Valeraldehyde

Structural formula
General
Surname	Valeraldehyde
other names	n -Pentanal ( IUPAC ) Amylaldehyde VALERALDEHYDE ( INCI )
Molecular formula	C 5 H 10 O
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 110-62-3 EC number 203-784-4 ECHA InfoCard 100.003.442 PubChem 8063 ChemSpider 7772 DrugBank DB01919 Wikidata Q420652
properties
Molar mass	86.13 g mol −1
Physical state	liquid
density	0.81 g cm −3 (20 ° C)
Melting point	−92 ° C
boiling point	103 ° C
Vapor pressure	36 hPa (20 ° C)
solubility	poorly soluble in water (14 g l −1 at 20 ° C)
Refractive index	1.3944 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-332-315-319-335 P: 210-233-302 + 352-304 + 340-305 + 351 + 338-403 + 235
MAK	Switzerland: 50 ml m −3 or 175 mg m −3
Toxicological data	4580 mg kg −1 ( LD 50 ,  rat ,  oral )
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

Valeraldehyde (according to IUPAC nomenclature: n- pentanal , more rarely also called amylaldehyde ) is an organic-chemical compound from the group of aldehydes . With its isomeric compounds isovaleraldehyde , 2-methylbutyraldehyde and pivalaldehyde , it forms the group of pentanals .

Extraction and presentation

Valeraldehyde is industrially by hydroformylation of 1-butene at temperatures of 70 - 200 bar made - 150 ° C and pressures of from 10th The catalyst systems used are usually rhodium bisphosphite complexes with sterically hindered organic secondary amines which have a selectivity for n- pentanal of at least 90%. The complete reaction takes place in bubble column reactors or stirred tank reactors . C4 mixtures such as the so-called raffinate II obtained in steam cracking can also be used as starting material .

properties

Valeraldehyde forms highly flammable vapor-air mixtures. The compound has a flash point of 6 ° C. The lower explosion limit (LEL) is 1.1 vol.% (50 g · m ⁻³ ). The ignition temperature is 205 ° C. The substance therefore falls into temperature class T3.

use

Valeraldehyde is used in various flavors (e.g. fruit flavors) and as a vulcanization accelerator. 2-Propyl-2-heptenal is obtained from valeraldehyde by aldol condensation , which is hydrogenated to the saturated branched alcohol 2-propylheptanol (2-PH) . This serves as a starting material for the PVC plasticizer di-2-propylheptyl phthalate and, after ethoxylation with 5 or 7 EO units, for nonionic APEO (alkylphenol ethoxylate) -free detergents.

safety instructions

The fumes are irritating to the eyes, respiratory tract and skin. Long exposure can lead to pulmonary edema . Polymerization occurs with amines, ammonia and alkaline substances.

Individual evidence

1. ↑ Entry on VALERALDEHYDE in the CosIng database of the EU Commission, accessed on May 6, 2020.
2. ↑ ^{a b c d e f g h i j k l} Entry on valeraldehyde in the GESTIS substance database of the IFA , accessed on August 21, 2017(JavaScript required) .
3. ↑ 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. 3-414.
4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 110-62-3 or valerianaldehyde ), accessed on September 30, 2019.
5. ↑ WO 2009/146985 Evonik OXENO GmbH .
6. ↑ Dirk Fridag, Robert Franke, Dieter Hess, Markus Schwarz, Katrin Marie Dyballa, Hans-Gerd Lueken, Bart Hamers, Uwe Ernst: Long-term stable process for the production of C5 aldehydes. In: Google Patents. Evonik Degussa GmbH, October 12, 2012, accessed on December 22, 2018 (German, English, French). 
7. ^ ^{A b} E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.