112-34-5

Basic information

• Product Name: Butyldiglycol
• Synonyms: 2-(2-Butoxyethoxy)ethanol, Butyldiglycol, DB Solvent;2-(2-Butoxyethoxy)ethanol, Butyldiglycol;2-(2-Butoxyethoxy)ethanol, Butyldiglycol, DOWANOL(R) DB;O-Butyl diethyl glycol;2-(2-Butoxyetoxy)ethanol;Butyldiglycol DB Solvent;Diethylene glycol monobutyl ether,2-(2-Butoxyethoxy)ethanol, Butyldiglycol;Diethylene glycol monobutyl ether, synthesis grade
• CAS NO: 112-34-5
• Molecular Formula: C₈H₁₈O₃
• Molecular Weight: 162.23
• EINECS: 203-961-6
• Product Categories: Alcohols;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Colorless liquid with a mild pleasant odor. Mixes with water.;Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 112-34-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: -68 °C(lit.)
• Boiling Point: 231 °C(lit.)
• Flash Point: 212 °F
• Appearance: colourless liquid
• Density: 0.967 g/mL at 25 °C(lit.)
• Vapor Density: 5.6 (vs air)
• Vapor Pressure: 30 mm Hg ( 130 °C)
• Refractive Index: n20/D 1.432
• Storage Temp.: Store below +30°C.
• PKA: 14.37±0.10(Predicted)
• Explosive Limit: 0.7-5.9%(V)
• Water Solubility: soluble
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,1557
• BRN: 1739225
• CAS DataBase Reference: Butyldiglycol(CAS DataBase Reference)
• NIST Chemistry Reference: Butyldiglycol(112-34-5)
• EPA Substance Registry System: Butyldiglycol(112-34-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 24-26
• WGK Germany: 1
• RTECS: KJ9100000
• TSCA: Yes
• Hazardous Substances Data: 112-34-5(Hazardous Substances Data)

Usage

Reactivity Profile

Butyldiglycol is a ether-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

General Description

Colorless liquid with a mild pleasant odor. Mixes with water.

Uses

Solvent.

Chemical Properties

Diethylene glycol monobutyl ether is a colorless, high-boiling liquid with a mild odour. It is miscible in proportions with water, alcohol (methanol), ketones (acetone), ethers (ethyl ether), aromatic hydrocarbons (benzene), paraffinic hydrocarbons (n-heptane), and halogenated hydrocarbons (carbon tetrachloride). As it is an ether-alcohol type compound it possesses solvent action for many substances such as oils, dyes, gums, and natural and synthetic resins. It is used as a high-boiling solvent in nitrocellulose lacquers and other synthetic coatings, baking lacquers, flash-dry printing inks, and dye bath.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Mddly toxic by skin contact. A severe eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, CO2, or dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Contact allergens

This organic solvent belongs to the carbitols group and is included in waterbased liquids such as paints, surface cleaners, polishes, and disinfectants. It is considered to be an exceptional allergen.

Uses

Diethylene glycol monobutyl ether (DGBE)is used as a solvent for cellulose ester,lacquers, varnishes, and dyes; as a primarycomponent of the aqueous film-forming foam that is used by the U.S. Navy in shipboardfirefighting systems (Hobson et al. 1987).

Health Hazard

DGBE showed low toxicity in test species.Toxic symptoms are similar to those ofother glycol ethers containing two etherealoxygen atoms. The routes of entry into thebody are ingestion and absorption throughthe skin. Hobson and coworkers (1987)investigated the subchronic oral toxicity ofDGBE in rats. The toxic effects observedwere lowering of food consumption, elevatedliver and spleen weights, lowered redblood cell counts and lymphocyte counts,and a dose-related decrease in corpuscularhemoglobin concentration. The high dosescaused pulmonary congestion. No renaldamage was reported.LD50 value, oral (guinea pigs): 2000 mg/kgDGBE is an eye irritant. There is no reporton teratogenicity of this compound.

Purification Methods

Dry the ether with anhydrous K2CO3 or CaSO4, filter and fractionally distil it. Peroxides can be removed by refluxing with stannous chloride or a mixture of FeSO4 and KHSO4 (or, less completely, by filtration under slight pressure through a column of activated alumina). [Beilstein 1 IV 2394.]

Waste Disposal

DGBE is mixed with a combustible solventand burned in a chemical incinerator. Smallamounts may be disposed down the drainwith large amounts of water.

Health Hazard

Inhalation for brief periods has no significant effect. Contact with liquid causes moderate irritation of eyes and corneal injury. Prolonged contact with skin causes only minor irritation.

Fire Hazard

Butyldiglycol is combustible.

Air & Water Reactions

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Water soluble.

InChI:InChI=1/C8H18O.C4H10O3/c1-3-5-7-9-8-6-4-2;5-1-3-7-4-2-6/h3-8H2,1-2H3;5-6H,1-4H2

Synthetic route

oxirane (75-21-8) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With potassium aluminum sulfate at 170℃; for 24h; Reagent/catalyst; Autoclave;	A 93.1% B 6.63%

n-Butyl chloride (109-69-3) + diethylene glycol (111-46-6) → Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With sodium hydroxide; water at 100℃; for 24h;	70%

oxirane (75-21-8) + butan-1-ol (71-36-3) → Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With boron trifluoride diethyl etherate at 50℃;

butan-1-ol (71-36-3) + diethylene glycol (111-46-6) → Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
sulfuric acid In toluene Heating;

1-bromo-butane (109-65-9) + sodium diethylene glycolate → Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With diethylene glycol

oxirane (75-21-8) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5) + triethyleneglycol monobutyl ether (143-22-6)

Conditions	Yield
2,4,6-trimethyl-pyridine at 160℃; under 2311.54 - 3345.86 Torr; for 2.5h; Product distribution / selectivity; Inert atmosphere;
sodium butanolate at 140℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;	A 20.16 %Chromat. B 9.07 %Chromat. C 6.10 %Chromat.
catalyst of invention (Sb2O3, copper acetate, hydrogen peroxide; calcined) at 140℃; under 30003 Torr; for 24 - 120h; Product distribution / selectivity;	A 76 - 77 %Chromat. B 13 - 14 %Chromat. C 9 %Chromat.

pyrene (129-00-0) → phthalic anhydride (85-44-9) + xanth-9-one (90-47-1) + pentadecane (629-62-9) + n-docosane (629-97-0) + n-hexacosane (630-01-3) + tetradecane (629-59-4) + Hexadecane (544-76-3) + Diethylene glycol monobutyl ether (112-34-5) + n-butyl isobutyrate (97-87-0) + heneicosane (629-94-7) + n-tricosane (638-67-5) + tetracosane (646-31-1) + n-pentacosane (629-99-2) + cyclopenta[def]phenanthrene (203-63-4) + 1,2-benzenedicarboxylic acid diisooctyl ether + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + Diethyl phthalate (84-66-2) + Phthalic acid dibutyl ester (84-74-2) + 4H-Cyclopenta[def]phenanthrene (203-64-5) + benzyl n-butyl phthalate (85-68-7) + 1,1'-Biphenyl-2,2',6,6'-tetracarboxaldehyde (4371-26-0) + 4,5-phenanthrene-8,9-dicarbaldehyde (16162-34-8) + 1-hexadecylcarboxylic acid (57-10-3) + 6-propyltridecane

Conditions	Yield
With oxygen; ozone In water for 0.25 - 2h;

...Expand

Tetraethylene glycol (112-60-7) + ethylene glycol (107-21-1) + butyraldehyde (123-72-8) + diethylene glycol (111-46-6) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 2-propyl-1,3-dioxolane (3390-13-4) + 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5) + triethyleneglycol monobutyl ether (143-22-6) + tetraethylene glycol monobutyl ether (1559-34-8) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h;

...Expand

butyraldehyde (123-72-8) + diethylene glycol (111-46-6) → Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 200℃; under 51716.2 Torr; for 2h; Inert atmosphere;	94.5 %Chromat.
With palladium 10% on activated carbon; hydrogen at 200℃; under 51755.2 Torr; for 2h;	94.5 %Chromat.

Diethylene glycol monobutyl ether (112-34-5) + p-toluenesulfonyl chloride (98-59-9) → diethylene glycol monobutyl ether tosylate (50964-16-4)

Conditions	Yield
Stage #1: Diethylene glycol monobutyl ether; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; Stage #2: With triethylamine In dichloromethane at 20℃;	100%
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h;	85%
With pyridine In dichloromethane at 20℃; for 3h;	57%
With pyridine

Diethylene glycol monobutyl ether (112-34-5) + 2-hexyldecanoic acid (25354-97-6) → 2-(2-butoxyethoxy)ethyl 2-hexyldecanoate

Conditions	Yield
With p-toluenesulfonic acid monohydrate	99%
With p-toluenesulfonic acid monohydrate	99%

Diethylene glycol monobutyl ether (112-34-5) + Methyl decanoate (110-42-9) → 1-Decanol (112-30-1)

Conditions	Yield
With sodium borohydrid In 5,5-dimethyl-1,3-cyclohexadiene	98%

Diethylene glycol monobutyl ether (112-34-5) + 2-Bromoacetyl bromide (598-21-0) → 2-(2-butoxyethoxy)ethyl 2-bromoacetate (56521-78-9)

Conditions	Yield
With sodium carbonate In dichloromethane at -5 - 20℃; for 12h; Green chemistry;	98%
With triethylamine In dichloromethane at -78℃; Inert atmosphere;	72%

Diethylene glycol monobutyl ether (112-34-5) + acrylonitrile (107-13-1) → 3-[2-(2-butoxyethoxy)ethoxy]propanenitrile (35633-48-8)

Conditions	Yield
With sodium methylate for 1.16667h;	97%

Adipic acid (124-04-9) + 2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + Diethylene glycol monobutyl ether (112-34-5) → methyldiglycol butyldiglycol adipate

Conditions	Yield
toluene-4-sulfonic acid In toluene at 118 - 145℃; for 6.5h; Heating / reflux;	96.9%

Diethylene glycol monobutyl ether (112-34-5) + paracetaldehyde (123-63-7) → 2-butoxyethyl 2-ethoxyethyl ether (3895-17-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 160℃; under 760 Torr; for 18h; Etherification;	96%
With hydrogen; palladium on activated charcoal at 160℃; for 10h; atmospheric pressure;	96%

Diethylene glycol monobutyl ether (112-34-5) → 1-[2-(2-chloroethoxy)-ethoxy]butane (1120-23-6)

Conditions	Yield
With pyridine; thionyl chloride In chloroform for 10h; Reflux;	95%
With pyridine; thionyl chloride

Diethylene glycol monobutyl ether (112-34-5) + Octanal (124-13-0) → 2-butoxyethyl 2-(octoxy)ethyl ether (101433-27-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 160℃; under 760 Torr; for 18h; Etherification;	95%
With hydrogen; palladium on activated charcoal at 160℃; for 10h; atmospheric pressure;	95%

Diethylene glycol monobutyl ether (112-34-5) + Acetic formic anhydride (2258-42-6) → 2-(2-butoxyethoxy)ethyl formate

Conditions	Yield
With pyridine 1.) 0 deg C, 5 h, 2.) rt, 12 h;	90%

Diethylene glycol monobutyl ether (112-34-5) + trans-1,2-Diaminocyclohexane (1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7) → C38H74N6O10

Conditions	Yield
Stage #1: Diethylene glycol monobutyl ether; Hexamethylene diisocyanate; dibutyltin dilaurate In hexane at 20 - 45℃; Stage #2: trans-1,2-Diaminocyclohexane In hexane at 15 - 20℃; for 0.5h;	88.8%

Diethylene glycol monobutyl ether (112-34-5) + 1,3-Diiodobenzene (626-00-6) → 1,3-Bis-[2-(2-butoxy-ethoxy)-ethoxy]-benzene (71784-21-9)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;	86%

formaldehyd (50-00-0) + Diethylene glycol monobutyl ether (112-34-5) + rccc-2,8,14,20-tetrakis-(iso-butyl)-resorcin[4]arene (118600-20-7, 134731-86-5) → C80H128O20

Conditions	Yield
With iminodiacetic acid In acetonitrile	81%

Diethylene glycol monobutyl ether (112-34-5) + vanadium(V) oxychloride (7727-18-6) → dichloro(2-(2-butoxyethoxy)ethanolate)oxovanadium(V)

Conditions	Yield
In pentane byproducts: HCl; N2, equimol., V compd. added dropwise to a soln. of alcohol, stirred for2 h, heated on water bath; decanted, concd., stored at 0°C, ppt. collected, dried (vac.); elem. anal.;	80%

Diethylene glycol monobutyl ether (112-34-5) + 1-Iodonaphthalene (90-14-2) → 1-(2-(2-butoxyethoxy)ethoxy)naphthalene

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 26h; Inert atmosphere;	79%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 26h; Inert atmosphere;	79%

Diethylene glycol monobutyl ether (112-34-5) + 2-Phenylpropanal (34713-70-7) → (E/Z)-(1-(2-(2-butoxyethoxy)ethoxy)prop-1-en-2-yl)benzene

Conditions	Yield
With methanesulfonic acid; methanesulfonic acid sodium salt In toluene for 15h; Inert atmosphere; Reflux; Dean-Stark;	79%

Diethylene glycol monobutyl ether (112-34-5) + [2-(2-chloro-2-oxoethoxy)phenoxy]acetyl chloride (31250-16-5) → Dibutoxyethoxyethyl 1,2-phenylenedioxydiacetate

Conditions	Yield
In tetrachloromethane Ambient temperature;	76%

5-(chloromethyl)-6-propyl-1,3-benzodioxole (1938-32-5) + Diethylene glycol monobutyl ether (112-34-5) → Piperonyl butoxide (51-03-6)

Conditions	Yield
Stage #1: Diethylene glycol monobutyl ether With sodium hydroxide In water Reflux; Stage #2: 5-(chloromethyl)-6-propyl-1,3-benzodioxole In water for 5h; Reflux;	75%
With sodium hydroxide at 30℃; for 5h;	230 g

Diethylene glycol monobutyl ether (112-34-5) + 1,2-Diiodobenzene (615-42-9) → 1,2-bis(2-(2-(butyloxy)ethoxy)ethoxy)benzene (71784-20-8)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 40h; Reflux; Inert atmosphere;	75%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere;	4 g

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + Diethylene glycol monobutyl ether (112-34-5) → C26H38O8

Conditions	Yield
With NAH In tetrahydrofuran at 80℃; Inert atmosphere;	71%

Diethylene glycol monobutyl ether (112-34-5) + 2-(2-methoxyphenoxy)acetyl chloride (40926-73-6) → Butoxyethoxyethyl o-methoxyphenoxyacetate

Conditions	Yield
In chloroform for 12h; Heating;	69.01%

Diethylene glycol monobutyl ether (112-34-5) + 3-{[(4-bromobutyl)oxy]methyl}-3-methyloxetane (103781-33-5) → 3-(2,7,10,13-tetraoxaheptadecyl)-3-methyloxetane

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In hexane for 5h; Heating;	68%

2-iodoacetyl chloride (38020-81-4) + Diethylene glycol monobutyl ether (112-34-5) → 2-(2-butoxyethoxy)ethyl-2-iodoacetate (56521-91-6)

Conditions	Yield
With sodium carbonate In dichloromethane at -5 - 20℃; for 12h; Green chemistry;	68%

Diethylene glycol monobutyl ether (112-34-5) + 2-(2-nitrophenoxy)acetyl chloride (20142-87-4) → Butoxyethoxyethyl o-nitrophenoxyacetate

Conditions	Yield
In chloroform for 12h; Heating;	66.89%

2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine (940-71-6) + Diethylene glycol monobutyl ether (112-34-5) → C24H51Cl3N3O9P3 (1245625-50-6) + C24H51Cl3N3O9P3 (1245625-47-1) + C24H51Cl3N3O9P3 (1245625-36-8)

Conditions	Yield
With sodium hydride In tetrahydrofuran at -60 - 20℃; for 3.5h; Inert atmosphere;	A 20% B 16% C 64%

Diethylene glycol monobutyl ether (112-34-5) → C24H51Cl3N3O9P3 (1245625-50-6) + C24H51Cl3N3O9P3 (1245625-47-1) + C24H51Cl3N3O9P3 (1245625-36-8)

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran at -60 - 20℃; for 3.5h; Inert atmosphere;	A 20% B 16% C 64%
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran at -60 - 20℃; for 3.5h; Inert atmosphere;	A 20% B 16% C 64%

Diethylene glycol monobutyl ether (112-34-5) + (5,10,15,20-tetraphenylporphinato)dichlorophosphorus(V) chloride → di(3,6-dioxadecyloxo)tetraphenylporphyrinatophosphorus(V) chloride

Conditions	Yield
With pyridine In acetonitrile for 24h; Reflux;	60%
With pyridine In acetonitrile for 24h; Reflux;

Diethylene glycol monobutyl ether (112-34-5) + 2-methyl-2-octyldodecanoic acid → C29H58O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Dean-Stark; Reflux;	60%

Upstream product

• 111-76-2 2-Butoxyethanol 
• 67-56-1 Methanol 
• 64-17-5 Etanol 

Downstream Products

• 124-17-4 2-(2-Butoxyethoxy)ethyl acetate 
• 51-03-6 Piperonyl butoxide 

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