Butyl ether

log Kow= 3.21

3.21

0.767 at 68 °F (USCG, 1999) - Less dense than water; will float

0.7684 at 20 °C/4 °C

% In saturated air: 0.9 at 25 °C, 760 mm Hg; density of saturated air: 1.1 at 25 °C, 760 mm hg (air= 1)

Density (at 20 °C): 0.8 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

0.7689 @25 °C

0.0069 poise (20 °C)

0.86 mm²/s at 20 °C

less than 1 mg/mL at 72.5 °F (NTP, 1992)

Miscible with benzene and most org solvents

Sol in all prop in alc, ether; very sol in acetone

Miscible with oxygenated solvents

In water, 300 mg/L at 25 °C

Solubility in water, g/100ml:

77 °F (NTP, 1992)

37 °C (CLOSED CUP)

25 °C c.c.

288 °F at 760 mmHg (NTP, 1992)

140.8 °C

142 °C

142 °C @760 [mm Hg]

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Warning

H226 (99.9%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: Butane, 1,1'-oxybis-

Butane, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butane, 1,1'-oxybis- 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: 16-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11808

Butane, 1,1'-oxybis-: HSNO Approval: HSR001076 Approved with controls

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.)

Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)

Flammable. Above 25 °C explosive vapour/air mixtures may be formed.

May form explosive peroxides; [Hawley] A skin, eye, and respiratory tract irritant; May have effects on CNS and liver; Defats the skin; [ICSC] A skin and eye irritant; [eChemPortal: ERMA] An irritant; Effects in high-dose animal studies include general anesthesia and fatty liver degeneration; [MSDSonline]

Ethers, such as N-BUTYL ETHER can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.

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

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

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Use dry chemical, foam, carbon dioxide or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool.

Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal.

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 of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

/DUE TO FIRE HAZARD, ETHERS/ ... SHOULD BE KEPT COOL & CONTAINERS ELECTRICALLY GROUNDED TO AVOID SPARKS ... . /ETHERS/

Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, sunlight, and acids.

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.

Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.

Environmental considerations-air spill: Apply water spray or mist to knock down vapors.

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.

Incineration

The following wastewater treatment technologies have been investigated for butyl ether: Concentration process: Activated carbon.

Used ether containers, which are suspected of containing ether crystals or solids, are especially hazardous and may require bomb-squad assistance for their disposal. /Short alkyl-chain ethers/

This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Cover the spilled material with foam. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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.

TO PREVENT EXPOSURE OF WORKERS TO HARMFUL CONCN OF SOLVENT VAPOR, MOST EFFECTIVE MEASURE IS ENCLOSURE OF PROCESS. LOCAL EXHAUST VENTILATION SHOULD BE INSTALLED ON ENCLOSURE ... /IF/ THIS IS NOT PRACTICABLE OPERATIONS MAY BE CONDUCTED UNDER HOOD FITTED WITH EXHAUST VENTILATION ... . /SOLVENTS INDUST/

... COMMON /ETHERS/ ... ARE EASILY IGNITED & HAVE LOW FLASH POINTS. IT IS NECESSARY TO CONTROL SMOKING, OPEN FLAMES OR HOT PLATES IN AREAS WHERE LOW MOL WT ETHERS ARE APT TO REACH 1% CONCN OR MORE IN AIR. /ETHERS/

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.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

LC50 Cyprinodon variegatus (Sheepshead minnows, juvenile 14-28 days old) above 430 ppm/24, 48, 72 and 96 hr, seawater at 25-31 °C, static bioassay

LC50 Pimephales promelas (fathead minnow) 32.5 mg/L 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/L CaCO3, temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation

LC50 Pimephales promelas (fathead minnow) 52 mg/L for 96 hr /Conditions of bioassay not speicifed/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static, pH 8.0; Concentration: 150 mg/L for 24 hr; Effect: behavior, equilibrium

For more Ecotoxicity Values (Complete) data for DIBUTYL ETHER (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a structure estimation method(2), indicates that dibutyl ether is expected to have high mobility in soil(SRC). Volatilization of dibutyl ether from moist soil surfaces may be important(SRC) given a Henry's Law constant of 6.0X10-3 atm-cu m/mole(3). Volatilization of dibutyl ether from dry soil surfaces is expected(SRC) based upon an extrapolated vapor pressure of 6.0 mm Hg at 25 °C(4). Biodegradation of dibutyl ether in soil is expected to be a slow process(SRC), based upon its slow biodegradation in aqueous screening studies(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a structure estimation method(2), indicates that dibutyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Dibutyl ether is expected to volatilize from water surfaces(3) based on a Henry's Law constant of 6.0X10-3 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 3.5 hours and 4.6 days, respectively(SRC). According to a classification scheme(5), BCFs ranging from 30 to 114 measured in carp(6), suggest that bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation of dibutyl ether in water is expected to be a slow process(SRC), based upon its slow biodegradation in aqueous screening studies(6,7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl ether, which has an extrapolated vapor pressure of 6.0 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dibutyl 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 13 hours(SRC) calculated from its rate constant of 2.88X10-11 cu cm/molecule-sec at 25 °C(3). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(4).

Cough. Sore throat.

Dry skin.

Redness. Pain.

Burning sensation. Nausea. Sore throat.

Dibutyl ether has been detected in 1 out of 63 samples of industrial effluents collected from a wide variety of industries across the U.S. at a concn of <10 ug/L (dates not reported)(1). Dibutyl ether was tentatively identified, but not quantified, in an advanced waste treatment concentrate from Lake Tahoe, CA, sampled in Oct 1974(2). Dibutyl ether was detected at concn of 5.6 and 0.2 ug/L in 2 of 7 sites sampled in Feb 1979 for standing water and impoundments which were discharged into Wilson Creek from a hazardous waste dump site called "Valley of the Drums" in Bullitt County, KY(3).

The substance is harmful to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment. Bioaccumulation of this chemical may occur along the food chain, for example in fish.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dibutyl ether can be estimated to be 51(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibutyl ether is expected to have high mobility in soil(SRC).

/SIGNS AND SYMPTOMS/ ... humans exposed to 100 ppm of dibutyl ether estimated it satisfactory for 8 hr exposures. At 200 ppm for 15 min the vapors produced a sensation of irritation to the eyes and nose, although at 300 ppm the odor was not objectionable to the majority of subjects.

/SIGNS AND SYMPTOMS/ Dibutyl ether, although not highly toxic orally, seems to have a greater toxicity by inhalation than the lower ethers of the series. It is also more irritating to the skin.

AEROBIC: Dibutyl ether achieved 16% of its theoretical BOD in screening tests which utilized acclimated mixed microbial cultures over a 5 day incubation period(1). Many ethers are known to be resistant to biodegradation(2). Dibutyl ether at 100 mg/L reached 3 to 4% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(3).

ANAEROBIC: 0% loss of dibutyl ether was observed in landfill leachate impacted aquifer slurries amended with sulfate or nitrate after 244 and 85 days incubation, respectively(1). Dibutyl ether was not biodegraded in aquifer slurries prepared from the methanogenic portion of a shallow anoxic aquifer polluted by municipal landfill leachate(2).

BCFs of 47 to 83 and 30 to 114 were measured for carp exposed to 200 and 20 ug/L of dibutyl ether over the course of a 6 week incubation period(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is moderate to high, provided the compound is not metabolized by the organism(SRC).

Used as solvent (hydrocarbons, resins, fats, oils, organic acids, alkaloids, esters, and gums), extracting agent , intermediate, reaction medium, and in plutonium separation processes; [HSDB]

Solvent for hydrocarbons, fatty materials; extracting agent, used especially for separating metals, solvent purification, organic synthesis (reaction medium).

Solvent ... for esters, gums, hydrocarbons, alkaloids, oils, org acids, & resins

Has limited use as a solvent in the preparation of Grignard reagents.

Proposed as high-cetane diesel additive

For more Uses (Complete) data for DIBUTYL ETHER (7 total), please visit the HSDB record page.

2023: 1,000,000 - <5,000,000 lb

Butane, 1,1'-oxybis- 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#1011]

AVAILABLE AS A BY-PRODUCT IN MFR OF BUTYL ESTERS.

Hydrolysis of butyl bromide at 130-180 °C and 350-700 kPa.

n-Butyl ether is prepared by the dehydration of n-butyl alcohol by sulphuric acid or by catalytic dehydration over ferric chloride, copper sulfate, silica or alumina at high temperatures.

Di-n-butyl ether is produced by dehydrating 1-butanol with sulfuric acid. It is also obtained as a byproduct during the synthesis of the butyl esters of higher acids; it occurs in the recovered alcohol and can be obtained by extractive distillation with water, drying, and rectification.

Synthetic Rubber Manufacturing

Butane, 1,1'-oxybis-: ACTIVE

Autooxidation produces di-n-butyl hydroperoxy ether