MORPHOLINE (CAS 110-91-8)

Morpholine (Cas 110-91-8), also known as 1, 4-oxazepine and diethylenimine oxide, is a kind of colorless alkaline oily liquid. 
Morpholine (Cas 110-91-8) smells of ammonia and has hygroscopicity. 
Morpholine (Cas 110-91-8) could evaporate with water vapor and miscible with water. 

CAS:    110-91-8
MF:    C4H9NO
MW:    87.12
EINECS:    203-815-1

Synonyms
1,4-Oxazinan;1,4-oxazine,tetrahydro-;2H-1,4-Oxazine, tetrahydro-;4H-1,4-Oxazine, tetrahydro-;BASF 238;basf238;Diethylenimide oxide;diethylenimideoxide;MORPHOLINE;110-91-8;1-Oxa-4-azacyclohexane;Diethylene oximide;Tetrahydro-1,4-oxazine;Diethylenimide oxide;Diethyleneimide oxide;Diethylene imidoxide;Drewamine;Tetrahydro-2H-1,4-oxazine;Tetrahydro-p-oxazine;p-Isoxazine, tetrahydro-;morpholin;Tetrahydro-1,4-isoxazine;BASF 238;138048-80-3;Caswell No. 584;2H-1,4-Oxazine, tetrahydro-;4H-1,4-Oxazine, tetrahydro-;NSC 9376;Tetrahydro-p-isoxazine;CCRIS 2482;HSDB 102;EINECS 203-815-1;UNII-8B2ZCK305O;EPA Pesticide Chemical Code 054701;BRN 0102549;8B2ZCK305O;DTXSID2025688;CHEBI:34856;AI3-01231;NSC-9376;MFCD00005972;C4H9NO;Tetrahydro-4H-1-4-oxazine;DTXCID305688;EC 203-815-1;4-27-00-00015 (Beilstein Handbook Reference);MORPHOLINE (IARC);MORPHOLINE [IARC];tetrahydro-14-iso-xazine;1,4-oxazinane;CAS-110-91-8;MORPHOLINE,REAG;MORPHOLINE, PRACT;UN2054;morphline;Morpholine; Molsidomine Imp. E (EP); Molsidomine Impurity E;morpho line;morpholine-;6LR;Morpholine (BASF);4H-1, tetrahydro-;MORPHOLINE [MI];Morpholine [UN2054] [Flammable liquid];MORPHOLINE [FCC];DIEYTHYLENE OXIMIDE;MORPHOLINE [HSDB];Morpholine on Rasta Resin;WLN: T6M DOTJ;NCIMech_000154;Tetrahydro-1, 4-isoxazine;NCIOpen2_007748;Oprea1_317540;Tetryhydro-2H-1,4-oxazine;Tetrahydro-4H-1,4-Oxazine;BIDD:ER0297;Morpholine, analytical standard;CHEMBL276518;NSC9376;BCP24054;STR00194;Tox21_202450;Tox21_303240;STL182843;TETRAHYDRO-2H-1, 4-OXAZINE;AKOS000118829;Morpholine, ACS reagent, >=99.0%;Morpholine, ReagentPlus(R), >=99%;DB13669;NA 2054;UN 2054;USEPA/OPP Pesticide Code: 054701;NCGC00249227-01;NCGC00256942-01;NCGC00259999-01;Morpholine, p.a., ACS reagent, 99.0%;DB-030063;Morpholine [UN2054] [Flammable liquid];M0465;NS00010190;EN300-18064;Morpholine purified by distillation from glass;Morpholine, purified by redistillation, >=99.5%;Q410243;1-Oxa-4-azacyclohexane; Tetrahydro-2H-1,4-oxazine;J-522715;1-Oxa-4-azacyclohexane ; Tetrahydro-2H-1,4-oxazine;F2190-0339;InChI=1/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H;ScavengePore(TM) phenethyl morpholine, macroporous, 40-70 mesh, extent of labeling: 0.7-1.5 mmol/g loading;StratoSpheres(TM) PL-MPH resin, 50-100 mesh, extent of labeling: 3.0-4.0 mmol/g loading, 1 % cross-linked

Morpholine (Cas 110-91-8) is Soluble in acetone, benzene, ether, pentane, methanol, ethanol, carbon tetrachloride, propylene glycol and other organic solvents. 
Morpholine (Cas 110-91-8) could form an explosive mixture with air and the explosion limit is 1.8% to 15.2% (volume fraction). 
Morpholine (Cas 110-91-8) is a secondary amine, and at the same time it has the property of inorganic acid and organic acid, so that it can generate salt and amide.
Morpholine (Cas 110-91-8) contains secondary amine groups and it has all the typical reaction characteristics of the secondary amine groups. 
Morpholine (Cas 110-91-8) can react with inorganic acid to form a salt, and also can react with organic acid to form salt or amide. 
Morpholine (Cas 110-91-8) can carry out alkylation reactions and it also carry out ketone reaction or Willgerodt reaction with ethylene oxide. 
Because of the unique chemical properties of Morpholine (Cas 110-91-8), it has become one of the important petrochemical products with important commercial application. 

Morpholine (Cas 110-91-8) can be applied to produce rubber vulcanization accelerators such as NOBS, DTOS and MDS. 
And Morpholine (Cas 110-91-8) is also applied to produce anti-corrosives, anti-corrosion agents, detergents, detergents, analgesics, local anesthetics, sedatives, respiratory and vascular stimulants, surfactants, optical bleach, fruit preservatives, and textile dyeing auxiliaries. 
Morpholine (Cas 110-91-8) also has a wide range of applications in the field of rubber, pharmaceuticals, pesticides, dyes, coatings and other industries. 
In medication Morpholine (Cas 110-91-8) could be applied in the production of morpholine guanidine, virus Ling, ibuprofen, cough must, naproxen, dichloroaniline, sodium phenylacetate and other important drugs.
The two main production method of Morpholine (Cas 110-91-8) are DEA method (diethanolamine method) and DEA method (diethylene glycol method)
Morpholine (Cas 110-91-8) is noteworthy that new polymer monomer acrylic morpholine has obtained a rapid development in recent years. 
Morpholine (Cas 110-91-8) could be produced from the reaction between acrylic acid and morpholine. 
And Morpholine (Cas 110-91-8) is a kind of water-soluble monomer, and it is still water-soluble after the polymerization. 

So Morpholine (Cas 110-91-8) could be applied for the modification of aqueous polymers. 
Besides, Morpholine (Cas 110-91-8) is widely used as a reactive diluent for UV curable resins. 
With the deepening of applied research, many new specific uses have been developed and Morpholine (Cas 110-91-8) becomes polymer monomer with rapid development.
Morpholine (Cas 110-91-8) is an organic heteromonocyclic compound whose six-membered ring contains four carbon atoms and one nitrogen atom and one oxygen atom that lies opposite to each other; the parent compound of the morpholine family. 
Morpholine (Cas 110-91-8) is a saturated organic heteromonocyclic parent and a member of morpholines. 
Morpholine (Cas 110-91-8) is a conjugate base of a morpholinium.
Morpholine (Cas 110-91-8) is an organic heteromonocyclic compound whose six-membered ring contains four carbon atoms and one nitrogen atom and one oxygen atom that lies opposite to each other; the parent compound of the morpholine family. 
Morpholine (Cas 110-91-8) has a role as a NMR chemical shift reference compound. 
Morpholine (Cas 110-91-8) is a saturated organic heteromonocyclic parent and a member of morpholines. 
Morpholine (Cas 110-91-8) is a conjugate base of a morpholinium.

Morpholine (Cas 110-91-8) is an organic chemical compound having the chemical formula O(CH2CH2)2NH. 
This heterocycle features both amine and ether functional groups. 
Because of the amine, Morpholine (Cas 110-91-8) is a base; its conjugate acid is called morpholinium. 
For example, treating Morpholine (Cas 110-91-8) with hydrochloric acid generates the salt morpholinium chloride. 
Morpholine (Cas 110-91-8) is a colorless liquid with a weak, ammonia- or fish-like odor.
The naming of Morpholine (Cas 110-91-8) is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.
Morpholine (Cas 110-91-8) is a cyclic organic compound with the chemical formula C4H9NO. 
Morpholine (Cas 110-91-8) is a colorless liquid with a distinct amine-like odor. 
Morpholine (Cas 110-91-8) is widely used in various industries, including pharmaceuticals, agrochemicals, rubber, and water treatment, due to its unique chemical properties and versatility.

Morpholine (Cas 110-91-8) Chemical Properties
Melting point: -7--5 °C (lit.)
Boiling point: 126.0-130.0 °C 129 °C (lit.)
Density: 0.996 g/mL at 25 °C (lit.)
Vapor density: 3 (vs air)
Vapor pressure: 31 mm Hg ( 38 °C)
Refractive index: n20/D 1.454(lit.)
Fp: 96 °F
Storage temp.: Store below +30°C.
Solubility water: miscible
Form: Liquid
pka: 8.33(at 25℃)
Color: APHA: ≤15
Specific Gravity: 0.996
Odor: Characteristic amine-like odor
PH: 11.2 (H2O)(undiluted)
Explosive limit: 1.4-15.2%(V)
Water Solubility: MISCIBLE
FreezingPoint: -4.9℃
Sensitive: Hygroscopic
Merck: 14,6277
BRN: 102549
Dielectric constant: 7.3（25℃）
Exposure limits    TLV-TWA 20 ppm (～70 mg/m3) (ACGIH, MSHA, and OSHA); STEL skin 30 ppm (ACGIH); IDLH 8000 ppm.
Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides. Hygroscopic.
InChIKey: YNAVUWVOSKDBBP-UHFFFAOYSA-N
LogP: -0.860
CAS DataBase Reference: 110-91-8(CAS DataBase Reference)
NIST Chemistry Reference: Morpholine (Cas 110-91-8)
IARC: 3 (Vol. 47, 71) 1999
EPA Substance Registry System: Morpholine (Cas 110-91-8)

Morpholine (Cas 110-91-8) is colorless water-absorbing oily liquid and it smells ammonia. 
Morpholine (Cas 110-91-8) is soluble in water and methanol, ethanol, benzene, acetone, ether, ethylene glycol and other commonly used solvents.
Morpholine (Cas 110-91-8) is a colorless to yellow liquid with a weak ammonia or fish-like odor.
The odor threshold is 0.01 ppm. 
The reactivity of Morpholine (Cas 110-91-8) is mainly due to its secondary amine group. 
Morpholine (Cas 110-91-8) readily undergoes organic condensations, alkylations, and arylations, resulting in the formation of various N-substituted morpholine compounds. 
Ethers are relatively chemically inert, hence the oxygen is of relatively little consequence except as a member of the heterocyclic ring.
Colorless, mobile, oily, hygroscopic, flammable liquid with a weak ammonia-like odor. Experimentally determined detection and recognition odor threshold concentrations were 40 μg/m3 (11 ppbv) and 25 μg/m3 (70 ppbv), respectively. 
Forms explosive vapors at temperatures >35 °C.

Uses    
(1) For medicine, Morpholine (Cas 110-91-8) used as the raw materials for rubber accelerator and fluorescent whitening agent.
(2) Morpholine (Cas 110-91-8) is the intermediates of fungicide dimethomorph and flumorpholine and organophosphate insecticide phosalphos.
(3) Morpholine (Cas 110-91-8) is Mainly used for the production of rubber vulcanization accelerator, but also for surfactant, textile auxiliaries, pharmaceuticals, pesticide synthesis. 
(4) Morpholine (Cas 110-91-8) also used as a catalyst for polymerization of butadiene, corrosion inhibitors, optical bleach, the goods are dyes, resins, wax, early glue, casein and other solvents. 
At present, the total production of Morpholine (Cas 110-91-8) in the world is 3-4 million t/a.
(5) Morpholine (Cas 110-91-8) salts are also widely used. 
Morpholine (Cas 110-91-8) salts like morpholine hydrochloride (10024-89-2) are the organic synthesis of intermediates. 
Morpholine (Cas 110-91-8) fatty acid salt can be used as the coating agent of fruits or vegetables epidermal coating agent, and it could inhibit the base respiration and prevent the epidermis from evaporation of water and epidermal atrophy.

(6) Morpholine (Cas 110-91-8) is the main raw materials of accelerator NOBS. for analysis reagents and resins, wax, shellac and other solvents, used in the production of sodium sulfate. 
Water glass and ultramarine. 
Also used in the manufacture of glass. 
Paper. Detergent. Soap. Dye. Synthetic fiber. Tanning.
Medicine and ceramics industries. 
Analysis reagents, such as nitrogen determination, dehydrating agent.
(7) Morpholine (Cas 110-91-8) is used for the analysis of reagents and resins, wax, casein, shellac and a variety of solvents solvent.
(8) Morpholine (Cas 110-91-8) could produce salt after reacting with inorganic acid, and it also could produce salt or amide after reacting with organic acid. 
Morpholine (Cas 110-91-8) also can be alkylated, and it also could come up a ketone reaction or Willgerodt reaction with ethylene oxide.

Morpholine (Cas 110-91-8) is made by dehydrating ethanolamines. 
Morpholine (Cas 110-91-8)'s main use is as a rubber accelerator in manufacturing tires. 
This process requires high temperature (300°F) and pressure, which increase the hazards. 
Morpholine (Cas 110-91-8) is also used as a boiler water additive, brightener for detergents, and corrosion inhibitor, in the preservation of book paper, in waxes and polishes, and in organic synthesis.

Industrial uses    
The total industrial consumption of morpholine is 11,000 metric tons/year. 
The largest usage for Morpholine (Cas 110-91-8) (33%) is in the rubber industry as an intermediate in the production of delayed-action accelerators for the polymerization of rubber, as stabilizers against heat-aging effects, and as bloom inhibitors in butyl rubber vulcanization. 
A second large proportion (25%) of Morpholine (Cas 110-91-8) production is used as an inhibitor to combat carbonic acid corrosion in condensate return lines of steam boiler systems. 
Morpholine (Cas 110-91-8) is an intermediate in the manufacture of optical brighteners utilized by the soap and detergent industry. 
Morpholine (Cas 110-91-8) reacts readily with fatty acids, forming soaps used in the formulation of self-polishing waxes and polishes and in coatings for the food industry. 
N-methyl morpholine and TV-ethyl morpholine are used as catalysts in the manufacture of polyurethane foams. 
Morpholine (Cas 110-91-8) derivatives are utilized in pharmaceutical applications, as bactericides, fungicides, and herbicides, and as separating agents for oils. 
Other derivatives are utilized in the textile and printing industry as adjuvants, whitening agents, stabilizers, ink eradicators, and paper conditioners.

Metal Corrosion Inhibitors    
As a kind of metal corrosion inhibitor, Morpholine (Cas 110-91-8) is mainly applied for the anti-corrosion of iron, copper, zinc, lead and other metals.
Morpholine (Cas 110-91-8) remains at its starting stage in China, but outside the country, a considerable proportion of Morpholine are used as a kind of anti-rust agent for metal gas to prevent the metal corrosion caused by atmosphere and Morpholine (Cas 110-91-8) has been widely used in the field of mechanical instruments, automobiles, medical equipment and others. 
The metal atmospheric rust inhibitor used earlier such as dicyclohexylamine nitrite and cyclohexylamine do harm to the human body and they are more environmentally toxic. 
Instead, Morpholine (Cas 110-91-8) as a metal gas-liquid corrosion inhibitor, it has the advantages of low toxicity, so the foreground is prosperous.

Rubber Vulcanization Accelerator    
Before 1990's, in Europe, the United States, Japan and other developed areas, the consumption of rubber vulcanization accelerator accounted for more than 50% of the total demand for morpholine. 
At present, more than 30% consumption of rubber vulcanization accelerator is used for NOBS.
In recent years, the toxicity issue of the harmful nitrosamines in the accelerator which produced during rubber processing is driving more attention internationally. 
A number of restrictive laws and regulations are introduced all around the world. 
For example, in Germany as early as 1982, the law about the regulations issued nitrosamine content control was established. 
The United States, Japan, France, the United Kingdom actively developed new vulcanization accelerator which don’t produce nitrosamine, and they have stopped using nitrosamine which will produce vulcanization accelerator. 

Therefore, the consumption of morpholine in foreign countries has decreased with banning of the accelerator NOBS year by year. 
But China has joined the WTO, due to a large number of foreign enter and high requirement about additives localization, Morpholine (Cas 110-91-8) requires more environmental protection in China's rubber vulcanization accelerator. 
Using non-toxic promoter and replacing NOBS becomes the general trend. 
China's demand for NOBS is significantly reduced in recent years. 
China will no longer use basic decomposition of nitrosamine secondary amine accelerator. 
As the main substitute of NOBS, NS (N-tert-butyl-2-benzothiazole sulfonamide), which does not produce nitrosamines, has a large production capacity. 
In 2005, the output was 14,000 tons and it is 10.1%, of the total amount. 
So there was good development momentum.

Production Method    
(1) Morpholine (Cas 110-91-8) could be produced by diethanolamine dehydration cyclization derived from sulfuric acid. 
Add diethanolamine to the water reaction pot and drop sulfuric acid in the temperature of 60 ℃, then when the temperature heat at 185-195 ℃, incubate it for 30min. 
Cool Morpholine (Cas 110-91-8) to under 60℃ and drop sodium hydroxide solution to pH = 11. 
The next steeps are cooling, filtering, filtrating distillation, collecting the following fractions below 130℃. 
The content of spermine is suppose to reach more than 99.5%. 
The method is easy to obtain raw materials, so it has become the main method of producing Morpholine (Cas 110-91-8) in the world.
Morpholine (Cas 110-91-8) also could be produced in the catalytic reaction between dioxane and ammonia gas.

(2) The preparation method is that we could get Morpholine (Cas 110-91-8) from the presence of sulfuric acid dehydration cyclization diethanolamine In the presence of sulfuric acid ; then add diethanolamine into the reaction kettle and add H2SO4 at a temperature of below 6 °C, then heat it to 185-195 °C for 30 minutes, cool to 60 °C. 
Drop NaOH solution to pH = 11, and the last two steeps is cooling and filtrating. 
Morpholine could be collected from the fraction below 130 °C.
The method is easy to obtain raw materials, thus Morpholine (Cas 110-91-8) is the main method of producing morpholine around the world.

Production Methods    
Morpholine (Cas 110-91-8) is produced by reacting diethylene glycol, ammonia, and a small amount of hydrogen over a hydrogenation catalyst at 150-400°C and 30-400 atmospheres with the morpholine being recovered by fractional distillation.
Various byproducts include 2-(2-aminoethoxy)ethanol and Af-alkylmorpholines.
Morpholine (Cas 110-91-8) is often produced industrially by the dehydration of diethanolamine with concentrated sulfuric acid.
Alternatively, Morpholine (Cas 110-91-8) can be made from bis(2-chloroethyl)ether in a reaction with ammonia, by which also ammonium chloride is formed.