3-butenoic acid
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| Surname | 3-butenoic acid | ||||||||||||||||||
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| Molecular formula | C 4 H 6 O 2 | ||||||||||||||||||
| Brief description |
colorless liquid |
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| properties | |||||||||||||||||||
| Molar mass | 86.09 g · mol -1 | ||||||||||||||||||
| Physical state |
liquid |
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| density |
1.01 g cm −3 (20 ° C) |
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| Melting point |
−39 ° C |
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| boiling point |
163 ° C |
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| pK s value |
4.34 (25 ° C) |
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| solubility |
Fully miscible with water |
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| Refractive index |
1.4239 (20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | |||||||||||||||||||
3-butenoic acid is a short-chain unsaturated carboxylic acid . It is a light yellow, clear liquid with a flash point of 65 ° C.
synthesis
3-Butenic acid can be produced by the hydrolysis of allyl cyanide , which in turn is synthesized from allyl bromide and copper (I) cyanide .
The reaction of the corresponding Grignard compound with carbon dioxide also gives 3-butenic acid.
Large-scale production is possible via a catalytic reaction from allyl alcohol and carbon monoxide .
Reactions
3-Butenic acid can be reduced to 3-buten-1-ol with lithium aluminum hydride .
In the vapor phase, 3-butenic acid is decarboxylated to propene and carbon dioxide at higher temperatures .
The bromination of 3-butenoic acid with elemental bromine mainly leads to 3,4-dibromobutanoic acid , but an intramolecular condensation reaction also produces the corresponding lactone with elimination of hydrogen bromide .
The hydroformylation of 3-butenoic acid basically gives a mixture of isomers, but the regioselectivity of the reaction can be controlled through the choice of suitable catalysts.
With nickel (II) chloride and sodium hypochlorite in dichloromethane , fumaric acid can be produced by double oxidation .
With trinitromethane is 3-methyl-4,4,4-Trinitrobuttersäure forms.
The condensation of 3-butenic acid with aromatic 2-hydroxyaldehydes gives 3-vinyl coumarins.
Cycloadditions also take place with oximes under suitable conditions:
See also
Individual evidence
- ↑ a b Data sheet 3-butenoic acid (PDF) from Merck , accessed on May 19, 2010.
- ↑ 3-Butenic acid data sheet from Acros, accessed on May 19, 2010.
- ↑ a b Data sheet 3-Butenoic acid from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-43.
- ↑ Data sheet 3-butenoic acid from AlfaAesar, accessed on May 19, 2010 ( PDF )(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-74.
- ↑ a b Entry on 3-butenoic acid in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
- ^ A b E. Rietz: Vinylacetic acid In: Organic Syntheses . 24, 1944, p. 96, doi : 10.15227 / orgsyn.024.0096 ; Coll. Vol. 3, 1955, p. 851 ( PDF ).
- ↑ JV Supniewski, PL Salzberg: Allyl cyanide In: Organic Syntheses . 8, 1928, p. 4, doi : 10.15227 / orgsyn.008.0004 ; Coll. Vol. 1, 1941, p. 46 ( PDF ).
- ↑ Process for the manufacture of vinyl acetic acid - Patent 4140865 . www.freepatentsonline.com. Retrieved June 23, 2010.
- ^ CC Lee, AJ Cessna: Reactions of Cyclopropylcarbinol in dilute hydrochloric acid . In: Canadian Journal of Chemistry . 58, 1980, pp. 1075-1079, doi : 10.1139 / v80-168 .
- ^ GG Smith, SE Blau: "Decarboxylation. I. Kinetic Study of the Vapor Phase Thermal Decarboxylation of 3-Butenoic Acid" in J. Phys. Chem. 1964 , 68 (5), pp. 1231-1234. doi : 10.1021 / j100787a506
- ↑ K. Pels, V. Dragoljovic: Solvent-free phase-vanishing reactions with PTFE (Teflon) as a phase screen , in Beilstein Journal of Organic Chemistry 2009 , 75 (5). doi : 10.3762 / bjoc.5.75
- ^ BC Gates: Advances in Catalysis . Academic Press, 2011, ISBN 0-12-387773-3 , pp. 80 ( limited preview in Google Book search).
- ↑ JM Grill, JW Ogle, SA Miller: "An Efficient and Practical System for the Catalytic Oxidation of Alcohols, Aldehydes, and α, β-Unsaturated Carboxylic Acids" in J. Org. Chem. 2006 , 71 (25), pp. 9291-9296. doi : 10.1021 / jo0612574
- ↑ LT Eremenko, VI Grigos: "Reaction of nitroform with vinylacetic acid" in Russian Chemical Bulletin 1967 , 16 (6), pp. 1301-1302. doi : 10.1007 / BF00908296
- ↑ J. Gordo, J. Avo, AJ Parola, JC Lima, A. Pereira, PS Branco: "Convenient Synthesis of 3-Vinyl and 3-Styryl Coumarins" in Organic Letters 2011 , 13 (19), pp. 5112-5115 . Full text
- ↑ J. Wityak, C.-B. Xue, TM Sielecki-Dzurdz, RE Olson, WF Degrado, GA Cain: "Novel isoxazoline and isoxazole fibrinogen receptor antagonists", EP 0730590; EP 0832076; JP 1997505590; JP 1999504651; US 5849736; WO 9514683; WO 9638426. Full text