| 词条 | Morpholine |
| 释义 |
| Watchedfields = changed | verifiedrevid = 477503302 | Reference = [1] | Name = Morpholine | ImageFileL1 = Morpholine numbering.svg | ImageNameL1 = numbered skeletal formula of the morpholine molecule | ImageFileR1 = Morpholine-stereo-2D-skeletal.png | ImageNameR1 = perspective skeletal formula of the morpholine molecule | ImageFileL2 = Morpholine-from-xtal-3D-balls-B.png | ImageNameL2 = ball-and-stick model of the morpholine molecule | ImageFileR2 = Morpholine-from-xtal-3D-vdW-B.png | ImageNameR2 = space-filling model of the morpholine molecule | PIN = Morpholine | OtherNames = Diethylenimide oxide 1,4-Oxazinane Tetrahydro-1,4-oxazine Diethylene imidoxide Diethylene oximide Tetrahydro-p-oxazine |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 8B2ZCK305O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 34856 | ChemSpiderID = 13837537 | SMILES = C1CNCCO1 | InChI = 1/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2 | InChIKey = YNAVUWVOSKDBBP-UHFFFAOYAU | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YNAVUWVOSKDBBP-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 110-91-8 | RTECS = QD6475000 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 276518 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C14452 |Section2={{Chembox Properties | C=4 | H=9 | N=1 | O=1 | Appearance = Colorless liquid | Odor = Weak ammonia-like or fish-like[2] | Density = 1.007 g/cm3 | Solubility = miscible | MeltingPtC = −5 | BoilingPtC = 129 | pKa = 8.36[2] (of conjugate acid) | VaporPressure = 6 mmHg (20 °C)[2] | MagSus = -55.0·10−6 cm3/mol |Section7={{Chembox Hazards | ExternalSDS = hazard.com | MainHazards = Flammable, Corrosive | NFPA-H = 3 | NFPA-F = 3 | NFPA-R = 0 | FlashPtC = 31 | AutoignitionPtC = 275 | RPhrases = {{R10}} {{R20/21/22}} {{R34}} | SPhrases = {{S1/2}} {{S23}} {{S36}} {{S45}} | PEL = TWA 20 ppm (70 mg/m3) [skin][3] | ExploLimits = 1.4%–11.2%[3] | IDLH = 1400 ppm[3] | LC50 = 365 ppm (mouse, 2 hr)[4] | LD50 = 1220 mg/kg (mammal, oral) 525 mg/kg (mouse, oral) 1050 mg/kg (rat, oral)[4] | REL = TWA 20 ppm (70 mg/m3) ST 30 ppm (105 mg/m3) [skin][3] }} 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. ProductionMorpholine is often produced industrially by the dehydration of diethanolamine with sulfuric acid:[5] UsesIndustrial applicationsMorpholine 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 synthesisMorpholine 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).[6] It is commonly used to generate enamines.[7] 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. AgricultureAs a fruit coatingMorpholine 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.[8] The European Union has forbidden the use of morpholine in fruit coating.[9][10] As a component in fungicidesMorpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.
See also
References1. ^{{cite web | author=National Institute for Occupational Safety and Health | year=2000 | title=Morpholine | work=International Chemical Safety Cards | url=https://www.cdc.gov/niosh/ipcsneng/neng0302.html | accessdate=5 November 2005}} 2. ^{{cite journal | last = Hall | first = H. K. | journal = J. Am. Chem. Soc. | year = 1957 | volume = 79 | pages = 5441 | doi = 10.1021/ja01577a030 | issue = 20}} 3. ^1 2 3 4 5 {{PGCH|0437}} 4. ^1 {{IDLH|110918|Morpholine}} 5. ^{{cite book | title = Industrial Organic Chemistry |first1=Klaus |last1=Weissermel |first2=Hans-Jürgen |last2=Arpe |first3=Charlet R. |last3=Lindley |first4=Stephen |last4=Hawkins | publisher = Wiley-VCH | year = 2003 | isbn = 3-527-30578-5 | pages = 159–161 | chapter = Chapter 7. Oxidation Products of Ethylene}} 6. ^{{OrgSynth | last1= Lindsay Smith |first1=J. R. |last2=McKeer |first2=L. C. |last3=Taylor |first3=J. M. | title = 4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene | collvol = 8 | collvolpages = 167 | year = 1993 | prep = CV8P0167}} 7. ^{{OrgSynth | authorlink = Ryoji Noyori|last1=Noyori |first1=R. |last2=Yokoyama |first2=K. |last3=Hayakawa |first3=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}} 8. ^{{cite journal |first1=Raymond G. |last1=McGuire |first2=Dimitrios A. |last2=Dimitroglou | url = http://www.informaworld.com/smpp/content~content=a713655919~db=all | title = Evaluation of Shellac and Sucrose Ester Fruit Coating Formulations that Support Biological Control of Post-harvest Grapefruit Decay | journal = Bio-control Science and Technology | volume = 9 | issue = 1 | year = 1999 | pages = 53–65}} 9. ^{{cite web | url = http://www.salltd.co.uk/news_item.jsp?file=2010-09-29%20Morpholine%20residues%20detected%20in%20apples%20from%20Chile.html | title = Morpholine | publisher = Scientific Analysis Laboratories Ltd | deadurl = yes | archiveurl = https://web.archive.org/web/20120426070141/http://www.salltd.co.uk/news_item.jsp?file=2010-09-29%20Morpholine%20residues%20detected%20in%20apples%20from%20Chile.html | archivedate = 2012-04-26 | df = }} 10. ^{{cite web | url = http://www.nwhort.org/UKCountryAlert.html | title = Morpholine Issues in the United Kingdom | date = September 28, 2010 | publisher = Northwest Horticultural Council | deadurl = yes | archiveurl = https://web.archive.org/web/20120426070141/http://www.nwhort.org/UKCountryAlert.html | archivedate = April 26, 2012 | df = }} External links
3 : Morpholines|Ether solvents|Amine solvents |
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