Diethyl sulfate

Structural formula
General
Surname	Diethyl sulfate
other names	Sulfuric acid diethyl ester
Molecular formula	C 4 H 10 O 4 S
Brief description	colorless liquid with an ester-like odor
External identifiers / databases
EC number	200-589-6
ECHA InfoCard	100,000,536
PubChem	6163
ChemSpider	5931
Wikidata	Q421338
properties
Molar mass	154.19 g mol −1
Physical state	liquid
density	1.18 g cm −3 (25 ° C)
Melting point	−24 ° C
boiling point	208 ° C (with decomposition)
Vapor pressure	16 Pa (20 ° C)
solubility	little in water (7 g l −1 at 20 ° C) with slow hydrolysis; Miscible with ethanol, ether and most polar organic solvents;
Refractive index	1.3989 (20 ° C)
safety instructions
H and P phrases	H: 302 + 332-311-314-340-350
	P: 201-260-280-303 + 361 + 353-305 + 351 + 338-308 + 313
Authorization procedure under REACH	particularly worrying : carcinogenic, mutagenic ( CMR )
MAK	No MAK, as it is carcinogenic ; Switzerland: 0.03 ml m −3 or 0.2 mg m −3 ;
Toxicological data	880 mg kg −1 ( LD 50 , rat , oral ) ; 706 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 647 mg kg −1 ( LD 50 , mouse , 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

Diethyl sulfate is a toxic, colorless, oily liquid with a characteristic peppermint odor.

properties

The colorless substance is liquid at room temperature, but not very volatile. Diethyl sulfate is poorly soluble in water, and slowly hydrolyzes with the formation of sulfuric acid and ethanol . This reaction occurs much faster in hot water. Diethyl sulfate is miscible with ethanol, ether and most polar organic solvents.

use

Diethyl sulfate is used for alkylation of phenols , amines and thiols used.

Manufacturing

In the laboratory, diethyl sulfate can be produced with good yield from sulfuryl chloride and excess absolute ethanol in the presence of a base at 20 to 35 ° C:

{\ displaystyle \ mathrm {SO_ {2} Cl_ {2} +2 \ EtOH + 2 \ B. \ longrightarrow}}

{\ displaystyle \ mathrm {Et_ {2} SO_ {4} +2 \ B.HCl \}}

However, diethyl sulfate is industrially obtained from ethene and fuming sulfuric acid under pressure and cooling:

{\ displaystyle \ mathrm {H_ {2} SO_ {4} +2 \ CH_ {2} {=} CH_ {2} \ longrightarrow}}

{\ displaystyle \ mathrm {Et_ {2} SO_ {4} \}}

The crude product is purified by vacuum distillation .

safety instructions

Diethyl sulfate is poisonous and has a corrosive effect . It causes severe burns on skin contact. Inhalation can cause pulmonary edema . The substance has been shown to be carcinogenic in animal experiments, but there is a reasonable suspicion of carcinogenicity in humans. According to Appendix II, No. 6 of the German Hazardous Substances Ordinance (GefStoffV), the substance is classified as a particularly dangerous carcinogenic substance and may only be manufactured or used in closed facilities.

If the liquid evaporates, it forms explosive mixtures with the air up to a volume fraction of 12%.

The substance is flammable, but very difficult to ignite due to the low vapor pressure.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethyl sulphate in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ ^a ^b ^c ^d Entry on diethyl sulfate. In: Römpp Online . Georg Thieme Verlag, accessed on January 16, 2014.
↑ ^a ^b ^c ^d Entry on diethyl sulfate in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ 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. 3-172.
↑ Entry on diethyl sulphate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 64-67-5 or diethyl sulfate ), accessed on November 2, 2015.
↑ Hazardous Substances Ordinance (GefStoffV) - as of April 2017 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethyl sulphate in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[roempp-2] Entry on diethyl sulfate. In: Römpp Online . Georg Thieme Verlag, accessed on January 16, 2014.

[chemid-3] Entry on diethyl sulfate in the ChemIDplus database of the United States National Library of Medicine (NLM)

[CRC90_3_172-4] 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. 3-172.

[CLP_100.000.536-5] Entry on diethyl sulphate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-6] Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.

[7] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 64-67-5 or diethyl sulfate ), accessed on November 2, 2015.

[8] Hazardous Substances Ordinance (GefStoffV) - as of April 2017 .