2-Butyne-1,4-diol

Other Classes -> Other Organic Compounds

Reactive agents - 1st degree

1.07 at 68 °F (USCG, 1999) - Denser than water; will sink

Relative density = 1.115 at 20 °C

Relative density (water = 1): 1.1

1.115 @ 20°C

Plates from benzene and ethyl acetate

White, orthorhombic crystals

WHITE TO LIGHT YELLOW

Yellow scaley solid at 20 °C and 1,013 hPa

Insoluble in benzene; slightly soluble in ethyl ether, choroform; very soluble in ethanol, acetone, methanol

Soluble in aqueous acids.

In water, 3.74X10+6 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 75 (good)

263 °F (USCG, 1999)

128 °C

263 °F (OPEN CUP)

152 °C

460 °F at 760 mmHg (USCG, 1999)

238 °C

No boiling point at normal pressure; decomposes at >160 °C

238 °C @760 [mm Hg]

50 °C

58 °C

50 °C

0.000556 [mmHg]

5.56X10-4 mm Hg at 25 °C

Vapor pressure, Pa at 20 °C: 0.2

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: 2-Butyne-1,4-diol

2-Butyne-1,4-diol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butyne-1,4-diol 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)

Status: Active Update: 30-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13224

2-Butyne-1,4-diol: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Risk of explosion on contact with bases, oxidizing agents or halogens.

May cause dermatitis. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

A severe skin and eye irritant; [HSDB] Toxic by inhalation, ingestion, and skin contact; [CAMEO] May cause skin burns and sensitization; [eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May cause skin sensitization; Causes liver, brain, and reproductive injury in high-dose animal studies; [MSDSonline] Danger of cutaneous absorption; Danger of skin sensitization; [MAK]

European Chemicals Bureau; IUCLID Dataset, But-2-yne-1,4-diol (110-65-6) (2000 CD-ROM edition). Provides information on usage patterns, toxicity, and environmental effects supplied by industry to the European Union. Available from the database query page: http://ecb.jrc.it/esis/esis.php as of September 09, 2006.

Pure 1,4-BUTYNEDIOL is non-explosive. Small amounts of certain impurities-alkali hydroxides, alkaline earth hydroxides, halides-may cause explosive decomposition upon distillation. Butynediol should not be treated with basic catalysts in the absence of a solvent at room temperature, and its stability is less with elevated temperatures. In strong acids, contamination with mercury salts can also result in violent decomposition. [NFPA 491M 1991].

Fire Extinguishing Agents: Water, alcohol foam, dry chemical, or carbon dioxide (USCG, 1999)

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

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

SKIN CONTACT: wash affected skin area thoroughly with water.

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

0.1 [ppm]

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams fo water may be ineffective Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

The storage temperature should be kept below 40 °C and storage times longer than a few months should be avoided because the butynediol flakes tend to set up.

... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT, MOISTURE, ACIDS, OR ACID FUMES, SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF ... FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED.

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.

Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

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.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.

EC50 Daphnia magna 26.8 mg/L48 hr (nominal concentration) immobilization, static test. NOTE: At 100 mg/L all daphnids were immobile after 48 hours.

LC50 Pimephales promelas (Fathead minnow) 53.6 mg/L/96 hr (confidence limit 49.3-58.3 mg/L), flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 6.8 mg/L, hardness 46.5 mg/L calcium carbonate, alkalinity 43.5 mg/L calcium carbonate, and pH 7.7

EC50 Pimephales promelas (Fathead minnow) 53.6 mg/L/96 hr (confidence limit 49.3-58.3 mg/L), flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 6.8 mg/L, hardness 46.5 mg/L calcium carbonate, alkalinity 43.5 mg/L calcium carbonate, and pH 7.7. Effect: loss of equilibrium was not observed prior to death.

LC50 Leuciscus idus (fresh-water cyprinoid fish) 46 mg/L/96 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for 1,4-BUTYNEDIOL (7 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a water solubility of 3.74X10+6 mg/L(2) and a regression-derived equation(3), indicates that 1,4-butynediol is expected to have very high mobility in soil(SRC). Volatilization of 1,4-butynediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.56X10-4 mm Hg(4), and water solubility(2). 1,4-Butynediol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). 1,4-Butynediol has been shown to biodegrade 90% in 4 days using a sewage sludge(5); therefore, biodegradation is expected to be 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 water solubility of 3.74X10+6 mg/L(2) and a regression-derived equation(3), indicates that 1,4-butynediol 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 1.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.56X10-4 mm Hg(4), and its water solubility(2). According to a classification scheme(5), an estimated BCF of 0.12(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,4-Butynediol has been shown to biodegrade 90% in 4 days using a sewage sludge(6); therefore, biodegradation is expected to be an important environmental fate profcess in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-butynediol, which has a vapor pressure of 5.56X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-butynediol 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,4-Butynediol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

/AQUATIC SPECIES/ ... The test results on /the freshwater fish/ Leuciscus idus /showed that among/ the selected test concentrations (10, 21.5, 46.4 and 100 mg/L) only at the highest two lethal effects were observed. After 96 hours the mortality was 5% at 46.4 mg/L and 100% at 100 mg/L and therefore the LC50 is between 46.4 and 100 mg/Ll. The NOEC was 21.5 mg/L.

/AQUATIC SPECIES/ The population growth impairment testing was done in the /protozoa/ Tetrahymena pyriformis batch system ... This is a two-day assay using population density measured spectrophotometrically at 540 nm as the endpoint. An EC50 inhibition of growth of 1,343 mg/L after 48 hours was obtained.

/AQUATIC SPECIES/ In a test ... with /the freshwater algae/ Scenedesmus subspicatus after 96 hours an EC50 of 433 mg/L and an EC20 of 218 mg/L were derived for the reduction of biomass measured fluorometrically.

/AQUATIC SPECIES/ Using continuous flow diluters, the 96 hr LC50 values were determined for 16 acetylenic alcohols in the fathead minnow (Pimephales promelas). The observed LC50 value for butyn-1,4-diol was 53.6 (49.3-58.3) mg/L. This was 4740 times greater than the predicted LC50 of 254,000 mg/L based on quantitative structure activity relationships (QSAR) for ... /CNS depressant/ lethality.

/OTHER TERRESTRIAL SPECIES/ In a test with /the soil bacterium/ Pseudomonas putida ... after 17 hours an EC50 of 3,935 mg/L and an EC10 of 1993 were obtained for cell multiplication inhibition measured at 436 nm.

Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.

Redness. Pain. Skin burns.

Redness. Pain. Burns.

Burns in mouth and throat. Burning sensation in the throat and chest. Abdominal pain.

The Koc of 1,4-butynediol is estimated as 1(SRC), using a water solubility of 3.74X10+6 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,4-butynediol is expected to have very high mobility in soil.

/HUMAN EXPOSURE STUDIES/ Ten workers with suspicion of allergic contact eczema who were probably accidentally exposed to butynediol were asked for voluntary patch testing for possible sensitisation; 6 of these 10 workers were willing to undergo the test. Pure butynediol and technical grade butynediol were applied as a 0.5% aqueous solution. Furthermore, formaldehyde which is a precursor for synthesis and an impurity in technical grade butynediol was also tested. Whereas formaldehyde did not show a positive reaction in these individuals, 4/4 tested in 2001 showed clear evidence of sensitisation. Two other workers tested in 1990 and 1994 had positive patch test reactions ...

/SIGNS AND SYMPTOMS/ ... Reported to be severely irritating to eyes and to penetrate skin and cause severe irritation.

/CASE REPORTS/ A 20-year old patient whose occupation involved nickel-plating developed itchy dermatitis on the dorsum of his left hand, extending to the upper arm. By patch testing butynediol (1% in water) was identified as the causative agent ...

/CASE REPORTS/ A 54-yr old male worker developed an itchy dermatitis on his hands and lower arms. Eczematous eruption was seen and contact allergy suspected. He was patch tested. The only substance to give a two plus positive reaction at 48 hr was a 2% butin diol soln in water. At the 72 hr reading, the reaction had increased in severity.

/CASE REPORTS/ A 41-year-old female cleaner developed dermatitis on the face, hands and forearms after having used a new cleaning agent for a few months. The dermatitis appeared about 12 hours after contact with the agent and settled when she was not using it. Patch testing with the components of the cleaning agent produced a strong reaction to butynediol. The compound was present in the cleaning agent at low concentration (0.7%) as corrosion inhibitor. Patch testing of 55 control persons with 1% butynediol in water was negative ...

1,4-Butynediol's production and use as an intermediate, corrosion inhibitor, electroplating brightener, polymerization accelerator, stabilizer for chlorinated hydrocarbons and cosolvent for paint and varnish removal(1) may result in its release to the environment through various waste streams. Its use as a defoliant(1) (not regristered for this application in the US(2)) will result in its direct release to the environment(SRC).

It can be anticipated that in a first metabolic step butynediol is enzymatically activated to the corresponding reactive aldehyde capable of reacting with biologically relevant nucleophiles. Using purified horse liver and rainbow trout hepatic cytosol alcohol dehydrogenase (ADH) preparations, the propensity of butynediol to inhibit enzyme activity, in both the presence and the absence of reduced glutathione, was ascertained ... The involvement of ADH in the metabolic activation was additionally shown by inhibition experiments with rat liver extracts. Pyrazole, an inhibitor of ADH, competitively inhibited the oxidation of butynediol ... Cytochrome P450-dependent metabolism can not be excluded, because a low increase of aminopyrine demethylase activity was detected.

Used to produce flame retardants and other chemicals; Also used as a corrosion inhibitor, pickling agent, paint remover, cleansing agent, descaling agent, electroplating brightener, defoliant, polymerization accelerator, and stabilizer for chlorinated hydrocarbons; [HSDB]

Electroplating [Category: Plate]

... Hydrogenation in aqueous solution to butanediol and butenediol is the main application area ... Less than 2% of the production volume of butynediol are ... used as an external intermediate for the production of flame retardants or as a corrosion inhibitor and pickling agent in metal surface treatment ... Butynediol is reported to serve as an intermediate for the synthesis of polyols, insecticides, pharmaceuticals and auxiliaries for the paint and textile industry ... Butynediol is ... a component in cleaning solutions to remove scale by means of acids, in acid pickles and in organic paint removers. The following consumer products may contain butynediol ... cleansing agents for sanitary installations ... car cleansing products ... building facade cleansers ... disinfectants for sanitary installations ... pipe descaling agents ... descaling agents ...

Intermediate; corrosion inhibitor; electroplating brightener; defoliant /SRP: Not registered for USE in USA/; polymerization accelerator; stabilizer for chlorinated hydrocarbons; cosolvent for paint and varnish removal.

2023: 100,000,000 - <500,000,000 lb

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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3759]

All Other Chemical Product and Preparation Manufacturing

2-Butyne-1,4-diol: ACTIVE

Butynediol is produced by Reppe synthesis. The reaction of acetylene and formaldehyde is carried out in closed systems at 80 to 100 °C using an aqueous formaldehyde solution (30-50%) and a partial pressure of acetylene of 1 to 6 X10+5 Pa ... The crude product contains 33 to 55% butynediol, 1 to 2% propargyl alcohol, 0.4 to 1% of unreacted formaldehyde and 1 to 2% heavy by-products.

At 2 sites in the European Union ... produced at tonnages of >1,000 tonnes/annum, the maximum production volume at a single site is 100,000 tonnes/annum. The maximum cumulative production volume is indicated in IUCLID amounts to 200,000 tonnes/annum, from 1993 to 1996 around 185,000 tonnes were annually produced. Less than 200 tonnes/annum were exported outside the European Union.