| Revision as of 10:11, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477325098 of page 1,2-Diaminopropane for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 17:42, 6 July 2024 edit GünniX (talk | contribs)Extended confirmed users311,836 editsm Double pipe in a linkTag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 477343147 |
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| ImageFile = 1,2-Diaminopropane.svg |
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| ImageFile = 1,2-Diaminopropane.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = |
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| IUPACName = |
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| ImageSize = 160 |
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| ImageName = Skeletal formula of 1,2-diaminopropane with some implicit hydrogens shown |
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| OtherNames = |
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| PIN = Propane-1,2-diamine |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 1,2-Propanediamine |
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| CASNo = |
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|Section1={{Chembox Identifiers |
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| ChEBI = 30630 |
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| PubChem = |
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| CASNo = 78-90-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChemSpiderID = 13849260 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = CC(N)CN |
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| UNII = 2A4P522UGO |
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| InChI = 1/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 |
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| PubChem = 6567 |
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| InChIKey = AOHJOMMDDJHIJH-UHFFFAOYAH |
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| PubChem1 = 447820 |
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| StdInChI = 1S/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 |
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| PubChem1_Comment = <small>''R''</small> |
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| StdInChIKey = AOHJOMMDDJHIJH-UHFFFAOYSA-N |
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| PubChem2 = 642322 |
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}} |
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| PubChem2_Comment = <small>''S''</small> |
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| Section2 = {{Chembox Properties |
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| ChemSpiderID = 13849260 |
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| C = 3 | H = 10 | N = 2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance = |
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| Density = |
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| ChemSpiderID1 = 394801 |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| MeltingPt = |
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| ChemSpiderID1_Comment = <small>''R''</small> |
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| BoilingPt = |
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| ChemSpiderID2 = 557530 |
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| Solubility = |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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}} |
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| ChemSpiderID2_Comment = <small>''S''</small> |
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| Section3 = {{Chembox Hazards |
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| EINECS = 201-155-9 |
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| MainHazards = |
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| FlashPt = |
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| UNNumber = 2258 |
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| MeSHName = 1,2-diaminopropane |
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| Autoignition = |
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| ChEBI = 30630 |
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}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| RTECS = TX6650000 |
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| Beilstein = 605274 |
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| Gmelin = 25709 |
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| SMILES = CC(N)CN |
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| StdInChI = 1S/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = dAOHJOMMDDJHIJH-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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| C=3 | H=10 | N=2 |
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| Appearance = Colourless liquid |
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| Odor = Fishy, ammoniacal |
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| Density = 870 mg mL{{sup|−1}} |
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| MeltingPtK = 236.0 |
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| BoilingPtK = 392.7 |
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| VaporPressure = 1.9 kPa (at 20 °C) |
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| RefractIndex = 1.446 |
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| MagSus = -58.1·10{{sup|−6}} cm{{sup|3}}/mol |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −98.2–−97.4 kJ mol{{sup|−1}} |
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| DeltaHc = −2.5122–−2.5116 MJ mol{{sup|−1}} |
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| Entropy = 247.27 J K{{sup|−1}} mol{{sup|−1}} |
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| HeatCapacity = 205.64 J K{{sup|−1}} mol{{sup|−1}} |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|226|302|312|314}} |
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| PPhrases = {{P-phrases|280|305+351+338|310}} |
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| FlashPtC = 34 |
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| AutoignitionPtC = 360 |
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| ExploLimits = 1.9–11.1% |
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| LD50 = {{Unbulleted list|434 mg kg{{sup|−1}} <small>(dermal, rabbit)</small>|2.23 g kg{{sup|−1}} <small>(oral, rat)</small>}} |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = alkanamines |
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| OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]|]}} |
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| OtherCompounds = ] |
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}} |
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}} |
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'''1,2-Diaminopropane''' ('''propane-1,2-diamine''') is ] with the formula CH{{sub|3}}CH(NH{{sub|2}})CH{{sub|2}}NH{{sub|2}}. A colorless liquid, it is the simplest chiral ]. It is used as a bidentate ligand in coordination chemistry. |
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==Preparation== |
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Industrially, this compound is synthesized by the ] of ]:<ref name="ref1">{{cite journal |author1=Bartkowiak, M. |author2=Lewandowski, G. |author3=Milchert, E. |author4=Pelech, R. | title = Optimization of 1,2-Diaminopropane Preparation by the Ammonolysis of Waste 1,2-Dichloropropane | journal = Ind. Eng. Chem. Res. | year = 2006 | volume = 45 |issue=16 | pages = 5681–5687 | doi = 10.1021/ie051134u}}</ref> |
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:CH{{sub|3}}CHClCH{{sub|2}}Cl + 4 NH{{sub|3}} → CH{{sub|3}}CH(NH{{sub|2}})CH{{sub|2}}NH{{sub|2}} + 2 NH{{sub|4}}Cl |
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This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ].<ref name="ref1" /> |
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The racemic mixture of this chiral compound may be separated into enantiomers by conversion into the diastereomeric tartaric acid ammonium salt. After purification of the diastereomer, the diamine can be regenerated by treatment of the ammonium salt with sodium hydroxide.<ref>{{cite journal |author1=Romanowski, G. |author2=Wera, M. | title = Mononuclear and dinuclear chiral vanadium(V) complexes with tridentate Schiff bases derived from R(−)-1,2-diaminopropane: Synthesis, structure, characterization and catalytic properties | journal = Polyhedron | year = 2010 | volume = 29 |issue=13 | pages = 2747–2754 | doi = 10.1016/j.poly.2010.06.030}}</ref> Alternate reagents for ] include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.<ref>{{cite patent | invent1 = Sakie, N. | invent2 = Haruyo, S. | title = Production of Optically Active 1,2-propanediamine | country = JP | status = application | number = 04-018057}}</ref> |
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==Uses== |
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===Metal deactivator=== |
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1,2-Diaminopropane is used in the synthesis of ], a ]-type ], usually abbreviated as salpn, that is used as a ] additive in ]s.<ref>{{Ullmann | author1 = Dabelstein, W.|author2= Reglitzky A.|author3= Schutze A.|author4= Reders, K. | title = Automotive Fuels | doi = 10.1002/14356007.a16_719.pub2}}</ref> |
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==Related compounds== |
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/* Uses */ Two chiral 1,2-diamines are ] and ]. |
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==References== |
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{{Reflist}} |
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{{Antioxidants}} |
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{{DEFAULTSORT:Diaminopropane, 1, 2-}} |
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] |
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] |
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] |
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] |