问题：The synthesis of methyl propiolate
类型：求助 (悬赏分:3分)
提问：gumption
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时间：2005-05-13 18:27:35 编辑加入/取消收藏订制/取消短消息举报该贴

丙炔酸甲酯(methyl propiolate)较贵,小弟需要大量合成,请问哪位老兄知道怎样制备?紧急!

回复人：zhangquee,▲▲▲▲ (药物合成) 时间：2005-05-13 22:47:33 编辑

1楼

RCB_CT,405985Entry Name: 2-Propynoic acid, 9CI
Synonym(s): Propiolic acid, 8CI. Acetylenecarboxylic acid. Propargylic acid
Chapman Hall Number: DFP35-Y
CAS Registry Number: 471-25-0
Related CAS Registry Numbers(s): 920-38-7
HCCCOOH

Molecular Formula: C3H2O2
Molecular Weight: 70.048
Accurate Mass: 70.00548
Percentage Composition: C 51.44%; H 2.88%; O 45.68%
Physical Description: Cryst. or liq. with odour resembling acetic acid
Melting Point: Mp 18
Boiling Point: Bp 144 dec.. Bp50 83-84
Solubility: Misc. H2O
Dissociation Constant: pKa 1.89 (25)
Other Data: Forms a monohydrate, Mp 0.3, and a hydrate with 1/3 H2O, Mp 10
Hazard Toxicity: Reacts with ammoniacal Cu(I) or Ag(I) solutions to form explosive ppt.
RTECS Accession Number: UD9300000

Aldrich: P5140-0
Fluka: 81860
Sigma:
RCB_CT,405986Derivative: K salt
Chapman Hall Number: DFP36-Z
CAS Registry Number: 1968-46-3
Physical Description: Cryst. + 1H2O
Other Data: Dec. at 105
RCB_CT,405987Derivative: Me ester
Synonym(s): Methyl 2-propynoate. Propiolic ester
Chapman Hall Number: DFP37-A
CAS Registry Number: 922-67-8
Molecular Formula: C4H4O2
Molecular Weight: 84.074
Accurate Mass: 84.02113
Percentage Composition: C 57.14%; H 4.80%; O 38.06%
Boiling Point: Bp 102
Hazard Toxicity: Lachrymator
RTECS Accession Number: UE0050000
Aldrich: 17185-9
Fluka:
RCB_CT,405988Derivative: Et ester
Synonym(s): Ethyl 2-propynoate
Chapman Hall Number: MHL23-I
CAS Registry Number: 623-47-2
Molecular Formula: C5H6O2
Molecular Weight: 98.101
Accurate Mass: 98.03678
Percentage Composition: C 61.22%; H 6.16%; O 32.62%
Boiling Point: Bp 119
Aldrich: E4660-7
Fluka:
RCB_CT,405989Derivative: Chloride
Synonym(s): 2-Propynoyl chloride. Propiolyl chloride
Chapman Hall Number: MGK56-I
CAS Registry Number: 50277-65-1
Molecular Formula: C3HClO
Molecular Weight: 88.493
Accurate Mass: 87.971592
Percentage Composition: C 40.72%; H 1.14%; Cl 40.06%; O 18.08%
Physical Description: Liq.
Boiling Point: Bp 58-60
Other Data: Fumes slightly in air. Yellows at
RCB_CT,405990Derivative: Amide
Synonym(s): 2-Propynamide, 9CI. Propiolamide, 8CI
Chapman Hall Number: DFP39-C
CAS Registry Number: 7341-96-0
Molecular Formula: C3H3NO
Molecular Weight: 69.063
Accurate Mass: 69.021464
Percentage Composition: C 52.17%; H 4.38%; N 20.28%; O 23.17%
Physical Description: Needles or plates (Et2O)
Melting Point: Mp 61-62
RCB_CT,405991Derivative: Methylamide
Chapman Hall Number: LNO40-F
CAS Registry Number: 2682-32-8
Molecular Formula: C4H5NO
Molecular Weight: 83.09
Accurate Mass: 83.037114
Percentage Composition: C 57.82%; H 6.07%; N 16.86%; O 19.26%
Physical Description: Cryst. solid
Melting Point: Mp 88
RCB_CT,405992Derivative: Nitrile
see Cyanoacetylene, MFV56-E
Chapman Hall Number: DFP40-
RCB_CT,405993Derivative: Anhydride
Chapman Hall Number: DFP38-B
CAS Registry Number: 4672-74-6
Molecular Formula: C6H2O3
Molecular Weight: 122.08
Accurate Mass: 122.000395
Percentage Composition: C 59.03%; H 1.65%; O 39.32%
Boiling Point: Bp16 56
References:
Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 943A; 944B; 944C, (ir)
Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 524C; 526B; 526C, (nmr)
Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1595B; 1595D; 1596A, (ir)
Wilson, C.J., J.A.C.S., 1935, 57, 1265, (synth, props)
Owen, L.N. et al., J.C.S., 1949, 3109, (synth)
Maerkl, G., Angew. Chem., Int. Ed., 1962, 1, 160, (synth)
Balfour, W.J. et al., J.O.C., 1974, 39, 725, (chloride)
Rhinesmith, H.S., J.O.C., 1975, 40, 1773, (synth)
Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1977, 6, 495
Kalabin, G.A. et al., Zh. Org. Khim., 1983, 19, 476, (cmr)
Jung, M.E. et al., J.A.C.S., 1989, 110, 3965, (esters, amide)
Nuvole, A. et al., J.C.S. Perkin 1, 1989, 1007, (amide)
Coppola, G.M. et al., Synth. Commun., 1993, 23, 2003, (amides)
Hay, L.A. et al., J.O.C., 1998, 63, 5050-5058, (amide, methylamide, synth, ir, pmr, cmr)
Bretherick, L., Handbook of Reactive Chemical Hazards, 4th edn., Butterworths, 1990, 1020; 1354
Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MOS875; PMT275; PMT300

回复人：hubeiliji,▲ (天道酬勤！) 时间：2005-05-14 01:28:46 编辑

2楼

将30毫升无水甲醇,冷却下与3.5克发烟硫酸小心混合,等冷却后,将7克丙炔酸加入,搅拌下反应,维持反应温度在40度左右,5小时后加入无水硫酸镁6克,搅拌下反应20小时后,将反应液倾入20克冰水中,加入40毫升乙醚提取,将乙醚提取液用饱和碳酸氢钠溶液洗涤2次,每次用10毫升,水相合并后,用乙醚提取3次,每次30毫升,将提取液用20毫升饱和碳酸氢钠洗涤后,与前一有机相合并再用20毫升水洗一次,用无水硫酸钠干燥,将干燥过的乙醚溶液蒸去乙醚后,收取90至103度馏分7.5克,产率为89%.

回复人：gumption,▲ () 时间：2005-05-14 10:08:31 编辑	3楼
谢谢!可丙炔酸还是贵得吓人啊!

回复人：quhe,▲▲▲▲ (我已成实验室动物，可没钱做化学实验是真难!!!其实我更喜欢花草,若不做化学人,就做植物人儿!!) 时间：2005-05-14 19:23:58 编辑	4楼
炔基氯化镁和二氧化碳作用可以合成炔酸。

回复人：4968135,▲ () 时间：2005-05-14 21:46:36 编辑	5楼
楼上说的对

回复人：admin,★ (论坛管理员-欢迎大家访问化学化工论坛) 时间：2005-06-06 21:24:29 编辑	6楼
接受答案了。

得分人：zhangquee-1,hubeiliji-1,quhe-1,

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