| 词条 | 1,2-Diaminopropane |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477343147 | ImageFile = 1,2-Diaminopropane.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 160 | ImageName = Skeletal formula of 1,2-diaminopropane with some implicit hydrogens shown | PIN = 1,2-Propanediamine | SystematicName = Propane-1,2-diamine |Section1={{Chembox Identifiers | CASNo = 78-90-0 | CASNo_Ref = {{cascite|changed|??}} | PubChem = 6567 | PubChem1 = 447820 | PubChem1_Comment = R | PubChem2 = 642322 | PubChem2_Comment = S | ChemSpiderID = 13849260 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 394801 | ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1_Comment = R | ChemSpiderID2 = 557530 | ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID2_Comment = S | EINECS = 201-155-9 | UNNumber = 2258 | MeSHName = 1,2-diaminopropane | ChEBI = 30630 | ChEBI_Ref = {{ebicite|correct|EBI}} | RTECS = TX6650000 | Beilstein = 605274 | Gmelin = 25709 | SMILES = CC(N)CN | StdInChI = 1S/C3H10N2/c1-3(5)2-4/h3H,2,4-5H2,1H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = dAOHJOMMDDJHIJH-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} }} |Section2={{Chembox Properties | C=3 | H=10 | N=2 | Appearance = Colourless liquid | Odor = Fishy, ammoniacal | Density = 870 mg mL{{sup|−1}} | MeltingPtK = 236.0 | BoilingPtK = 392.7 | VaporPressure = 1.9 Pa (at 20 °C) | RefractIndex = 1.446 | MagSus = -58.1·10{{sup|−6}} cm{{sup|3}}/mol }} |Section3={{Chembox Thermochemistry | DeltaHf = −98.2–−97.4 kJ mol{{sup|−1}} | DeltaHc = −2.5122–−2.5116 MJ mol{{sup|−1}} | Entropy = 247.27 J K{{sup|−1}} mol{{sup|−1}} | HeatCapacity = 205.64 J K{{sup|−1}} mol{{sup|−1}} }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|226|302|312|314}} | PPhrases = {{P-phrases|280|305+351+338|310}} | FlashPtC = 34 | AutoignitionPtC = 360 | ExploLimits = 1.9–11.1% | LD50 = {{Unbulleted list|434 mg kg{{sup|−1}} (dermal, rabbit)|2.23 g kg{{sup|−1}} (oral, rat)}} }} |Section5={{Chembox Related | OtherFunction_label = alkanamines | OtherFunction = {{Unbulleted list|Ethylamine|Ethylenediamine|Propylamine|Isopropylamine|1,3-Diaminopropane|Isobutylamine|tert-Butylamine|n-Butylamine|sec-Butylamine|Putrescine}} | OtherCompounds = 2-Methyl-2-nitrosopropane }} }} 1,2-Diaminopropane (1,2-propanediamine) is organic compound with the formula CH{{sub|3}}CH(NH{{sub|2}})CH{{sub|2}}NH{{sub|2}}. A colorless liquid, it is the simplest chiral diamine. It is used as a bidentate ligand in coordination chemistry. PreparationIndustrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane:[1] This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia:[1] 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 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.[2] Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.[3] UsesMetal deactivator1,2-Diaminopropane is used in the synthesis of N,N′-disalicylidene-1,2-propanediamine, a salen-type ligand, usually abbreviated as salpn, that is used as a metal deactivating additive in motor oils.[4] References1. ^1 {{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 | pages = 5681–5687 | doi = 10.1021/ie051134u}} {{Antioxidants}}{{DEFAULTSORT:Diaminopropane, 1, 2-}}2. ^{{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 | pages = 2747–2754 | doi = 10.1016/j.poly.2010.06.030}} 3. ^{{cite patent | invent1 = Sakie, N. | invent2 = Haruyo, S. | title = Production of Optically Active 1,2-propanediamine | country = JP | status = application | number = 04-018057 }} 4. ^{{Ullmann | author1 = Dabelstein, W.|author2= Reglitzky A.|author3= Schutze A.|author4= Reders, K. | title = Automotive Fuels | doi = 10.1002/14356007.a16_719.pub2}} 4 : Diamines|Chelating agents|Fuel antioxidants|Corrosion inhibitors |
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