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Home > Encyclopedia > Diethylene glycol monohexyl ether

Diethylene glycol monohexyl ether

Diethylene glycol monohexyl ether structure

Diethylene glycol monohexyl ether 

structure
  • CAS No:

    112-59-4

  • Formula:

    C10H22O3

  • Chemical Name:

    Diethylene glycol monohexyl ether

  • Synonyms:

    Ethanol,2-[2-(hexyloxy)ethoxy]-;2-[2-(Hexyloxy)ethoxy]ethanol;Diethylene glycol monohexyl ether;n-Hexoxyethoxyethanol;Hexyl Carbitol;Diethylene glycol hexyl ether;3,6-Dioxa-1-dodecanol;Ucar Filmer EHC;DEGHE;NSC 403666;HEDG;Kyowanol HX 20;Hexyl diglycol;2-(2-Hexoxyethoxy)ethanol

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Clear colorless liquidWater-white liquid.


Diethylene glycol n-hexyl ether is a water-white liquid. (USCG, 1999)|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Diethylene glycol n-hexyl ether is a water-white liquid. (USCG, 1999)

Diethylene glycol monohexyl ether Basic Attributes

190.28

190.28

203-988-3

Z6X09N6YJL

1572

403666

DTXSID4026921

Water-white liquid

29094400

Characteristics

38.69000

1.50

Diethylene glycol n-hexyl ether is a water-white liquid. (USCG, 1999)

0.935 g/cm3 @ Temp: 25 °C

-40 °C

259.1 °C @ Press: 760 Torr

>230 °F

n 20/D 1.4381(lit.)

H2O: 17g/l;soluble in water. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.

<0.01 hPa (20 °C)

Relative vapour density (air = 1): 6.6

LD50 orally in Rabbit: 2400 mg/kg LD50 dermal Rabbit 1395 mg/kg

1.1-6.3%(V)

Henry's Law constant = 8.9X10-11 atm-cu m/mol at 25 °C (est)

1 mg/L = 128.5 ppm at 25 °C, 760 mm Hg; 1 ppm = 7.78 mg/cu m at 25 °C, 760 mm Hg|7.8 lb/gal; freezing point: -33 °C. Combustible|Hydroxyl radical reaction rate constant = 4.04X10-11 cu cm/molec-sec at 25 °C (est)

Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.

Ethers

Peroxidizable Compound

Ethers, such as DIETHYLENE GLYCOL N-HEXYL ETHER can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Safety Information

NONH for all modes of transport

1

R21

26-36/37-46-36/37/39

KL2625000

Xn

Separated from strong oxidants.

P280-P305 + P351 + P338

H312-H318

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. (USCG, 1999)|Combustible.

|Danger|H312: Harmful in contact with skin [Warning Acute toxicity, dermal]|P280, P302+P352, P305+P351+P338, P310, P312, P322, P363, and P501|H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]|Aggregated GHS information provided by 554 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, and P501|Warning|P264, P280, P302+P352, P305+P351+P338, P312, P322, P337+P313, P363, and P501

Fire Extinguishing Agents Not to Be Used: Water. Fire Extinguishing Agents: Dry chemical, alcohol foam, or carbon dioxide. (USCG, 1999)|Use water spray, powder, foam, carbon dioxide.

Full impervious protective clothing, including boots and gloves. Where splashing is possible wear full face shield or chemical safety goggles. Use approved respirator to protect against vapors. (USCG, 1999)

Combustible

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|...BECAUSE OF ITS TOXICITY, /IT/ SHOULD BE HANDLED WITH CARE & CAUTION TO PREVENT EYE CONTACT. IT WOULD SEEM WISE ALSO TO EXERCISE CARE TO AVOID PROLONGED OR REPEATED INHALATION EXPOSURE, ESP IF IT IS HANDLED HOT OR IF OPERATIONS CALL FOR AGITATED OR NEBULIZATION SO THAT FOG OR MIST IS GENERATED.

Severely irritating to the eyes and can cause marked corneal injury that may be slow to heal. It is mildly irritating to the skin by acute contact; however, prolonged or occluded contact can cause severe irritation.

Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Personal protection: face shield.

Separated from strong oxidants.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

The substance is severely irritating to the eyes. The substance is irritating to the skin.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety goggles.

Toxicity

LD50 Rat oral 4.92 mL/kg (male) and 3.73 mL/kg (female)|LD50 Rabbit dermal 1500 mg/kg|LD50 Rabbit percutaneous 2.14 mL/kg (males) and 2.37 mL/kg (females).

Diethylene glycol hexyl ether's production and use as a high boiling solvent(1) 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 200(SRC), determined from a log Kow of 1.70(2) and a regression-derived equation(3), indicates that diethylene glycol hexyl ether is expected to have moderate mobility in soil(SRC). Volatilization of diethylene glycol hexyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.18X10-3 mm Hg(4), and water solubility, 1.7X10+4 mg/L(5). Diethylene glycol hexyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation of diethylene glycol hexyl ether may take place based on a study using pure culture Pseudomonas sp 4-5-3 which degraded diethylene glycol hexyl ether 34% in 7 days at 30 °C(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.70(2) and a regression-derived equation(3), indicates that diethylene glycol hexyl ether is 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 1.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.18X10-3 mm Hg(4), and water solubility, 1.7X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 4(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation of diethylene glycol hexyl ether may take place based on a study using pure culture Pseudomonas sp 4-5-3 which degraded diethylene glycol hexyl ether 34% in 7 days at 30 °C(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol hexyl ether, which has an estimated vapor pressure of 1.18X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol hexyl ether 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 9.5 hours(SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Alcohols and ethers do not contain chromophores that absorb at wavelengths >290 nm and therefore diethylene glycol hexyl ether is not expected to be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of diethylene glycol hexyl ether with photochemically-produced hydroxyl radicals has been estimated as 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diethylene glycol hexyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Alcohols and ethers do not contain chromophores that absorb at wavelengths >290 nm and therefore diethylene glycol hexyl ether is not expected to be susceptible to direct photolysis by sunlight(3).

An estimated BCF of 4 was calculated in fish for diethylene glycol hexyl ether(SRC), using a log Kow of 1.70(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of diethylene glycol hexyl ether is estimated as 200(SRC), using a log Kow of 1.70(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol hexyl ether is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for diethylene glycol hexyl ether is estimated as 1.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.18X10-8 mm Hg(1), and water solubility, 1.7X10+4 mg/L(2). This Henry's Law constant indicates that diethylene glycol hexyl ether is expected to be essentially nonvolatile from water surfaces(3). Diethylene glycol hexyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 18 workers (0 of these are female) are potentially exposed to diethylene glycol hexyl ether in the US(1). Occupational exposure to diethylene glycol hexyl ether may occur through inhalation and dermal contact with this compound at workplaces where diethylene glycol hexyl ether is produced or used(SRC).

Drug Information

Exposure can cause irritation of eyes, nose and throat. (USCG, 1999)

Get medical attention. INHALATION: Remove to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen. EYES: Flush with water for at least 15 min., lifting lids occasionally. SKIN: Remove contaminated clothing and shoes. Wash with soap and water. (USCG, 1999)


Fresh air, rest.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


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

/SIGNS AND SYMPTOMS/ IT IS MILDLY TO MODERATELY IRRITATING TO THE SKIN BUT SHOULD CAUSE NO SERIOUS INJURY UNLESS THE EXPOSURE IS PROLONGED & SEVERE.|/SIGNS AND SYMPTOMS/ 1. CENTRAL NERVOUS DEPRESSION... 3. NAUSEA, VOMITING, & SOMETIMES DIARRHEA. 4. ...HEADACHE. LATER ABDOMINAL & LUMBAR PAIN & COSTOVERTEBRAL ANGLE TENDERNESS. 5. TRANSIENT POLYURIA & THEN OLIGURIA, PROGRESSING TO ANURIA. 6. ACUTE RENAL FAILURE... /DIETHYLENE GLYCOL & ITS MONOETHERS/|/SIGNS AND SYMPTOMS/ ... PATHOLOGICAL LESIONS MAY APPEAR IN BRAIN, LUNGS, LIVER, MENINGES & HEART. /DIETHYLENE GLYCOL & ITS MONOETHERS/

DGHE

The substance can be absorbed into the body through the skin.

Redness. Pain.


Redness. Pain.

Diethylene glycol monohexyl ether Use and Manufacturing

Methods of Manufacturing

REACTION OF ETHYLENE OXIDE WITH 1-HEXANOL (PRODUCT IS ISOLATED FROM THE REACTION MIXT BY VACUUM DISTILLATION); REACTION OF DIETHYLENE GLYCOL WITH 1-HEXANOL|Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethylene Glycol Monoethers/

Uses

Solvents (for cleaning and degreasing)

Production

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5445]|(2006): 1,612 million lb annual capacity /Glycol ethers/|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

All other basic organic chemical manufacturing|Ethanol, 2-[2-(hexyloxy)ethoxy]-: ACTIVE

EPA Safer Chemical Functional Use Classes -> Solvents|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues

Computed Properties

Molecular Weight:190.28
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:10
Exact Mass:190.15689456
Monoisotopic Mass:190.15689456
Topological Polar Surface Area:38.7
Heavy Atom Count:13
Complexity:86.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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