Misplaced Pages

Crotonaldehyde: Difference between revisions

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 10:24, 11 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'KEGG', 'CASNo').← Previous edit Latest revision as of 15:28, 25 December 2024 edit undoSandcherry (talk | contribs)Extended confirmed users8,092 edits Could not confirm process with manufacturing engineer 
(69 intermediate revisions by 40 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Verifiedfields = changed |Verifiedfields = changed
|Watchedfields = changed
| verifiedrevid = 401969288
|verifiedrevid = 460108375
| Reference=<ref>'']'', 11th Edition, '''2599'''</ref>
|Reference=<ref>'']'', 11th Edition, '''2599'''</ref>
| ImageFile = Crotonaldehyde.png
|ImageFile = Crotonaldehyde.png
| ImageName = Skeletal formula
|ImageAlt = Skeletal formula of crotonaldehyde
| ImageSize = 180px
|ImageSize = 180px
| ImageFile1 = Crotonaldehyde-3D-balls.png
|ImageFile1 = Crotonaldehyde-3D-balls.png
| ImageName1 = Ball-and-stick model
|ImageAlt1 = Ball-and-stick model of (Z)-crotonaldehyde
| IUPACName = (2''E'')-but-2-enal
|IUPACName = (2''E'')-but-2-enal
| OtherNames = Crotonaldehyde<br/>crotoinic aldehyde<br/>β-Methacrolein
|OtherNames = Crotonaldehyde<br/>Crotonic aldehyde<br/>β-Methacrolein<br/>β-Methyl acrolein<br/>2-butenal<br/>Propylene aldehyde
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| Abbreviations =
|IUPHAR_ligand = 6288
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 394562
|ChemSpiderID = 394562
| InChIKey = MLUCVPSAIODCQM-NSCUHMNNBQ
|InChIKey = MLUCVPSAIODCQM-NSCUHMNNBQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
|StdInChI = 1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MLUCVPSAIODCQM-NSCUHMNNSA-N
|StdInChIKey = MLUCVPSAIODCQM-NSCUHMNNSA-N
| CASNo_Ref = {{cascite|changed|??}}
|CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 123-73-9
|CASNo = 4170-30-3
| EINECS =
|CASNo_Comment = (''E/Z'')
| PubChem = 447466
| ChEMBL_Ref = {{ebicite|changed|EBI}} |CASNo1_Ref = {{cascite|correct|CAS}}
| ChEMBL = 1086445 |CASNo1 = 123-73-9
|CASNo1_Comment = (''E'')
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
|CASNo2_Ref = {{cascite|correct|CAS}}
| DrugBank = DB04381
|CASNo2 = 15798-64-8
| SMILES = O=C/C=C/C
|CASNo2_Comment = (''Z'')
| InChI = 1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
|UNII_Ref = {{fdacite|correct|FDA}}
| RTECS =
|UNII = 9G72074TUW
| MeSHName =
|UNII_Comment = (''E/Z'')
| ChEBI_Ref = {{ebicite|changed|EBI}}
|UNII1_Ref = {{fdacite|correct|FDA}}
| ChEBI = 41607
|UNII1 = 6PUW625907
| KEGG_Ref = {{keggcite|changed|kegg}}
|UNII1_Comment = (''E'')
| KEGG = <!-- blanked - oldvalue: C19377 -->
|UNII2_Ref = {{fdacite|correct|FDA}}
| ATCCode = }}
|UNII2 = RB9WCA91QT
| Section2 = {{Chembox Properties
|UNII2_Comment = (''Z'')
| C = 4 | H = 6 | O = 1
|UNNumber = 1143
| Appearance = Colorless liquid
|EINECS = 204-647-1
| Density = 0.846 g/cm<sup>3</sup>
|PubChem = 447466
| MeltingPtC = -76.5
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| Melting_notes =
|ChEMBL = 1086445
| BoilingPtC = 104.0
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| Boiling_notes =
|DrugBank = DB04381
| Solubility =
| pKa = |SMILES = O=C/C=C/C
|InChI = 1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
| pKb =
|RTECS =GP9499000
| IsoelectricPt =
|ChEBI_Ref = {{ebicite|correct|EBI}}
| SpecRotation =
|ChEBI = 41607
| RefractIndex = 1.4362
|KEGG_Ref = {{keggcite|changed|kegg}}
| Viscosity =
| Dipole = }} |KEGG = C19377
}}
| Section3 = {{Chembox Structure
|Section2={{Chembox Properties
| CrystalStruct =
|C=4 | H=6 | O=1
| Coordination =
|Appearance = colourless liquid
| MolShape =
|Odor = pungent, suffocating odor
| Dipole = }}
|Density = 0.846 g/cm<sup>3</sup>
| Section4 = {{Chembox Thermochemistry
| DeltaHf = |MeltingPtC = -76.5
| DeltaHc = |BoilingPtC = 104.0
|Solubility = 18% (20°C)<ref name=PGCH/>
| Entropy =
|SolubleOther = very soluble in ], ], ] <br/> soluble in ] <br/> miscible in ]
| HeatCapacity = }}
|RefractIndex = 1.4362
| Section5 = {{Chembox Pharmacology
|VaporPressure = 19 mmHg (20°C)<ref name=PGCH/>
| AdminRoutes =
}}
| Bioavail =
|Section3={{Chembox Hazards
| Metabolism =
| HalfLife = |NFPA-H = 4
|NFPA-F = 3
| ProteinBound
| Excretion = |NFPA-R = 2
|NFPA-S = -
| Legal_status =
|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| Legal_US =
|GHSSignalWord = Danger
| Legal_UK =
|HPhrases = {{H-phrases|225|301|310|311|315|318|330|335|341|373|400}}
| Legal_AU =
|PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|261|262|264|270|271|273|280|281|284|301+310|302+350|302+352|303+361+353|304+340|305+351+338|308+313|310|312|314|320|321|322|330|332+313|361|362|363|370+378|391|403+233|403+235|405|501}}
| Legal_CA =
| PregCat = |FlashPtC = 13
|AutoignitionPtC = 207
| PregCat_AU =
|ExploLimits = 2.1-15.5%
| PregCat_US = }}
|PEL = TWA 2 ppm (6 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0157}}</ref>
| Section6 = {{Chembox Explosive
|IDLH = 50 ppm<ref name=PGCH/>
| ShockSens =
|REL = TWA 2 ppm (6 mg/m<sup>3</sup>)<ref name=PGCH/>
| FrictionSens =
|LC50 = 600 ppm (rat, 30 min)<br/>1375 ppm (rat, 30 min)<br/>519 ppm (mouse, 2 hr)<br/>1500 ppm (rat, 30 min)<ref name=IDLH>{{IDLH|123739|Crotonaldehyde}}</ref>
| ExplosiveV =
|LCLo = 400 ppm (rat, 1 hr)<ref name=IDLH/>
| REFactor = }}
}}
| Section7 = {{Chembox Hazards
|Section4={{Chembox Related
| ExternalMSDS =
|OtherFunction_label = alkenals
| EUClass =
|OtherFunction = ]<br />
| EUIndex =
| MainHazards =
| NFPA-H = 4
| NFPA-F = 3
| NFPA-R = 2
| NFPA-O = &nbsp;
| RPhrases = {{R11}} {{R24/25}} {{R26}} {{R37/38}} {{R41}} {{R48/22}} {{R50}} {{R68}}
| SPhrases = {{S26}} {{S28}} {{S36/37/39}} {{S45}} {{S61}}
| RSPhrases =
| FlashPt =
| Autoignition =
| ExploLimits =
| PEL = }}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| Function = alkenals
| OtherFunctn = ]<br />
]<br /> ]<br />
] ]
| OtherCpds = }} |OtherCompounds =}}
}} }}


'''Crotonaldehyde''' is a ] with the ] CH<sub>3</sub>CH=CHCHO. The compound is usually sold as a mixture of the ''E''- and ''Z''-isomers, which differ with respect to the relative position of the ] and ] groups. The ''E''-isomer is more common (data given in Table is for the ''E''-isomer). This ] liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in ]. It occurs in a variety of foodstuffs, e.g. ]s.<ref name=Schulz>R. P. Schulz, J. Blumenstein, C. Kohlpaintner "Crotonaldehyde and Crotonic Acid" ''Ullmann's Encyclopedia of Chemical Technology'', Wiley-VCH, Weinheim: 2005. {{DOI|10.1002/14356007.a08_083}}</ref> '''Crotonaldehyde''' is a ] with the ] CH<sub>3</sub>CH=CHCHO. The compound is usually sold as a mixture of the ''E''- and ''Z''-isomers, which differ with respect to the relative position of the ] and ] groups. The ''E''-isomer is more common (data given in Table is for the ''E''-isomer). This ] liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in ]. It occurs in a variety of foodstuffs, e.g. ]s.<ref name=Schulz>{{Ullmanns |author=R. P. Schulz |author2=J. Blumenstein |author3=C. Kohlpaintner|title=Crotonaldehyde and Crotonic Acid|year=2005|doi=10.1002/14356007.a08_083}}</ref>


==Production and uses== ==Production and reactivity==
Crotonaldehyde is produced by the ] of ]: Crotonaldehyde is produced by the ] of ]:
:2 CH<sub>3</sub>CHO → CH<sub>3</sub>CH=CHCHO + H<sub>2</sub>O :2 CH<sub>3</sub>CHO → CH<sub>3</sub>CH=CHCHO + H<sub>2</sub>O
Its main application is as a precursor to fine chemicals. ], a food preservative, and trimethylhydroquinone, a precursor to the vitamin E, are prepared from crotonaldehyde. Other derivatives include crotonic acid and 3-methoxybutanol.<ref name=Schulz/>


Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is an excellent ] dienophile.<ref>{{OrgSynth | author = Longley, Jr., R. I..; Emerson, W. S.; Blardinelli, A. J. | title = 3,4-Dihydro-2-methoxy-4-methyl-2H-pyran | collvol = 4 | collvolpages = 311 | year = 1963 | prep = CV4P0311}}</ref> It is a ]. Addition of ] affords 3-penten-2-ol.<ref>{{OrgSynth | author = Coburn, E. R. | title = 3-Penten-2-ol | collvol = 3 | collvolpages = 696 | year = 1955 | prep = CV3P0696}}</ref> Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is a ] dienophile.<ref>{{cite journal | author = Longley Jr., R. I.. | author2 = Emerson, W. S. | author3 = Blardinelli, A. J. | title = 3,4-Dihydro-2-methoxy-4-methyl-2H-pyran |journal= Org. Synth.|year=1954|volume=34|page=29|doi=10.15227/orgsyn.034.0029}}</ref> It is a ]. Addition of ] produces 3-penten-2-ol.<ref>{{cite journal | author = Coburn, E. R. | title = 3-Penten-2-ol |journal= Org. Synth.|year=1947|volume=27|page=65|doi= 10.15227/orgsyn.027.0065}}</ref>

==Uses==
] is a specialty fertilizer.<ref name=Ull>{{Ullmann|doi= 10.1002/14356007.n10_n01 |title= Fertilizers, 2. Types |year=2009 |last1=Dittmar |first1=Heinrich |last2=Drach |first2=Manfred |last3=Vosskamp |first3=Ralf |last4=Trenkel |first4=Martin E. |last5=Gutser |first5=Reinhold |last6=Steffens |first6=Günter}}</ref>]]
It is a precursor to many fine chemicals. A prominent industrial example is the crossed aldol condensation with ] to give trimethylcyclohexenone, this can be easily converted to trimethylhydroquinone, which is a precursor to the ].<ref>{{cite journal |last1=Müller |first1=Marc-André |last2=Schäfer |first2=Christian |last3=Litta |first3=Gilberto |last4=Klünter |first4=Anna-Maria |last5=Traber |first5=Maret G. |last6=Wyss |first6=Adrian |last7=Ralla |first7=Theo |last8=Eggersdorfer |first8=Manfred |last9=Bonrath |first9=Werner |title=100 Years of Vitamin E: From Discovery to Commercialization |journal=European Journal of Organic Chemistry |date=6 December 2022 |volume=2022 |issue=45 |doi=10.1002/ejoc.202201190|url=https://pure.rug.nl/ws/files/373357775/100_Years_of_Vitamin_E.pdf }}</ref> Other derivatives include crotonic acid, 3-methoxybutanol and the food preservative ]. Condensation with two equivalents of ] gives a ] derivative that is employed as a ].
<ref name=Schulz/>


==Safety== ==Safety==
Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an {{LD50}} of 174 mg/kg (rats, oral).<ref name=Schulz/>
Crotonaldehyde is an irritant. It is listed as an "]" as defined by the U.S. ]. It occurs widely in nature.


==See also== ==See also==
Line 127: Line 114:


==References== ==References==
{{Reflist}}
<references/>


==External links== ==External links==
* *
*


{{Chemical agents}}
]
]
]


{{Authority control}}
]

]
]
]
]
]
]
]
]
]
]
]
]
Crotonaldehyde: Difference between revisions Add topic