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Home > Encyclopedia > 2-Butyne-1,4-diol

2-Butyne-1,4-diol

2-Butyne-1,4-diol structure

2-Butyne-1,4-diol 

structure
  • CAS No:

    110-65-6

  • Formula:

    C4H6O2

  • Chemical Name:

    2-Butyne-1,4-diol

  • Synonyms:

    2-Butyne-1,4-diol;1,4-Butynediol;Butynediol;Bis(hydroxymethyl)acetylene;2-Butynediol;1,4-Dihydroxy-2-butyne;NSC 834

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

yellow solidChEBI: A butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.White to light-brown solid or brownish-yellow aqueous solution. Solid sinks and mixes with water.


1,4-butynediol appears as white to light-brown solid or brownish-yellow aqueous solution. Solid sinks and mixes with water. (USCG, 1999)|Liquid; OtherSolid; OtherSolid, Liquid|YELLOW SOLID IN VARIOUS FORMS.


1,4-butynediol appears as white to light-brown solid or brownish-yellow aqueous solution. Solid sinks and mixes with water. (USCG, 1999)|But-2-yne-1,4-diol is a butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.

2-Butyne-1,4-diol Basic Attributes

86.09

86.09

1071237

203-788-6

AXH202FPQM

1733

834

2716

DTXSID4021921

Plates from benzene and ethyl acetate|White, orthorhombic crystals|WHITE TO LIGHT YELLOW|Yellow scaley solid at 20 °C and 1,013 hPa

29053980

Characteristics

40.5

-0.73

slightly brown Crystalline Platelets or Flakes

1.1

58 °C

238 °C @ Press: 760 Torr

306 °F

1.4804

H2O: 3740 g/L (20 ºC)

Refrigerator

<0.1 mm Hg ( 55 °C)

Relative vapour density (air = 1): 3.0

Oral-Rat LD50: 104 mg/kg; Oral-Mouse LD50: 105 mg/kg

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

Explosive reaction with traces of alkalies, alkali earth hydroxides, halide salts, strong acids, mercury salts plus strong acids.

Henry's Law constant = 1.684X10-11 atm-cu m/mol at 25 °C (est)

SOLN IS STRAW TO AMBER COLOR|Hydroxyl radical reaction rate constant = 3.38X10-11 cu cm/molec-sec at 25 °C (est)

Soluble in water.

Alcohols and Polyols

Pure 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].

335 °C

Safety Information

III

6.1

UN 2716 6.1/PG 3

2

21-23/25-34-43-48/22

25-26-36/37/39-45-46

ES0525000

T,C

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Explosive when mixed with oxidant; explosive when exposed to heat; explosive when reacted with trace alkali metal or alkaline earth metal hydroxide, strong acid, chloride salt, mercury salt + strong acid; moderately explosive

Stable. Highly flammable solid. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong acids, strong bases.

P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P363, P403+P233, P405, P501

H301

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.

The pure diol may be distilled unchanged, but traces of alkali or alkaline earth hydroxides or halides may cause explosive decomposition during distillation. In presence of strong acids, mercury salts may cause violent decomposition of the diol.

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.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Risk of explosion on contact with bases, oxidizing agents or halogens.|Reactive - 1st degree

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P363, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 343 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Neoprene rubber gloves and safety goggles or face shield. (USCG, 1999)|Neoprene rubber gloves and safety goggles or face shield

Explosive reaction with traces of alkalies, alkali earth hydroxides, halide salts, strong acids, mercury salts plus strong acids.

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.

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.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for 1,4-BUTYNEDIOL (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

... Reported to be severely irritating to eyes and to penetrate skin and cause severe irritation.

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.

Separated from incompatible materials. See Chemical Dangers. Cool. Store in an area without drain or sewer access.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

Corrosive. Inhalation may cause lung oedema, but only after initial corrosive effects on eyes and/or airways have become manifest. Medical observation is indicated.

The substance may have effects on the blood. This may result in anaemia. The substance may have effects on the kidneys and liver. This may result in tissue lesions. Repeated or prolonged contact may cause skin sensitization.

NO open flames.

STRICT HYGIENE!

Use ventilation (not if powder).

Protective clothing. Protective gloves.

Wear face shield or eye protection in combination with breathing protection if powder.

1,4-Butynediol was reported at 5304 ng/uL of extract in 1 occurrence from the organics and plastics industry(1).

Toxicity

highly toxic

Toxic action of 1,4-butynediol was prevented by pretreatment with pyrazole which competitively inhibited oxidation of 1,4-butynediol by rat liver alcohol dehydrogenase indicating that toxicity is due to products of oxidative metabolism.

LD50 Guniea pig oral 130 mg/kg|LD50 Rabbit oral 150 mg/kg|LD50 Mouse oral 105 mg/kg|LD50 Rat oral 104 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1,4-BUTYNEDIOL (9 total), please visit the HSDB record page.

/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.

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).

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).

The rate constant for the vapor-phase reaction of 1,4-butynediol with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,4-butynediol 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 382 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). 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(3).

An estimated BCF of 0.12 was calculated in fish for 1,4-butynediol(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 BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

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.

The Henry's Law constant for 1,4-butynediol is estimated as 1.7X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 5.56X10-4 mm Hg(1), and water solubility, 3.74X10+6 mg/L(2). This Henry's Law constant indicates that 1,4-butynediol is expected to be essentially nonvolatile from water surfaces(3). 1,4-Butynediol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 16,528 workers (4,756 of these are female) are potentially exposed to 1,4-butynediol in the US(1). Occupational exposure to 1,4-butynediol may occur through dermal contact with this compound at workplaces where 1,4-butynediol is produced or used(SRC). The general population may be exposed to 1,4-butynediol via dermal contact with products containing 1,4-butynediol(SRC).

Drug Information

... /Can/ penetrate skin ...

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.

< 0.5% water; 1% butane-1,4-diol

May cause dermatitis. (USCG, 1999)

SKIN CONTACT: wash affected skin area thoroughly with water. EYE CONTACT: immediately wash with water for at least 15 minutes and get medical attention. (USCG, 1999)


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.

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 shock and treat if necessary ... . Monitor for pulmonary edema 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 ... . /Higher alcohols (>3 carbons) and related compounds/|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 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 ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

/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 ...

2-butin-1,4-diol

The substance can be absorbed into the body by inhalation, through the skin and by ingestion. Serious local effects by all routes of exposure.

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


Redness. Pain. Skin burns.


Redness. Pain. Burns.

2-Butyne-1,4-diol Use and Manufacturing

Methods of Manufacturing

The synthesis 2-butyne-1,4-diol ... is carried out by reaction under pressure of acetylene and an aqueous solution of formaldehyde, catalyzed by copper acetylide.

Uses

Basic brightener in nickel electroplating baths,also an important intermediate for organic synthesis 2-Butyne-1,4-diol is used to produce butanedioland butenediol, in metal plating andpickling baths, and in making the carbamateherbicide Barban (Carbyne).


Corrosion inhibitors and anti-scaling agents


Metal products not covered elsewhere

Production

100,000,000 - 250,000,000 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#3761]

Grade: crystalline solid, 97%; aqueous solution 35%

All other basic organic chemical 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.

POLYSORB-1 COLUMNS & POLYETHYLENE GLYCOL ADIPATE AS IMMOBILE LIQ PHASE USED IN DETECTION OF 2-BUTYNE-1,4-DIOL & ITS HYDROGENATION PRODUCTS.

Fire Hazards -> Reactive - 1st degree

Computed Properties

Molecular Weight:86.09
XLogP3:-1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:86.036779430
Monoisotopic Mass:86.036779430
Topological Polar Surface Area:40.5
Heavy Atom Count:6
Complexity:66
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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