ethane-1,2-diol

ethane-1,2-diol - Names and Identifiers

Name	Ethylene glycol
Synonyms	Inhibitory ethylene glycol EG MEG dowtherm ethane-1, dowthermsr1 Athylenglykol Dowtherm SR 1 Aliphatic diol 1,2-Ethanediol Ethylene glycol ethane-1,2-diol Dihydroxyethane 2-Hydroxyethanol Monoethylene glycol monoethylene-glycol glycol, 1,2-Dihydroxyethane
CAS	107-21-1
EINECS	203-473-3
InChI	InChI=1/C2H4.2H2O/c1-2;;/h1-2H2;2*1H2

ethane-1,2-diol - Physico-chemical Properties

Molecular Formula	C2H6O2
Molar Mass	62.07
Density	1.113 g/mL at 25 °C (lit.)
Melting Point	-13 °C (lit.)
Boling Point	195-198 °C
Specific Rotation(α)	n20/D 1.431 (lit.)
Flash Point	230°F
Water Solubility	miscible
Solubility	Miscible with water, miscible with ethanol, ether, etc.
Vapor Presure	0.08 mm Hg ( 20 °C)
Vapor Density	2.1 (vs air)
Appearance	Colorless transparent viscous liquid
Color	blue
Odor	Odorless
Exposure Limit	Ceiling limit in air for vapor and mist50 ppm (~125 mg/m3) (ACGIH); TWA 10mg/m3 (particulates) (MSHA).
Maximum wavelength(λmax)	['λ: 260 nm Amax: ≤0.03', , 'λ: 280 nm Amax: ≤0.01']
Merck	14,3798
BRN	505945
pKa	14.22(at 25℃)
PH	6-7.5 (100g/l, H2O, 20℃)
Storage Condition	2-8°C
Sensitive	Hygroscopic
Explosive Limit	3.2%(V)
Refractive Index	n20/D 1.431(lit.)
MDL	MFCD00002885
Physical and Chemical Properties	Characteristics of colorless transparent viscous liquid, sweet, with hygroscopicity. boiling point 198 ℃ freezing point -11.5 ℃ relative density 1.1088 refractive index 1.4318 flash point 116 ℃ solubility, lower aliphatic alcohols, glycerol, acetic acid, acetone and similar ketones, aldehydes, pyridine and similar coal tar alkali miscible, slightly soluble in ether, almost insoluble in benzene and its homologs, chlorinated hydrocarbons, petroleum ether and oils.
Use	Mainly used for the production of synthetic resins, surfactants and explosives, also used as antifreeze

ethane-1,2-diol - Risk and Safety

Hazard Symbols	Xn - Harmful
Risk Codes	R22 - Harmful if swallowed R36 - Irritating to the eyes R41 - Risk of serious damage to eyes
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
UN IDs	UN 1219 3/PG 2
WGK Germany	3
RTECS	KW2975000
FLUKA BRAND F CODES	3
TSCA	Yes
HS Code	29053100
Toxicity	LD50 in rats, guinea pigs (g/kg): 8.54, 6.61 orally (Smyth); in mice (ml/kg): 13.79 orally (Bornmann)

ethane-1,2-diol - Upstream Downstream Industry

Raw Materials	Ethylene Oxide Oxygen Ethylene
Downstream Products	Ethyl Alcohol Glyoxal Oxalic acid 1,2-Dibromoethane Ethyl chrysanthemumate, mixture of cis andtrans carbendazim Bromoadiolone

ethane-1,2-diol - Reference

Reference

1. Li Li Wang Jiayu Gaoshan et al. GC Simultaneous Determination of Five Volatile Impurities in Polysorbate 80 [J]. Northwest Journal of Pharmacy 2015(04):364-367.
2. Qin Liqin, Yang Huanggen, Tao Pingfang, et al. Polyhedral CaWO4:Dy 3 ,M (M = Li,Na,K) Preparation and Luminescence Properties of Phosphor [J]. Chinese Ceramics, 2019(2):18-22.
3. Zhang Xifeng, Wang Xinxin, Zhang Qingting, Luo Guanghong. Temperature-sensitive eutectic solvent aqueous two-phase extraction separation of peony seed meal polysaccharides for oil [J]. China grease, 2020,45(12):93-99.
4. Cheng, Qi-Bin, and Li-Wei Zhang. "Highly efficient enzymatic preparation of daidzein in deep eutectic solvents." Molecules 22.1 (2017): 186.https://doi.org/10.3390/molecules22010186
5. [IF = 4.411] Hui Wang et al."Deep Eutectic Solvent-Based Ultrahigh Pressure Extraction of Baicalin from Scutellaria baicalensis Georgi." Molecules. 2018 Dec;23(12):3233
6. [IF = 4.411] Qi-Bin Cheng et al."Highly Efficient Enzymatic Preparation of Daidzein in Deep Eutectic Solvents." Molecules. 2017 Jan;22(1): 186
7. [IF = 3.517] Juan Wu et al."pH-sensitive magnetic drug delivery system via layer-by-layer self-assembly of CS/PEG and its controlled release of DOX." J Biomat Sci-Polym E. 2020;31(8):1057-1070
8. [IF = 2.494] Xi feng Zhang et al."A green and highly efficient method of extracting polyphenols from Lilium davidii var. unicolor Salisb using deep eutectic solvents." Chemical Engineering Communications. 2021 Jan 04

ethane-1,2-diol - Nature

Open Data Verified Data

colorless, transparent, slightly viscous liquid. The taste was slightly sweet. Easy to absorb moisture. With water, glycerol, acetone, acetic acid, aldehydes, pyridine, ethanol phase miscible, slightly soluble in ether, insoluble in benzene, petroleum ether, oil. The melting point in the case of open flame, high heat or contact with the oxidant, the risk of causing combustion explosion. In case of high fever, the internal pressure of the container increases, and there is a risk of cracking and explosion.

Last Update：2024-01-02 23:10:35

ethane-1,2-diol - Preparation Method

ethylene glycol can be produced from ethylene oxide by hydration reaction, and then purified ethylene glycol can be obtained by vacuum distillation.

Last Update：2024-04-28 13:48:49

ethane-1,2-diol - Introduction

Sweet, hygroscopic, can reduce the freezing point of water, soluble in water, lower alcohols, glycerin, acetone, acetic acid, pyridine and aldehydes, slightly soluble in ether, almost insoluble in benzene and benzene homologs, Chlorinated hydrocarbons, petroleum ethers, oils. Toxic, median lethal dose (rat, oral) 8.54 g/kg. It is absorbent and flammable.

Last Update：2022-10-16 17:11:50

ethane-1,2-diol - Use

Open Data Verified Data

gas chromatography analysis reagent. For the determination of calcium oxide in water, as a capacitance medium, solvent and antifreeze. Used in the manufacture of resins, plasticizers, synthetic fibers, cosmetics and explosives.

Last Update：2022-01-01 09:25:06

ethane-1,2-diol - Safety

Open Data Verified Data

belongs to low toxicity class. Rat, guinea pig oral LD50:8.54, 6.61g/kg; Mouse oral: 13. 79ml/kg. Staff should be protected and immediately rinsed with running water when touching eyes and skin. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Keep the container sealed. Should be stored separately from oxidants and acids.

Last Update：2022-01-01 09:25:06

ethane-1,2-diol - Reference Information

relative polarity	0.79
freezing point	-11.5 ℃
LogP	-1.36 at 25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
Diol	Ethylene glycol, also known as glycol, is the simplest aliphatic glycol with the chemical properties of alcohols, such as ether, ester, It can be oxidized to form aldehydes or acids, and can be condensed to form ethers. It can also be replaced by halogen. Reacts with acid chloride or acid anhydride to generally form diesters. Heating under the action of a catalyst (manganese dioxide, alumina, zinc oxide or sulfuric acid) can dehydrate intramolecular or intermolecular to form cyclic ethylene glycol acetaldehyde, which reacts with nitric acid to form ethylene glycol dinitrate (an explosive). Ethylene glycol is the raw material for the production of polyester resin, alkyd resin and polyester fiber. It is also used as automobile antifreeze and aircraft engine refrigerant. In 1980, the consumption of ethylene glycol used in antifreeze in the United States was equal to that used in the production of polyester. In addition, polymer compounds such as polyester fibers can also be synthesized. The combination of ethylene glycol dinitrate and nitroglycerin can reduce the freezing point of explosives. Ethylene glycol can also be used as raw materials and high boiling point solvents for medicines and plastics. In industry, ethylene is used as raw material, which is first converted into ethylene oxide and then hydrolyzed to produce ethylene glycol. This product has the hazards of fire and explosion. It is irritating to the skin and mucous membranes, inhaled vapor or percutaneous absorption, which has an anesthetic effect on the central nervous system and also causes renal disorders. Rats LD508540 mg/kg orally. The maximum allowable concentration in the workplace is 5 × 10-6.
traits	colorless transparent viscous liquid
use	ethylene glycol is mainly used as the raw material of polyester fiber, and is used in other polyester resins, unsaturated polyester resins and 1730 polyester lacquer. Many types of surfactants can be derived from ethylene glycol and polyethylene glycol. The dinitro compound dinitro ethyl Diol is an explosive. Ethylene glycol can reduce the freezing point of aqueous solution, so it is often used as antifreeze. It is mainly used to produce polyester resin, alkyd resin, plasticizer, antifreeze, and also used in cosmetics and explosives Used as analytical reagent, chromatographic analysis reagent and capacitance medium Ethylene glycol is the intermediate of fungicide pentacyclazole and hajmezol. Ethylene glycol is mainly used to prepare antifreeze for automobile cooling system and produce polyethylene terephthalate (raw material for polyester fiber and polyester plastic). It can also be used to produce synthetic resin, solvent, lubricant, surfactant, softener, humidification agent, explosive, etc. Ethylene glycol can often be used instead of glycerin, and is used as a water mixture and solvent in the leather and pharmaceutical industries, respectively. Ethylene glycol has a strong dissolving ability, but it is easy to metabolize and oxidize to produce toxic oxalic acid, so it cannot be widely used as a solvent. Adding ethylene glycol to the hydraulic fluid can prevent the erosion of the rubber in the system by the oil-based hydraulic fluid; the water-based hydraulic fluid with ethylene glycol as the main component is a kind of non-combustible hydraulic fluid, which is used in airplanes and automobiles. Molding machines for high-temperature operations. Ethylene glycol has many important derivatives. Low molecular weight polyethylene glycol (monoethylene glycol, diethylene glycol, triethylene glycol or diethylene glycol, triethylene glycol, tetraethylene glycol respectively) is actually ethylene oxide Hydration to produce by-products of ethylene glycol. Diethylene glycol can be used as a humidifier, plasticizer, sizing agent, printing ink solvent, natural gas dehydration desiccant and aromatic extraction solvent. Diethylene glycol dinitrate is similar to ethylene glycol dinitrate and is also an important industrial explosive. High molecular weight polyethylene glycol is also a useful derivative depending on the molecular weight, from colorless transparent viscous liquid to waxy solid. Used as lubricants, moisture retention agents, solvents, and intermediates in the rubber and food industries. It is also used to prepare cosmetics, as well as additives in the fields of textiles and papermaking. There are many varieties of ethylene glycol esters and they are widely used as solvents. Ethylene glycol esters of long-chain fatty acids have surface improvement properties and can be used alone or shared with surfactants as emulsifiers, stabilizers, dispersants, humidification agents, foaming agents and suspending agents. Ethylene glycol reacts with urea to form cycloethylene urea, which is used in the textile industry. Glycol disodium reacts with 1, 2-dibromoethane to form dioxane, which is a special solvent. Different oxidants or reaction conditions are used for ethylene glycol. After oxidation, glycolaldehyde, glyoxal, glycolic acid, oxalic acid, etc. can be obtained. It is mainly used for the production of synthetic resins, surfactants and explosives, and also used as antifreeze Gas chromatography stationary liquid (the maximum service temperature is 50 ℃, the solvent is chloroform), separation and analysis of low boiling point oxygenates, Amine compounds, nitrogen or oxygen heterocyclic compounds. Determination of calcium oxide, solvent, antifreeze in cement, manufacturing polyester resin, plasticizer, cosmetics, explosives, cold-resistant lubricating oil, surfactant, varnish, dye, ink, etc., organic synthesis.
poisoning first aid	ethylene glycol is a low toxicity category. The LD50 of rats is 5.5ml/kg ~ 8.54ml/kg. One oral LD50 is 80g ~ 100g. The concentration of ethylene glycol in blood is 2.4g/L, which can cause acute renal failure. It can be absorbed by the digestive tract, skin and respiratory tract, and is discharged from the kidney in its original shape or oxidized to oxalate (oxalate). The oxidation of ethylene glycol to carbon dioxide is discharged from the respiratory tract. Although ethylene glycol is highly toxic, its volatility is very small, so it is unlikely to cause serious poisoning by inhalation in production. The manifestations of inhalation poisoning are confusion, nystagmus, protein, calcium oxalate crystals and red blood cells in the urine. Oral poisoning can be divided into three clinical stages: the first stage is mainly the symptoms of the central nervous system, such as the manifestations of ethanol poisoning; the second stage is the main symptoms of dyspnea, cyanosis, and various manifestations of pulmonary edema or bronchopneumonia; The third stage of kidney disease is obvious, including low back pain, kidney pain, renal damage, proteinuria, hematuria, calcium oxalate crystals in the urine, oliguria and even anuria, and acute renal failure. Those who take it by mistake shall be treated according to the general principle of first aid for oral poisoning, and 600ml of 1/6mol sodium lactate solution and 10ml of 10% calcium gluconate can be given intravenous drip. Artificial kidney dialysis can be used for patients with severe poisoning. The container containing ethylene glycol should be marked with "poison". This product should be sealed and exhausted when heated to prevent inhalation of this product vapor or aerosol. Avoid direct skin contact with this product for a long time.
production method	1. direct water method of ethylene oxide is the only method for producing ethylene glycol on an industrial scale at present. Ethylene oxide and water are directly hydrated in liquid phase in a tubular reactor under pressure (2.23MPa) and 190-200°C to produce ethylene glycol, while by-producing diethylene glycol, diethylene glycol and polyethylene glycol. The ethylene glycol dilute solution obtained by the reaction is concentrated by a thin film evaporator, and then dehydrated and refined to obtain qualified ethylene glycol products and by-products. 2. Ethylene oxide sulfuric acid catalysis water-catalyzed ethylene oxide and water under sulfuric acid catalysis, at 60-80 ℃, 9.806-19.61kPa pressure to produce ethylene glycol. The reaction liquid is neutralized with liquid alkali, evaporated to remove water through an evaporator to obtain 80% ethylene glycol, which is then refined in a rectification tower to obtain more than 98% finished products. This method is an early development method. Due to corrosion, pollution and product quality problems, coupled with the complexity of the refining process, countries have gradually stopped using it and switched to direct water law. 3. Ethylene is directly synthesized from ethylene glycol without ethylene oxide. 4. Dichloroethane hydrolysis method. 5. Formaldehyde method. The preparation of ethylene glycol is industrially based on chloroethanol method, ethylene oxide hydration method and ethylene direct water method. Various methods have their own characteristics, which are described below. Chloroethanol method is obtained by hydrolysis of chloroethanol as raw material in alkaline medium. The reaction is carried out at 100 ℃ to form ethylene oxide, and then hydrolyzed under pressure at 1.01 MPa to form ethylene glycol. Ethylene oxide water legal There are catalytic hydration and direct water legal. The hydration process can be carried out under normal pressure or under pressure. Atmospheric water method generally uses a small amount of inorganic acid as catalyst, and the reaction is carried out at 50~70 ℃. The molar ratio of ethylene oxide to water under pressurized water is higher than 1: 6 to reduce the side reaction of ether formation. The reaction temperature is 150 ℃ and the pressure is 147kPa. Hydration yields ethylene glycol. At present, there is a gas-phase catalytic water method, with silver oxide as catalyst and alumina as carrier, reacting at 150~240 ℃ to generate ethylene glycol. Ethylene direct water method Ethylene is oxidized in acetic acid solution in the presence of a catalyst (such as antimony oxide TeO2, palladium catalyst) to form monoacetate or diacetate, and further hydrolysis to obtain ethylene glycol. The above methods are better with ethylene oxide water, simple process and suitable for industrialization.
category	flammable liquid
toxicity classification	poisoning
acute toxicity	oral-rat LD50: 4700 mg/kg; Oral-mouse LD50: 5500 mg/kg
stimulation data	skin-rabbit 555 mg mild; Eye-rabbit 500 mg/24 hours mild
explosive hazard characteristics	blastable when mixed with air
flammability hazard characteristics	combustible in case of open flame, high temperature and strong oxidant; Stimulating smoke produced by combustion
storage and transportation characteristics	warehouse ventilation and low temperature drying
fire extinguishing agent	foam, carbon dioxide, mist water, sand
occupational standard	TWA 60 mg/m3; STEL 120 mg/m3
auto-ignition temperature	752 °F
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)