PRODUCTS

MORPHOLINE

Morpholine is used as an intermediate for water treatment, the production of pharmaceutical and agrocultural products as well as optical brightness.
Morpholine is commonly used to generate enamines.
Morpholine is widely used in organic synthesis.

CAS Number: 110-91-8
EC Number: 203-815-1
MDL number: MFCD00005972
Molecular Formula: C4H9NO

SYNONYMS:
Morpholine, Tetrahydro-1,4-oxazine, Diethylene Imidoxide, 1-Oxa-4-azacyclohexane, Diethylene Oxazine, Morpholin, 1,4-Oxazine, Tetrahydro, p-Isoxazine, tetrahydro-, BASF 238, Diethylene Imidoxide, Diethylene oximide, Diethylenimide oxide, Tetrahydro-p-oxazine, Tetrahydro-1,4-oxazine, Tetrahydro-2H-1,4-oxazine, 1-Oxa-4-azacyclohexane, 2H-1,4-Oxazine, tetrahydro-, 4H-1,4-Oxazine, tetrahydro-, Diethyleneimide oxide, Tetrahydro-1,4-isoxazine, Drewamine, NA 2054, UN 2054, NSC 9376, diethylene imidoxide, diethylene oximide, tetrahydro-1,4-oxazine, tetrahydro-p-oxazine, p-Isoxazine, tetrahydro-, BASF 238, Diethylene Imidoxide, Diethylene oximide, Diethylenimide oxide, Tetrahydro-p-oxazine, Tetrahydro-1,4-oxazine, Tetrahydro-2H-1,4-oxazine, 1-Oxa-4-azacyclohexane, 2H-1,4-Oxazine, tetrahydro-, 4H-1,4-Oxazine, tetrahydro-, Diethyleneimide oxide, Tetrahydro-1,4-isoxazine, Drewamine, NA 2054, UN 2054, NSC 9376, 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, Diethylenimide oxide, 1,4-Oxazinane, Tetrahydro-1,4-oxazine, Diethylene imidoxide, Diethylene oximide, Tetrahydro-p-oxazine, 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, 61791-40-0, 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

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.
Morpholine appears as a colorless liquid with a fishlike odor.
Flash point of Morpholine is 100 °F.

Morpholine is less dense than water and soluble in water.
Vapors of Morpholine are heavier than air.
Morpholine 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 has a role as a NMR chemical shift reference compound.
It is a saturated organic heteromonocyclic parent and a member of morpholines.
Morpholine is a conjugate base of a morpholinium.

Morpholine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
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 generates the salt morpholinium chloride.

Morpholine is a colorless liquid with a weak, ammonia- or fish-like odor.
The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.
Morpholine is a versatile intermediate with a variety of applications.

Morpholine’s an amine-ether compound, a derivative of both ammonia and nitrogen.
Morpholine is a base as opposed to an acid.
And although it is used in medicine, Morpholine is not chemically related to morphine.

But if someone mistakenly thinks Morpholine is, they’re in good company.
Ludwig Knorr, the accomplished German chemist who discovered morpholine in the late 1800s, also made that mistake initially.
Because morpholine is so versatile, this article will not attempt to cover all of its uses.

Instead, we’ll focus on industrial applications.
This aspect of morpholine itself offers a rich cross section of uses, and industry is the place where morpholine is the most indispensable.

USES and APPLICATIONS of MORPHOLINE:
Morpholine is widely used in organic synthesis.
For example, it is a building block in the preparation of the antibiotic linezolid and the anticancer agent gefitinib (Iressa).
Morpholine is used as a chemical emulsifier in the process of waxing fruit.

Fruits make waxes naturally to protect against insects and fungal contamination, but this can be lost by means of the food processing companies when they clean the fruit.
As a result, an extremely small amount of new wax is applied and morpholine is then added and used as an emulsifier to evenly coat a fruit with the wax.

In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.
As a component in fungicides: Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.
Morpholine is an important building block for rubber chemicals and finds a multitude of applications in other industries.

For example, Morpholine 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.

Morpholine is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Morpholine is used in the following products: adhesives and sealants, coating products, inks and toners, anti-freeze products, biocides (e.g. disinfectants, pest control products), fuels, photo-chemicals, polishes and waxes, washing & cleaning products and paper chemicals and dyes.

Other release to the environment of Morpholine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Other release to the environment of Morpholine is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials), outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)), indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints).

Morpholine can be found in complex articles, with no release intended: Vehicles (e.g. personal vehicles, delivery vans, boats, trains, metro or planes)), machinery, mechanical appliances and electrical/electronic products e.g. refrigerators, washing machines, vacuum cleaners, computers, telephones, drills, saws, smoke detectors, thermostats, radiators, large-scale stationary industrial tools), vehicles and machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines).

Morpholine can be found in products with material based on: metal (e.g. cutlery, pots, toys, jewellery), metal used for large surface area articles (e.g. construction and building materials used for roof sheets, pipes), metal used for packaging (excluding food packaging), metal used for furniture & furnishings (e.g. outdoor furniture, benches, tables), wood used for large surface area articles (e.g. construction and building materials for floors, claddings), wood used for furniture & furnishings and wood.

Morpholine is used as an intermediate for organic synthesis, especially for rubber chemicals for vulcanization and stabilization, Corrosion inhibitors and so on.
Morpholine is used to make other chemicals, as a corrosion inhibitor, and in detergents.

Chemical Intermediate: Morpholine is used in the production of rubber chemicals, pharmaceuticals, and agrochemicals
Corrosion Inhibitor: Morpholine is commonly added to boiler water for pH control and preventing corrosion
Solvent: Morpholine is employed in coatings, resins, and dyes manufacturing

Surfactants and Emulsifiers: Morpholine is used in the formulation of detergents and cleaning products
Pharmaceuticals uses of Morpholine: Intermediate in drug synthesis due to its heterocyclic structure
Morpholine is widespread uses by professional workers

Morpholine is used in the following products: washing & cleaning products.
Morpholine is used in the following areas: building & construction work.
Morpholine is used for the manufacture of: chemicals and fabricated metal products.

Morpholine is widely used in organic synthesis.
For example, Morpholine is a building block in the preparation of the antibiotic linezolid, the anticancer agent gefitinib (brand name 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.
Morpholine is used in the following products: adhesives and sealants, coating products, fillers, putties, plasters, modelling clay, finger paints, metal surface treatment products, non-metal-surface treatment products and inks and toners.

Release to the environment of Morpholine can occur from industrial use: formulation of mixtures, formulation in materials, in processing aids at industrial sites, in the production of articles, as processing aid and of substances in closed systems with minimal release.
Morpholine is used in the following products: washing & cleaning products, pH regulators and water treatment products and polymers.

Morpholine has an industrial use resulting in manufacture of another substance (use of intermediates).
Morpholine is used in the following areas: building & construction work.
Morpholine is used for the manufacture of: chemicals and fabricated metal products.

Release to the environment of Morpholine can occur from industrial use: in processing aids at industrial sites, in the production of articles, of substances in closed systems with minimal release and as an intermediate step in further manufacturing of another substance (use of intermediates).
Release to the environment of Morpholine can occur from industrial use: manufacturing of the substance.

Morpholine is used as an important building block mainly in
rubber, optical brighteners, pharma, agro industry, solvent for the fibre industry.
Other applications of Morpholine include, inter alia, water treatment

Morpholine is incredibly common but a surprisingly little-known substance.
Morpholine has applications as diverse as cleaning, rubber production, construction, heating and cooling, personal care, agriculture, and so much more.

And yet, for all its usefulness, morpholine is strangely invisible.
People don’t often think or write about morpholine, and it really is practically invisible, as it is a colorless, easily soluble substance.

-Agriculture uses of Morpholine:
*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.

-Industrial applications of Morpholine:
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.
Morpholine's 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.

-Agriculture uses of Morpholine:
*As a fruit coating
In nature, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned.

Hence a small amount of new wax, made from shellac, is applied to replace it.
Morpholine is sometimes used as an emulsifier and solubility aid for this new 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.

-Industrial applications of Morpholine:
Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems.

COMMON INDUSTRIAL USES FOR MORPHOLINE:
As mentioned earlier, morpholine’s most common and important applications are all in industry.
Here is a rundown of some of the major industrial uses of morpholine:

*Cleaning products:
Morpholine is used as an abrasive cleaner and a brightening agent in cleaning solutions and heavy duty detergents.
Morpholine’s particularly useful in dry cleaning.
As an emulsifier, morpholine helps industrial waxes and polishes maintain their consistency.

*Coatings and Sealants
Morpholine is the active ingredient in the resin base for curable inks, coatings, and adhesives.
Morpholine also is an accelerant for the vulcanization of rubber, including rubber seals.

*Metalwork
Morpholine serves as a component in dual lubricant and cooling fluids that are used to keep metal from getting excessively hot while it is machined, ground, and crafted into different pieces for use.
Morpholine can also be applied as an anti-corrosive for steel and tin.

*Heating and Cooling
Morpholine helps stabilize heat transfer fluids– conductive liquids in heating systems such as boiler water.
One of the chief ways morpholine does this is by acting as a base that neutralizes acid contamination in heat transfer systems.
This keeps the heat transferring liquid from becoming corrosive and damaging the heating systems.

*Paper and cardboard
Due to morpholine’s fungicidal nature, many paper and cardboard products have a morpholine coating that prevents mildew and rot.
Morpholine also reduces foaming, a common reaction in paper and cardboard production, acting as an anti-foaming agent and paper mills.

ORGANIC SYNTHESIS OF MORPHOLINE:
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, Morpholine forms a stable chloramine.

PROPERTIES OF MORPHOLINE:
*Heterocyclic amine with both hydrophilic and hydrophobic characteristics
*Stable under normal conditions but reacts with acids and oxidizing agents
*Volatile and can form salts with acids

BENEFITS OF MORPHOLINE:
*Highly versatile in industrial and chemical applications
*Helps in corrosion control, extending equipment life
*Useful as a solvent due to its miscibility and stability

PRODUCTION OF MORPHOLINE:
Morpholine may be produced by the dehydration of diethanolamine with sulfuric acid.
Morpholine is commonly used to generate enamines.
Morpholine is often produced industrially by the dehydration of diethanolamine with concentrated sulfuric acid.

Alternatively, Morpholine can be made from bis(2-chloroethyl)ether in a reaction with ammonia, by which also ammonium chloride is formed.
Morpholine is also produced industrially from diethylene glycol and ammonia, under high temperature and pressure, in the presence of hydrogen and a suitable catalyst.

HOW IS MORPHOLINE MADE?
There are three common methods for making morpholine.

*Dehydration of Diethanolamine With Acid
In this process, morpholine is derived from diethanolamine, an organic compound created by mixing ethylene oxide and ammonia.
A strong acid is heated to at least 150 Celsius and added to the diethanolamine.

This reaction is then neutralized with an alkali or other base.
The resulting liquid contains morpholine, which is distilled through the use of a solvent.

This is ultimately a “dehydration” process in chemical terms, because the hydrogen and oxygen atoms that make water are removed from diethanolamine’s structure, leaving behind morpholine molecules.

*Hydrogenating and Vaporizing Diethylene Glycol and Ammonia
This method, developed in the 1980s, has become the most common way to make morpholine, due to its speed and efficiency.

Diethylene glycol and ammonia are combined with hydrogen. A catalyst substance (typically a metal such as copper, nickel or cobalt) is also in the mix to trigger the hydrogenation– the molecular infusion of hydrogen– of the diethylene glycol and ammonia.

The whole mixture is then heated to between 150 and 400 Celsius and pressurized.
The resulting chemical reaction creates a solution that contains morpholine molecules.

The morpholine is then extracted from the mixture by vaporization.
The morpholine escapes in the vapor and is collected.
(In chemistry, this kind of vaporization extraction method is also known as a stripping operation.)

*Combining Ether and Dry Ammonia
Here, ether, specifically a bis (2-chloroethy1) ether compound is mixed with dry, water-free ammonia and a chemically compatible solvent.
These chemicals are stored together in warm but not boiling temperatures of 50 Celsius for 24 hours.

The mix is stored in a completely sealed, sturdily rigid container– a closed vessel in chemistry terms– so that the mixture doesn’t increase in volume while the chemical and heat reactions happen.

Once the vessel is unsealed, excess ammonia is vented, and the reaction leaves behind ammonium chloride and morpholine.
The morpholine is then distilled from the solution.

PHYSICAL and CHEMICAL PROPERTIES of MORPHOLINE:
Chemical Name: Morpholine
Molecular Formula: C4H9NO
Molecular Weight: 87.12 g/mol
EC Number: 203-815-1
CAS Number: 110-91-8
Appearance: Clear, colorless liquid
Density: ~1.0 g/cm³ at 20°C
Melting Point: -5°C
Boiling Point: 129°C
Flash Point: 38°C (closed cup)

Solubility: Fully miscible with water,
soluble in most organic solvents
Odor: Ammonia-like
Molecular Weight: 87.12 g/mol
XLogP3: -0.9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 87.068413911 g/mol
Monoisotopic Mass: 87.068413911 g/mol
Topological Polar Surface Area: 21.3 Å²

Heavy Atom Count: 6
Formal Charge: 0
Complexity: 34.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Chemical Formula: C4H9NO
Molar Mass: 87.122 g/mol
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
Physical Description: Colorless liquid with a weak,
ammonia- or fish-like odor.

Boiling Point: 264 °F
Molecular Weight: 87.12 g/mol
Freezing Point/Melting Point: 23.2 °F
Vapor Pressure: 6 mmHg
Flash Point: 98 °F (open cup)
Vapor Density: 3
Specific Gravity: 1.007
Ionization Potential: 8.88 eV
Lower Explosive Limit (LEL): 1.8%
Upper Explosive Limit (UEL): 10.8%
NFPA Health Rating: 3
NFPA Fire Rating: 3
NFPA Reactivity Rating: 1

FIRST AID MEASURES of MORPHOLINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of MORPHOLINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of MORPHOLINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of MORPHOLINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of MORPHOLINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of MORPHOLINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .
-Possibility of hazardous reactions:
No data available