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Home > Encyclopedia > Bis(2-hydroxypropyl) ether

Bis(2-hydroxypropyl) ether

Bis(2-hydroxypropyl) ether structure

Bis(2-hydroxypropyl) ether 

structure
  • CAS No:

    110-98-5

  • Formula:

    C6H14O3

  • Chemical Name:

    Bis(2-hydroxypropyl) ether

  • Synonyms:

    2-Propanol,1,1′-oxybis-;2-Propanol,1,1′-oxydi-;1,1′-Oxybis[2-propanol];Bis(2-hydroxypropyl) ether;1,1′-Oxydi-2-propanol;1,1′-Dimethyldiethylene glycol;NSC 8688;4-Oxaheptane-2,6-diol;1,1′-Oxybis-2-propanol;1-(2-Hydroxypropoxy)propan-2-ol;1,1′-Oxybis(propan-2-ol)

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Clear liquid


Liquid|SLIGHTLY VISCOUS COLOURLESS LIQUID.

Bis(2-hydroxypropyl) ether Basic Attributes

134.17

134.17

246-770-3

D5SV08985Z

1055

8688

DTXSID7026863

Colorless, slightly viscous liquid

29094400

Characteristics

49.7

-0.4

Liquid

1.0252 g/cm3 @ Temp: 20 °C

-40 °C

233 °C

138 °C

1.44-1.442

Solubility in water: miscible

Store in a cool, dry place. Store in a tightly closed container.

Vapour pressure, Pa at 25°C: 4

Relative vapour density (air = 1): 4.63

LD50 orl-rat: 14,850 mg/kg 34ZIAG -,731,69

vol% in air: 2.22.6

Nearly odorless

Henry's Law constant = 3.6X10-9 atm-cu m/mole at 25 °C (est)

Greater solvent power for castor oil & some other organic materials than other glycols|Conversion factors: 1 ppm = 5.49 mg/cu m; 1 mg/L = 182 ppm|Hydroxyl radical reaction rate constant = 3.1X10-11 cu cm/molecule-sec at 25 °C (est)

310 °C

Safety Information

36/37/38

24/25

UB8785000

Well closed.

Stable under normal temperatures and pressures.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

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.

...can react vigorously with oxidizing materials.

Dipropylene glycol is an indirect food additive for use only as a component of adhesives.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision for Propylene Glycol and Dipropylene Glycol, EPA 739-R-06-002 (September 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of August 12, 2015: http://www.epa.gov/pesticides/reregistration/status.htm]

Combustible.

Not Classified

Combustible when exposed to heat or flame, can react vigorously with oxidizing materials.

Explosive limits , vol% in air: 2.2-12.6

Alcohol foam, carbon dioxide, dry chemical.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

A skin and eye irritant.

Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.

Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is mildly irritating to the eyes and skin.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety spectacles.

| 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.

The major hazards encountered in the use and handling of 1,1'-oxydi-2-propanol stem from its toxicologic properties. Exposure to this practically odorless, colorless, slightly viscous liquid may occur from its use as a solvent in the manufacture of printing inks, resins, plastics, and antifreeze. Effects from exposure may include liver and kidney damage, and CNS depression. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus. 1,1'-Oxydi-2-propanol is only slightly flammable and must be preheated before ignition can occur. For fires involving this substance, extinguish with dry chemical, CO2, alcohol foam, or water spray (applied gently to the surface).

2,2'-Dihydroxydi-n-propyl ester is listed as an ingredient found in >25 products including arts and crafts, home maintenance and personal care products that consist of mostly hair colorants(1).

Toxicity

IDENTIFICATION AND USE: 1,1'-Oxydi-2-propanol is a colorless slightly viscous liquid that is nearly odorless. Commercial dipropylene glycol is composed of 3 isomers and is typically 98% pure. The commercial product is typically composed of up to 48% of the isomer 1,1'-oxydi-2-propanol. 1,1'-Oxydi-2-propanol is registered for use as an approved pesticide in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is also used as a solvent and in the production of polyester and alkyd resins, reinforced plastics, and plasticizers. Uses for dipropylene glycol include in printing industry, in antifreeze, and air sanitation, since its vapor is highly germicidal. HUMAN EXPOSURE AND TOXICITY: There is no human toxicity data reported for 1,1'-oxydi-2-propanol. ANIMAL STUDIES: All toxicity data reported is for the related chemical dipropylene glycol. Although more acutely depressant to the central nervous system than ethylene, diethylene or propylene glycol, dipropylene glycol is still low in toxicity to animals, especially to the liver. It is not irritating to the skin and is not absorbed in toxic amounts through intact skin. Dipropylene glycol did cause death from kidney injury when administered at 10%. Chronic administration to rats caused degeneration of tubular epithelium in the kidneys and liver degeneration of parenchyma. In dogs, repeated gastric dosage of dipropylene glycol resulted in moderate degenerative changes in kidney and only minimal evidence of liver damage.

LD50 Guinea pig oral 17,600 mg/kg|LD50 Dog iv 11,500 mg/kg|LD50 Mice ip 4494 mg/kg|LD50 Rat iv 5800 mg/kg|For more Non-Human Toxicity Values (Complete) data for 2,2'-Dihydroxydi-n-propyl ether (6 total), please visit the HSDB record page.

2,2'-Dihydroxydi-n-propyl ester's production and use in hydraulic and brake fluids, inks, paint and as a plasticizer and lubricant(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 1(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxydi-n-propyl ester is expected to have very high mobility in soil(SRC). Volatilization of 2,2'-dihydroxydi-n-propyl ester from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 3.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2,2'-Dihydroxydi-n-propyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 1% of theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxydi-n-propyl ester 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 3.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 2,2'-Dihydroxydi-n-propyl ester 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(4), BCFs of <2.2-4.6 and 0.3-1.4 reported in carp (Cyprinus carpio) exposed over a 6 week period to 0.3 and 3 mg/L of 2,2'-dihydroxydi-n-propyl ester(5), respectively, suggest bioconcentration in aquatic organisms is low(SRC). A 1% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2'-dihydroxydi-n-propyl ester, which has an estimated vapor pressure of 6.3X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,2'-dihydroxydi-n-propyl ester 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 12 hours(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). 2,2'-Dihydroxydi-n-propyl ester 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).

The rate constant for the vapor-phase reaction of 2,2'-dihydroxydi-n-propyl ester with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,2'-Dihydroxydi-n-propyl ester is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,2'-Dihydroxydi-n-propyl ester does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

4.57|BCFs of <2.2-4.6 and 0.3-1.4 were reported in carp (Cyprinus carpio) exposed over a 6 week period to 0.3 and 3 mg/L of 2,2'-dihydroxydi-n-propyl ester, respectively(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is low(SRC).

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

The Henry's Law constant for 2,2'-dihydroxydi-n-propyl ester is estimated as 3.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2'-dihydroxydi-n-propyl ester is expected to be essentially nonvolatile from moist soil and water surfaces(2). 2,2'-Dihydroxydi-n-propyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-3 mm Hg(SRC), determined from a fragment constant method(1).

DRINKING WATER: 2,2'-Dihydroxydi-n-propyl ester was qualitatively detected in drinking water concentrates collected in Cincinnati, OH on Oct 17, 1978 and Jan 14, 1980(1).|GROUND WATER: 2,2'-Dihydroxydi-n-propyl ester was qualitatively detected in ground water samples collected from a well adjacent to a landfill facility in Norman, OK. The occurrence of 2,2'-dihydroxydi-n-propyl ester in the well water is probably the result of leaching from the landfill(1).

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of 2,2'-dihydroxydi-n-propyl ester in the United States may be 25-49 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 3536 workers (1385 of these are female) were potentially exposed to 1,1-oxydi-2-propanol in the US(1). Occupational exposure to 2,2'-dihydroxydi-n-propyl ester may occur through inhalation and dermal contact with this compound at workplaces where 2,2'-dihydroxydi-n-propyl ester is produced or used. Monitoring data indicate that the general population may be exposed to 2,2'-dihydroxydi-n-propyl ester via ingestion of contaminated drinking water, and dermal contact with consumer products containing 2,2'-dihydroxydi-n-propyl ester(SRC).

Drug Information

It is ...not absorbed in toxic amt through intact skin. /Dipropylene Glycol/|Dipropylene glycol is not utilized by liver or stored as glycogen ... found that dipropylene glycol disappeared from the blood in approximately 24 hr ... . /Dipropylene glycol/

Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


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

/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/

The substance can be absorbed into the body by inhalation of its aerosol.

Redness.


Redness.

Bis(2-hydroxypropyl) ether Use and Manufacturing

Methods of Manufacturing

It is obtained by condensation of 1, 2-propanediol and propylene oxide. 1, 2-Propanediol and propylene oxide are subjected to condensation reaction under the action of 85% sulfuric acid. The reaction solution was neutralized with sodium hydroxide solution, filtered, distilled under reduced pressure, and then rectified under normal pressure, collecting 229-233°C fraction to obtain dipropylene glycol. Raw material consumption quota: 1300kg/t for propylene glycol, 1500kg/t for propylene oxide, 100kg/t for sulfuric acid (98%), and 100kg/t for caustic soda (95%).

Uses

Bis(2-hydroxypropyl) Ether is commonly used as a plasticizer, an intermediate in industrial chemical reactions.


Odor agents


Air care products

Production

2-Propanol, 1,1'-oxybis- is listed as a High Production Volume (HPV) chemical (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).|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Propanol, 1,1'-oxybis-. National Production Volume: 146,990 lb/yr.

Grade: Technical|Purge Air Sanitizer (Amrep, Inc): Active ingredient: dipropylene glycol 4.0%; alkyl* dimethyl benzyl ammonium chloride *(50�4, 40�2, 10�6) 0.2%; and triethylene glycol 6.0%. /Dipropylene glycol/|Saginaw (Clorox Professional Products Company): Active ingredient: ethanol 66.34%; dipropylene glycol 5.31%. /Dipropylene glycol/|Clorox Aerosol (The Clorox Company): Active ingredient: ethanol 66.34%; dipropylene glycol 5.31%. /Dipropylene glycol/|The commercial dipropylene glycol substance (CAS No. 25265-71-8; mixed isomers) occurs as a mixture of three different isomers, each of which has the same chemical formula with atoms connected differently in the dipropylene glycol molecule. These component isomers are identified as follows: CAS No. 110-98-5: 1,1'-oxybis-2-propanol (2,2'-dihydroxydipropylether); CAS No. 108-61-2: 2,2'-oxybis-1-propanol (2,2'-dihydroxydiisopropylether); CAS No. 106-62-7: 2-(2-hydroxypropoxy)-1-propanol (2-hydroxypropyl-2'-hydroxyisopropylether).

All other chemical product and preparation manufacturing|2-Propanol, 1,1'-oxybis-: ACTIVE|... the exact composition of the commercial product is not known. /Dipropylene glycol/|Commercial dipropylene glycol (CAS # 25265-71-8) is composed of 3 isomers and is typically 98% pure. The commercial product is typically composed of up to 48% of /the/ isomer /1,1'-oxydi-2-propanol/ (CAS #110-98-5).

EPA Safer Chemical Functional Use Classes -> Solvents|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Cosmetics -> Solvent

Computed Properties

Molecular Weight:134.17
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:134.094294304
Monoisotopic Mass:134.094294304
Topological Polar Surface Area:49.7
Heavy Atom Count:9
Complexity:57.3
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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