Morpholine
1733679
216108558
2008-05-31T02:57:14Z
Cacycle
83784
+ [[Category:Ethers]] + [[Category:Amines]]
{{Chembox new
| References = <ref>{{cite web | author=National Institute for Occupational Safety and Health | year=2000 | title=MORPHOLINE | work=International Chemical Safety Cards | url=http://www.cdc.gov/niosh/ipcsneng/neng0302.html | accessdaymonth=5 November | accessyear=2005}}</ref>
| Name = Morpholine
| ImageFileL1 = Morpholine numbering.svg
| ImageNameL1 = Morpholine
| ImageSizeL1 = 100px
| ImageFileR1 = Morpholine-stereo-2D-skeletal.png
| ImageNameR1 = Morpholine
| ImageSizeR1 = 100px
| ImageFile2 = Morpholine-3D-vdW.png
| ImageName2 = Morpholine
| ImageSize2 = 150px
| IUPACName = Morpholine
| OtherNames = Diethylenimide Oxide; tetrahydro-1,4-oxazine
| Section1 = {{Chembox Identifiers
| SMILES = O(CCNC1)C1
| CASOther = 110-91-8
| RTECS = QD6475000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>9</sub>NO
| MolarMass = 87.1 g/mol
| Appearance = Colorless liquid
| Density = 1.007 g/cm<sup>3</sup>
| Solubility = miscible
| MeltingPt = -5 °C
| BoilingPt = 129 °C
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/MO/morpholine.html Oxford MSDS]
| MainHazards = Flammable, Corrosive
| NFPA-H = 3
| NFPA-F = 3
| NFPA-R =
| FlashPt = 31 °C
| Autoignition = 275 °C
| RPhrases = 10-20/21/22-34
| SPhrases = (1/2-)23-36-45
}}
}}
'''Morpholine''' is an [[Organic compound|organic]] [[chemical compound]] having the [[chemical formula]] [[oxygen|O]]([[carbon|C]][[hydrogen|H]]<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>[[nitrogen|N]]H. This [[heterocycle]], pictured at right, features both [[amine]] and [[ether]] [[functional group]]s. Because of the amine, morpholine is a [[base (chemistry)|base]]; its [[conjugate acid]] is called morpholinium. For example, when morpholine is neutralized by [[hydrochloric acid]], one obtains the [[salt]] morpholinium chloride.
<!-- how is this stuff made?-->
==Production==
Morpholine may be produced by the dehydration of [[diethanolamine]] with [[sulfuric acid]]:<ref name = weissermel>{{cite book | title = Industrial Organic Chemistry | author = Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, Stephen Hawkins | publisher = [[Wiley-VCH]] | year = 2003 | isbn = 3527305785 | pages = 159-161 | chapter = Chap. 7. Oxidation Products of Ethylene}}</ref>
:[[Image:Morpholine from DEA.png|400px]]
==Uses==
===Industrial applications===
Morpholine is a common additive, in ppm [[concentration]]s, for [[pH]] adjustment in both [[fossil fuel power plant|fossil fuel]] and [[nuclear power plant]] [[steam]] systems. Morpholine is used because its [[Volatility (chemistry)|volatility]] is about the same as [[water (molecule)|water]], so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam [[phase (matter)|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]] even at the high [[temperature]]s and [[pressure]]s in these steam systems.
===Organic synthesis===
Morpholine undergoes most [[chemical reaction]]s typical for other secondary [[amine]]s, 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).<ref>{{OrgSynth | author = Lindsay Smith, J. R.; McKeer, L. C.; Taylor, J. M. | title = 4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene | collvol = 8 | collvolpages = 167 | year = 1993 | prep = CV8P0167}}</ref>
It is commonly used to generate [[enamine]]s.<ref>{{OrgSynth | author = [[Ryoji Noyori|Noyori, R.]]; Yokoyama, K.; Hayakawa, Y. | title = Cyclopentenones from α,α'-Dibromoketones and Enamines: 2,5-Dimethyl-3-Phenyl-2-Cyclopenten-1-one | collvol = 6 | collvolpages = 520 | year = 1988 | prep = CV6P0520}}</ref>
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 inhibitor]]s.
*[[Fenpropimorph]]
*[[Tridemorph]]
==References==
<references/>
[[Category:Morpholines| ]]
[[Category:Ethers]]
[[Category:Amines]]
[[Category:Ether solvents]]
[[Category:Amine solvents]]
[[de:Morpholin]]
[[fr:Morpholine]]
[[ja:モルホリン]]
[[pl:Morfolina]]
[[ru:Морфолин]]
[[zh:吗啉]]