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Home > Encyclopedia > Propiolic acid

Propiolic acid

Propiolic acid structure

Propiolic acid 

structure
  • CAS No:

    471-25-0

  • Formula:

    C3H2O2

  • Chemical Name:

    Propiolic acid

  • Synonyms:

    2-Propynoic acid;Propiolic acid;Acetylenecarboxylic acid;Propargylic acid;Propynoic acid;Carboxyacetylene;Acetylenemonocarboxylic acid;2-Propyne-1-carboxylic acid;NSC 16152

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

viscous yellow liquid


Solid


Propynoic acid is a terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond. It has a role as a xenobiotic metabolite. It is an acetylenic fatty acid, a monounsaturated fatty acid, a short-chain fatty acid, a terminal acetylenic compound and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a propynoate.

Propiolic acid Basic Attributes

70.047

70.05

207-437-8

P2QW39G9LZ

16152

DTXSID6060050

Crystals from carbon disulfde|Crystals or liquid

2916190090

Characteristics

37.30000

0.31

Solid

1.1435 g/cm3 @ Temp: 15 °C

9 °C

57 °C

58.9±0.0 °C

1.456

miscible

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8 deg C

3.5 mm Hg at 25 deg C (est)

Odor resembling acetic acid

When heated to decompostion it emits acrid smoke and irritating fumes|Hydroxyl radical reaction rate constant = 2.97X10-12 cu cm/molec-sec at 25 °C (est)

Safety Information

II

8

UN 2920 8/PG 2

3

R25;R34

S26-S36/37/39-S45-S24/25

UD9300000

T:Toxic

Stable. Incompatible with bases, oxidizing agents, reducing agents. Combustible.

P280-P302 + P350-P305 + P351 + P338-P310

H226-H301-H310-H314

This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.|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.

Reacts with solutions of copper(I) or silver salts in ammonia to form an explosive precipitate.

|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P310, P312, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Tightly fitting safety goggles. Faceshield (8-inch minimum).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Accidental Release Measures. Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods for cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Handle with gloves. Choose body protection according to the amount and concentration of the dangerous substance at the work place.|Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|If inhaled, move person into fresh air. If not breathing give artificial respiration. Consult a physician. In case of skin contact, take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Take victim immediately to hospital. Consult a physician. In case of eye contact, continue rinsing eyes during transport to hospital. Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed DO NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Toxicity

LD50 Rat oral 100 mg/kg|LD50 Rat ip 25 mg/kg|LD50 Mouse oral 100 mg/kg|LD50 Mouse ip 25 mg/kg|LD50 Guinea pig skin 100 mg/kg

Propiolic acid's production and use as laboratory reagent(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 propiolic acid is expected to have very high mobility in soil(SRC). The pKa of propiolic acid is estimated as 1.89(3), indicating that this compound will exist entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). Propiolic acid is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that propiolic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 1.89(3) indicates propiolic acid will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.19(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Propiolic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Biodegradation data were not available(SRC, 2010).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propiolic acid, which has an estimated vapor pressure of 3.5 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 propiolic acid 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 5 days(SRC), calculated from its rate constant of 3.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase propiolic acid is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 380 days(SRC), calculated from its rate constant of 3.0X10-20 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Propiolic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of propiolic acid with photochemically-produced hydroxyl radicals has been estimated as 3.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of propiolic acid with ozone has been estimated as 3.0X10-20 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 380 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Propiolic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Propiolic acid contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for propiolic acid(SRC), using an estimated log Kow of -0.19(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of propiolic acid can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that propiolic acid is expected to have very high mobility in soil. The pKa of propiolic acid is 1.89(3), indicating that this compound will exist entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

A pKa of 1.89(1) indicates propiolic acid will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces and moist soil is not expected to be an important fate process(SRC). Propiolic acid is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5 mm Hg(SRC), determined from a fragment constant method(2).

Occupational exposure to propiolic acid may occur through inhalation and dermal contact with this compound at workplaces where propiolic acid is produced or used. (SRC)

Drug Information

/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. /Organic acids 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 respirations 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 ... . 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids 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. Early intubation, at the first sign of upper airway obstruction, may be necessary. 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 (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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/SIGNS AND SYMPTOMS/ Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin., Cough, Shortness of breath, Headache, Nausea|/SIGNS AND SYMPTOMS/ Causes eye burns. Causes skin burns. May be fatal if absorbed through skin.

propiolic acid

Propiolic acid Use and Manufacturing

Methods of Manufacturing

Propiolic acid, acetylenecarboxylic acid, is produced electrochemically from propargyl alcohol ...

Uses

Propiolic acid is an intermediate in monohalogenated acetylene synthesis and a corrosion inhibitor for steel.

2-Propynoic acid: ACTIVE

Computed Properties

Molecular Weight:70.05
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:70.005479302
Monoisotopic Mass:70.005479302
Topological Polar Surface Area:37.3
Heavy Atom Count:5
Complexity:84.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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