Glycolaldehyde
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Glycolaldehyde | |||||||||||||||
other names |
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Molecular formula | C 2 H 4 O 2 | |||||||||||||||
Brief description |
colorless syrupy liquid with a sweetish taste |
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properties | ||||||||||||||||
Molar mass | 60.05 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.366 g cm −3 (100 ° C ) |
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boiling point |
96-97 ° C |
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solubility |
soluble in chloroform |
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Refractive index |
1.4772 (20 ° C) |
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safety instructions | ||||||||||||||||
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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 |
Glycolaldehyde is the simplest compound in the group of hydroxyaldehydes . It has an aldehyde and a hydroxyl group . So it can be formally assigned to the carbohydrates (aldodiosis).
Occurrence
Glycolaldehyde is produced when ethylene glycol breaks down in the human body. Furthermore, glycolaldehyde was detected in space, among others in the star system IRAS 16293–2422 . It is formed from formaldehyde through the formose reaction and may therefore have arisen in the prebiotic phase of evolution .
Extraction and presentation
There are a number of ways to prepare glycolaldehyde, for example by carefully oxidizing ethylene glycol using hydrogen peroxide in the presence of ferrous sulfate .
Glycolaldehyde can be produced from a C 1 building block by catalytic umpolung of formaldehyde . This reaction is important in order to make the C 1 raw material basis (natural gas, coal, methane hydrate from the deep sea) usable for syntheses.
properties
Glycolaldehyde tends to dimerize to 2,5-dihydroxy-1,4-dioxane (m.p .: 96 ° C, easily soluble in water). It also reacts with propenal to form ribose , an essential component of ribonucleic acid , and is therefore considered to be a precursor to the origin of life.
use
Glycolaldehyde is used to make polymers that contain free hydroxyl groups and as an intermediate for various esters and amino alcohols .
Web links
- Biological Magnetic Resonance Data Bank: Glycolaldehyde
Individual evidence
- ↑ a b c Entry on glycolaldehyde. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
- ↑ 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. 3-270.
- ↑ a b David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 296 ( limited preview in Google Book search).
- ↑ a b Data sheet Glycolaldehyde dimer, crystalline, mixture of stereoisomers. Melts between 80 and 90 ° C depending on stereoisomeric composition from Sigma-Aldrich , accessed on February 23, 2019 ( PDF ).
- ↑ A relative of an amino acid discovered in space. Max Planck scientists find aminoacetonitrile near the galactic center (press release of March 26, 2008).
- ↑ Hans Peter Latscha, Uli Kazmaier and Helmut Alfons Klein: Organic Chemistry: Basic Chemistry II . Springer, Berlin; 6th, completely revised edition 2008, ISBN 978-3-540-77106-7 , p. 217.
- ↑ Patent application DE4212264A1 : Process for the catalytic production of condensation products of formaldehyde. Registered on April 11, 1992 , published on October 14, 1993 , applicant: BASF, inventor: Eugen Gehrer, Wolfgang Harder, Klaus Ebel.
- ↑ External identifiers or database links for 1,4-dioxane-2,5-diol : CAS number: 23147-58-2, EC number: 607-202-3, ECHA InfoCard: 100.108.667 , PubChem : 186078 , ChemSpider : 161748 , Wikidata : Q72472673 .