硫酸ジエチル

Diethyl Sulfate

HCID 6163CAS 64-67-5

基本情報

標準SMILES
CCOS(=O)(=O)OCC
InChIKey
DENRZWYUOJLTMF-UHFFFAOYSA-N
分子式
C4H10O4S
平均分子量
154.19 g/mol
単同位体質量
154.0299798

概要

Diethyl Sulfate can cause cancer according to an independent committee of scientific and health experts.

名称と識別子

優先名称
Diethyl Sulfate
IUPAC
diethyl sulfate
現地名
硫酸ジエチル
英語名
Diethyl sulfate
分子式
C4H10O4S
分子量
154.18

名称と別名

Diethyl sulfate64-67-5Diethyl sulphateSulfuric acid, diethyl esterDIETHYLSULFATEDiaethylsulfatSulfuric acid diethyl esterDiethyl tetraoxosulfateDiethylester kyseliny siroveK0FO4VFA7INSC-56380CHEBI:34699
名称をさらに表示
硫酸ジエチル硫酸エチルジエチル=スルファートジエチルスルファートジエチル硫酸硫酸エチル(硫酸ジエチル)DSETHYL SULFATEDHYSMIG13EthylsulpateDiethylsulfat
NSC56380RefChem:133445Sufuric Acid Diethyl Ester200-589-6Montelukast Impurity 15MFCD00009099NSC 56380DTXSID1024045

データベース識別子

CAS
64-67-5
PubChem CID
6163
DTXSID
DTXSID1024045
ChEMBL
CHEMBL163100
ChEBI
CHEBI:34699
UNII
K0FO4VFA7I
EC Number
200-589-6
Nikkaji
J2.811H

物性

構造計算による物性

XLogP
1.1
極性表面積
61 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
4
重原子数
9

実験および物理化学的性質

Chemical Classes · 3 件

Hazardous Air Pollutants (HAPs)

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Carcinogens

SpringerMaterials PropertiesBoiling point
PesticidesPesticide -> EPA IRIS
LogP · 3 件

log Kow= 1.14

1.14

1.14

Odor · 2 件

Peppermint odor

Faint ethereal odor

Density · 4 件

1.1803 at 68 °F (USCG, 1999) - Denser than water; will sink

1.172 g/cu cm @ 25 °C

Relative density (water = 1): 1.2

1.172 @25 °C

物理化学的性質

融点
-24 °C · -24 °C (lit.)
沸点
208 °C · 208 °C (lit.)
比重(密度)
1.177 g/mL · 1.177 g/mL at 25 °C (lit.)
蒸気密度
5.3 · 5.3 (vs air)
蒸気圧
0.01 mm · <0.01 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.399(lit.)
化学的性質 · 2 件

化学的特性Diethyl sulfate is a colorless, oily liquid with a faint peppermint- like odor, which darkens with age (Budavari, 1996). It is miscible with alcohol and ether (O'Neil, 2006). At higher temperatures, DES rapidly decomposes into monoethyl sulfate and alcohol (NTP, 2011).

化学性质沸点93~93.2℃(13mmHg)

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Danger

H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Sulfuric acid, diethyl ester

Hazard Traits - Carcinogenicity; Genotoxicity

Sulfuric acid, diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Sulfuric acid, diethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 26-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24081

Substance: Diethyl sulphate

Diethyl sulphate: HSNO Approval: HSR002968 Approved with controls

Other Safety InformationIMAP assessments - Sulfuric acid, diethyl ester: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 3 件

Special Hazards of Combustion Products: Highly toxic fumes contaning sulfur oxides may be generated along with thermal decomposition products such as ethyl ether and ethylene. Sulfuric acid may be produced in the presence of moisture.

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialCombustible when exposed to heat or flame... .
Health Hazards · 2 件

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. (USCG, 1999)

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give nothing to drink. Refer immediately for medical attention.

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 件

INHHALATION: Remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.

General First Aid:

Safe StorageSeparated from food and feedstuffs. Dry. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based upon the hydrolysis of diethylsulfate in aqueous environments(1), diethylsulfate is expected to hydrolyze in moist soils(SRC). Volatilization from soil surfaces and adsorption to soil are not expected to be important processes because of hydrolysis(SRC).

AQUATIC FATE: If released to water, diethylsulfate is expected to hydrolyze rapidly(SRC). A hydrolysis rate constant of 1.15X10-4/sec at 25 °C(1) translates to a half-life of 1.7 hours at pH 7(SRC). The rate of hydrolysis will increase in both acidic and basic waters as the reaction is catalyzed under these conditions(2). Volatilization from water surfaces, adsorption to suspended solids and sediments, biodegradation, and bioconcentration are not expected to be important fate processes in aquatic systems because of hydrolysis(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylsulfate, which has a vapor pressure of 0.212 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylsulfate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-lives for this reaction in air is estimated to be about 9 days(SRC), calculated from its rate constant of 1.8X10-12 cu cm/molecule-sec at 25 °C(3). Diethylsulfate also reacts rapidly with water in the atmosphere, with an estimated half-life of <1 day(3).

Adverse Effects · 1 件

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Exposure RoutesThe substance can be absorbed into the body by inhalation, by ingestion and through the skin.
Ecotoxicity Excerpts · 1 件

/PLANTS/ Diethyl sulfate induced unscheduled DNA synthesis in pollen of petunia hybrida. It induced chromosomal aberrations in meiotic cells and chlorophyll mutations in rice, ring chromosomes in Allium sativum root tips and anaphase and telophase aberrations in Papaver somniferum root meristemic cells.

Signs and Symptoms · 4 件

Cough. Sore throat. Laboured breathing. Shortness of breath. Symptoms may be delayed.

Redness. Pain. Serious skin burns.

Redness. Pain. Severe burns.

Burns in mouth and throat. Burning sensation behind the breastbone. Abdominal pain. Shock or collapse.

Effluent ConcentrationsIn 1989, total land releases of diethylsulfate in the US were estimated at approximately 114 kg and total air emissions were estimated as approximately 4 tons from 28 locations(1).

法規制情報

Atmospheric Standards · 2 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diethyl sulfate is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Diethyl sulfate is included on this list.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

安全データ

wgk
3
tsca
TSCA listed
rtecs
WS7875000
ridadr
UN 1594
毒性
LD50 orally in rats: 0.88 g/kg (Smyth)
hs_code
29209090

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

ETHYLMERCAPTURIC ACID WAS IDENTIFIED AS A URINARY METABOLITE OF SC, IP, OR ORAL DIETHYL SULFATE, ALSO ISOLATED FROM URINE WAS THE DICYCLOHEXYLAMMONIUM SALT IN 2.4% YIELD.

After male CFE albino rats were administered 1 ml of a 5% (v/v) solution of diethyl sulfate in arachis oil by gavage or by intraperitoneal or subcutaneous injection, ethylmercapturic acid and a sulfoxide were identified as metabolites.

MeSH Pharmacological Classification · 2 件

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

用途と製造

Uses · 6 件

Diethyl sulfate is primarily used as an ethylating agent, and also as an accelerator in the sulfation of ethylene and in some sulfonations. Diethyl sulfate is also a chemical intermediate for ethyl derivatives of phenols, amines, and thiols, and as an alkylating agent.

Used mainly to make dyes; Also used as an ethylating agent (pigment production), a finishing agent (textile manufacturing), a dye-set agent (carbonless paper), and an accelerator (sulfation of ethylene); Also used in agricultural chemicals, household products, pharmaceuticals, and cosmetics; [HSDB]

Pulp and Paper Processing [Category: Industry]

Chiefly as an ethylating agent; as an accelerator in the sulfation of ethylene; in some sulfonations.

Chemical intermediate for ethyl derivatives of phenols, amines, and thiols and as an alkylating agent.

The principal uses are as an intermediate in dye manufacture, as an ethylating agent in pigment production, as a finishing agent in textile manufacture and as a dye-set agent in carbonless paper. Smaller applications are in agricultural chemicals, in household products, in the pharmaceutical and cosmetic industries, as a laboratory reagent, as an accelerator in the sulfation of ethylene and in some sulfonation processes.

U.S. Production · 3 件

2023: 2,500,000 - <4,000,000 lb

(1972) PROBABLY GREATER THAN 4.5X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesPigment
Methods of ManufacturingPrepared from ethanol + sulfuric acid; by absorption of ethylene in sulfuric acid; from diethyl ether and fuming sulfuric acid.
Formulations/Preparations · 2 件

GRADES: TECHNICAL

Diethyl sulfate is available as a technical grade product that contains 99.5% active ingredient or as a laboratory chemical with a purity of 95% to >98%.

応用分野 · 5 件

用途強力なエチル化剤で染料、医薬品、農薬、ファインケミカル工業で広範な用途がある 第4級アンモニウム塩化合物合成剤

用途染料、医薬品、農薬、合成剤

用途強力なエチル化剤、染料医薬農薬等の用途

使用The primary use of diethyl sulfate is as a chemical intermediate (ethylating agent) in synthesis of ethyl derivatives of phenols, amines, and thiols; as an accelerator in the sulfation of ethylene; and in some sulfonation processes. It is used to manufacture dyes, pigments, carbonless paper, and textiles. It is an intermediate in the indirect hydration (strong acid) process for the preparation of synthetic ethanol from ethylene. Smaller quantities are used in household products, cosmetics, agricultural chemicals, pharmaceuticals, and laboratory reagents (IARC 1992, 1999, HSDB 2009). In 1966, it was used as a mutagen to create the Luther variety of barley (IARC 1974).

一般的な説明Diethyl sulfate appears as a clear colorless liquid with a peppermint odor. Burns, though may be difficult to ignite. Corrosive to metals and tissue. It is a potent alkylating agent.

調製方法

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

純化方法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.]

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補足説明

定義ChEBI: Diethyl sulfate is the diethyl ester of sulfuric acid. It has a role as a carcinogenic agent, an apoptosis inducer, an alkylating agent and a mutagen.

関連反応

344 件

関連ノート

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