Этилен гликол химические свойства, назначение, производство
Описание
Ethylene glycol was first synthesized in 1859; however, it did
not become a public health concern until after World War II. In
fact, the first published series of deaths from ethylene glycol
consumption involved 18 soldiers who drank antifreeze as
a substitute for ethanol. Despite the early recognition that
patients who drank ethanol in addition to ethylene glycol had
prolonged survival when compared to those drinking ethylene
glycol alone, antidotal treatment of ethylene glycol toxicity
with ethanol was not evaluated until the 1960s. Today,
ethylene glycol poisoning continues to be a public health
problem, particularly in the southeastern United States. In
2009, US poison control centers received 5282 calls about
possible ethylene glycol exposures, and the toxicology
community believes these exposures are underreported.
Химические свойства
Ethylene glycol,CH20HCH20H, also known as glycol,ethylene alcohol, glycol alcohol, and dihydric alcohol, is a colorless liquid. It is soluble in water and in alcohol. Ethyleneglycol has a low freezing point,-25°C (-13 OF), and is widely used as an antifreeze in automobiles and in hydraulic fluids. It is used as a solvent for nitrocellulose and in the manufacture of acrylonitrile, dynamites, and resins.
Использование
Ethylene glycol is used as an antifreeze inheating and cooling systems (e.g., automobileradiators and coolant for airplane motors).It is also used in the hydraulic brake fluids;as a solvent for paints, plastics, and inks; as a softening agent for cellophane; and in themanufacture of plasticizers, elastomers, alkydresins, and synthetic fibers and waxes.
Методы производства
Historically, ethylene glycol has been manufactured by
hydrolyzing ethylene oxide. Presently, it is also produced
commercially by oxidizing ethylene in the presence of acetic
acid to form ethylene diacetate, which is hydrolyzed to the
glycol, and acetic acid is recycled in the process .
Определение
ChEBI: A 1,2-glycol compound produced via reaction of ethylene oxide with water.
Подготовка
Ethylene glycol is prepared by the hydration of ethylene oxide:
This reaction is carried out in a manner comparable to that described for the
preparation of propylene glycol from propylene oxide .
Ethylene glycol is a colourless liquid, b.p. 197??C.
Реакции
Glycol reacts (1) with sodium to form sodium glycol, CH2OH · CH2ONa, and disodium glycol, CH2ONa·CH2ONa; (2) with phosphorus pentachloride to form ethylene dichloride, CH2Cl·CH2Cl (3) with carboxy acids to form mono- and disubstituted esters, e.g., glycol monoacetate, CH2OH·CH2OOCCH3, glycol diacetate, CH3COOCH2 · CH2OOCCH3; (4) with nitric acid (with sulfuric acid), to form glycol mononitrate, CH2OH·CH2ONO2, glycol dinitrate, CH2ONO2 · CH2ONO2; (5) with hydrogen chloride, heated, to form glycol chlorohydrin (ethylene chlorohydrin, CH2OH·CHCl); (6) upon regulated oxidation to form glycollic aldehyde, CH2OH·CHO, glyoxal, CHO · CHO, glycollic acid, CH2OH·COOH, glyoxalic acid, CHO·COOH, oxalic acid, COOH·COOH.
Общее описание
Ethylene glycol is a clear, colorless syrupy liquid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Since Ethylene glycol is a liquid Ethylene glycol can easily penetrate the soil and contaminate groundwater and nearby streams.
Профиль реактивности
Mixing Ethylene glycol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, sulfuric acid, [NFPA 1991].
Опасность
Questionable carcinogen. Toxic by ingestion and inhalation. Lethal dose reported to be
100 cc.
Угроза здоровью
Inhalation of vapor is not hazardous. Ingestion causes stupor or coma, sometimes leading to fatal kidney injury.
Пожароопасность
Ethylene glycol is combustible.
Профиль безопасности
Human poison by
ingestion. (Lethal dose for humans reported
to be 100 mL.) Moderately toxic to humans
by an unspecified route. Moderately toxic
experimentally by ingestion, subcutaneous,
intravenous, and intramuscular routes.
Human systemic effects by ingestion and
inhalation: eye lachrymation, general
anesthesia, headache, cough, respiratory
stimulation, nausea or vomiting, pulmonary,
kidney, and liver changes. If ingested it
causes initial central nervous system
stimulation followed by depression. Later, it
causes potentially lethal kidney damage.
Very toxic in particulate form upon
inhalation. An experimental teratogen.
Other experimental reproductive effects.
Human mutation data reported. A skin, eye,
and mucous membrane irritant.
Combustible when exposed to heat or
flame; can react vigorously with oxidants. Moderate explosion hazard when exposed
to flame. Iptes on contact with chromium
trioxide, potassium permanganate, and
sodium peroxide. Mixtures with ammonium
dichromate, silver chlorate, sodium chlorite,
and uranyl nitrate ipte when heated to
100°C. Can react violently with
chlorosulfonic acid, oleum, H2SO4, HClO4,
and Pass. Aqueous solutions may ignite
silvered copper wires that have an applied
D.C. voltage. To fight fire, use alcohol foam,
water, foam, CO2, dry chemical. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Возможный контакт
Ethylene glycol is used in antifreeze (especially as car radiator antifreeze) and in production of polyethylene terephthalate fibers and films; in hydraulic fluids; antifreeze and coolant mixtures for motor vehicles; electrolytic condensers; and heat exchangers. It is also used as a solvent and as a chemical intermediate for ethylene glycol dinitrate, glycol esters; resins, and for pharmaceuticals.
Экологическая судьба
Ethylene glycol is considered an inert ingredient in pesticides. It
typically enters the environment through waste streams after
use of deicing products, where it is highly mobile in soil and
contaminates groundwater. Ethylene glycol is considered
‘readily biodegradable.’ It biodegrades relatively quickly; its
half-life (t1/2) is 2–12 days in soil.
Ethylene glycol is biodegraded in water under both aerobic
and anaerobic conditions within a day to a few weeks. In the
atmosphere, ethylene glycol photochemically degrades with
a t1/2 of approximately 2 days.
Растворимость в органика
Miscible
with water and alcohol, soluble in lower atifatic alcohols and ketones, Propylene glycol and
Glycerin, poorly soluble in Hydrocarbons such
as Terpenes as well as in Terpene alcohols,
esters, etc.
Перевозки
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Методы очистки
It is very hygroscopic, and also likely to contain higher diols. Dry it with CaO, CaSO4, MgSO4 or NaOH and distil it under vacuum. Dry further by reaction with sodium under nitrogen, reflux for several hours and distil. The distillate is then passed through a column of Linde type 4A molecular sieves and finally distil under nitrogen, from more molecular sieves. Then fractionally distil it. [Beilstein 1 IV 2369.]
Несовместимости
Reacts with sulfuric acid, oleum, chlorosulfonic acid; strong oxidizing agents; strong bases; chromium trioxide; potassium permanganate; sodium peroxide.
Hygroscopic (i.e., absorbs moisture from the air)
Утилизация отходов
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. Alternatively, ethylene glycol can be recovered
from polyester plant wastes
Этилен гликол препаратная продукция и сырье
сырьё
препарат
2,4-DIAMINO-6-MERCAPTOPYRIMIDINE
2 - (2-бромэтил) -1,3-диоксолан
tussah silk fabric aftertreatment finishing agent
3-аминофталгидразид
Щавелевая кислота дигидрат чда
2-Этил-5-метилтиофен
4-формилфенилборная кислота
5-хлороксиндола
Polyester Filament
PolyesterPolyol
3-BENZOYL PROPIOPHENONE
Dye-fixing agent,no formaldehyde
solid alcohol
N-Винил-2-пирролидон
6-Azathymine
21-Iodo-16-methylpregna-1,4,9(11)-trien-17-ol-3,20-dione
Ethylene glycol diglycidyl ether
1-CHLORO-2-METHYL-1-PROPENE
2,3-THIOPHENEDICARBOXALDEHYDE
4-(Hydroxymethyl)phenylboronic acid
Ethylene brassylate
2-(2,4-DINITROPHENOXY)ETHANOL
Antifreeze
16,17-Эпоксипрегна-5,9(11)-диен-3,20-дион циклический бис(1,2-этандиилацеталь)
Saponified soluble oil
16-Methylpregna-1,4,9(11)-trien-17-ol-3,20-dione
9-Bromo-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione-21-acetate
16-Methylpregna-4,9(11)-dien-17-ol-3,20-dione
17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal
17,21-dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate
4,5-DIMETHYLTHIOPHENE-2-CARBOXYLIC КИСЛОТА
5-[(1,3-диоксо-1,3-дигидро-2H-изоиндол-2-ил)метил]-2-фуральдегид
2,4-DIMETHYLTHIOPHENE
2,3-диметилтиофен
2-фенил-2-имидазолин
4,5-диметилтиофена-2-карбоксальдегид
2-фторэтанол
Дексаметазон ацета
9,11β-Epoxy-17-hydroxy-16β-methyl-3,20-dioxo-9β-pregna-1,4-diene-21-yl Acetate
2-cyano-2-[2,3-dihydro-3-(tetrahydro-2,4,6-trioxo-5(2H)-pyrimidinylidene)-1H-isoindol-1-ylidene]-N-methylacetamide