| Revision as of 20:19, 17 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validatio← Previous edit |
Latest revision as of 09:08, 25 October 2023 edit undoCitation bot (talk | contribs)Bots5,393,097 edits Removed proxy/dead URL that duplicated identifier. | Use this bot. Report bugs. | #UCB_CommandLine |
| (62 intermediate revisions by 39 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 366075525 |
|
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 445391168 |
|
| ImageFile = Methyldiethanolamine.svg |
|
| ImageFile = Methyldiethanolamine.svg |
|
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFileSize = |
|
|
| ImageFile1 = |
|
| ImageSize = 160 |
|
|
| ImageName = Skeletal formula of methyl diethanolamine |
|
| ImageFileSize1 = |
|
|
|
| PIN = 2,2′-(Methylazanediyl)di(ethan-1-ol) |
|
| ImageFile2 = |
|
|
|
| OtherNames = Bis(2-hydroxyethyl)(methyl)amine |
|
| ImageFileSize2 = |
|
|
|
|Section1={{Chembox Identifiers |
|
| ImageFile3 = |
|
|
| ImageFileSize3 = |
|
|
| IUPACName = Bis(2-hydroxyethyl)methylamine |
|
|
| OtherNames = 2,2′-(Methylimino)bis-ethanol<br/>Diethanolmethylamine<br/>Bis(2-hydroxyethyl)methylamine |
|
|
| Abbreviations = MDEA |
|
|
| Section1 = {{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite}} |
|
|
| CASNo = 105-59-9 |
|
| CASNo = 105-59-9 |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| EINECS = |
|
|
|
| ChEMBL = 3185149 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 3IG3K131QJ |
|
| PubChem = 7767 |
|
| PubChem = 7767 |
|
| SMILES = |
|
| ChemSpiderID = 7479 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| InChI = |
|
|
|
| EINECS = 203-312-7 |
|
|
| MeSHName = N-methyldiethanolamine |
|
| RTECS = KL7525000 |
|
| RTECS = KL7525000 |
|
| MeSHName = |
|
| Beilstein = 1734441 |
|
|
| SMILES = CN(CCO)CCO |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
|
|
| StdInChI = 1S/C5H13NO2/c1-6(2-4-7)3-5-8/h7-8H,2-5H2,1H3 |
|
| ChEBI = |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = CRVGTESFCCXCTH-UHFFFAOYSA-N |
|
| KEGG = |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| ATCCode = }} |
|
|
|
}} |
|
| Section2 = {{Chembox Properties |
|
|
|
|Section2={{Chembox Properties |
|
| Formula = CH<sub>3</sub>N(C<sub>2</sub>H<sub>4</sub>OH)<sub>2</sub> |
|
|
|
| C=5 | H=13 | N=1 | O=2 |
|
| MolarMass =119.163 g/mol |
|
|
| Appearance = Clear, colorless, 150 APHA max. |
|
| Appearance = Colorless liquid |
|
|
| Odor = Ammoniacal |
|
| Density = 1.043 g/cm<sup>3</sup> |
|
|
|
| Density = 1.038 g mL<sup>−1</sup> |
|
| MeltingPt = -21°C |
|
|
|
| MeltingPtK = 252.15 |
|
| Melting_notes = |
|
|
| BoilingPt = 247°C |
|
| BoilingPtK = 520.2 |
|
|
| Solubility = Miscible |
|
| Boiling_notes = |
|
|
|
| VaporPressure = 1 Pa (at 20 °C) |
|
| Solubility = complete |
|
|
| SolubleOther = ], ] |
|
|
| Solvent = |
|
|
| pKa = |
|
|
| pKb = |
|
|
| IsoelectricPt = |
|
|
| SpecRotation = |
|
|
| RefractIndex = 1.4694 |
|
| RefractIndex = 1.4694 |
|
| Viscosity = 101 cP @ 20°C |
|
| Viscosity = 101 mPa s (at 20°C) |
|
|
}} |
|
| Dipole = }} |
|
|
| Section3 = {{Chembox Structure |
|
|Section3={{Chembox Pharmacology |
|
| CrystalStruct = |
|
| AdminRoutes = Oral |
|
|
}} |
|
| Coordination = |
|
|
|
|Section4={{Chembox Hazards |
|
| MolShape = |
|
|
|
| GHSPictograms = {{gHS exclamation mark}} |
|
| Dipole = }} |
|
|
|
| GHSSignalWord = '''WARNING''' |
|
| Section4 = {{Chembox Thermochemistry |
|
|
|
| HPhrases = {{h-phrases|319}} |
|
| DeltaHf = |
|
|
|
| PPhrases = {{p-phrases|305+351+338}} |
|
| DeltaHc = |
|
|
| Entropy = |
|
|
| HeatCapacity = }} |
|
|
| Section5 = {{Chembox Pharmacology |
|
|
| AdminRoutes = Ingestion |
|
|
| Bioavail = |
|
|
| Metabolism = |
|
|
| HalfLife = |
|
|
| ProteinBound |
|
|
| Excretion = |
|
|
| Legal_status = |
|
|
| Legal_US = |
|
|
| Legal_UK = |
|
|
| Legal_AU = |
|
|
| Legal_CA = |
|
|
| PregCat = |
|
|
| PregCat_AU = |
|
|
| PregCat_US = }} |
|
|
| Section6 = {{Chembox Explosive |
|
|
| ShockSens = |
|
|
| FrictionSens = |
|
|
| ExplosiveV = |
|
|
| REFactor = }} |
|
|
| Section7 = {{Chembox Hazards |
|
|
| ExternalMSDS = |
|
|
| EUClass = |
|
|
| EUIndex = |
|
|
| MainHazards = |
|
|
| NFPA-H = 1 |
|
| NFPA-H = 1 |
|
| NFPA-F = 1 |
|
| NFPA-F = 1 |
|
| NFPA-R = 0 |
|
| NFPA-R = 0 |
|
| NFPA-O = |
|
| FlashPtC = 127 |
|
| RPhrases = |
|
| AutoignitionPtC = 410 |
|
| SPhrases = |
|
| ExploLimits = 1.4-8.8% |
|
|
| LD50 = 1.945 g kg<sup>−1</sup> <small>(oral, rat)</small> |
|
| RSPhrases = |
|
|
| FlashPt = 135°C ] |
|
|
| Autoignition = 265°C |
|
|
| ExploLimits = 0.9-8.4 vol% in air |
|
|
| PEL = }} |
|
|
| Section8 = {{Chembox Related |
|
|
| OtherAnions = |
|
|
| OtherCations = |
|
|
| OtherFunctn = |
|
|
| Function = |
|
|
| OtherCpds = }} |
|
|
}} |
|
}} |
|
|
|Section5={{Chembox Related |
|
|
| OtherFunction_label = alkanols |
|
|
| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]}} |
|
|
| OtherCompounds = ] |
|
|
}} |
|
|
}} |
|
|
'''Methyldiethanolamine''', also known as ''N''-methyl diethanolamine and more commonly as MDEA, is the ] with the formula CH<sub>3</sub>N(C<sub>2</sub>H<sub>4</sub>OH)<sub>2</sub>. It is a colorless liquid with an ] odor. It is ] with water, ] and ]. A tertiary ], it is widely used as a sweetening agent in chemical, oil ], ] production and ].<ref name=Ullmann>Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke "Ethanolamines and Propanolamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.{{doi|10.1002/14356007.a10_001}}</ref> |
|
|
|
|
|
|
Similar compounds are ] (MEA), a primary amine, and ] (DEA), a secondary amine, both of which are also used for ]. MDEA's defining characteristic when compared to these other amines is its ability to preferentially remove H<sub>2</sub>S (and strip CO<sub>2</sub>) from ] streams.<ref name=Ullmann/> |
|
'''Methyl diethanolamine''' is a clear, colorless or pale yellow liquid with an ] odour. It is ] with water, ] and ]. Methyl diethanolamine is also known as N-Methyl diethanolamine and more commonly as MDEA. It has the formula CH<sub>3</sub>N (C<sub>2</sub>H<sub>4</sub>OH)<sub>2</sub>. MDEA is a tertiary ] and is widely used as a sweetening agent in chemical, oil ], ] production and ]. This compound should not be confused with the similarly named commercial drug ]. |
|
|
|
|
|
|
|
MDEA's popularity as a solvent for gas treating stems from several advantages it has when compared to other alkanolamines. One of these advantages is a low vapor pressure, which allows for high amine compositions without appreciable losses through the absorber and regenerator. MDEA is also resistant to thermal and chemical degradation and is largely immiscible with hydrocarbons. MDEA is a common base note in perfumes to allow the fragrance to last. Lastly, MDEA has a relatively low heat of reaction with hydrogen sulfide and carbon dioxide, which allows for lower reboiler duties, thus lower operating costs. |
|
MDEA's popularity as a solvent for gas treating stems from several advantages it has over other alkanolamines, especially its ability to preferentially remove H<sub>2</sub>S (and slip CO<sub>2</sub>) from sour gas streams. |
|
|
|
|
|
|
|
==MDEA blends== |
|
Similar compounds are monoethanolamine (MEA), a primary amine, and diethanolamine (DEA), a secondary amine, both of which are also used for ]. |
|
|
|
|
|
|
|
MDEA is less reactive towards CO<sub>2</sub>, but has an equilibrium loading capacity approaching 1 mole CO<sub>2</sub> per mole amine.<ref name="Idem2006">{{cite journal|last1=Idem|first1=Raphael|title=Pilot Plant Studies of the CO<sub>2</sub> Capture Performance of Aqueoues MEA and Mixed MEA/MDEA Solvents at the University of Regina CO<sub>2</sub> Capture Technology Development Plant and the Boundary Dam CO<sub>2</sub> Capture Demonstration Plant|journal=Ind. Eng. Chem. Res.|volume=45|issue=8|year=2006|pages=2414–2420|doi=10.1021/ie050569e}}</ref> It also requires less energy to regenerate.<ref name="Idem2006"/> To combine the advantages of MDEA and the smaller amines, MDEA is usually mixed with a catalytic promoter such as piperazine, PZ, or a fast reacting amine such as MEA to retain reactivity, but lower regeneration costs. Activated MDEA or aMDEA uses ] as a catalyst to increase the speed of the reaction with CO<sub>2</sub>. It has been commercially successful.<ref>{{cite journal | title = Piperazine – Why It's Used and How It Works | journal = The Contactor | date = 2008 | publisher = Optimised Gas Treating, Inc. | volume = 2 | issue = 4 | url = http://www.ogtrt.com/files/contactors/vol_2_issue_4.pdf | access-date = 2013-10-23 | url-status = dead | archive-url = https://web.archive.org/web/20141129012009/http://www.ogtrt.com/files/contactors/vol_2_issue_4.pdf | archive-date = 2014-11-29}}</ref> Many tests have been done on the performance of MDEA/MEA or MDEA/piperazine mixtures compared to single amines. CO<sub>2</sub> production rates were higher than MEA for the same heat duty and total molar concentration when experiments were performed in the University of Regina pilot plant, which is a modeled after a natural gas plant. There were also insignificant trace amounts of degradation products detected.<ref name="Idem2006"/> However, when the same control variables and tests were conducted at the ] plant, the CO<sub>2</sub> production rate for the mixed solvent was lower than MEA.<ref name="Idem2006"/> This was a result of the reduction in the capacity of the solvent to absorb CO<sub>2</sub> after degradation. Because the Boundary Dam plant is a coal-fired power plant, it operates under harsher environments and produces an impure flue gas containing, fly ash, SO<sub>2</sub>, and NO<sub>2</sub> that are fed into carbon capture. Even with flue gas pretreatment, there is still enough to produce degradation products such as |
|
|
straight chain amines and sulfur compounds, which accumulate so it is no longer possible to regenerate MEA and MDEA.<ref name="Idem2006"/> For these blends to be successful in reducing heat duty, their chemical stabilities must be maintained. |
|
|
|
|
|
===Degradation=== |
|
|
|
|
|
Main oxidative degradation products of MDEA include monoethanol amine (MEA), methyl-aminoethanol (MAE), diethanolamine (DEA), amino acids bicine, glycine and hydroxyethyl sarcosine (HES), formyl amides of MAE and DEA, ammonia, and stable salts formate, glycolate, acetate, and oxalate.<ref name="Handford2014">{{cite journal|last1=Boot-Handford|first1=M.E.|title= Carbon capture and storage update|journal= Energy Environ. Sci.|volume=7|issue=1|year=2014|pages=130–189|doi=10.1039/c3ee42350f|s2cid=97132693}}</ref> In an industrial plan that utilizes MDEA, oxidative degradation is most likely to shift to the cross exchanger where temperatures are greater than 70 °C.<ref name="Handford2014"/> Higher temperatures and higher CO<sub>2</sub> loading accelerate the rate of degradation, resulting in an increase of alkalinity loss as well as total formate production. While MDEA is more resistant to degradation as a standalone compared to MEA, MDEA is preferentially degraded when in an MDEA/MEA blend.<ref name="Handford2014"/> Because of the formation of DEA and MAE, which could form nitroso-compounds or diethylnitrosamine and diethylnitraine, the blend could potentially have an adverse impact in terms of atmospheric admissions.<ref name="Handford2014"/> In the Boundary Dam plant, emissions increased when CO<sub>2</sub> loading of lean amine increased for the blend and MEA.<ref name="Handford2014"/> However, decreasing the lean loading increases the reboiler heat duty, which results in an obvious tradeoff between emissions and heat duty or energy costs. |
|
|
|
|
|
This compound should not be confused with the recreational drug ] which is also abbreviated MDEA. |
|
|
|
|
|
==Production== |
|
|
MDEA is produced by ] of methylamine using ]:<ref name=Ullmann/> |
|
|
:CH<sub>3</sub>NH<sub>2</sub> + 2 C<sub>2</sub>H<sub>4</sub>O → CH<sub>3</sub>N(C<sub>2</sub>H<sub>4</sub>OH)<sub>2</sub> |
|
|
Another route involves ] of diethanolamine followed by hydrogenolysis. |
|
==See also== |
|
==See also== |
|
* ] |
|
* ] |
|
|
|
|
|
==References== |
|
==References== |
|
|
{{Reflist}} |
|
* The GPSA Databook |
|
* The GPSA Databook |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
|
|
] |
|
|
] |
|
|
] |
|