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Home > Encyclopedia > Tetraethylene glycol

Tetraethylene glycol

Tetraethylene glycol structure

Tetraethylene glycol 

structure
  • CAS No:

    112-60-7

  • Formula:

    C8H18O5

  • Chemical Name:

    Tetraethylene glycol

  • Synonyms:

    Ethanol,2,2′-[oxybis(2,1-ethanediyloxy)]bis-;Tetraethylene glycol;2,2′-[Oxybis(2,1-ethanediyloxy)]bis[ethanol];Hi-Dry;3,6,9-Trioxaundecane-1,11-diol;Bis[2-(2-hydroxyethoxy)ethyl] ether;TEG;NSC 1262;1,11-Dihydroxy-3,6,9-trioxaundecane;2-[2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy]ethanol;2,2′-((Oxybis(ethane-2,1-diyl))bis(oxy))diethanol;2-[2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy]ethan-1-ol;2,2′-[Oxybis(2,1-ethanediyloxy)]diethanol;2,2′-((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethanol);79688-08-7;1186024-61-2

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

PROTAC Linker 18 is a PROTAC linker, which refers to the alkyl/ether composition. PROTAC Linker 18 can be used in the synthesis of a series of PROTACs. PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[1].


Tetraethylene glycol is a colorless to straw-colored liquid with a mild odor. Sinks and mixes with water. (USCG, 1999)|Liquid


Tetraethylene glycol is a colorless to straw-colored liquid with a mild odor. Sinks and mixes with water. (USCG, 1999)|Tetraethylene glycol is a poly(ethylene glycol).

Tetraethylene glycol Basic Attributes

194.23

194.23

1634320

203-989-9

1262

DTXSID9026922

Liquid|Colorless liquid|Colorless to straw-colored liquid

29094919

Characteristics

68.2

-1.6

Clear slightly yellow Liquid

1.1285 g/cm3 @ Temp: 15 °C

-6.2 °C

327 °C @ Press: 760 Torr

400 °F

1.455

H2O: soluble

Store below +30°C.

<0.01 mm Hg

6.7 (vs air)

0.5-3.4%(V)

Mild odor

Henry's Law constant = 1.188X10-11 atm-cu m/mol at 25 °C (est)

Liquid Molar Volume = 0.173153 cu m/kmol|Hydroxyl radical reaction rate constant = 5.04X10-11 cu cm/molec-sec at 25 °C (est)

Water soluble.

Alcohols and Polyols

TETRAETHYLENE GLYCOL is a ether-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. May attack some forms of plastics (USCG, 1999).

-10.530 BTU/LB= -5.850 CAL/G= -245X10+5 JOULES/KG

62.63 kJ/mol at 760 mm Hg

Safety Information

NONH for all modes of transport

2

36/37/38

24/25

XC2100000

Stable. Incompatible with strong oxidizing agents, strong bases.

P264, P280, P305+P351+P338, P33, P313

H319

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated Packaging: Dispose of as unused product.

May attack some forms of plastics.|Materials to avoid: strong oxidizing agents, Strong bases.|Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid

European Chemicals Bureau; IUCLID Dataset, 3,6,9-Trioxaundecane-1,11-diol (CAS # 112-60-7)[Available from, as of February 23, 2007: http://esis.jrc.ec.europa.eu/]

|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 388 companies from 6 notifications to the ECHA C&L Inventory.|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P260, P261, P264, P271, P272, P280, P284, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P320, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 446 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Goggles or face shield and rubber gloves. (USCG, 1999)|Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Handle with gloves.|Impervious clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK (EU EN 14387) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Goggles or face shield & rubber gloves.

Combustible

Wear self-contained breathing apparatus for firefighting if necessary.|Alcohol foam, dry chemical or carbon dioxide.

Avoid breathing vapors, mist or gas.|Keep in suitable, closed containers for disposal.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

The dermal irritation of tetraethylene glycol was examined in humans. A group of 103 humans received 0.2 mL applied occlusively to the infrascapular area of the back, either to the right or left of the midline for 48 hours. Humans were examined at the end of the 48 hour period and 24 hours later. The primary irritation index was 15.5, indicating minimal irritation.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Tetraethylene glycol was not detected in tire wear particle or road dust particle samples but was detected in a brake lining particle sample at 403.6 ug/g(1).

Tetraethylene glycol is listed as an ingredient found in brake fluid and printer ink cartridges(1).

Toxicity

IDENTIFICATION AND USE: Tetraethylene Glycol (TetraEG) is colorless or straw-colored liquid with a mild odor. It is used as a solvent for nitrocellulose, plasticizer, lacquers, coating compositions. It is also used in ceramic paste/printing ink binder; as a lubricant (metalworking fluids/textile spin finishes), softening agent (paper tissue), and fragrance ingredient and viscosity decreasing agent in cosmetic formulations. HUMAN EXPOSURE AND TOXICITY: TetraEG caused minimal skin irritation and was not a skin sensitizer when tested in humans. ANIMAL STUDIES: TetraEG did not cause any adverse events when rats were exposed to vapors of this material for 8 hrs. Instillation of 0.1 mL of sample into rabbit eyes produced minor, transient irritation which did not involve the cornea. TetraEG exhibited no potential to produce dermal sensitization in the guinea pig. No treatment-related effects of toxicological significance were noted in rats administered TetraEG in the drinking water to provide up to 2000 mg/kg/d for 4 weeks. TetraEG did not produce significant mutagenic effect in the CHO gene mutation assay in the tests with and without metabolic activation and was negative in Ames (Salmonella) gene mutation test. However, it produced statistically significant increases of SCEs in tests with and without metabolic activation, but the increases did not occur with a dose-related trend characteristic of genotoxic agents. ECOTOXICITY STUDIES: For fish, snail, copepod, protozoan and fungi LC50 values of DMSO, ethlyene glycol, triethylene glycolmonomethyl ether and tetraethylene glycol were more than 30000 ppm. These solvents exhibit the lowest toxicity compared to other surfactants and their acceptable concentration was estimated at about 300 ppm.

LD50 Rabbit dermal = >18000 mg/kg|LD50 Rat oral = 30,000 mg/kg bw|LD50 Rat oral 33000 mg/kg bw|LD50 Rat oral 29 g/kg|LD50 Male and female Rats oral >16.0 mL/kg

/AQUATIC SPECIES/ ...Many kinds of surfactants have higher toxicity for phytoplankton than organic solvents. The least toxic surfactants for phytoplankton were the Tween (polyoxyethylene(20) sorbitan) series and polyoxyethylene(20)octyl ether and their acceptable concentration was estimated from 10 to 100 ppm. For the other organisms (fish, snail, copepod, protozoan and fungi), LC50 values of DMSO, ethlyene glycol, triethylene glycolmonomethyl ether and tetraethylene glycol were more than 30000 ppm, and these solvents exhibit the lowest toxicity and their acceptable concentration was estimated at about 300 ppm.

Tetraethylene glycol's production and use as a solvent for nitrocellulose, lacquers, and coating compositions, as a plasticizer(1), and in pigment/water based ink(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that tetraethylene glycol is expected to have very high mobility in soil(SRC). Volatilization of tetraethylene glycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), based upon its vapor pressure, 4.65X10-5 mm Hg(3), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(4). Tetraethylene glycol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Tetraethylene glycol is expected to biodegrade in soil based upon a 4% degradation in 5 days under unacclimated conditions to an 88% degradation in 20 days after acclimation, both using a wastewater inoculum(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that tetraethylene glycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 4.65X10-5 mm Hg(4), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(5). Tetraethylene glycol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of -2.02(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Tetraethylene glycol is expected to biodegrade in water based upon a 4% degradation in 5 days under unacclimated conditions to an 88% degradation in 20 days after acclimation, both using a wastewater inoculum(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetraethylene glycol, which has a vapor pressure of 4.65X10-5 mm Hg at 26 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tetraethylene glycol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.6 hours(SRC), calculated from its rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tetraethylene glycol may be removed from the air by wet and dry deposition(SRC). Tetraethylene glycol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of tetraethylene glycol with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tetraethylene glycol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Tetraethylene glycol does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for tetraethylene glycol(SRC), using an estimated log Kow of -2.02(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tetraethylene glycol can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetraethylene glycol is expected to have very high mobility in soil.

The Henry's Law constant for tetraethylene glycol is estimated as 1.2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 4.65X10-5 mm Hg(1), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(2). This Henry's Law constant indicates that tetraethylene glycol is expected to be essentially nonvolatile from moist soil and water surfaces(3). Tetraethylene glycol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

According to the 2012 TSCA Inventory Update Reporting data, eight reporting facilities estimate the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of tetraethylene glycol in the United States may be as low as <10 workers up to the range of 1000-9999 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 55,282 workers (1585 of these are female) were potentially exposed to tetraethylene glycol in the US(1). Occupational exposure to tetraethylene glycol may occur through inhalation and dermal contact with this compound at workplaces where tetraethylene glycol is produced or used. Monitoring and use data indicate that the general population may be exposed to tetraethylene glycol via dermal contact with consumer products containing tetraethylene glycol(SRC).

Drug Information

Compound is nonirritating. No symptoms observed by any exposure route. (USCG, 1999)

INGESTION: if large amounts are swallowed, induce vomiting; treat symptomatically. EYES: flush with water; get medical attention if ill effects develop. SKIN: wash with soap and water. (USCG, 1999)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ethylene glycol, glycols, and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/|Emergency and supportive measures. 1. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. 2. Treat coma, convulsions, cardiac arrhythmias, and metabolic acidosis if they occur. Observe the patient for several hours to monitor for development of metabolic acidosis, especially if the patient is symptomatic or there is known co-ingestion of ethanol. 3. Treat hypocalcemia with IV calcium gluconate or calcium chloride. /Ethylene glycol and other glycols/

/HUMAN EXPOSURE STUDIES/ The dermal irritation of tetraethylene glycol was examined in humans. A group of 103 humans received 0.2 mL applied occlusively to the infrascapular area of the back, either to the right or left of the midline for 48 hours. Humans were examined at the end of the 48 hour period and 24 hours later. The primary irritation index was 15.5, indicating minimal irritation.|/HUMAN EXPOSURE STUDIES/ The dermal sensitization potential of tetraethylene glycol /TetraEG/ was examined in humans. TetraEG was applied (0.2 mL) semiocclusively or occlusively to the skin of 397 individuals every 48 hours for 9 applications. Subjects removed patches after 24 hours. After a two-week rest phase, the challenge phase was initiated. Subjects removed patches 24 hrs after application and sites were graded at 48 and 72 hrs after application. TetraEG was not a human skin sensitizer.

tetraethylene glycol

Tetraethylene glycol Use and Manufacturing

Methods of Manufacturing

Produced as a coproduct of diethylene glycol manufacture|Tetraethylene glycol is prepared commercially by adding ethylene oxide to ethylene glycol, diethylene glycol, or water in the presence of a suitable catalyst.|Diethylene glycol + ethylene oxide (epoxidation)

Uses

Used as a new aromatic extraction solvent, cosmetic solvent, aircraft engine lubricant, brake oil admixture, etc.


Functional fluids (closed systems)


Anti-freeze and de-icing products

Production

10,000,000 - 50,000,000 lb|(1972) 5.36X10+9 GRAMS|(1975) 6.81X10+9 GRAMS|(1984) 9.80X10+9 g|(2006) 1,612 million lb annual capacity /Glycol ethers/|For more U.S. Production (Complete) data for TETRAETHYLENE GLYCOL (7 total), please visit the HSDB record page.

All other basic organic chemical manufacturing|Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-: ACTIVE

Method: NIOSH 5523, Issue 1; Procedure: gas chromatography with a flame ionization detection; Analyte: tetraethylene glycol; Matrix: air; Detection Limit: 14 ug/sample.

EPA Safer Chemical Functional Use Classes -> Solvents|Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern|Cosmetics -> Humectant; Solvent

Computed Properties

Molecular Weight:194.23
XLogP3:-1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:194.11542367
Monoisotopic Mass:194.11542367
Topological Polar Surface Area:68.2
Heavy Atom Count:13
Complexity:78.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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