Morpholine Identifiers CAS number UNII KEGG ChEMBL RTECS number QD6475000 Jmol-3D images Image 1 Properties Molecular formula C4H9NO Molar mass 87.1 g/mol Appearance Colorless liquid Density 1.007 g/cm3 Melting point
-5 °C, 268 K, 23 °F
129 °C, 402 K, 264 °F
Solubility in water miscible Acidity (pKa) 8.36 Hazards MSDS Oxford MSDS R-phrases S-phrases Main hazards Flammable, Corrosive NFPA 704 Flash point 31 °C Autoignition
275 °C (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle, pictured at right, features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, neutralizing morpholine with hydrochloric acid makes the salt morpholinium chloride.
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.
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 (CAS#23328-69-0).
In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.
Most (as above) is widespread in Europe and the USA; accordingly, producers in Europe and the USA are able to cover the domestic and export markets.
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.
As a component in fungicides
Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.
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- ^ Noyori, R.; Yokoyama, K.; Hayakawa, Y. (1988), "Cyclopentenones from α,α'-Dibromoketones and Enamines: 2,5-Dimethyl-3-Phenyl-2-Cyclopenten-1-one", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6P0520 ; Coll. Vol. 6: 520
- ^ Raymond G. McGuire; Dimitrios A. Dimitroglou,"Evaluation of Shellac and Sucrose Ester Fruit Coating Formulations that Support Biological Control of Post-harvest Grapefruit Decay". Bio-control Science and Technology, Volume 9, Issue 1 March 1999 , pages 53 - 65
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Morpholine — Général Nom IUPAC tétrahydro 1,4 oxazine No CAS … Wikipédia en Français
morpholine — morfolinas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė HN:(CH₂CH₂)₂:O atitikmenys: angl. morpholine rus. морфолин … Chemijos terminų aiškinamasis žodynas
morpholine — /mawr feuh leen , lin/, n. Chem. a colorless, hygroscopic liquid, C4H9NO, used chiefly as a solvent for dyes, resins, and waxes. [1885 90; MORPH + OL2 + INE2] * * * … Universalium
morpholine — noun A six membered, saturated heterocycle tetrahydro 1,4 oxazine containing four carbon atoms, one nitrogen and one oxygen atom; it has a number of industrial applications Syn: tetrahydrooxazine See Also: morpholinium … Wiktionary
morpholine — mor·pho·line mȯr fə .lēn, lən n an oily cyclic secondary amine C4H9NO made from ethylene oxide and ammonia and used chiefly as a solvent and emulsifying agent … Medical dictionary
morpholine — n. (Chemistry) colorless organic liquid used as a deacidifying agent (Na . (CH 2 ) 2 . O . (CH 2 ) 2) … English contemporary dictionary
morpholine — mor·pho·line … English syllables
morpholine — n.f. Fongicide … Le dictionnaire des mots absents des autres dictionnaires
morpholine — ˌlēn, lə̇n noun ( s) Etymology: International Scientific Vocabulary morphol (International Scientific Vocabulary morphine + ol) + ine; from a former belief that its molecular structure was similar to that of morphine : an oily cyclic secondary… … Useful english dictionary
110-91-8 — Morpholine Morpholine Général Nom IUPAC tétrahydro 1,4 oxazine No CAS … Wikipédia en Français