629-15-2

Basic information

• Product Name: 1,2-Diformyloxyethane
• Synonyms: 1,2-Ethanediol,diformate;1,2-ethanedioldiformate;diformiated’ethyleneglycol;Ethylene formate;ethyleneformate;Formic acid, ethylene ester;formicacid,ethyleneester;1,2-DIFORMYLOXYETHANE
• CAS NO: 629-15-2
• Molecular Formula: C₄H₆O₄
• Molecular Weight: 118.09
• EINECS: 211-077-7
• Mol File: 629-15-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 174-178 °C(lit.)
• Flash Point: 86.2 °C
• Appearance: water-white liquid
• Density: 1.226 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.17mmHg at 25°C
• Refractive Index: n20/D 1.415
• CAS DataBase Reference: 1,2-Diformyloxyethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diformyloxyethane(629-15-2)
• EPA Substance Registry System: 1,2-Diformyloxyethane(629-15-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KW5250000
• Hazardous Substances Data: 629-15-2(Hazardous Substances Data)

Usage

Chemical Properties

Water-white liquid. hydrolyzes slowly, liberating formic acid. Soluble in water, alcohol and ether. Combustible.

Uses

Embalming fluids.

General Description

A water-white liquid. More dense than water. Flash point 200°F. May be toxic by ingestion. Used in embalming fluids.

Air & Water Reactions

Soluble in water.

Reactivity Profile

1,2-Diformyloxyethane reacts exothermically with acids. With strong oxidizing acids; the heat may ignite the reaction products. Also reacts exothermically with basic solutions. Generates hydrogen with with strong reducing agents (alkali metals, hydrides).

Hazard

Toxic by ingestion.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion. A severe eye irritant. Flammable when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C4H6O4/c5-3-7-1-2-8-4-6/h3-4H,1-2H2

Synthetic route

formic acid (64-18-6) + ethylene glycol (107-21-1) → ethylene glycol diformate (629-15-2)

Conditions	Yield
ammonium cerium(IV) nitrate In chloroform at 55 - 60℃;	98%
Stage #1: formic acid With silica gel at 20℃; for 0.0166667h; Stage #2: ethylene glycol With silica gel at 110℃; for 0.166667h;	96%
phosphoric acid In benzene Acylation; Heating;	93.2%

1,4-Bis(1-hydroxyethoxy)-2-butyne diformate → ethylene glycol diformate (629-15-2)

Conditions	Yield
In formic acid Mechanism; Heating;	92%

1,4-Bis(1-hydroxyethoxy)-2-butyne diformate + formic acid → ethylene glycol diformate (629-15-2)

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium for 2h; Heating;	92%

2,3,8,8a-Tetrahydro-cis-4aH-pyrano<2,3-b>-<1,4>dioxin-7(6H)-on-ethylenacetal (127817-98-5) → ethylene glycol diformate (629-15-2) + 2,3,8,8a-Tetrahydro-cis-4aH-pyrano<2,3-b>-<1,4>dioxin-7(6H)-on (127817-99-6)

Conditions	Yield
With formic acid for 6h; Ambient temperature;	A n/a B 49.3%

1,4-dioxene (543-75-9) + p-benzoquinone (106-51-4) → ethylene glycol diformate (629-15-2) + spiro<2.3.5.7.10-pentaoxabicyclo<4.4.0>decane-4,1'-cyclohexa-2',5'-dien-4'-one> (108165-10-2)

Conditions	Yield
With oxygen In tetrachloromethane at -5℃; under 7600 Torr; for 4h; Irradiation;	A 34% B 20%

benzophenone (119-61-9) + 1,4-dioxene (543-75-9) → 7,7-diphenyl-2,5,8-trioxatricyclo<4.2.0> octane (108165-08-8) + ethylene glycol diformate (629-15-2) + cis-2,3,5,7,10-pentaoxa-4,4-diphenylbicyclo<4.4.0>dodecane (108165-09-9)

Conditions	Yield
With oxygen In tetrachloromethane at -5℃; under 7600 Torr; for 6h; Irradiation;	A 9% B 24% C 7%

ethylene glycol monoformate (628-35-3) → ethylene glycol diformate (629-15-2) + ethylene glycol (107-21-1)

Conditions	Yield
With 1-Methylpyrrolidine; ruthenium(II) bis(triphenylphosphine) dichloride at 140℃; for 15h;	A 12% B 12%

oxirane (75-21-8) + formic acid (64-18-6) → ethylene glycol diformate (629-15-2)

Conditions	Yield
With sulfuric acid

1,4-dioxane (123-91-1) + Cyclopentane (287-92-3) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → ethylene glycol diformate (629-15-2)

Conditions	Yield
at 132℃; under 20594.2 Torr; Behandeln mit Luft;

1,4-dioxane (123-91-1) → ethylene glycol diformate (629-15-2)

Conditions	Yield
With clorine; oxygen; nitrogen(II) oxide at 21.9℃; under 700 Torr; Product distribution; Mechanism; FTIR study of atmospheric fate of title comp.;
With air; Cyclopentane; cobalt(II) acetate at 132℃; under 22065.2 Torr;
With OH radicals; nitrogen(II) oxide Kinetics; Oxidation; UV-irradiation;

oxalic acid (144-62-7) + ethylene glycol (107-21-1) → ethylene glycol diformate (629-15-2)

ethylene glycol (107-21-1) + Acetic formic anhydride (2258-42-6) → ethylene glycol diformate (629-15-2)

sodium formate (141-53-7) + 1,2-dichloro-ethane (107-06-2) → ethylene glycol diformate (629-15-2)

Conditions	Yield
With methanol at 165℃;

1,4-dioxene (543-75-9) → ethylene glycol diformate (629-15-2)

Conditions	Yield
(i) O2, (ii) (thermolysis); Multistep reaction;
With 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin for 1h; Irradiation; Atmospheric conditions;	77 %Spectr.

C11H11N2O4 → formaldehyd (50-00-0) + ethylene glycol monoformate (628-35-3) + ethylene glycol diformate (629-15-2) + 4-cyanonitrosobenzene (31125-07-2) + 1,4-dioxane-2-ol (22347-47-3) + p-dioxanone (3041-16-5)

Conditions	Yield
With dinitrogen monoxide In water Mechanism; Product distribution; Rate constant; Ambient temperature; Irradiation; other ethers;

formic acid (64-18-6) + ethylene glycol (107-21-1) → ethylene glycol monoformate (628-35-3) + ethylene glycol diformate (629-15-2)

Conditions	Yield
With acid at 20℃; Esterification;

sodium formate (141-53-7) + ethylene dibromide (106-93-4) → ethylene glycol monoformate (628-35-3) + ethylene glycol diformate (629-15-2)

Conditions	Yield
In formic acid for 30h; Substitution; Heating;

ethylene glycol (107-21-1) + CO → ethylene glycol diformate (629-15-2) + ethylene glycol monoformate

Conditions	Yield
With sodium ethane-1,2-diolate at 70 - 100℃; under 147102 - 294203 Torr;

1,4-dioxane (123-91-1) → formaldehyd (50-00-0) + formic acid (64-18-6) + ethylene glycol diformate (629-15-2) + 2-methoxyacetic acid (625-45-6)

Conditions	Yield
With water; oxygen at 25℃; for 2h; pH=7.5; Kinetics; Product distribution; Further Variations:; ultrasonic frequencies; sparge gases: Ar/O2 mixtures, pure Ar; Decomposition; ultrasonic irradiation;

ethylene glycol divinyl ether (764-78-3) → formaldehyd (50-00-0) + ethylene glycol diformate (629-15-2)

Conditions	Yield
With ozone at 24.84℃; under 760.051 Torr; Kinetics; Concentration; Time; Gas phase;	A 47 %Chromat. B 50 %Chromat.

sec-butyl formate (589-40-2) + ethylene glycol (107-21-1) → ethylene glycol diformate (629-15-2)

Conditions	Yield
With potassium carbonate at 100 - 130℃; for 6h; Reagent/catalyst; Concentration; Reflux;

Methyl formate (107-31-3) → methanol (67-56-1) + ethylene glycol diformate (629-15-2) + carbon dioxide (124-38-9) + carbon monoxide (201230-82-2)

Conditions	Yield
With oxygen at 560℃; under 15001.5 Torr;

6-methoxyquinolin-8-amine (90-52-8) + ethylene glycol diformate (629-15-2) + 5-diethylamino-2-pentanone (105-14-6) → pamaquine (491-92-9)

ethylene glycol diformate (629-15-2) → formic acid ethyl ester (109-94-4)

Conditions	Yield
With di-tert-butyl peroxide at 140℃; for 3h; conversion, concentration of products;

ethylene glycol diformate (629-15-2) → formic acid (64-18-6) + carbon monoxide (201230-82-2) + formic anhydride (1558-67-4)

Conditions	Yield
With OH radicals; chlorine Kinetics; Product distribution; Oxidation; UV-irradiation;

ethylene glycol diformate (629-15-2) → ethene (74-85-1) + carbonic-acid (463-79-6) + water (7732-18-5) + carbon monoxide

Conditions	Yield
at 220 - 240℃;

ethylene glycol diformate (629-15-2) + N-ethyl-N(2-formyloxyethyl)formamide (93625-19-5) → N-formyldiethylamine (617-84-5) + formic acid ethyl ester (109-94-4) + CO2

Conditions	Yield
With di-tert-butyl peroxide In chlorobenzene at 140℃; for 1.5h; Product distribution;

ethylene glycol diformate (629-15-2) → N-formyldiethylamine (617-84-5) + octyl formate (112-32-3) + N-ethyl-N-octyl formamide (93625-20-8) + formic acid ethyl ester (109-94-4) + CO2

Conditions	Yield
With competition reaction with N-ethyl-N(2-formyloxyethyl)formamide and 1-hexene In chlorobenzene at 140℃; for 1.5h; Product distribution;

ethanol (64-17-5) + ethylene glycol diformate (629-15-2) → formic acid ethyl ester (109-94-4) + ethylene glycol monoformate

ethylene glycol diformate (629-15-2) + vanadyl phosphate intercalated with 2-propanol → vanadyl phosphate intercalated with ethylene glycol diformate

Conditions	Yield
In not given react. by refluxing 1 h;

Upstream product

• 123-91-1 1,4-dioxane 
• 287-92-3 Cyclopentane 
• 71-48-7 cobalt(II) acetate 
• 144-62-7 oxalic acid 
• 107-21-1 ethylene glycol 
• 2258-42-6 formyl acetic anhydride 
• 141-53-7 sodium formate 
• 107-06-2 1,2-dichloro-ethane 
• 127817-98-5 2,3,8,8a-Tetrahydro-cis-4aH-pyrano<2,3-b>-<1,4>dioxin-7(6H)-on-ethylenacetal 
• 628-35-3 ethylene glycol monoformate 
• 106-93-4 ethylene dibromide 
• 107-31-3 Methyl formate 
• 589-40-2 sec-butyl formate 
• 764-78-3 ethylene glycol divinyl ether 

Downstream Products

• 74-85-1 ethene 
• 463-79-6 carbonic-acid 
• 7732-18-5 water 
• 617-84-5 N-formyldiethylamine 
• 109-94-4 formic acid ethyl ester 
• 112-32-3 octyl formate 
• 93625-20-8 N-ethyl-N-octyl formamide 
• 67-56-1 methanol 
• 107-21-1 ethylene glycol 
• 64-18-6 formic acid 
• 201230-82-2 carbon monoxide 
• 1558-67-4 formic anhydride 

Relevant articles and documents

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Industrial method for preparing ethylene glycol diformate

The invention relates to an industrial method for preparing ethylene glycol diformate (EGDF). The method comprises the following steps: completing esterification reaction of raw materials namely ethylene glycol and formic acid, in a composite solvent medium in the presence of an acid catalyst in an esterification reactor of a production device shown in drawings; and sequestially performing normalpressure desolventizing, reduced pressure low boiling removal and rectification treatment on esterification liquid, thereby obtaining the qualified EGDF. The ester content of the product is more thanor equal to 98%, the saponification value is 800-910mgKOH/g, and the product yield is more than 80%. Due to use of the composite solvent, the reaction temperature is decreased, and the reaction time is shortened. The distillation and rectification separation technology is utilized, and the esterification liquid after-treatment process is improved, so that the solvent and excessive formic acid canbe recycled. Therefore, the method disclosed by the invention has the advantages that the process is novel, the product quality is excellent, the yield is high, economic benefits are excellent, emission of three wastes is few and the method accords with the green chemical development direction.

A glycol dimethyl ester synthesis process

The invention relates to a method for preparing glycol diformate. The method comprises the following steps of (1) adding organic solvent, reactant glycol, 50% of formic acid aqueous solution (industrial formic acid) and an acid catalyst into a reactor and raising the temperature of a reaction system to divide water; and (2) collecting fraction with the temperature of 150-170 DEG C after a period of reaction time to obtain a glycol diformate product. The method is stable in reaction, safe, high in yield, low in cost, simple in process and easy to industrialize.