MORPHOLINE

Morpholine 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 is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride. 
The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

Morpholine appears as a colorless liquid with a fishlike odor. Flash point 100°F. Corrosive to tissue. Less dense than water and soluble in water. Vapors heavier than air. Used to make other chemicals, as a corrosion inhibitor, and in detergents.
Morpholine is a saturated organic heteromonocyclic parent and a member of morpholines.

Morpholine is an important building block for rubber chemicals and finds a multitude of applications in other industries. It is used as an intermediate for water treatment, the production of pharmaceutical and agrocultural products as well as optical brightners.

Morpholine (1,4-tetrahydro-oxazine) is a simple heterocyclic compound that has great industrial importance and a wide range of applications. This chemical compound and its derivatives have been used as rubber additives, corrosion inhibitors, solvents, optical brighteners, antioxidants and in the manufacture of a range of drugs and herbicides.

PRODUCT USE
Solvent for resins, waxes, casein, dyes. Morpholine fatty acid salts are used as surface active agents and emulsifiers. Other morpholine
compounds are used as corrosion inhibitors, antioxidants, plasticisers. Morpholine compounds are also used as viscosity improvers,
insecticides, fungicides, herbicides, local anaesthetics and antiseptics. Morpholine has a volatility similar to water. It is therefore widely used
as a neutralising amine in combating carbonic acid corrosion in condensate return lines in steam boiler systems as well as in aqueous
hydraulic liquids and similar systems. Morpholine vapours protect silver and other metals against corrosion and tarnish by acid fumes such as
SO2 and H2S. Corrosion of metal aerosol containers and valves can also be prevented by the use of low levels of morpholine. Morpholine is
effective in hydraulic system fluids based on glycols, where various metals are in contact with the fluid at the same time. Morpholine
derivatives have been used as corrosion inhibitors in mineral lubricating oil, turbine oils, for protecting storage tanks, pipes and other devices
used in handling petroleum distillates, and for inhibiting the corrosive action of grease-proof paper on steel and other metals Intermediate

SYNONYMS
C4-H9-O-N, C4-H9-O-N, OCH2-CH2-NHCH2-CH2, "diethyleneimide oxide", "diethylene imideoxide", "diethylene oximide", "diethylenimide
oxide", Drewamine, "p-isoxamine, tetrahydro-", "p-isoxamine, tetrahydro-", 1-oxa-4-azacyclohexane, 1-oxa-4-azacyclohexane, "2H-1,
4-oxazine, tetrahydro-", "2H-1, 4-oxazine, tetrahydro-", "4H-1, 4-oxazine, tetrahydro-", "4H-1, 4-oxazine, tetrahydro-", "tetrahydro-1,
4-isoxazine", "tetrahydro-1, 4-isoxazine", tetrahydro-p-oxazine, tetrahydro-p-oxazine, "tetrahydro-2H-1, 4-oxazine", "tetrahydro-2H-1,
4-oxazine", "BASF 238"

CAS Number: 110-91-8;EINECS 263-172-8; IUPAC name: Morpholine. Other names:Diethylenimide oxide; 1,4-Oxazinane; Tetrahydro-1,4-oxazine; Diethylene imidoxide; Diethylene oximide; Tetrahydro-p-oxazine
Synonyms & Trade Names: Diethylene imidoxide, Diethylene oximide, Tetrahydro-1,4-oxazine, Tetrahydro-p-oxazine

Chemical formula: C4H9NO
Molar mass: 87.122 g·mol−1
Appearance :Colorless liquid
Odor: Weak ammonia-like or fish-like
Density: 1.007 g/cm3
Melting point: −5 °C (23 °F; 268 K)
Boiling point: 129 °C (264 °F; 402 K)
Solubility in water: miscible
Vapor pressure: 6 mmHg (20 °C)
Acidity (pKa):8.36 (of conjugate acid)
Magnetic susceptibility (χ): -55.0·10−6 cm3/mol
Main hazards: Flammable, Corrosive

Odor: characteristic
Use: Due to morpholine's chemical stability and similar volatility to water, it makes an excellent corrosion inhibitor for steam boilers and water treatment systems. Morpholine is also used as a common emulsifier used in fruit waxes to protect against fungal and insect contamination. Morpholine can be used as a pH modifier for fossil and nuclear fuels, in rubber accelerants, as a descaling agent, antiseptic, textile printing and dyeing agent, antioxidant, deodorizer, and in medicines and pesticides.

Applications:Corrosion inhibitor in steam condensate ( Boiler), Optical brighteners, pharmaceuticals.

Morpholine is an organic chemical compound, which is used as a corrosion inhibitor, additive and used to synthesize other chemicals. The molecular formula of Morpholine is C4H9NO. Morpholine is a heterocyclic chemical compound, which has amine and ether functional groups. Morpholine is a base due to the presence of the amine. Morpholine is colorless and free of suspended matter. Morpholine is commonly used as a solvent in organic synthesis, reactions and chemical industry research due to its low cost and polarity.

APPLICATIONS

1. ADDITIVES AND CATALYSTS
Morpholine is used as an additive for adjusting pH in nuclear power plant steam systems and fossil fuels. Morpholine is also used for corrosion protection of boiler water stream systems in chemical plants. Morpholine is used for the preparation of alumina catalysts. They are prepared in the form of a gelling agent for the treatment of hydrocarbons.
2. ORGANIC SYNTHESIS
Morpholine is commonly used for the synthesis of enamines. It is an important ingredient to produce linezolid, which is an antibiotic used for treating infections caused by gram-positive bacteria. It is also used in gefitinib, a cancer drug. Morpholine is also used in the analgesic dextromoramide. Morpholine salts such as morpholine hydrochloride are used for the organic synthesis of intermediates.
3. AGRICULTURE
Morpholine in the form of a chemical emulsifier is used for the protection of fruits. This is achieved through the process of waxing, where a wax layer is applied onto the fruits. This coating protects fruits from insects and fungal infestation. Ergosterol biosynthesis inhibitors are the derivatives of morpholine, which are used as fungicides in cereals. Some of the morpholine based fungicides used on cereal crops are amorolfine, fenpropimorph and tridemorph.
4. RUBBER INDUSTRY
Morpholine is widely used as an intermediate in the rubber industry to produce rubber vulcanization accelerators such as DTOS, MDS and NOBS. Over 50% of the demand for morpholine is from rubber vulcanization accelerators, and about 30% of rubber vulcanization accelerators are used for NOBS. 
5. METAL CORROSION INHIBITORS
Morpholine is used as a corrosion inhibitor for metals such as copper, iron, lead, zinc and other metals. It is widely used in areas such as automobiles, mechanical instruments and medical equipment. Morpholine in its gas-liquid state has lower toxicity towards the environment when compared to its forerunners like cyclohexylamine and dicyclohexylamine nitrite. 
6. MANUFACTURING 
Morpholine is used in the manufacture of paper, glass, soap, detergent, dye and synthetic fibre. It is used to manufacture analysis reagents for nitrogen determination. Morpholine also finds applications in pharmaceuticals, tanning, textiles, household care and ceramics industries. 

SCOPE 
In recent times, drug discovery efforts have unveiled numerous interesting morpholine based compounds. There is still a lot to be explored when it comes to the synthesis of drugs and intermediates. With the advancement in technology, morpholine will find more applications in various industries. 

Uses
Industrial applications: Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. 
Morpholine decomposes reasonably slowly in the absence of oxygen at the high temperatures and pressures in these steam systems.

Organic synthesis
Morpholine undergoes most chemical reactions typical for other secondary amines, though the presence of the ether oxygen withdraws electron density from the nitrogen, rendering it less nucleophilic (and less basic) than structurally similar secondary amines such as piperidine. For this reason, it forms a stable chloramine.

It is commonly used to generate enamines.

Morpholine is widely used in organic synthesis. For example, it is a building block in the preparation of the antibiotic linezolid, the anticancer agent gefitinib (Iressa) and the analgesic dextromoramide.

In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.

Agriculture
As a fruit coating
Morpholine is used as a chemical emulsifier in the process of waxing fruit. Naturally, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned. A small amount of new wax is applied to replace it. Morpholine is used as an emulsifier and solubility aid for shellac, which is used as a wax for fruit coating. The European Union has forbidden the use of morpholine in fruit coating.

As a component in fungicides
Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.

Description
This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Oxazinanes
Sub Class: Morpholines
Direct Parent: Morpholines
Alternative Parents: Oxacyclic compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents: Aliphatic heteromonocyclic compound / Amine / Azacycle / Dialkyl ether / Ether / Hydrocarbon derivative / Morpholine / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework: Aliphatic heteromonocyclic compounds
External Descriptors: morpholines, saturated organic heteromonocyclic parent (CHEBI:34856)
Morpholine is a pale hygroscopic liquid with the chemical formula of O(CH2CH2)2NH free of foreign matter. It bears its characteristic amine odour that is detectable above 0.1 ppm concentration in boiler feed. It is a widely used neutralizing amine in combating carbonic acid corrosion in condensate return lines of steam boiler systems. It volatilizes and condenses with the steam from the boilers, thereby affording protection to the lines, which otherwise would be subjected to corrosion from the carbonic acid present in the steam condensate. Its vapours protect silver and other metals against corrosion and tarnishing by acrid fumes, such as  sulphur dioxide and hydrogen sulfide.

Morpholine is used as a boiler water treatment additive in steam systems of power plants and refineries. It forms an even wax like coating as morpholine oleate. It prevents decomposition of a chlorinated hydrocarbon in a composition containing the chlorinated hydrocarbon and a large amount of water. It is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile boiler water treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of oxygen at the high temperatures and pressures in these steam systems. Because of its volatility being the same as water, upon addition to water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities become more distributed throughout the steam plant to provide corrosion protection.

Key Features & Benefits of Morpholine:
Prevents corrosion due to stress cracking
Reduces blow down requirement
Compatible with other boiler water treatment chemicals
Returns to the feed line with the condensate return so raises the feed water pH
Corrosion of metal aerosol containers and valves can be prevented by use of low levels of morpholine. It increases the pH of boiler water to protect boiler against corrosion. Due to its amine based formulation, it does not add salt to the boiler and hence does not contribute to the TDS, which results in reduced blow down and fuel savings. Morpholine can be used in all types, size and pressure of boilers.
ATAMAN KIMYA provides high quality Morpholine for boiler water treatment globally.
www.atamankimya.com

Morpholine, an organic compound with both amine and ether groups, obtained by dehydrating diethanolamine with sulphuric acid. Morpholine can be adapted to many different activities for many important applications. Some of its different adaptation can be seen in following applications like it functions as an intermediate in the production of rubber chemicals even as optical brighteners. It acts as an effective corrosion inhibitor in steam boiler systems. Morpholines can utilized as pharma chemicals and antioxidants for lubricating oils. 
Morpholines can be used as emulsifiers in waxes and polishes processing industries.

Morpholine is a very good pH adjuster which is very effective for nuclear power plants. One more reason for it to be used is because of its rate of vapourization which is quiet similar to water; so what happens is when it is added to water, it disperses accordingly in water in both of its liquid and vapour phases. It can also be used as an ingredient in fungicides and bactericides.

Key Features and Benefits
Prevents stress cracking corrosion
Reduces blow down requirement
Returns to the feed line with the condensate return so raises the feed water pH
Saves power & downtime
Compatible with other treatment chemicals
Versatile applications
Physicochemical Data
Properties: Typical Value
Form: Clear liquid
Appearance:Colourless
Odour:Amine like
Assay as Morpholine:99.0% min.
Solubility: Completely soluble with water
Application Areas
Rubber Chemicals:Delayed action accelator
Catalysts:Temperature sensitive polymerization inhibitor
Gelling agent
Optical Brighteners
Stabler than chlorine bleaches
Pharma Chemicals: Morpholine derivatives as analgesics and anesthetics
Choleretics, antispasmodics, analeptics, antimalarials
Corrosion Inhibitors:Neutralizing Amine
Antioxidants
Separating Agents: Wax Emulsifier
Self polishing waxes and polishes: Surface tension depressor
Scrubbing organic sulphur compounds from fuel gas
Purification procedures
Biocide
Bacteriostatic/ bactericidal properties
Anti-fungal
Processing Industries
Processing Industries (Non-food)
Water Treatment
Handling Measures and Precautions: DG Cargo. Morpholine is hazardous in nature. Proper human safety products such as splash goggles, lab coat, dust and vapour respirator, NIOSH approved gloves and boots should be worn while handling and applying chemicals. Splashes on the skin should be washed off with water immediately. In case of splashing into the eyes, flush them with fresh water and obtain medical attention. Should not be injected. Kindly refer SDS for more details.

Storage
Morpholine should be stored in original vented containers, away from heat, direct sunlight and combustibles. Store in a cool and dry place. Kindly refer SDS for details.

1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethyleneimide oxide
Diethylenimide oxide
Drewamine
Morpholine
MORPHOLINE
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-isoxazine
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine

MORPHOLINE
Morfolin
110-91-8
1-Oxa-4-azacyclohexane
Tetrahydro-1,4-oxazine
Diethylene oximide
Diethylenimide oxide
Diethyleneimide oxide
Drewamine
Diethylene imidoxide
morpholin
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-isoxazine
BASF 238
Caswell No. 584
Morpholine, 4-soya alkyl derivs.
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
EINECS 203-815-1
UN2054
C4H9NO
EPA Pesticide Chemical Code 054701
BRN 0102549
Tetrahydro-4H-1-4-oxazine
61791-40-0
Morpholine [UN2054] [Flammable liquid]
Morpholine, 99+%, extra pure
CAS-110-91-8
MORPHOLINE,REAG
Tetrahydro-p-isoxazine
MORPHOLINE, PRACT
morphline
morpho line
morpholine-
EINECS 263-172-8
4H-1, tetrahydro-
PubChem15002
Morpholine 
1,4$l^{2}-oxazinane
Tetrahydro-1, 4-isoxazine
Oprea1_317540
Tetryhydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
4-27-00-00015 (Beilstein Handbook Reference)
Morpholine, analytical standard

morfoliin (et)
Morfoliini (fi)
morfolin (cs)
morfolin (hr)
morfolin (hu)
morfolin (no)
morfolin (sl)
morfolin (sv)
morfolina (es)
morfolina (it)
morfolina (pl)
morfolina (pt)
morfolina (ro)
morfolinas (lt)
morfoline (nl)
morfolín (sk)
morfolīns (lv)
morpholin (da)
Morpholin (de)
morpholine (fr)
morfolin (tr)
morfolin (türkçe)

tetrahidro-1,4-oxazina (es)

tetrahydro-1,4-oksazyna (pl)

μορφολίν (el)

мoрфолин (bg)

CAS names
Morpholine

IUPAC names
2-chloro-1-morpholin-4-ylethanone
4H-1,4-Oxazine, tetrahydro-
Morpholin
MORPHOLINE
Morpholine
morpholine
tetrahydro 1.4 oxazine
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetraidro-1,4-ossazina

Trade names
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethylenimide oxide
Drewamine
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine

102549 [Beilstein]
110-91-8 [RN]
203-815-1 [EINECS]
8B2ZCK305O
MFCD00005972 [MDL number]
Morfolina [Italian]
Morfolina [Portuguese]
Morpholin [German] [ACD/IUPAC Name]
Morpholine [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
Morpholine [French] [ACD/Index Name] [ACD/IUPAC Name]
QD6475000
Tetrahydro-1,4-oxazine
UNII:8B2ZCK305O
Морфолин [Russian]
モルホリン [Chinese]
吗啉 [Chinese]
吗啡啉 [Chinese]
138048-80-3 [RN]
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4-27-00-00015 (Beilstein Handbook Reference) [Beilstein]
4H-1,4-Oxazine, tetrahydro-
Diethylene imidoxide
Diethylene oximide
Diethyleneimide oxide
diethylenimide oxide
Drewamine
Morpholine-d8
N-Vinylbenzylmorpholine-divinylbenzene Copolymer
Oprea1_317540
p-Isoxazine, tetrahydro-
ST5213815
STR00194
T6M DOTJ [WLN]
Tetrahydro-1, 4-isoxazine
Tetrahydro-1,4-isoxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
Tetrahydro-4H-1-4-oxazine
Tetrahydro-P-isoxazine
Tetrahydro-p-oxazine
Tetryhydro-2H-1,4-oxazine
UN 2054
UNII-8B2ZCK305O
WLN: T6M DOTJ

Other identifiers
CAS number
1357848-50-0
CAS number
1357848-50-0
Deleted CAS number
147366-31-2
CAS number
147366-31-2
Deleted CAS number
613-028-00-9
Index Number
854893-20-2
CAS number
854893-20-2
Deleted CAS number
88542-81-8
CAS number
88542-81-8
Deleted CAS number
96122-95-1
CAS number
96122-95-1
Deleted CAS number
99108-56-2
CAS number
99108-56-2
Deleted CAS number

Morpholine is a heterocycle featured in numerous approved and experimental drugs as well as bioactive molecules. It is often employed in the field of medicinal chemistry for its advantageous physicochemical, biological, and metabolic properties, as well as its facile synthetic routes. The morpholine ring is a versatile and readily accessible synthetic building block, it is easily introduced as an amine reagent or can be built according to a variety of available synthetic methodologies. This versatile scaffold, appropriately substituted, possesses a wide range of biological activities. There are many examples of molecular targets of morpholine bioactive in which the significant contribution of the morpholine moiety has been demonstrated; it is an integral component of the pharmacophore for certain enzyme active‐site inhibitors whereas it bestows selective affinity for a wide range of receptors. A large body of in vivo studies has demonstrated morpholine's potential to not only increase potency but also provide compounds with desirable drug‐like properties and improved pharamacokinetics. In this review we describe the medicinal chemistry/pharmacological activity of morpholine derivatives on various therapeutically related molecular targets, attempting to highlight the importance of the morpholine ring in drug design and development as well as to justify its classification as a privileged structure.

Morpholine
Morpholine is a colorless, hygroscopic liquid with a characteristic amine-like odor. It is completely miscible with water and a large number of organic solvents, and is itself a solvent for a large variety of organic materials, including resins, dyes, waxes, shellac, and casein.

Molecular Formula : C4H9NO

Usage
Morpholine are mainly used to manufacture rubber accelerant (such as NOBS, OTOS and MDS), sulfuration agent (like DT-DM), cleanser, descaling agent, anti rust, anti-scorching agent, antiseptic, surfactant, textile printing & dyeing agent, optical bleaching agent, chemical plating bath, antioxidant, hydrolyzing agent, initiator, developer, fruit preserving agent, deodorizer, brightener and organic solvents. It is widely used in many industries such as medicine, pesticide, animal medicine, petroleum and extraction of coke aromatic hydrocarbon.