Glycolaldehyde

Structural formula
General
Surname	Glycolaldehyde
other names	Glycolaldehyde; Hydroxyacetaldehyde; 2-hydroxyethanal; Bios;
Molecular formula	C 2 H 4 O 2
Brief description	colorless syrupy liquid with a sweetish taste
External identifiers / databases
EC number	205-484-9
ECHA InfoCard	100,004,987
PubChem	756
Wikidata	Q899877
properties
Molar mass	60.05 g mol −1
Physical state	liquid
density	1.366 g cm −3 (100 ° C )
boiling point	96-97 ° C
solubility	soluble in chloroform
Refractive index	1.4772 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	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

Commons : Glycolaldehyde - Collection of pictures, videos, and audio files

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 .

[Römpp-1] Entry on glycolaldehyde. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.

[CRC90_3_270-2] 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.

[David_R._Lide-3] 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).

[Sigma-4] 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 ).

[5] A relative of an amino acid discovered in space. Max Planck scientists find aminoacetonitrile near the galactic center (press release of March 26, 2008).

[6] 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.

[7] 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. ‌

[8] 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 .