the reaction with ethylene oxide, a ketone, or the wilgerodt reaction may be performed. |
| production method | is obtained by dehydration-cyclization of diethanolamine with sulfuric acid. Diethanolamine was added to the water reaction pot, and sulfuric acid was added dropwise below 60 °c. After addition, the temperature was raised at 185-195 °c for 30min. Cool to below 60 ℃, Dropwise add sodium hydroxide solution to pH = 11, cool, filter, filtrate distillation, collect the fraction below 130 ℃, the refined morpholine content can reach more than 99.5%. The raw materials of this method are easy to obtain, and it has become the main method for the production of morpholine in the world. Morpholine can be obtained by the phase catalytic reaction of dioxane and ammonia. The preparation method is obtained by dehydration cyclization of diethanolamine in the presence of sulfuric acid. Diethanolamine was added into the reaction Pan, H2SO4 was added dropwise below 60 ℃, and the temperature was increased to 185~195 ℃ for 30min, cooled to 60 ℃, and NaOH solution was added dropwise, pH = 11, cooling filtration, filtrate distillation, collecting 130 deg C below the fraction is Morpholine. Morpholine can also be prepared using diethylene glycol and ammonia in the presence of a catalyst and under pressure. The raw material of this method is easy to obtain, and it has become the main method for producing morpholine in the world. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 1050 mg/kg; Oral-mouse LD50: 525 mg/kg |
| stimulation data | Skin-rabbits 995 mg/24 h severe; eye-rabbit 2 mg severe |
| explosive hazard characteristics | mixture of vapor and air can be exploded |
| flammability hazard characteristics | flammable; Toxic chloride gas from combustion |
| storage and transportation characteristics | warehouse ventilation and drying at low temperature; Anti-Flame, friction, Spark, separate from oxidant |
| extinguishing agent | dry powder, carbon dioxide, foam, water mist |
| Occupational Standard | TLV-TWA 70 mg/m3; Tel 105 mg/m3 |
| spontaneous combustion temperature | 590 ° F. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-and health-threatening concentrations | 1,400 ppm [10% LEL] |
Last Update：2024-04-09 15:16:44
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