グリコロニトリル

Odorless

Odor similar to that of hydrogen cyanide

1.1 at 66 °F (NIOSH, 2024) - Denser than water; will sink

1.10

Relative density (water = 1): 1.1

1.1 @25 °C

(66 °F): 1.10

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

Very soluble in water, ethanol, and ethyl ether; insoluble in benzene.

Soluble in water, ethanol, and diethyl ether but insoluble in chloroform and benzene.

Solubility in water: good

Soluble

greater than 200 °F (NTP, 1992)

Flash point > 200 °F

361 °F at 760 mmHg with slight decomposition (EPA, 1998)

183 °C (slight decomp)

183 °C

183 °C @760 [mm Hg]

361 °F (Decomposes)

Less than -98 °F (EPA, 1998)

less than -72 °C

-72 °C

<-98 °F

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 94 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Acetonitrile, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetonitrile, 2-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Acetonitrile, hydroxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Moderate explosion hazard when exposed to heat or by spontaneous chemical reaction in the presence of alkalies if uninhibited. When heated to decomposition, it emits highly toxic fumes of cyanide and nitrogen oxides. Unstable, may explode on standing. Hazardous polymerization may occur. avoid the presence of alkalis, and exposure to heat. (EPA, 1998)

Combustible.

(Non-Specific -- Acetonitrile) Cool containers with flooding quantities of water. Apply water from as far away as possible. Avoid breathing vapors. Keep upwind. Wear self-contained breathing apparatus. Avoid bodily contact with the material. Wear boots, protective gloves, and goggles.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Fresh air, rest. No mouth-to-mouth artificial respiration. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

Warning: Formaldehyde cyanohydrin exposure by any route (oral, dermal, inhalation) may produce cyanide poisoning.

(General first aid procedures)

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number D003 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanide cmpd/

A poor candidate for incineration. /Cyanides/

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water. Do NOT let this chemical enter the environment. Personal protection: complete protective clothing including self-contained breathing apparatus.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/

For more Preventive Measures (Complete) data for GLYCOLONITRILE (7 total), please visit the HSDB record page.

The toxic mechanism of nitriles (including propionitrile) and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were dosed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles. /Nitriles/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glycolonitrile is expected to have very high mobility in soil(SRC). Volatilization of glycolonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(3). Glycolonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.8 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glycolonitrile is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.4X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 61 hrs and 30 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 0.5(SRC), from an estimated log Kow of -1.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glycolonitrile, which has an estimated vapor pressure of 0.8 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase glycolonitrile 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 21 days(SRC), calculated from its rate constant of 7.61X10-11 cu cm/molecule-sec at 25 °C(3).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Dizziness. Lethargy. Headache. Shortness of breath. Weakness. Blue lips, fingernails and skin.

MAY BE ABSORBED! Further see Inhalation.

MAY BE ABSORBED! Redness. Pain. Blurred vision. Further see Inhalation.

See Inhalation.

irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting

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

... STUDIES ... INDICATE THAT IT IS A HIGHLY TOXIC SUBSTANCE & EXPOSURE BY ANY ROUTE MUST BE STRICTLY AVOIDED. DIRECT CONTACT WITH EXPOSED SKIN GIVES NO IMMEDIATE /SENSATION/. IT IS ABSORBED THROUGH SKIN, & IF NOT IMMEDIATELY REMOVED, MAY HAVE FATAL CONSEQUENCES.

EXPOSURE TO TOXIC NITRILES MAY RAPIDLY CAUSE DEATH BY ASPHYXIATION SIMILAR TO THAT RESULTING FROM ... HYDROGEN CYANIDE. /NITRILES/

BEECH-NUT MEAL CONTAMINATED WITH GLYCOLONITRILE LED TO PROLONGED DEADLY POISONING WITH HYDROCYANIC ACID IN 3 PERSONS. HISTOTOXIC HYPOXYDOSIS WAS EXPRESSED BY SYMMETRIC NECROSIS OF NUCLEUS LENTIFORMIS WHICH WAS DISTINGUISHABLE FROM OTHER HISTOLOGICAL BRAIN CHANGES.

NITRILES ARE ORG CYANIDES. ACRYLONITRILE, PROPIONITRILE & SOME OTHERS RESEMBLE CYANIDES IN TOXICITY. OTHER NITRILES SUCH AS CYANAMIDES & CYANATES HAVE NO CYANIDE EFFECT. /NITRILES/

For more Human Toxicity Excerpts (Complete) data for GLYCOLONITRILE (8 total), please visit the HSDB record page.

An estimated BCF of 0.5 was calculated for glycolonitrile(SRC), using an estimated log Kow of -1.6(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.

The Henry's Law constant for glycolonitrile is estimated as 7.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that glycolonitrile is not expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 61 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 30 days(SRC). Glycolonitrile's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Glycolonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.8 mm Hg(3).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Formaldehyde cyanohydrin is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.

IN THE CASE OF ALIPHATIC NITRILES, IT IS PROBABLE THAT HYDROLYSIS TAKES PLACE WITH THE RELEASE OF THE CN GROUP. THE RAPIDITY WITH WHICH THIS PROCESS OCCURS MAY DETERMINE THE RELATIVE TOXICITY OF THE VARIOUS ALIPHATIC NITRILES. /ALIPHATIC NITRILES/

Used to produce pharmaceuticals and synthetic resins; [HSDB]

MANUFACTURE OF INTERMEDIATES IN PHARMACEUTICAL PRODUCTION & AS COMPONENT OF SYNTHETIC RESINS

Solvent and organic intermediate

2023: 10,000,000 - <50,000,000 lb

(1972) PROBABLY GREATER THAN 9.08X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

REACTION OF FORMALDEHYDE AND AQUEOUS SODIUM CYANIDE IN THE PRESENCE OF MINERAL ACID

Formaldehyde and hydrogen cyanide.

Formed in 79.5% yield when 37% formaldehyde is mixed with a stoichiometric amount of aqueous hydrogen cyanide for 1 hr at 2 °C in the presence of sodium hydroxide as a catalyst.

Patents ... describe synthesis by (1) heating formaldehyde with hydrogen cyanide at 250 °C or in the presence of sulfur dioxide at pH 1.5-2.0 in an aqueous medium and (2) by reacting acetonitrile with oxygen and with or without water at high pressure in the presence of various vanadium oxides.

All Other Basic Organic Chemical Manufacturing

Acetonitrile, 2-hydroxy-: ACTIVE