Trimethyl orthoformate

Structural formula
General
Surname	Trimethyl orthoformate
other names	Trimethoxymethane; Trimethyl orthoformate; Orthocarbonic acid methyl ester; TMOF;
Molecular formula	C 4 H 10 O 3
Brief description	colorless liquid with a pungent odor
External identifiers / databases
EC number	205-745-7
ECHA InfoCard	100.005.224
PubChem	9005
Wikidata	Q408190
properties
Molar mass	106.12 g mol −1
Physical state	liquid
density	0.97 g cm −3
Melting point	−53 ° C
boiling point	104 ° C
Vapor pressure	10 hPa (7 ° C); 255 hPa (50 ° C);
solubility	soluble under hydrolysis in water (10 g l −1 at 20 ° C); soluble in ethanol and ether;
Refractive index	1.379 (20 ° C)
safety instructions
H and P phrases	H: 225-319
	P: 210-233-260-262-305 + 351 + 338-403 + 235
	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

Trimethyl orthoformate is a chemical compound from the group of orthoesters . It is an ester of the hypothetical orthoformic acid HC (OH) ₃ .

Extraction and presentation

Trimethyl orthoformate can be obtained by reacting chloroform with sodium methoxide .

properties

Trimethyl orthoformate is a highly flammable, volatile, colorless liquid with a pungent odor. At normal pressure , the compound boils at 104 ° C. The heat of vaporization is 38.2 kJ mol ⁻¹ . Hydrolysis takes place in water to form methyl formate and methanol . The reaction is slightly exothermic with a heat of reaction of −9.6 kJ mol ⁻¹ .

use

Trimethyl orthoformate can be used as an intermediate in the production of other chemical compounds (e.g. acetals or compounds such as benzimidazole , vitamin B1 ).

safety instructions

Trimethyl orthoformate forms highly flammable vapor-air mixtures. The compound has a flash point of 13 ° C. The explosion range is between 1.4 vol.% As the lower explosion limit (LEL) and 44.6 vol.% As the upper explosion limit (UEL). The limit gap width was determined to be 0.79 mm (50 ° C). This results in an assignment to explosion group IIA. The ignition temperature is 255 ° C. The substance therefore falls into temperature class T3.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on trimethoxymethane in the GESTIS substance database of the IFA , accessed on February 2, 2016(JavaScript required) .
↑ Entry on trimethyl orthoformate at TCI Europe, accessed on June 27, 2011.
↑ Trimethyl orthoformate data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

↑ Process for the distillation of a TMOF-containing electrolysis output

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 88th edition. (Internet version: 2008), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-504.

↑ ^a ^b ^c J. Hine, AW Klueppet: Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters. In: J. Am. Chem. Soc. 96, 1974, pp. 2924-2929, doi: 10.1021 / ja00816a043 .

↑ ^a ^b ^c ^d E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

Web links

Electrochemical process for the production of trimethyl orthoformate or orthocarbonic acid methyl ester

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on trimethoxymethane in the GESTIS substance database of the IFA , accessed on February 2, 2016(JavaScript required) .

[2] Entry on trimethyl orthoformate at TCI Europe, accessed on June 27, 2011.

[Sigma-3] Trimethyl orthoformate data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

[4] Process for the distillation of a TMOF-containing electrolysis output

[CRC-5] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 88th edition. (Internet version: 2008), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-504.

[Hine-6] J. Hine, AW Klueppet: Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters. In: J. Am. Chem. Soc. 96, 1974, pp. 2924-2929, doi: 10.1021 / ja00816a043 .

[Brandes-7] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.