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Home > Encyclopedia > 1-Phenoxy-2-propanol

1-Phenoxy-2-propanol

1-Phenoxy-2-propanol structure

1-Phenoxy-2-propanol 

structure
  • CAS No:

    770-35-4

  • Formula:

    C9H12O2

  • Chemical Name:

    1-Phenoxy-2-propanol

  • Synonyms:

    2-Propanol,1-phenoxy-;1-Phenoxy-2-propanol;Propylene phenoxetol;2-Phenoxy-1-methylethanol;Phenoxyisopropanol;β-Phenoxyisopropanol;(±)-1-Phenoxy-2-propanol;rac-1-Phenoxy-2-propanol;NSC 24015;2-Hydroxypropyl phenyl ether;130890-76-5;207275-03-4

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

colourless liquid


Liquid

1-Phenoxy-2-propanol Basic Attributes

152.19000

152.19

212-222-7

24015

DTXSID9027312

Colorless to yellow liquid

29094990

Characteristics

29.46000

1.44620

Liquid

1.0622 g/cm3 @ Temp: 20 °C

<25 °C

242.7 °C

98.304ºC

1.519

In water, 15.1 g/L at 20 deg C

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

0.02mmHg at 25°C

5.27 (Air = 1)

LD50 orl-rat: 2830 mg/kg NTIS** OTS0539745

Mild odor

Henry's Law constant = 2.9X10-8 atm-cu m/mol at 25 °C (est)

log Kow = 1.41|Hydroxyl radical reaction rate constant = 3.7X10-11 cu cm/molec-sec at 25 °C (est)

30.4 kJ/g at 25 °C (est)

319 J/g at normal boiling point

Safety Information

NONH for all modes of transport

1

R36

S23-S26

UB8886500

Xi

Stable. Flammable. Incompatible with strong oxidizing agents.

P280-P305 + P351 + P338-P337 + P313

H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

PPh is incompatible with strong acids, strong bases, and strong oxidizers and contact should be avoided.

U.S. Chemical Safety Board; Freedom Industries Chemical Release. Accident Description: A leak originating from a storage tank at Freedom Industries contaminated the local water supply leaving hundreds of thousands of West Virginia residents without clean drinking water. The CSB's investigation is currently ongoing. No related Recommendations found.[U.S. Chemical Safety Board; Freedom Industries Chemical Release. Available from, as of July 17, 2014: http://www.csb.gov/freedom-industries-chemical-release-/]|CDC: Summary Report of Short-term Screening Level Calculation and Analysis of Available Animal Studies for Dipropylene Glycol Phenyl Ether (DiPPH) and Propylene Glycol Phenyl Ether (PPH)[CDC: Summary Report of Short-term Screening Level Calculation and Analysis of Available Animal Studies for Dipropylene Glycol Phenyl Ether (DiPPH) and Propylene Glycol Phenyl Ether (PPH); Available from, as of March 6, 2014: http://emergency.cdc.gov/chemical/MCHM/westvirginia2014/pdf/DiPPH-PPH-calculation.pdf]|OECD; Screening Information Dataset (SIDS) Inital Assessment Report for SIDS Initial Assessment Meeting (SIAM) 18, Proplylene Glycol Phenyl Ether (CAS 770-35-4) (2006). Summarize the literature on high production chemicals and provides an initial assessment.[Available from, as of August 14, 2014: http://www.inchem.org/pages/sids.html]|West Virginia Poison Center and Mid-Atlantic Center for Children's Health & the Environment; Factsheet February 10, 2014.[West Virginia Poison Center and Mid-Atlantic Center for Children's Health & the Environment; Factsheet February 10, 2014; Available from, as of April 3, 2014: http://www.childrensnational.org/files/PDF/MACCHE/Charleston_WV_Health_Professionals_Factsheet.pdf]

|Warning|H319 (93.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 1434 companies from 4 notifications to the ECHA C&L Inventory.|Danger|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P261, P271, P280, P304+P340, P305+P351+P338, P310, P312, P403+P233, P405, and P501

Do not use a direct water stream; it may spread the fire. Use water fog or fine spray, carbon-dioxide or dry-chemical extinguishers, or foam. Water fog applied gently may be used as a blanket to extinguish the fire.|Wear positive-pressure, self-contained breathing apparatus (SCBA) and protective fire-fighting clothing or fight the fire from a safe distance.

If a large spill does occur, contain spilled material if possible. Pump the contained material into suitable and properly labeled containers using appropriate safety equipment.

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.

... Potential for severe eye irritation but is not significantly irritating to skin after acute exposure.

The typical propylene glycol phenyl ether concentration in paint is 2 to 10%, in cosmetics and soaps 0.1 to 1%(1).

Toxicity

LD50 Rabbit dermal >2000 mg/kg|LD50 Rat oral 2830 mg/kg|LC50 Rat inhalation (4 hr) > 5400 mg/cu m

Propylene glycol phenyl ether's production and use as a solvent in paints, coatings, inks and adhesives, as a latex coalescent and dye carrier, and as an antibacterial agent in soaps and cosmetics(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 23(SRC), determined from a structure estimation method(2), indicates that propylene glycol phenyl ether is expected to have very high mobility in soil(SRC). Volatilization of propylene glycol phenyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given a an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00218 mm Hg(3), and water solubility, 1.51X10+4 mg/L(4). Propylene glycol phenyl ether enters the environment through evaporation from solvent or coating applications(5); therefore, it is expected to volatilize from dry soil surfaces(SRC). Propylene glycol phenyl ether biodegraded rapidly in aerobic soil degradation studies with initial half-lives of <5 days in two sandy loam soils(5); initial half-lives in a sandy soil ranged from <5 to <23 days(5). Biodegradation was much slower in anaerobic soil tests(5). Using OECD Guideline 301F (Manometric Respirometry Test), propylene glycol phenyl ether had a 60% degradation in 9.8 days and 72% degradation in 28 days which met the criteria for being classified as readily biodegradable(5). Propylene glycol phenyl ether was also readily biodegradable in Zahns-Wellens tests done in accordance with OECD guidelines(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 23(SRC), determined from a structure estimation method(2), indicates that propylene glycol phenyl ether 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 2.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00218 mm Hg(4), and water solubility, 1.51X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 2.5(SRC), from its log Kow of 1.50(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Propylene glycol phenyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Using OECD Guideline 301F (Manometric Respirometry Test), propylene glycol phenyl ether had a 60% degradation in 9.8 days and 72% degradation in 28 days which met the criteria for being classified as readily biodegradable(7). Propylene glycol phenyl ether was also readily biodegradable in Zahns-Wellens tests done in accordance with OECD guidelines(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propylene glycol phenyl ether, which has a vapor pressure of 0.00218 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase propylene glycol phenyl 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 about 10 hours(SRC), calculated from its rate constant of 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Propylene glycol phenyl ether 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 propylene glycol phenyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Propylene glycol phenyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Propylene glycol phenyl ether 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).

An estimated BCF of 2.5 was calculated in fish for propylene glycol phenyl ether(SRC), using a log Kow of 1.50(1) and a regression-derived equation(2). 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 propylene glycol phenyl ether can be estimated to be 23(SRC). According to a classification scheme(2), this estimated Koc value suggests that propylene glycol phenyl ether is expected to have very high mobility in soil.

The Henry's Law constant for propylene glycol phenyl ether is estimated as 2.9X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 0.00218 mm Hg(1), and water solubility, 1.51X10+4 mg/L(2). This Henry's Law constant indicates that propylene glycol phenyl ether is expected to be essentially nonvolatile from water surfaces(3). Propylene glycol phenyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Propylene glycol phenyl ether enters the environment through evaporation from solvent or coating applications(4); therefore, it is expected to volatilize from dry soil surfaces(SRC).

Occupational exposure to propylene glycol phenyl ether may occur through inhalation and dermal contact with this compound at workplaces where propylene glycol phenyl ether is produced or used(SRC). Worker exposure is most likely to occur while applying coating products containing propylene glycol phenyl ether to various surfaces(1). Use data indicate that the general population may be exposed to propylene glycol via inhalation of ambient air and dermal contact with products containing this compound(2). Limited population exposure may occur via ingestion of and dermal contact with contaminated water in the vicinity of a spill site(SRC).

Drug Information

PPh is rapidly absorbed, distributed throughout the body, metabolized, and eliminated. The major routes of elimination are via the urine and feces.

The following urinary metabolites were tentatively identified within Liquid Chromatography (LC) peaks using HPLC/ESI/MS and HPLC/ESI/MS/MS techniques: LC Peak A (<1%) - Glucuronide conjugate of hydroquinone LC Peak B (1-2%) - Not identified LC Peak C (1.3-3.8%) - Not identified LC Peak D (<1%) - Not identified LC Peak E/F (60-63%) - Sulfate and glutathione conjugates of phenol; Sulfate and glucuronide conjugates of PPh, sulfate conjugates of ring-hydroxylated PPh and 1- phenoxy-2-propanone LC Peak G (<1%) - Not identified LC Peak H (1-2%) - Not identified LC Peak I (4-5%) - Glucuronide conjugate of PPh LC Peak J (<1%) - Not identified LC Peak K (8-9%) - Glucuronide conjugate of PPh LC Peak L (9- 10%) - Sulfate conjugate of PPh Based on comparisons of chromatographic retention times with authentic materials, acid hydrolysis of urine yielded free phenol (61%), hydroquinone (1.5%), and parent PPh (13%).|PPh is rapidly absorbed, distributed, and quickly metabolized and eliminated in male rats. Virtually all the administered dose is eliminated within 48 hours in the urine and feces. The three major routes of metabolism are 1) cleavage of PPh by O-dealkylation, yielding propylene glycol and phenol, followed by excretion of phenol as a sulfate, or glutathione conjugate in the urine; 2) direct sulfate or glucuronide conjugation of parent PPh and excretion into the urine; and 3) ring hydroxylation of parent PPh or its oxidized propanone metabolite, followed by sulfate conjugation and excretion into the urine. Minor urinary metabolites included the glucuronide conjugate of hydroquinone.

Propylene glycol phenyl ether has a minimum purity of 93%. At least 93% of commercial propylene glycol phenyl ether is comprised of a mixture of 1-phenoxy-propan-2-ol and 2-phenoxypropan- 1-ol, with the former isomer as the major constituent. The individual isomers are not separated nor produced as individual chemicals. The remaining 7% consists of up to 7% di-PPh, 0.1% phenol and 0.35% water. Of the 93% that is a mixture of the two isomers, 1-phenoxy-propan- 2-ol (CAS No. 770-35-4) constitutes > 85% of the mixture (is the thermodynamically favored isomer) and 2-phenoxy-propan-1-ol (CAS No. 4169-04-4) constitutes < 15%.

/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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/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 needed. 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ ... an in vitro chromosome aberration assay was conducted with PPh using human lymphocytes ... Concentrations of PPh up to 400 ug/mL were incubated with human lymphocytes, with and without metabolic activation. No increases in chromosomal aberrations were detected in this assay.|/OTHER TOXICITY INFORMATION/ Individuals applying paint or other PPh-containing coatings may be exposed to this propylene glycol ether. Dermal contact through minor spills or usage contact is a source of exposure, as is inhalation from aerosol or vapor generated during application or usage. General population exposure also is possible through inhalation of ambient air containing low concentrations of PPh that may be released from industrial processes or through evaporation of coatings or other products containing it. The rapid photochemical degradation of PPh would suggest that this means of exposure to the general population would be low. Ingestion of drinking water containing PPh as a contaminant (e.g., from a spill) also is possible. The ready biodegradability of PPh, again, would suggest that exposure of the general population to such a source of PPh would be low.

propylene phenoxetol

1-Phenoxy-2-propanol Use and Manufacturing

Uses

1-Phenoxy-2-propanol is a useful synthetic intermediate. It was used in the preparation of acylarylthiocarbamates as nonnucleoside reverse transcriptase inhibitors.


Finishing agents


Fabric, textile, and leather products not covered elsewhere

Production

1,000,000 - 10,000,000 lb|2-Propanol, 1-phenoxy- 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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8175]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Propanol, 1-phenoxy-. Aggregated National Production Volume: 10 to < 50 million pounds.|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-phenoxy-. National Production Volume: 208,306 pounds lb/yr.

DOWANOL PPH Glycol Ether; Propylene glycol phenyl ether >99.5%

Paint and coating manufacturing|2-Propanol, 1-phenoxy-: ACTIVE

The following urinary metabolites were tentatively identified within Liquid Chromatography (LC) peaks using HPLC/ESI/MS and HPLC/ESI/MS/MS techniques: LC Peak A (<1%) - Glucuronide conjugate of hydroquinone LC Peak B (1-2%) - Not identified LC Peak C (1.3-3.8%) - Not identified LC Peak D (<1%) - Not identified LC Peak E/F (60-63%) - Sulfate and glutathione conjugates of phenol; Sulfate and glucuronide conjugates of PPh, sulfate conjugates of ring-hydroxylated PPh and 1- phenoxy-2-propanone LC Peak G (<1%) - Not identified LC Peak H (1-2%) - Not identified LC Peak I (4-5%) - Glucuronide conjugate of PPh LC Peak J (<1%) - Not identified LC Peak K (8-9%) - Glucuronide conjugate of PPh LC Peak L (9- 10%) - Sulfate conjugate of PPh Based on comparisons of chromatographic retention times with authentic materials, acid hydrolysis of urine yielded free phenol (61%), hydroquinone (1.5%), and parent PPh (13%).

EPA Safer Chemical Functional Use Classes -> Specialized Industrial Chemicals|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Cosmetics -> Preservative; Solvent

Computed Properties

Molecular Weight:152.19
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:152.083729621
Monoisotopic Mass:152.083729621
Topological Polar Surface Area:29.5
Heavy Atom Count:11
Complexity:97.7
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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