PRODUCTS

DEO (DIETHYL OXALATE)

DEO (Diethyl Oxalate) is a chemical intermediate used in the manufacture of API and various dyes.
DEO (Diethyl Oxalate) can be used as a solvent for a number of synthetic and natural resins.
DEO (Diethyl Oxalate) is also used as a cost effective additive based in the dye-sensitized solar cells (DSSCs).

CAS Number: 95-92-1
EC Number: 202-464-1
IUPAC Name: diethyl oxalate
Chemical Formula: C6H10O4

Other names: 95-92-1, Ethyl oxalate, Oxalic ether, Ethyl oxalate (VAN), NSC 8851, Diethylester kyseliny stavelove, HSDB 2131, EINECS 202-464-1, UNII-860M3ZWF6J, Diethyl ester of oxalic acid, UN2525, Diethylester kyseliny stavelove [Czech], BRN 0606350, 860M3ZWF6J, DTXSID2044472, ETHYL OXOLATE, NSC-8851, C2H5OCOCOOC2H5, Ethanedioic acid, 1,2-diethyl ester, DIETHYL OXALATE [MI], DIETHYL OXALATE [HSDB], DTXCID0024472, EC 202-464-1, 4-02-00-01848 (Beilstein Handbook Reference), ETHANEDIOC ACID, DIETHYL ESTER, UN 2525, DIETHYL OXALATE [INCI], ETHANEDIOIC ACID,DIETHYL ESTER (DIETHYLOXALATE), 202-464-1, inchi=1/c6h10o4/c1-3-9-5(7)6(8)10-4-2/h3-4h2,1-2h, wyacbzdahnbppb-uhfffaoysa-n, diethyloxalate, Ethanedioic acid, diethyl ester, Diethyl ethanedioate, Oxalic acid, diethyl ester, Oxalic Acid Diethyl Ester, MFCD00009119, diethyl ethane-dioate, oxalic acid diethylester, 1,2-diethyl ethanedioate, Diethyl oxalate, >=99%, SCHEMBL7262, WLN: 2OVVO2, CHEMBL3183226, NSC8851, Diethyl oxalate, analytical standard, Tox21_302109, BBL011413, STL146519, Ethyl oxalate [for Spectrophotometry], AKOS000120214, Ethyl oxalate [UN2525] [Poison], FD03598, CAS-95-92-1, NCGC00255767-01, AS-14315, BP-13324, Diethyl oxalate, purum, >=99.0% (GC), NS00009607, O0078, O0120, EN300-19207, F87445, Q904612, 5-pentyl-5-tetrahydropyran-2-yl-imidazolidine-2,4-dione, ETHANEDIOIC ACID,DIETHYL ESTER (DIETHYLOXALATE), F1908-0115, Z104473164, Ethanedioic Acid 1,2-Diethyl Ester; Oxalic Acid Diethyl Ester; Diethyl Ethanedioate; Ethyl Oxalate; NSC 8851

Due to DEO (Diethyl Oxalate) chemical characteristic, DEO (Diethyl Oxalate) (DEOX) is miscible with alcohols, ether and other common organic solvents.
DEO (Diethyl Oxalate) is slightly soluble in water.
DEO (Diethyl Oxalate) is a Diester of ethyl alcohol and oxalic acid.
DEO (Diethyl Oxalate) appears as a colorless liquid.

DEO (Diethyl Oxalate) is slightly denser than water and insoluble in water.
DEO (Diethyl Oxalate) undergoes transesterification with phenol in the liquid phase over very efficient MoO3/TiO2 solid-acid sol-gel catalysts to form diphenyl oxalate.
DEO (Diethyl Oxalate) undergoes Claisen condensation with active methylene group of ketosteroids to form glyoxalyl derivatives.
DEO (Diethyl Oxalate) undergoes hydrogenation in the presence of high copper contented mesoporous Cu/SBA-15 catalysts to yield ethylene glycol.

Form of DEO (Diethyl Oxalate) is liquid.
A sustainable process based on carbon monoxide (CO) coupling reaction has been considered as an alternative method for DEO

DEO (Diethyl Oxalate) appears as a colorless liquid.
DEO (Diethyl Oxalate) is slightly soluble in water.

DEO (Diethyl Oxalate) is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 tonnes per annum.
DEO (Diethyl Oxalate) is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

DEO (Diethyl Oxalate) may have a promising industrial application for coal to ethylene glycol production.
DEO (Diethyl Oxalate) is a clear colorless liquid with characteristic.

Ethyl oxalyl Chloride is manufactured by hydrolysis of DEO (Diethyl Oxalate) with Potassium Carbonate.
DEO (Diethyl Oxalate) is a chemical used to pre-treat wood chips in order to refine and prepare them for further processing (such as obtaining wood pulp).

DEO (Diethyl Oxalate) is also used as a starting material to synthesize Ethylene glycol (E890140) by means of catalytic hydrogenation.
DEO (Diethyl Oxalate) is a chemical intermediate used in the manufacture of API and various dyes.

Applications of DEO (Diethyl Oxalate):
DEO (Diethyl Oxalate) is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates.
DEO (Diethyl Oxalate) is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics.

DEO (Diethyl Oxalate) is involved in the transesterification reaction with phenol to get dipheny oxalate.
DEO (Diethyl Oxalate) is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives.

Further, DEO (Diethyl Oxalate) is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine.
In addition to this, DEO (Diethyl Oxalate) is utilized in the microemulsion synthesis of zinc oxide nanoparticles.

DEO (Diethyl Oxalate) was used in microemulsion synthesis of ZnO nanoparticles.

Uses of DEO (Diethyl Oxalate):
DEO (Diethyl Oxalate) is used especially for production of pesticides and also as a starting material of so-called oxalate syntheses used in many areas, such as in pharmaceutical industry (production of steroids, barbiturates), in dyeing industry (Tartrazin dyestuff) and other specialised chemicals and in PU and plastic industry.

DEO (Diethyl Oxalate) is used to make pharmaceuticals, plastics, dyes, and dyestuff intermediates.
DEO (Diethyl Oxalate) is also used as a solvent for cellulose esters, ethers, resins, perfumes, and lacquers for electronics.

DEO (Diethyl Oxalate) is a chemical used to pre-treat wood chips in order to refine and prepare them for further processing (such as obtaining wood pulp).
DEO (Diethyl Oxalate) is also used as a starting material to synthesize Ethylene glycol (E890140) by means of catalytic hydrogenation.

DEO (Diethyl Oxalate) uses and applications include:
Solvent for cellulose esters and ethers, many natural and synthetic resins, paint stripping;
radio-tube cathode fixing lacquers;
perfumes;
chelating agent;
cleaner for polymeric residues;
pigment dispersant;
intermediate for organic synthesis, pharmaceuticals, barbiturates (CNS depressants), dyes;
in food packaging adhesives
Suggested storage of DEO (Diethyl Oxalate):
Moisture-sensitive

Use and Manufacturing:
Manufacture of phenobarbital,
Ethylbenzyl malonate,
Triethylamine, & similar chemicals;
Manufacture of plastics,
Dyestuff intermediates;
Solvent for cellulose esters
Organic syntheses,
Esp in mfr of pharmaceuticals;
Solvent for ethers & resins
Olvent for perfumes & for natural & synthetic resins (cellulose esters);
Agent in radio tube cathode fixing lacquers; c
Hem int for pharmaceuticals,
Plastics & dyes.

Widespread uses by professional workers:
DEO (Diethyl Oxalate) is used in the following products: laboratory chemicals and polymers.
DEO (Diethyl Oxalate) is used in the following areas: building & construction work.
Other release to the environment of DEO (Diethyl Oxalate) is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).

Uses at industrial sites:
DEO (Diethyl Oxalate) is used in the following products: polymers and laboratory chemicals.
DEO (Diethyl Oxalate) has an industrial use resulting in manufacture of another substance (use of intermediates).

DEO (Diethyl Oxalate) is used in the following areas: building & construction work, formulation of mixtures and/or re-packaging and scientific research and development.
DEO (Diethyl Oxalate) is used for the manufacture of: chemicals.
Release to the environment of DEO (Diethyl Oxalate) can occur from industrial use: in the production of articles, for thermoplastic manufacture, of substances in closed systems with minimal release and as an intermediate step in further manufacturing of another substance (use of intermediates).

Other Industry Uses:
Intermediates
Processing aids, not otherwise listed
Agro chemical pesticide

Consumer Uses:
Apparel and footwear care products
Agro chemical pesticide

Other Uses:

Chelating:
Reacts and forms complexes with metal ions that could affect the stability and / or appearance of cosmetic products.

Hair conditioner:
Leaves hair easy to comb, soft, soft and shiny and / or confers volume, lightness and shine.

Masking:
Reduces or inhibits the odor or basic taste of the product.

Plasticiser:
Softens and softens another substance that otherwise could not easily be deformed, dispersed or worked.

Solvent:
Dissolves other substances.

Potential Uses:
Chelating agents, hair conditioning, plasticisers, solvents
DEO (Diethyl Oxalate) is used as a solvent for paint stripping and resins.

DEO (Diethyl Oxalate) is used as cleaner for polymeric residues.
DEO (Diethyl Oxalate) is used as pigment dispersant.
There are some specialty application of DEO (Diethyl Oxalate) as a solvent in nitrocellulose lacquers.

DEO (Diethyl Oxalate) is an important intermediate in chemical industry, especially in pharmaceutical industry, which can be utilized for the synthesis of high value drugs, dyestuff and as the useful solvent for spices.
DEO (Diethyl Oxalate) is used in microemulsion synthesis of ZnO nanoparticles.

DEO (Diethyl Oxalate) is used in the synthesis of sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine.
DEO (Diethyl Oxalate) can be used in Pharma & Life Science, Agriculture, Plastics, Cosmetics & Personal Care.
DEO (Diethyl Oxalate) can be applied as Agrochemicals.

DEO (Diethyl Oxalate) is widely used in fine chemical industry.
DEO (Diethyl Oxalate) can be added to unmodified vegetable oils in any ratio.

As heating oil, use can be made of a mixture which, as main component, consists of vegetable oils and up to 50% by volume DEO (Diethyl Oxalate).
DEO (Diethyl Oxalate) is used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.

As heating oil use can be made of a mixture which originates from the refining of crude oil and is admixed with up to 25% by volume DEO (Diethyl Oxalate).
DEO (Diethyl Oxalate) is widely utilized at industrial domains to synthesize a variety of significant fine chemicals, such as dyes, pharmaceuticals, solvents, extractants, various intermediates and ethylene glycol (EG).

DEO (Diethyl Oxalate) is necessary to dissolve DMO in anhydrous methanol or heat DMO to liquid state when DEO (Diethyl Oxalate) is applied to the production of ethylene glycol.
DEO (Diethyl Oxalate) is a liquid chemical at room temperature and convenient as raw material for the production of ethylene glycol by hydrogenation.

Benefits of DEO (Diethyl Oxalate):
Highly efficient
Highly stable
Contributes to sustainable ethylene glycol production

General Manufacturing Information of DEO (Diethyl Oxalate):
Industry Processing Sectors
All other basic organic chemical manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Plastic material and resin manufacturing

Solubility of DEO (Diethyl Oxalate):
Miscible with alcohols, ether and other common organic solvents.
Completely sol ether, alcohol and acetone; slightly sol hot water.

The solubility of dimethyl oxalate is similar, except that DEO (Diethyl Oxalate) is more soluble in water.
The solubilities of the other esters are similar in organic solvents, but they are insoluble in water.

Production of DEO (Diethyl Oxalate):

Dimethyl oxalate can be obtained by esterification of oxalic acid with methanol using sulfuric acid as a catalyst:
2CH3OH+(CO2H)2 → (CO2CH3)2+2H2O

Oxidative carbonylation route:

The preparation by oxidative carbonylation has attracted interest because DEO (Diethyl Oxalate) requires only C1 precursors:
4CH3OH+4 CO+O2→ 2 (CO2CH3)2+2H2O

The reaction is catalyzed by Pd2+.
The synthesis gas is mostly obtained from coal or biomass.

The oxidation proceeds via dinitrogen trioxide, which is formed according to (1) of nitrogen monoxide and oxygen and then reacts according to (2) with methanol forming methyl nitrite.

In the next step of dicarbonylation (3) carbon monoxide reacts with methyl nitrite to dimethyl oxalate in the vapor phase at atmospheric pressure and temperatures at 80-120 °C over a palladium catalyst.

This method is lossless with respect to methyl nitrite, which acts practically as a carrier of oxidation equivalents.
However, the water formed must be removed to prevent hydrolysis of the dimethyl oxalate product.
With 1% Pd/α-Al2O3 dimethyl oxalate is produced selectively in a dicarbonylation reaction, under the same conditions with 2% Pd/C dimethyl carbonate is produced by monocarbonylation.

Alternatively, the oxidative carbonylation of methanol can be carried out with high yield and selectivity with 1,4-benzoquinone as an oxidant in the system Pd(OAc)2/PPh3/benzoquinone with mass ratio 1/3/100 at 65 °C and 70 atm CO.

Production Methods of DEO (Diethyl Oxalate):
DEO (Diethyl Oxalate) is produced via esterification of ethanol and oxalic acid.
DEO (Diethyl Oxalate)is a preferred solvent for cellulose acetate and nitrate.

Due to DEO (Diethyl Oxalate)'s chemical characteristic, DEO (Diethyl Oxalate) is miscible with alcohols, ether and other common organic solvents.

Reactions of DEO (Diethyl Oxalate):
Dimethyl oxalate (and the related diethyl ester) is used in diverse condensation reactions.
For example, DEO (Diethyl Oxalate) condenses with cyclohexanone to give the diketo-ester, a precursor to pimelic acid.
With diamines, the diesters of oxalic acid condense to give cyclic diamides.

Quinoxalinedione is produced by condensation of dimethyloxalate and o-phenylenediamine:
C2O2(OMe)2 + C6H4(NH2)2 → C6H4(NHCO)2 + 2 MeOH

Hydrogenation gives ethylene glycol.
Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%).

The methanol formed is recycled in the process of oxidative carbonylation.
Other plants with a total annual capacity of more than 1 million tons of ethylene glycol per year are planned.

Decarbonylation gives dimethyl carbonate.

Diphenyl oxalate is obtained by transesterification with phenol in the presence of titanium catalysts, which is again decarbonylated to diphenyl carbonate in the liquid or gas phase.

Dimethyl oxalate can also be used as a methylating agent.
DEO (Diethyl Oxalate) is notably less toxic than other methylating agents such as methyl iodide or dimethyl sulfate.

Handling and Storage of DEO (Diethyl Oxalate):

Precautions for safe handling:

Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.
Keep in a well-ventilated place.
Keep locked up or in an area accessible only to qualified or authorized persons.

Stability and Reactivity of DEO (Diethyl Oxalate):
DEO (Diethyl Oxalate) is an ester.
Esters react with acids to liberate heat along with alcohols and acids.

Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products.
Heat is also generated by the interaction of esters with caustic solutions.
Flammable hydrogen is generated by mixing esters with alkali metals and hydrides

Chemical stability:
DEO (Diethyl Oxalate) is chemically stable under standard ambient conditions (room temperature).

First Aid Measures of DEO (Diethyl Oxalate):

General advice:
First aider needs to protect himself.

If inhaled:
Fresh air.
Call in physician.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.

In case of eye contact:
Rinse out with plenty of water.
Remove contact lenses.

If swallowed:
Make victim drink water.

Accidental Release Measures of DEO (Diethyl Oxalate):

Environmental precautions:
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.

Take up carefully with liquid-absorbent material.
Dispose of properly.
Clean up affected area.

Fire Fighting Measures of DEO (Diethyl Oxalate):

Extinguishing media:

Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder

Unsuitable extinguishing media:
For DEO (Diethyl Oxalate) no limitations of extinguishing agents are given.

Further information:
Remove container from danger zone and cool with water.
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Exposure Controls/personal Protection of DEO (Diethyl Oxalate):

Eye/face protection:
Use tightly fitting safety goggles.

Skin protection:
Full contact

Material: butyl-rubber
Minimum layer thickness: 0,7 mm
Break through time: 480 min

Splash contact:

Material: Nitrile rubber
Minimum layer thickness: 0,4 mm
Break through time: 10 min

Body Protection:
protective clothing

Control of environmental exposure:
Do not let product enter drains.

Molecular Weight: 146.14
XLogP3: 0.6
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 5

Exact Mass: 146.05790880
Monoisotopic Mass: 146.05790880
Topological Polar Surface Area: 52.6 Å²
Heavy Atom Count: 10

Complexity: 114
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes