Morpholine
Title: Morpholine
CAS Registry Number: 110-91-8
Additional Names: Tetrahydro-2H-1,4-oxazine; tetrahydro-1,4-oxazine; diethylene oximide; diethylene imidoxide
Molecular Formula: C4H9NO
Molecular Weight: 87.12
Percent Composition: C 55.15%, H 10.41%, N 16.08%, O 18.36%
Literature References: Prepd by dehydrating diethanolamine: Knorr, Ann. 301, 1 (1898); Jones, Burns, J. Am. Chem. Soc. 47, 2966 (1925); Hampton, Pollard, ibid. 58, 2338 (1936). Toxicity study: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 10, 61 (1954). Review of morpholine and derivatives: A. L. Wilson, Ind. Eng. Chem. 27, 867-871 (1935). Monograph: Morpholine Technical Bulletin, Jefferson Chemical Co. (New York, 1953).
Properties: Mobile, hygroscopic liquid. Characteristic amine odor. mp -4.9°. bp760 128.9°; bp6 20.0°. d420 1.007. nD20 1.4540. Volatile with steam. Does not form an azeotrope with water. Flash pt, open cup: 100°F (38°C). Surface tension (20°): 37.5 dynes/cm. Viscosity (20°): 2.23 cP. Dipole moment 1.58. Strong base, pKb 5.6. Immiscible with concd NaOH solns. Miscible with water with evolution of some heat, with acetone, benzene, ether, castor oil, methanol, ethanol, ethylene glycol, 2-hexanone, linseed oil, turpentine, pine oil. Will dissolve 109% dimethylamine; 34% trimethylamine; 33% methylamine; >5% naphtha; <1% paraffin oil; <5% sulfur. LD50 orally in female rats: 1.05 g/kg (Smyth).
Melting point: mp -4.9°
Boiling point: bp760 128.9°; bp6 20.0°
Flash point: Flash pt, open cup: 100°F (38°C)
pKa: pKb 5.6
Index of refraction: nD20 1.4540
Density: d420 1.007
Toxicity data: LD50 orally in female rats: 1.05 g/kg (Smyth)
 
Derivative Type: Hydrochloride
Molecular Formula: C4H9NO.HCl
Molecular Weight: 123.58
Percent Composition: C 38.88%, H 8.16%, N 11.33%, O 12.95%, Cl 28.69%
Properties: Crystals, dec 175-176°. Sol in water.
 
Derivative Type: Salicylate
CAS Registry Number: 147-90-0
Trademarks: Retarcyl (Delagrange); Deposal (Benvegna)
Molecular Formula: C11H15NO4
Molecular Weight: 225.24
Percent Composition: C 58.66%, H 6.71%, N 6.22%, O 28.41%
Properties: Crystals from ethanol, mp 110-111°. Soluble in water, methanol, ethanol, ethyl acetate, acetone, benzene, chloroform. Practically insol in toluene, xylene, petr ether, ether, carbon tetrachloride.
Melting point: mp 110-111°
 
Derivative Type: N-Methylmorpholine
Molecular Formula: C5H11NO
Molecular Weight: 101.15
Percent Composition: C 59.37%, H 10.96%, N 13.85%, O 15.82%
Properties: Mobile liquid, characteristic ammonia odor. bp764 116-117°; bp760 115.4°. d420 0.9168. nD20 1.4332. Miscible with water, alcohol, ether.
Boiling point: bp764 116-117°; bp760 115.4°
Index of refraction: nD20 1.4332
Density: d420 0.9168
 
CAUTION: Potential symptoms of overexposure to morpholine are irritation of eyes, skin, nose and respiratory system; visual disturbance; coughing. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 220.
Use: Cheap solvent for resins, waxes, casein, dyes. Morpholine fatty acid salts are used as surface-active agents and emulsifiers. Other morpholine compds are used as corrosion inhibitors, antioxidants, plasticizers, viscosity improvers, insecticides, fungicides, herbicides, local anesthetics and antiseptics.
Therap-Cat: Salicylate as analgesic; antipyretic; anti-inflammatory.

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