64-67-5

Basic information

• Product Name: Diethyl sulfate
• Synonyms: Diethyl sulfate (DES);Diaethylsulfat;Diethylester kyseliny sirove;diethylesterkyselinysirove;diethyltetraoxosulfate;DS;Ethylsulpate;sulfatediethylique
• CAS NO: 64-67-5
• Molecular Formula: C₄H₁₀O₄S
• Molecular Weight: 154.18
• EINECS: 200-589-6
• Product Categories: Pharmaceutical Intermediates;Organics
• Mol File: 64-67-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: -24 °C
• Boiling Point: 208 °C(lit.)
• Flash Point: 173 °F
• Appearance: Clear/Liquid
• Density: 1.177 g/mL at 25 °C(lit.)
• Vapor Density: 5.3 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.399(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Solubility: soluble in Ether,Alcohol
• Water Solubility: 5 g/L (20 ºC)
• Stability: Moisture sensitive. May react violently with oxidizing agents.
• Merck: 14,3130
• BRN: 1209714
• CAS DataBase Reference: Diethyl sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl sulfate(64-67-5)
• EPA Substance Registry System: Diethyl sulfate(64-67-5)

Safety Data

• Hazard Codes: T
• Statements: 45-46-20/21/22-34
• Safety Statements: 53-45
• RIDADR: UN 1594 6.1/PG 2
• WGK Germany: 3
• RTECS: WS7875000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 64-67-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Diethyl sulfate is used as a chemical intermediate for the synthesis of ethyl derivatives of phenols, amines, and thiols. It acts as an ethylating agent, transferring ethyl groups to other molecules, which is essential for the production of various chemicals.
Used in the Sulfation of Ethylene:
In the chemical industry, diethyl sulfate is used as an accelerator in the sulfation of ethylene. This process involves the reaction of ethylene with sulfur trioxide to produce ethylene sulfate, which is further used in the production of various chemicals.
Used in Sulfonation Processes:
Diethyl sulfate is also used in some sulfonation processes, where it acts as a sulfonating agent to introduce a sulfonic acid group into organic compounds.
Used in Manufacturing Dyes, Pigments, and Carbonless Paper:
Diethyl sulfate is utilized in the production of dyes, pigments, and carbonless paper. Its ethylating properties enable the synthesis of various colorants and other compounds used in these industries.
Used in Textile Industry:
In the textile industry, diethyl sulfate is used for various applications, such as the synthesis of dyes and other chemicals used in the production of textiles.
Used in the Preparation of Synthetic Ethanol:
Diethyl sulfate is an intermediate in the indirect hydration process for the preparation of synthetic ethanol from ethylene. This process involves the conversion of ethylene to ethanol using a strong acid catalyst.
Used in Household Products, Cosmetics, Agricultural Chemicals, Pharmaceuticals, and Laboratory Reagents:
Diethyl sulfate is used in smaller quantities in various industries, including household products, cosmetics, agricultural chemicals, pharmaceuticals, and laboratory reagents, due to its ethylating properties and reactivity.
Used in Mutagenesis:
In 1966, diethyl sulfate was used as a mutagen to create the Luther variety of barley, demonstrating its potential use in genetic research and plant breeding.

Preparation

Diethyl sulfate is produced from ethanol and sulfuric acid, from ethylene and sulfuric acid, or from diethyl ether and fuming sulfuric acid (Budavari, 1996).

Air & Water Reactions

Highly flammable. Slowly reacts with water to form ethyl alcohol, a flammable liquid, and ethyl sulfate, with eventual conversion to sulfuric acid.

Reactivity Profile

The presence of moisture in a metal container of Diethyl sulfate caused the formation of sulfuric acid which reacts with the metal to release hydrogen which pressurized and exploded the container [Chem. Abst. 28:2908(1934)].

Health Hazard

May be fatal if inhaled, swallowed or absorbed through skin. Inhalation causes nausea and vomiting. Causes burns to skin and eyes. Ingestion may cause nausea, vomiting abdominal pain and collapse.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by inhalation and subcutaneous routes. Moderately toxic by ingestion and sktn contact. A severe skin irritant. An experimental teratogen. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. Moisture causes liberation of H2SO4. Violent reaction with potassium tert-butoxide. Reacts violently with 3,8-dnitro-6-phenylphenanthridine + water. Reaction with iron + water forms explosive hydrogen gas. To fight fire, use alcohol foam, H2O foam, CO2, dry chemicals. When heated to decomposition it emits toxic fumes of SOx. See also SULFATES.

Carcinogenicity

Diethyl sulfate is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Purification Methods

Wash the ester with aqueous 3% Na2CO3 (to remove acidic material), then distilled water, dry (CaCl2), filter and distil it in a vacuum. It is an ethylating agent and blisters the skin. [Beilstein 1 IV 1236.]

InChI:InChI=1/C4H10.H2O4S/c1-3-4-2;1-5(2,3)4/h3-4H2,1-2H3;(H2,1,2,3,4)/p-2

Upstream product

• 60-29-7 diethyl ether 
• 74-85-1 ethene 
• 75-93-4 methyl bisulfate 
• 541-41-3 chloroformic acid ethyl ester 
• 540-82-9 ethyl sulfate 
• 3141-12-6 triethyl arsenite 
• 7446-11-9 sulfur trioxide 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 623-81-4 diethyl sulphite 
• 122-51-0 orthoformic acid triethyl ester 
• 13891-58-2 chloroethyl chlorosulfate 
• 625-01-4 ethyl chlorosulfate 
• 546-74-7 sodium ethyl sulfate 

Downstream Products

• 61310-53-0 3-ethoxyacrylonitrile 
• 2032-34-0 3,3-bis(ethyloxy)propanenitrile 
• 24741-99-9 3-ethoxy-5-methylphenol 
• 622-76-4 1-phenyl-1-butyne 
• 1131-52-8 3-ethoxy-4-methoxybenzaldehyde 
• 2029-94-9 3,4-diethoxybenzaldehyde 
• 6763-91-3 N-ethylhexamethyleneimine 
• 95112-14-4 2-ethyl-5-amino-tetrazole 
• 65258-53-9 1-ethyl-1H-tetrazole-5-amine 
• 109-65-9 1-bromo-butane 
• 110-54-3 hexane 
• 546-74-7 sodium ethyl sulfate 
• 59923-03-4 (E)-3-(2-ethoxyphenyl)prop-2-enoic acid 
• 53950-72-4 2-ethoxy-N-phenylaniline 

Relevant articles and documents

Environmentally-friendly diethyl sulfate production process,

The invention belongs to the field of chemical synthesis, and specially relates to an environmentally-friendly diethyl sulfate production process, which comprises: carrying out a reaction on a diethylsulfate intermediate (ethyl hydrogen sulfate or a mixture containing ethyl hydrogen sulfate) and sulfate or hydrochloride for 4-12 h at a temperature of 60-130 DEG C to generate a mixture of diethylsulfate and disulfate, cooling the mixture, dissolving with water, separating to obtain a disulfate solution and a diethyl sulfate crude product, and refining the diethyl sulfate crude product to obtain diethyl sulfate. According to the process of the invention, the reactants cannot be carbonized in the reaction process, the waste acid difficultly recycled is not generated, the product quality ishigh, the industrial production is easy to realize, and the process is an environmentally-friendly diethyl sulfate production process.

OPHTHALMIC SOLUTIONS

Disclosed are ophthalmic solutions such as packaging solutions for storing ophthalmic devices and lens care solutions for cleaning, disinfecting, rinsing and/or storing ophthalmic devices. The ophthalmic solutions contain at least a polymerization product obtained from a monomeric mixture comprising (a) a monomer bearing a center of permanent positive charge and (b) a non-ionic ethylenically unsaturated monomer, wherein the solution has an osmolality of at least about 200 mOsm/kg, and a pH of about 4 to about 9.

Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir

A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases.

REACTIONS OF DIMETHYL AND DIETHYL SULFATES WITH SULFUR TRIOXIDE

The composition of the products from the reaction of sulfur trioxide with dimethyl and diethyl sulfates and also with diethyl ether was investigated by 1H NMR spectroscopy.In addition to the main reaction leading to the formation of dialkyl polysulfates, in the case of the ethyl derivatives the side reaction involving sulfonation of the alkyl group at the β position is observed.This explains the preferred use of dimethyl sulfate in the syntheses of diaryl sulfones.

Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds

Compounds of the formula (I) STR1 optically active isomers thereof, and/or pharmaceutically acceptable acid addition salts thereof are disclosed, wherein R1 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, 2-hydroxyethyl, 3-hydroxypropyl and 4-hydroxybutyl, and wherein R is selected from the group consisting of STR2 in which R2, R3 R4 and R5 are the same or different and are each independently selected from the group consisting of hydrogen and methyl. Pharmaceutical preparations employing such compounds and method of using such compounds are also disclosed.

Reactions of Group V Metal Compounds with Sulfur Trioxide

Trialkylphosphines react with equimolar amounts of sulfuric trioxide to form the 1:1 adducts R3P(1+)-SO3(1-).Trialkylarsines and -stibines undergo sulfur trioxide insertion reaction across the metal-carbon bond to give the trisulfonates of the metal M(OSO2R)3 (M=As,Sb).The reactions of trialkyl phosphites, with sulfur trioxide yield trialkyl phosphonates, trialkyl thiophosates, dialkyl alkylphosphonates, dialkyl sulfates, and polymers which contain phosphorus atoms.The reactions of trialkoxyarsines and -stibines result in the insertion of sulfur trioxide across the metal-oxygen bond to form the alkoxymetal alkylsulfates (RO)3-nM(OSO3R)n (M=As,Sb; n=1,2,3) depending on the stoichiometric ratios of the reagents used.Pyrolysis of the metal sulfates gives dialkyl sulfates and undistillable residues containing the metals.

Benzoic acids, their derivatives and process for preparing them

Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.

Benz (c) fluoran compounds and recording sheet containing them

Novel benz[c]fluoran compounds such as 2-phenylamino-8-diethylamino-benz[c]fluoran, 2-(2',4',6'-trimethylphenylamino)-8-diethylamino-benz[c]fluoran and N-[8-diethylaminobenz[c]fluoran-2-yl]-N-[6-diethylaminofluoran-2-yl]amine, which are useful as a coloring material for record material systems such as pressure-sensitive copying paper or heat-sensitive copying paper, wherein colored images formed by an electron-donoracceptor color-forming reaction between coloring material and acidic material.