Ethyl formate

Structural formula
General
Surname	Ethyl formate
other names	Ethyl methanoate ( IUPAC ); Ethyl formate; Ethyl formate; Ethyl methanoate;
Molecular formula	C 3 H 6 O 2
Brief description	colorless liquid with an arrack-like odor
External identifiers / databases
EC number	203-721-0
ECHA InfoCard	100.003.384
PubChem	8025
ChemSpider	7734
Wikidata	Q422777
properties
Molar mass	74.08 g mol −1
Physical state	liquid
density	0.92 g cm −3 (20 ° C)
Melting point	−80 ° C
boiling point	54 ° C
Vapor pressure	256 h Pa (20 ° C); 408 hPa (30 ° C); 606 hPa (40 ° C); 872 hPa (50 ° C);
solubility	Easily soluble in water (105 g l −1 at 20 ° C)
Refractive index	1.3609 (20 ° C)
safety instructions
H and P phrases	H: 225-302 + 332-319-335
	P: 210-261-305 + 351 + 338
MAK	DFG : 100 ml m −3 or 310 mg m −3
Toxicological data	1850 mg kg −1 ( LD 50 , rat , oral ) ; > 18300 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

Ethyl formate (according to IUPAC nomenclature: ethyl methanoate , also ethyl formate ) is an organic-chemical compound from the group of carboxylic acid esters . It has a typical smell of rum or arrack .

Occurrence

As a natural flavoring substance , ethyl formate is found in many different plants. It has also been found to be one of the most complicated molecules in space, more precisely in the star- forming region Sagittarius B2 near the center of the Milky Way .

Extraction and presentation

Carbonylation of ethanol

Ethyl formate can industrially by carbonylation of ethanol with carbon monoxide at temperatures of 60-70 ° C and pressures of 40-50 bar are produced.

Metal alcoholates such as sodium ethanolate are usually used as catalysts .

Esterification

In the laboratory, ethyl formate can be produced by the acid-catalyzed esterification of formic acid with ethanol .

Due to the fact that formic acid can be easily dehydrated compared to other carboxylic acids, no strong desiccants such as. B. conc. Sulfuric acid can be used. According to the principle of Le Chatelier , separation of the water produced or the removal of the ester shifts the equilibrium to the product side (see also the law of mass action ).

properties

Physical Properties

Ethyl formate is a colorless liquid that boils at 54 ° C under normal pressure . The vapor pressure function results according to Antoine according to log ₁₀ (P) = A− (B / (T + C)) (P in kPa, T in K) with A = 6.1384, B = 1151.08 and C = −48 , 94 in the temperature range from 213 to 336 K or with A = 6.4206, B = 1326.4 and C = −26.867 in the temperature range from 327 to 498 K. The critical values are 506.8 K for the critical temperature, 4691 kPa for the critical pressure and 0.228 m ³ kmol ⁻¹ for the critical volume.

Chemical properties

The ester can be saponified , ie hydrolyzed , by reaction with water in the reverse of the formation reaction . The hydrolysis can be catalyzed by acids and then proceeds in the exact reverse of the esterification reaction; ethanol and formic acid are produced again. In the case of basic hydrolysis , on the other hand, ethanol and a salt of formic acid, a formate, are obtained.

Safety-related parameters

Ethyl formate forms highly flammable vapor-air mixtures. The compound has a flash point of −20 ° C. The explosion range is between 2.8 vol.% As the lower explosion limit (LEL) and 16 vol.% As the upper explosion limit (UEL). The limit gap width was determined to be 0.94 mm. This results in an assignment to explosion group IIA. The ignition temperature is 445 ° C. The substance therefore falls into temperature class T2. The electrical conductivity is rather low at 1.45 · 10 ⁻⁷ S · m ⁻¹ .

use

Ethyl formate is mainly used for the production of artificial rum and ark essences. It is also used as an additive to peach, banana, apple and pineapple flavors. It can also be used as a fungicide in cereal and tobacco crops. The use of ethyl formate in stored product protection was at least discussed. In Germany, Austria and Switzerland there is no approval of ethyl formate as a plant protection product.

Ethyl formate is used as an intermediate in various organic syntheses ( formylation ). In industry it is also used as a solvent for nitrocellulose and cellulose acetate .

safety instructions

The ester is very flammable and also reacts with many oxidizing agents . This can produce dangerous substances such as formic acid, formaldehyde and carbon monoxide . Ethyl formate can be absorbed both through the skin and the respiratory tract, causing irritation of the eyes, mucous membranes and respiratory tract. Higher concentrations or long-term intake can cause damage to the central nervous system and the lungs.

Web links

Commons : Ethyl Formate - Collection of pictures, videos and audio files

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v Entry on ethyl formate in the GESTIS substance database of the IFA , accessed on January 13, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g Entry on ethyl formate. In: Römpp Online . Georg Thieme Verlag, accessed on January 15, 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. 3-244.
↑ Entry on ethyl formats in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 13, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Wissenschaft-aktuell: Complex molecules in space ( Memento from June 10, 2009 in the Internet Archive ).
↑ Patent CN102746145B : Preparation method for ethyl formats. Published on October 8, 2014 , Applicant: Linhai Liansheng Chemical Co. Ltd., Inventor: Yijian Deng, Weiguo Huang; Haibo Hu. ‌
^ Jukka Hietala, Antti Vuori, Pekka Johnsson, Ilkka Pollari, Werner Reutemann, Heinz Kieczka: Formic Acid. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley ‐ VCH Verlag GmbH & Co. KGaA, March 21, 2016, accessed on January 13, 2019 (English).
^ ^A ^b Richard M. Stephenson, Stanislaw Malanowski: Handbook of the Thermodynamics of Organic Compounds , Elsevier 1987, ISBN 978-94-010-7923-5 , doi : 10.1007 / 978-94-009-3173-2 , p. 79 .
↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .
↑ Report on the 7th International Conference on Controlled Atmosphere and Fumigation of Stored Products - CAF2004: Storage Protection for Food - Quo vadis? .
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.
↑ Haritos VS, Damcevski KA, Dojchinov G: Improved efficacy of ethyl formats against stored grain insects by combination with carbon dioxide in a 'dynamic' application . In: Pest Manag. Sci. . 62, No. 4, April 2006, pp. 325-33. doi : 10.1002 / ps.1167 . PMID 16470681 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v Entry on ethyl formate in the GESTIS substance database of the IFA , accessed on January 13, 2019(JavaScript required) .

[Roempp-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on ethyl formate. In: Römpp Online . Georg Thieme Verlag, accessed on January 15, 2019.

[CRC90_3_244-3] 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. 3-244.

[CLP_100.003.384-4] Entry on ethyl formats in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 13, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Wissenschaft-aktuell: Complex molecules in space ( Memento from June 10, 2009 in the Internet Archive ).

[VERFAHREN-6] Patent CN102746145B : Preparation method for ethyl formats. Published on October 8, 2014 , Applicant: Linhai Liansheng Chemical Co. Ltd., Inventor: Yijian Deng, Weiguo Huang; Haibo Hu. ‌

[7] Jukka Hietala, Antti Vuori, Pekka Johnsson, Ilkka Pollari, Werner Reutemann, Heinz Kieczka: Formic Acid. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley ‐ VCH Verlag GmbH & Co. KGaA, March 21, 2016, accessed on January 13, 2019 (English).

[Stephenson_Malanowski-8] A ^b Richard M. Stephenson, Stanislaw Malanowski: Handbook of the Thermodynamics of Organic Compounds , Elsevier 1987, ISBN 978-94-010-7923-5 , doi : 10.1007 / 978-94-009-3173-2 , p. 79 .

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[10] Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .

[11] Report on the 7th International Conference on Controlled Atmosphere and Fumigation of Stored Products - CAF2004: Storage Protection for Food - Quo vadis? .

[PSM-12] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[13] Haritos VS, Damcevski KA, Dojchinov G: Improved efficacy of ethyl formats against stored grain insects by combination with carbon dioxide in a 'dynamic' application . In: Pest Manag. Sci. . 62, No. 4, April 2006, pp. 325-33. doi : 10.1002 / ps.1167 . PMID 16470681 .