Diethylene glycol monoethyl ether

Diethylene glycol monoethyl ether = Ethyl ether of diethylene glycol

DEGMEE

DEGEE

Diethylene glycol monoethyl ether (C8H16O4) an ethylene-series glycol ether. Diethylene glycol monoethyl ether is a colorless liquid with a mild odor. It is dissolvable in water and most organic solvents. Glycol ethers are primarily used as solvents in various formulations, such as: cleaning fluids, paints and wood stains, coatings and inks.

Chemical names: Carbitol, Carbitol solvent, Diethylene glycol monoethyl ether, 3,6-Dioxa-1-octanol, Diethylene glycol ethyl ether, Diethylene glycol monoethyl ether, Diglycol monoethyl ether, Dioxitol, Ethanol, 2,2′-oxybis-, monoethyl ether, Ethyl carbitol, Ethyl diethylene glycol, Ethyldigol

Trade names and abbreviations: Dowanol 17, Dowanol DE, Ektasolve DE, Solvolsol, Transcutol, Transcutol P, Transcutol HP, DEGEE, Carbitol; Carbitol Cellosolve; DEGEE; Poly-Solv; Solvosol; 2-(2-ethoxyethoxy)-ethanol

Linear Formula: C2H5OCH2CH2OCH2CH2OH

Formula: C₆H₁₄O₃

Chemical formula: HOCH₂CH₂OCH₂CH₂OC₂H₅

Molar Mass: 134.18 g/mol

HS Code: 2909 44 00

Physical form: Liquid with a mild, pleasant odour. Hydroscopic

Application Outlook: 

Paints, Coatings & Inks

Chemical intermediate

Floor Polish

Pharmaceutical & Personal Care

Diethylene glycol monomethyl ether is a product derived from ethylene oxide and methanol. Chemically, it is also known as methyl diglycol or 2-hydroxy-2-methoxy-diethyl ether. Commercially, it is known as methyl carbitol. Diethylene glycol monomethyl ether is a solvent which is excellent for application in various resins and pastes. It is a non-volatile solvent and hence, it is used only in special lacquer formulations. It is employed principally in nitrocellulose lacquers so as to improve characteristics of lacquers. It can be easily stabilized with the use of small quantities of additives such as 2, 6-ditert-butyl-4-methylphenol (0.005%). Diethylene glycol monomethyl ether has excellent dilution capacity. It is utilized in the aviation industry as FSII (fuel system icing inhibitor), which is also called anti-icing or dicing agent. It is also employed in the printing ink industry and in the production of ballpoint pen ink.

In addition to uses listed above, diethylene glycol monomethyl ether is used for applications such as architectural coatings, brake fluids, graphic arts, institutional cleaners, process solvents, protective coatings, textile, and wood coatings.

Diethylene glycol monoethyl ether, also known under many trade names, is the organic compound with the formula CH3CH2OCH2CH2OCH2CH2OH. 

Diethylene glycol monoethyl ether is a colorless liquid. DEGEE is a popular solvent for commercial applications.

Diethylene glycol monoethyl ether is produced by the ethoxylation of ethanol.

Diethylene Glycol Monoethyl Ether is a very polar, slow evaporating, water miscible solvent with a low odor. 

Diethylene Glycol Monoethyl Ether is an active solvent for cellulose acetate butyrate, nitrocellulose, epoxy resins, and other coating materials. 

Diethylene Glycol Monoethyl Ether solvent is used as a coalescent in latex paints and floor polishes, and as penetrating solvent in wood stains.

Applications

Diethylene glycol monoethyl ether is a solvent for dyes, nitrocellulose, paints, inks, and resins. 

Diethylene glycol monoethyl ether is a component of wood stains for wood, for setting the twist and conditioning yarns and cloth, in textile printing, textile soaps, lacquers, penetration enhancer in cosmetics, drying varnishes and enamels, and brake fluids. 

Diethylene glycol monoethyl ether used to determine the saponification values of oils and as a neutral solvent for mineral oil-soap and mineral oil-sulfated oil mixtures (giving fine dispersions in water)

Diethylene glycol monoethyl ether is a Solvent used to facilitate penetration into fibers and to promote the production of intense, bright shades; it features a high boiling point and low vapor pressure. Also an important solvent in nongrain-raising wood stains and serves as a component of industrial cleaners. 

Textile printing and dyeing processes utilize this product to facilitate penetration into fibers and to promote the production of intense, bright shades. 

These characteristics, as well as its high boiling point and low vapor pressure, make it useful for twist setting and yarn and cloth conditioning. 

Mineral oil-soap and mineral oil sulfonated oil mixtures require fast-acting mutual solvents. 

Small quantities of this product in these mixtures form translucent-to clear dispersions, in contrast to the usual turbid dispersion that indicates incomplete solubility.

Uses and Application Insights

Floor polish application dominated the diethylene glycol monoethyl ether market and accounted for over 30% of the global volume. 

DEGEE is known for its multifunctional properties to clean stains and add a glossy finish, especially on wooden flooring, which has resulted in a strong demand for the product.

Paints, coatings, and inks is the second-largest application for the product and the segment is anticipated to exhibit a CAGR of 5.5%, in terms of revenue. 

This growth can be attributed to the biodegradable property of the DEGEE-based paints and coatings. 

They are highly miscible in water and do not have any adverse effects on human health as well as the environment, which is expected to aid the product demand over the coming years.

Diethylene glycol monoethyl ether is used as a solvent in the manufacturing of industrial chemicals. 

Diethylene glycol monoethyl ether has gained preference as a chemical intermediate due to its compatibility with other chemicals. 

In the pharmaceutical and personal care sector, DEGEE is commonly termed as Transcutol. 

Diethylene glycol monoethyl ether is majorly used in skin treatment formulations in the form of topical creams or gels. 

Diethylene glycol monoethyl ether is considered to be a safe and tolerable pharmaceutical-grade glycol ether when used at 99.9% purity.

Diethylene glycol monoethyl ether is used in the formulation of various cosmeceutical products as it has skin treatment properties. 

Diethylene glycol monoethyl ether is particularly gaining importance in antimicrobial soaps, antiperspirants, nail polish removers, fragrances, hair dyes, and in products for treating acne, marks, and scars owing to its super solubilizing and efficacy boosting properties. 

Significantly ascending demand for anti-acne products can be attributed to various factors such as prevalence of hormone related diseases and unhealthy lifestyles and inappropriate eating habits of consumers. 

Furthermore, Diethylene glycol monoethyl ether is used in sunscreens and BB creams to enhance the properties of protective ingredients.

Diethylene glycol monoethyl ether is a solubiliser that ensures even distribution of the ingredients throughout a product, to help it work better

Diethylene glycol monoethyl ether is used in diverse industries such as textile, architecture and construction, chemical, automotive, personal care and pharmaceutical, and others. The increasing application of diethylene glycol monoethyl ether for the manufacturing of specialty paints, dyes, colorants, lacquer & stains has increased the demand for diethylene glycol monoethyl ether from the architecture and construction sector.

Diethylene glycol monoethyl ether is also used in the automotive sector for component manufacturing, coatings, and brake fluids. Factors such as the growing automotive industry, increasing adoption of electric vehicles, and rising need for modernization of vehicles boost the growth of the diethylene glycol monoethyl ether in the automotive industry. Rising urbanization, technological advancements, and an increase in the sale of passenger vehicles have resulted in increased applications of diethylene glycol monoethyl ether.

There has been increasing demand for diethylene glycol monoethyl ether from industries such as construction, chemical, and textile, thereby driving the market growth for diethylene glycol monoethyl ether

Benefits:

Excellent solvency

Great chemical stability

Compatible with water and a number of organic solvents

Synonym(s): Diethylene glycol ethyl ether, CARBITOL, 2-(2-Ethoxyethoxy)ethanol, Ethyldiglycol,  Ethoxydiglycol 

Other names: 3,6-dioxa-1-octanol, DEGEE, diethylene glycol monoethyl ether, Carbitol, Carbitol Cellosolve, Transcutol, Dioxitol, Polysolv DE, Dowanal DE, DE SOLVENT

INCI name: Ethoxydiglycol 

Preferred IUPAC name: 2-(2-Ethoxyethoxy)ethan-1-ol

APV

2-(BETA-ETHOXYETHOXY)ETHANOL

CARBITOL

CARBITOL CELLOSOLVE

CARBITOL SOLVENT

CARBITOL SOLVENT LOW

DIETHYLENE GLYCOL ETHYL ETHER

DIETHYLENE GLYCOL MONOETHYL ESTER

DIETHYLENE GLYCOL MONOETHYL ETHER

DIGLYCOL

DIGLYCOL MONOETHYL ETHER

3,6-DIOXA-1-OCTANOL

3,6-DIOXAOCTAN-1-OL

DIOXITOL

DOWANOL

DOWANOL DE

EKTASOLVE DE

ETHANOL, 2,2′-OXYBIS-, MONOETHYL ETHER

ETHANOL, 2-(2-ETHOXYETHOXY)-

ETHOXY DIGLYCOL

2-(2-ETHOXYETHOXY) ETHANOL

2-(ETHOXYETHOXY)ETHANOL

2-(2′-ETHOXYETHOXY)ETHANOL

2-(2-ETHOXYETHOXY)ETHANOL

ETHYL CARBITOL

ETHYL CELLOSOLVE

ETHYL DIETHYLENE GLYCOL

ETHYL DIGOL

ETHYLDIETHYLENE GLYCOL

ETHYLDIGOL

ETHYLENE DIGLYCOL MONOETHYL ETHER

1-HYDROXY-3,6-DIOXAOCTANE

LOSUNGSMITTEL APV

MONOETHYL ETHER OF DIETHYLENE GLYCOL

O-ETHYLDIGOL

POLY-SOLV

POLY-SOLV DE

SOLVOLSOL

TRANSCUTOL

Function and uses of Diethylene glycol monoethyl ether: 

Diethylene glycol monoethyl ether may be prepared from ethylene oxide and 2-ethoxyethanol in the presence of SO2.

Diethylene glycol monoethyl ether is used in the chemical and paint industries as a solvent for nitro cellulose, resins, and dyes. 

Diethylene glycol monoethyl ether is not used in food or detergent products.

Purified Diethylene glycol monoethyl ether (>99%) is used in cosmetics and dermatological preparations and as solvent in some medicine products. 

Diethylene glycol monoethyl ether enhances the percutaneous absorption through the skin and mucosal barriers. 

Diethylene glycol monoethyl ether is used in some drugs to enhance absorption.

According to the notification to the Commission DEGEE is used in cosmetic products in shampoos (rinse-off) in a concentration up to 5% and creams (leave-on) in a concentration up to 2%. 

Diethylene glycol monoethyl ether is used in toiletries, skin care, hair care or sun care products which may be applied on the whole body. 

Diethylene glycol monoethyl ether must not be used in products for oral hygiene and the eyes. 

The solvent diethylene glycol monoethyl ether (DEGEE) is currently used in over 500 cosmetic products and has enabled the formulation of a topical 5% dapsone gel for the treatment of acne. It is anticipated that this common cosmetic ingredient will be a component in numerous future prescription topical products approved for the US market. Dermatologists are already treating patients that apply products containing 5–40% of this solvent multiple times each day.

Diethylene Glycol Monoethyl Ether has low setting point and low viscocity at low temperature so it is used in manufacturing Brake Fluid. 

Ethyl Diglycol is used as a flow and gloss promoter in paint industries. 

The extendability of solution has also increased. Ethyl Carbitol is used in production of printing ink and as a cleaner in offset printing. Diethylene Glycol Monoethyl Ether is used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics. Ethyl Diglycol prevents the gel formation in liquid detergent and cleaner formulation. Diethylene Glycol Monoethyl Ether is also used a solubilizer in drilling and cutting coolants. Ethyl Diglycol is used in the production & formulation of pesticides & wood preservaties. Due to its low volatility property it is used in Indian & ink ball point pastes. It is also used in cosmetic & perfumary industry as a solvent. Ethyl diglycol (Ethyl Carbitol) does not attack rubber.

The established LVP-VOC exemption criteria, applicable in some states, can be reviewed in California’s Consumer Product Regulation. 

Visit the California Air Resource Board website for regulatory information.

The chemical substances for this product are listed as Inert Ingredients Permitted for Use in Nonfood Use Pesticide Products, and in Food Use Pesticide Products with limitations, under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA). 

Applications/uses of Diethylene Glycol Monoethyl Ether: 

Architectural coatings

Auto OEM

Auto refinish

Brake fluids

Cleaners

Cosmetics

Fabric care

Graphic arts

Hard surface care

Industrial cleaners

Institutional cleaners

Process solvents

Protective coatings

Textile

Wood coatings

 

Key attributes of Diethylene Glycol Monoethyl Ether: 

Good coupling efficiency

Good solvent activity

Inert – Food use with limitations

Inert – Nonfood use

Low odor

Low volatility/Low vapor pressure

LVP-VOC

Miscible with water and most organic liquids

REACH compliant

Readily biodegradable

Slow evaporation rate

Physicochemical Information

Boiling point: 202 °C (1013 hPa)

Density: 0.989 g/cm3 (20 °C)

Explosion limit: 1.8 – 12.2 %(V)

Flash point: 96 °C

Ignition temperature: 204 °C

Melting Point: -76 °C

Vapor pressure: 0.16 hPa (20 °C)

Toxicological Information

LD 50 oral: LD50 Rat 5900 – 6100 mg/kg

LD 50 dermal: LD50 Rabbit 8476 mg/kg

Safety Information according to GHS

Hazard Pictogram(s) Hazard Pictogram(s)

Hazard Statement(s)

H332: Harmful if inhaled.

Precautionary Statement(s)

P261: Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.

P271: Use only outdoors or in a well-ventilated area.

P304 + P340 + P312: IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.

Signal Word: Warning

RTECS: KK8750000

Storage class: 10 – 13 Other liquids and solids

WGK: WGK 1 slightly hazardous to water

Disposal 3

Relatively unreactive organic reagents should be collected in container A. 

If halogenated, they should be collected in container B. For solid residues use container C.

Carbitol solvent” (monoethyl ether of diethylene glycol) is of interest in dermatology because it is an ingredient of many commercial cosmetic products and of certain formulas recommended for use on the skin. 

It is said to confer a “vanishing effect, which appears to be esteemed in these preparations.

There has been a shift in preference toward coatings with low volatile organic compound (VOC) emissions and non-hazardous nature from automotive, packaging, and construction industries over the past few years. This has facilitated utilization of waterborne coatings in numerous end-use industries. 

This factor is anticipated to benefit the demand of DEGEE as a solvent in water-based coatings.

Ethylene oxide is an important intermediate product for manufacturing solvents, plastic, and surfactants. 

In addition, it is a raw material used for the chemical production of DEGEE. 

DEGEE market has gained acceptance by major regulatory bodies such as the U.S. Food and Drug Association (FDA) and the European Commission for its usage as an additive in topical products. 

Aczone (dapsone) gel is one of the products containing DEGEE and is commonly prescribed by dermatologists for acne treatment. 

Furthermore, Diethylene glycol monoethyl ether is highly water soluble and is likely to gain wider acceptance in the production of poorly water-soluble drugs.

Diethylene Glycol Monoethyl Ether has low setting point and low viscocity at low temperature so it is used in manufacturing Brake Fluid. 

Ethyl Diglycol is used as a flow and gloss promoter in paint industries. 

The extendability of solution has also increased. 

Ethyl Carbitol is used in production of printing ink and as a cleaner in offset printing.

Diethylene Glycol Monoethyl Ether is used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics. 

Ethyl Diglycol prevents the gel formation in liquid detergent and cleaner formulation. Diethylene Glycol Monoethyl Ether is also used a solubilizer in drilling and cutting coolants. 

Ethyl Diglycol is used in the production & formulation of pesticides & wood preservaties. Due to its low volatility property it is used in Indian & ink ball point pastes. 

It is also used in cosmetic & perfumary industry as a solvent. Ethyl diglycol (Ethyl Carbitol) does not attack rubber.

Synonyms:

Synonyms are alternative names that represent the same chemical substance.

Diethylene glycol ethyl ether (2);Diethylene glycol monoethyl ether;Ethanol, 2-(2-Ethoxyethoxy)-;Carbitol;Diglycol monoethyl ether;Ethanol, 2,2-oxybis-, monoethyl ether;Ethoxy diglycol;Ethoxyethoxyethanol;Ethyl diethylene glycol;Ethyl digol;Ethylene diglycol monoethyl ether;Diethylene glycol ethyl ether (1);Ethoxydiglycol;2-(2-Ethoxyethoxy)ethanol;Diethylene Glycol Monoethyl Ether [USAN]

111-90-0 [RN]

2-(2-Ethoxyethoxy)ethanol [ACD/IUPAC Name] [Wiki]

2-(2-Ethoxyethoxy)ethanol [German] [ACD/IUPAC Name]

2-(2-Éthoxyéthoxy)éthanol [French] [ACD/IUPAC Name]

2-(Ethoxyethoxy)ethanol

253-502-9 [EINECS]

A1A1I8X02B

Butyl CELLOSOLVE Solvent [Trade name]

CARBITOL [Trade name]

CARBITOL(TM)

Di(ethylene glycol) ethyl ether

diethylene glycol ethyl ether

diethylene glycol monoethyl ether [USAN]

Diglycol monoethyl ether

Dioxitol

Ethanol, 2-(2-ethoxyethoxy)- [ACD/Index Name]

Ethyldiglycol

KK8750000

MFCD00002872 [MDL number]

Poly-Solv DE

Transcutol

Transcutol HP, Highly purified, NF / EP [EINECS] [Formula] [INN] [NF] [RN] [Trade name] [USAN] [USP]

Transcutol P

(Ethoxyethoxy)ethanol

[111-90-0]

1-(2-METHOXY-ETHOXY)-2-{2-[2-(2-METHOXY-ETHOXY]-ETHOXY}-ETHANE

1219804-11-1 [RN]

149818-01-9 [RN]

15P

1-Ethoxy-2-(2-ethoxyethoxy)ethane [ACD/IUPAC Name]

1-ETHOXY-2-(2-HYDROXYETHOXY)ETHANE

1-hydroxy-3,6-dioxaoctane

1-METHOXY-2-[2-(2-METHOXY-ETHOXY]-ETHANE

1PE

2-(2-Ethoxyethoxy) ethanol

2-(2-ethoxyethoxy)ethan(2H)ol

2-(2-ethoxyethoxy)ethan-1-ol

2(2-Ethoxyethoxy)ethanol

2-(2-Ethoxyethoxy)-ethanol

2-(2-ethoxyethoxy)ethanol 99%

2(2-ethoxyethoxy)ethanol, 98+%

2-(2-ethoxyethoxy)ethanol, reagent

2-(2-エトキシエトキシ)エタノール [Japanese]

2-(β-Ethoxyethoxy)ethanol

2-[2-(1,1,2,2,2-Pentadeuterioethoxy)ethoxy]ethanol

2-{2-[2-(2-{2-[2-(2-ETHOXY-ETHOXY)-ETHOXY]-ETHOXY}-ETHOXY)-ETHOXY]-ETHOXY}-ETHANOL

3,6,9,12,15,18,21,24,27,30,33,36,39-Tridecaoxahentetracontane-1,41-diol [ACD/Index Name] [ACD/IUPAC Name]

3,6,9,12,15,18,21,24,27-Nonaoxanonacosane-1,29-diol [ACD/Index Name] [ACD/IUPAC Name]

3,6,9,12,15,18,21,24-Octaoxahexacosan-1-ol [ACD/Index Name] [ACD/IUPAC Name]

3,6,9,12,15-Pentaoxaheptadecane [ACD/Index Name] [ACD/IUPAC Name]

3,6-Dioxa-1-octanol

3,6-Dioxa-1-oktanol

3,6-Dioxa-1-oktanol [Czech]

3,6-Dioxaoctan-1-ol

3,6-DIOXAOCTANE-1-OL

4-01-00-02393 (Beilstein Handbook Reference) [Beilstein]

6JZ

Acetamide, N-5-(1,2-dihydroxyethyl)-4-hydroxy-3-pyrrolidinyl-, monohydrochloride, 3S-3α,4.beta

AE3

Aethyldiaethylenglycol [German]

C8E

Carbitol, 2-(2-Ethoxyethoxy)-ethanol, Ethyl diglycol

DE Solvent [Trade name]

Diethoxol

diethylene glycol monoethyl ether

diethylene glycol monoethyl ether, 98%

diethylene glycol monoethyl ether, 99%,

Diethylene glycol-monoethyl ether

Diethylene glycol-monoethylether

Diethyleneglycol monoethyl ether

Diethyleneglycol Monoethyl-d5 Ether

DiethyleneGlycolMonoethylEther

Dodecaethylene Glycol

Dowanol

Dowanol 17 [Trade name]

Dowanol DE

Eastman DE [Trade name]

Ehanol, 2,2′-oxybis-, monoethyl ether

EINECS 203-919-7

Ektasolve DE

Ethanol, 2,2′-oxybis-, monoethyl ether

Ethoxy diglycol

Ethoxydiglycol

ETHYL CARBITOL

Ethyl diethylene glycol

Ethyl digol

Ethyl Di-Icinol

Ethylene diglycol monoethyl ether

Glycol Ether DE

HEXAETHYLENE GLYCOL

https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:40572

Karbitol

Karbitol [Czech]

Losungsmittel APV

Monoethyl ether of diethylene glycol

Nonaethylene Glycol

O-ACETALDEHYDYL-HEXAETHYLENE GLYCOL

O-Ethyldigol

P3G

P4C

P6G

PE3

PE4

PE5

Pentaethylene Glycol

PG4

PG6

PGE

Polyethylene Glycol (N34)

Q2O2O2 [WLN]

Solvolsol

Tetraethylene glycol

Triethylene glycol [Wiki]

UNII:A1A1I8X02B

UNII-A1A1I8X02B

WLN: Q2O2O2

XPE

Diethylene glycol monomethyl ether is widely used in antiperspirants, nail paint removers, hair dyes, antimicrobial soaps, and in the treatment of acne, marks, and scars due to its solubilizing property and efficacy is fueling the market growth of Diethylene Glycol Monomethyl Ether market

The market for diethylene glycol monoethyl ether is projected to witness growth over the forecast period owing to increasing demand from the personal care sector, rising disposable income, and growing application in the manufacturing of textile fabrics. Increasing use in applications such as industrial cleaners, process solvents, protective coatings, and architectural coatings have also increased on account of its versatility, cost efficiency, and environment-friendly nature.

The demand for diethylene glycol monoethyl ether in the manufacturing of paints and inks is high. Diethylene glycol monoethyl ether is widely used in paints and inks owing to its affordable price, mass production, high miscibility in water, and high efficiency. It is also environment friendly, biodegradable, and versatile, which increases its application in the automotive, construction, and textile sectors.

Diethylene glycol monoethyl ether is used in diverse industries such as textile, architecture and construction, chemical, automotive, personal care and pharmaceutical, and others. The increasing application of diethylene glycol monoethyl ether for the manufacturing of specialty paints, dyes, colorants, lacquer & stains has increased the demand for diethylene glycol monoethyl ether from the architecture and construction sector.

Diethylene glycol monoethyl ether is also used in the automotive sector for component manufacturing, coatings, and brake fluids. Factors such as the growing automotive industry, increasing adoption of electric vehicles, and rising need for modernization of vehicles boost the growth of the diethylene glycol monoethyl ether in the automotive industry. Rising urbanization, technological advancements, and an increase in the sale of passenger vehicles have resulted in increased applications of diethylene glycol monoethyl ether.

There has been increasing demand for diethylene glycol monoethyl ether from industries such as construction, chemical, and textile, thereby driving the market growth for diethylene glycol monoethyl ether in Asia-Pacific. Increasing penetration of passenger vehicles coupled with rising application in paints and coatings fuels the market growth in this region.

Diethylene glycol monoethyl ether (DEGEE) is produced via the O-alkylation of ethanol with two ethylene oxide units, followed by distillation. It has a long history of safe use in food and personal-care products, and is used as an effective strong solubilizer in oral, topical, transdermal, and injectable human and veterinary pharmaceutical products. It has been used as a pharmaceutical solvent for many years under the trade name transcutol. DEGEE, a hydroalcoholic solvent, is gaining interest as a penetration/permeation enhancer, solubilizer, and surfactant for drug delivery systems. Area covered: The physicochemical properties of DEGEE, the solubility data for drugs in DEGEE or DEGEE-water mixtures, and the applications of DEGEE in the solubilization of poorly water-soluble drugs are summarized in this review. Expert opinion: DEGEE is a promising excipient as a solubilizer for many pharmaceutical products with enhanced drug absorption via oral, parenteral, and topical administration, as well as cosmetic products.

Synonyms: 2-(2-Ethoxyethoxy) ethanol; 2-(2-Ethoxyethoxy)ethanol; 3,6-Dioxa-1-octanol; 3,6-Dioxa-1-oktanol [Czech]; Aethyldiaethylenglycol [German]; Carbitol; Carbitol cellosolve; Carbitol solvent; DEGMEE; Diethylene glycol ethyl ether; Diethylene glycol monoethyl ether; Diethyleneglycol monoethyl ether; Diglycol monoethyl ether; Dioxitol; Dowanol 17; Dowanol DE; Ektasolve DE; Ethanol, 2,2′-oxybis-, monoethyl ether; Ethanol, 2-(2-ethoxyethoxy)-; Ethoxy diglycol; Ethyl carbitol; Ethyl diethylene glycol; Ethyl digol; Ethylene diglycol monoethyl ether; Karbitol [Czech]; Losungsmittel APV; Monoethyl ether of diethylene glycol; PM 1799; Poly-Solv DE; Solvolsol; Transcutol; Transcutol P; [ChemIDplus] DiEGEE; [AIHA] NA8027

Category: Glycol Ethers (E Series)

Description: A clear slightly viscous liquid with a mild pleasant odor; [CAMEO]

Sources/Uses

Diethylene glycol monoethyl ether is used in lubricating oil and braking fluid; [ChemIDplus] Used as a solvent for cellulose esters, lacquers, varnishes, enamels, dyestuffs, wood stains, gums, and resins; [Merck Index, 1800] Used in textile printing; [CHEMINFO] Used in photography (solvent for color processing); [www.ci.tucson.az.us/arthazards/medium.html]

Table 1: List of glycol ethers and abbreviations

Abbreviation Name

Ethylene-based

DEGBE Diethylene glycol butyl ether

DEGBEA Diethylene glycol (mono) n-butyl ether acetate

DEGDEE Diethylene glycol diethyl ether

DEGDME Diethylene glycol dimethyl ether

DEGEE Diethylene glycol (mono) ethyl ether

DEGEEA Diethylene glycol ethyl ether acetate

DEGHE Diethylene glycol (mono) hexyl ether

DEGME Diethylene glycol (mono) methyl ether

EGBE Ethylene glycol (mono) n-butyl ether

EGBEA Ethylene glycol (mono) n-butyl ether acetate

EGDEE Ethylene glycol diethyl ether

EGDME Ethylene glycol dimethyl ether

EGEE Ethylene glycol ethyl ether

EGEEA Ethylene glycol (mono) ethyl ether acetate

EGHE Ethylene glycol (mono) n-hexyl ether

EGiPE Ethylene glycol (mono) isopropyl ether

EGiPEA Ethylene glycol (mono) isopropyl ether acetate

EGME Ethylene glycol (mono) methyl ether

EGMEA Ethylene glycol (mono) methyl ether acetate

EGnPE Ethylene glycol (mono) n-propyl ether

EGnPEA Ethylene glycol (mono) n-propyl ether acetate

EGPhE Ethylene glycol (mono) phenyl ether

MAA Methoxyacetic acid a

TEGBE Triethylene glycol (mono) n-butyl ether

TEGDME Triethylene glycol dimethyl ether

TEGEE Triethylene glycol (mono) ethyl ether

TEGME Triethylene glycol (mono) methyl ether

Propylene-based

1PG2ME 1-Propylene glycol 2-methyl ether

1PG2MEA 1-Propylene glycol 2-methyl ether acetate

2PG1BE 2-Propylene glycol 1-n-butyl ether

2PG1EE 2-Propylene glycol (mono) 1-ethyl ether

2PG1EEA 2-Propylene glycol 1-ethyl ether acetate

2PG1ME 2-Propylene glycol 1-methyl ether

2PG1MEA 2-Propylene glycol 1-methyl ether acetate

2PG1PhE 2-Propylene glycol 1-phenyl ether

DPGBE Dipropylene glycol (mono) n-butyl ether

DPGEE Dipropylene glycol (mono) ethyl ether

DPGME Dipropylene glycol (mono) methyl ether

DPGPE Dipropylene glycol (mono) propyl ether

DPGTBE Dipropylene glycol tert-butyl ether

PGPE Propylene glycol n-propyl ether

PGTBE Propylene glycol tert-butyl ether

TPGBE Tripropylene glycol (mono) n-butyl ether

TPGME Tripropylene glycol (mono) methyl ether

a

 Not a glycol ether, but has similar toxicity 

Chemical Properties

Diethylene glycol monoethyl ether is a colorless, stable, hygroscopic liquid of a mild, pleasant odor. It is completely miscible with water, alcohols, ethers, ketones, aromatic and aliphatic hydrocarbons, and halogenated hydrocarbons. Owing to the fact that it contains an ether-alcohol-hydrocarbon group in the molecule, it has the power to dissolve a wide variety of substances such as oils, fats, waxes, dyes, camphor and natural resins like copal resin, kauri, mastic, rosin, sandarac, shellac, as well as several types of synthetic resins. It is used as a solvent in synthetic resin coating compositions, and in lacquers, where high-boiling solvents are desired.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Usually used as solvent for the polymer electrospinning.

Definition

ChEBI: A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.

Preparation

From ethyl alcohol plus ethylene oxide (Arctander, 1969).

General Description

A colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190°F. Used to make soaps, dyes, and other chemicals.

Air & Water Reactions

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

Reactivity Profile

Mixing 2(2-Ethoxyethoxy)ethanol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum, NFPA 1991.

Health Hazard

None expected.

Fire Hazard

2(2-Ethoxyethoxy)ethanol is combustible.

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: V; Inhibitor of Polymerization: Not pertinent.

Safety Profile

irritation, and unspecified eye effects, cough,

Metabolism

The major part of an administered dose of diethylene glycol monoethyl ether is oxidized in the body or excreted as the glucuronate, administration to rabbits orally or by sc injection being followed by a marked increase in the urinary content of glucuronic acid (Fellows, Luduena & Hanzlik, 1947).

Purification Methods

Ethylene glycol can be removed by extracting 250g in 750mL of *benzene with 5mL portions of water, allowing for phase separation, until successive aqueous portions show the same volume increase. Dry, and free from peroxides, as described for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2393.]

Glycol ethers, with the combination of ether, alcohol and hydrocarbon chain in one molecule, provide versatile solvency characteristics with both polar and non-polar properties. The chemical structure of long hydrocarbon chain resist to solubility in water, while ether or alcohol groups introduce the promoted hydrophilic solubility performance. This surfactant-like structure provides the compatibility between water and a number of organic solvents, and the ability to couple unlike phases. Glycol ethers are characterized by their wide range of hydrophilic/hydrophobic balances. glycol ethers are used as diluents and levelling agents in the manufacture of paints and baking finishes. Glycol ether series are used in the manufacture of nitrocellulose and combination lacquers. They are used as an additive in brake fluid. They are formulated for dying textiles and leathers and for insecticides and herbicides. They provides performance in cleaners products with oil-water dispersions. They are used in printing industries as they have a slow evaporation rate. They are used as a fixative for perfumes, germicides, bactericides, insect repellents and antiseptic. They are used as an additive for jet fuel to prevent ice buildup. Thje term of cellosolve refers to ethylene glycol monoethyl ether or a group of glycol ether solvent as below.

Glycol ether

Cellosolve

CAS RN

Tris(ethylene glycol monobutyl ether) phosphate Tributyl cellosolve phosphate 78-51-3

Ethylene glycol monoethyl ether acrylate Cellosolve acrylate 106-74-1

Ethylene glycol isopropyl ether

Isopropyl cellosolve

109-59-1

Ethylene glycol monomethyl ether

Methyl cellosolve

109-86-4

Ethylene glycol monomethyl ether acetate

Methyl cellosolve acetate

110-49-6

Ethylene glycol dimethyl ether

Dimethyl cellosolve

110-71-4

Ethylene glycol monoethyl ether

Cellosolve

110-80-5

Ethylene glycol monomethyl ether oleate Methyl cellosolve oleate 111-10-4

Ethylene glycol monoethyl ether acetate

Ethyl cellosolve acetate

111-15-9

Ethylene glycol monoallyl ether Allyl cellosolve 111-45-5

Ethylene glycol monobutyl ether

Butyl cellosolve

111-76-2

Diethylene Glycol Monoethyl Ether

Carbitol cellosolve

111-90-0

Ethylene glycol monobutyl ether acetate

Butyl cellosolve acetate

112-07-2

Ethylene glycol monohexyl ether Hexyl cellosolve 112-25-4

Diethylene glycol monobutyl ether

Butyl carbitol

112-34-5

Ethylene glycol dibutyl ether

Dibutyl cellosolve

112-48-1

Bis(ethylene glycol monomethyl ether) phthalate Dimethyl cellosolve phthalate 117-82-8

Bis(ethylene glycol monobutyl ether) phthalate Dibutyl cellosolve phthalate 117-83-9

Ethylene glycol o,p-Dichlorophenyl ether 2,4-Dichlorophenyl cellosolve 120-67-2

Ethylene glycol monophenyl ether

Phenyl cellosolve

122-99-6

Ethylene glycol monomethyl ether acetylricinoleate Methyl cellosolve acetylricinoleate 140-05-6

Bis(ethylene glycol monobutyl ether) adipate Dibutyl cellosolve adipate 141-18-4

Ethylene glycol monobenzyl ether

Benzyl cellosolve

622-08-2

Ethylene glycol diethyl ether

Diethyl cellosolve

629-14-1

Ethylene glycol monopropyl ether

Propyl cellosolve

2807-30-9

Ethylene glycol monomethyl ether acrylate Methyl cellosolve acrylate 3121-61-7

Ethylene glycol butyl ethyl ether Butyl ethyl cellosolve 4413-13-2

Ethylene glycol monoisobutyl ether Isobutyl cellosolve 4439-24-1

Ethyleneglycol 2-ethylbutyl ether Ethylbutyl cellosolve 4468-93-3

Ethylene glycol monobutyl ether acrylate Butyl cellosolve acrylate 7251-90-3

Ethylene glycol monoheptyl ether Heptyl cellosolve 7409-44-1

Ethylene glycol monomethylpentyl ether 2-Methylpentyl cellosolve 10137-96-9

Ethylene glycol o,p-Dichlorophenyl methyl ether 2,4-Dichlorophenyl methyl cellosolve 10140-84-8

Ethylene glycol monobutyl ether phosphate Butyl cellosolve phosphate 14260-98-1

Poly(cellosolve silicate) Poly(cellosolve silicate) 37338-04-8

Ethylene glycol monophenyl ether acrylate Phenyl cellosolve acrylate 48145-04-6

Ethylene glycol monoethyl ether oleate Cellosolve oleate 68134-05-4

Ethylene glycol monobutyl ether sebacate Butyl cellosolve sebacate 68186-66-3

Ethylene glycol monobutyl ether phosphate potassium salt Butyl cellosolve, phosphate potassium salt 68389-63-9

Ethylene glycol monobutyl ether polyphosphate Butyl cellosolve polyphosphate 68514-82-9

Ethylene glycol monohexyl ether phosphate Hexyl cellosolve phosphate 68814-14-2

The term of glyme refers to glycol dimethyl ether. Monoglyme, diglyme, triglyme are ethylene glycol dimethyl ether, Diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether respectively. Ethylene glycol dimethyl ether is readily soluble in water. Glymes, dimethyl ethers, have two terminal methyl groups which offer stability and high solvency. They are used as a higher boiling alternative to diethyl ether or THF. Glyme forms chelate and are useful as bidentate ligands. They are useful as solubilizers and phase transfer catalysts. Glymes offer the property required as an inert reaction medium chemical reaction due to their low chemical reactivity. They are suitable particularly for organometallic and polymerization reactions. Glycol ethers which contain hydroxyl group are also useful chemical intermediate. The hydroxyl group will undergo reaction with aldehydes (or ketones) to produce hemiacetals (or acetals), with epoxides to produce polyether alcohols, with halogenating agents to produce alkoxy alkyl halides, with carboxylic acid compounds or inorganic acids to produce a number of esters.

Glycol dimethyl ether

Glyme

CAS RN

Ethylene glycol dimethyl ether Monoglyme 110-71-4

Diethylene glycol dimethyl ether Diglyme 111-96-6

Diethylene glycol diethyl ether Ethyl diglyme 112-36-7

Triethylene glycol dimethyl ether Triglyme 112-49-2

Diethylene glycol dibutyl ether Butyl Diglyme 112-73-2

Tetraethylene glycol dimethyl ether Tetraglyme 143-24-8

Ethylene glycol diethyl ether Ethyl monoglyme 629-14-1

Polyethylene glycol dibutyl ether Polyglycol BB 31885-97-9

Dipropylene glycol dimethyl ether Proglyme 111109-77-4