109-86-4 Usage
Description
Methoxyethanol is a glycol ether that has been known since the
1920s, but its use significantly increased in the 1970s. Cellosolve
was a solvent product containing glycol ethers and
registered in the 1920s by Carbide and Carbon Chemicals
Corp. Glycol ethers are derived from either ethylene oxide
(E-series) or propylene oxide (p-series) combined with an
alcohol. Methoxyethanol is an E-series glycol ether derived
from methanol and ethylene oxide. Other commonly used
glycol ethers include ethoxyethanol, butoxyethanol, and
methoxypropanol. Use of methoxyethanol has declined in
recent years due to risk management procedures and replacement
by other substances.
Chemical Properties
2-Methoxyethanol is a colorless liquid with a slight ethereal odor. The Odor Threshold is 0.92.3 ppm. It is miscible with water and with aliphatic and aromatic hydrocarbons. It is a solvent for essential oils, lignin, dammar, Elemi Essential Oil, ester gum, kauri, mastic, rosin, sandarac resin, shellac, Zanzibar, nitrocellulose, cellulose acetate, alcohol-soluble dyes and many synthetic resins. Its solvency far cellulose esters is augmented when a ketone or a halogenated hydrocarbon i s added. The uses for 2-Methoxyethanol are as a solvent in quick-drying varnishes and enamels, in conjunction with aliphatic, aromatic and halogenated hydrocarbons, alcohols and ketones; in solvent mixtures and thinners for lacquers and dopes; in the manufacture of synthetic resin plasticizers and as a penetrating and leveling agent in dyeing processes, especially in the dyeing of leather, animal and vegetable fibers. Other uses are as o fixative in perfumes and as a solvent in odorless nail-polish lacquers. 2-Methoxyethanol should not be added to nitrocellulose lacquers containing coumarone resins or ester gum because it will cause incompatibility between these substances.
Physical properties
Colorless liquid with a mild, ether-like odor. Experimentally determined detection and recognition
odor threshold concentrations were <300 μg/m3 (<96 ppbv) and 700 μg/m3 (220 ppbv), respectively
(Hellman and Small, 1974).
Uses
Different sources of media describe the Uses of 109-86-4 differently. You can refer to the following data:
1. 2-Methoxyethanol is considered a non-comedogenic raw material. It is used as a solvent in nail products and as a stabilizer in cosmetic emulsions. It is able to penetrate the skin and may cause skin irritation.
2. The primary use of 2-methoxyethanol is as asolvent for cellulose acetate, certain syntheticand natural resins, and dyes. Other applications are in jet fuel deicing, sealing moisture-proof cellophane, dyeing leather, and use innail polishes, varnishes, and enamels.
3. Solvent for low-viscosity cellulose acetate, natural resins, some synthetic resins and some alcohol-soluble dyes; in dyeing leather, sealing moistureproof cellophane; in nail polishes, quick-drying varnishes and enamels, wood stains. In modified Karl Fischer reagent: Peters, Jungnickel, Anal. Chem. 27, 450 (1955).
Definition
ChEBI: A hydroxyether that is ethanol substituted by a methoxy group at position 2.
General Description
A clear colorless liquid. Flash point of 110°F. Less dense than water. Vapors are heavier than air.
Air & Water Reactions
Flammable. Water soluble.
Reactivity Profile
2-Methoxyethanol is incompatible with oxygen and strong oxidizing agents. Contact with bases may result in decomposition. Incompatible with acid chlorides and acid anhydrides. . 2-Methoxyethanol forms explosive peroxides.
Hazard
Toxic by ingestion and inhalation. Moderate fire risk. Toxic by skin absorption. Questionable
carcinogen.
Health Hazard
2-Methoxyethanol is a teratogen and a chronic inhalation toxicant. The target organs are blood, kidney,and the central nervous system. In addi tion to inhalation, the other routes of expo sure are absorption through the skin, and ingestion. Animal studies indicated that over-exposure to this compound produced anemia, hematuria, and damage to the testes.In humans, inhalation of EGME vapors cancause headache, drowsiness, weakness, irrita tion of the eyes, ataxia, and tremor. The acuteinhalation toxicity, however, is low and anytoxic effect may be felt at a concentration ofabout 25–30 ppm in air
The oral and dermal toxicities of thiscompound in test animals were found to belower than the inhalation toxicity. Ingestioncan produce an anesthetic effect and in alarge dosage can be fatal. An oral intake ofabout 200 mL may cause death to humans.
LC50 value (mice): 1480 ppm/7 h,
LD50 value (rabbits): 890 mg/kg
EGME is a teratogen exhibiting fetotoxi city, affecting the fertility and the litter size,and causing developmental abnormalities inthe urogenital and musculoskeletal systemsin test animals.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Flammable
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.
Safety Profile
Moderately toxic to humans by ingestion. Moderately toxic experimentally by ingestion, inhalation, shin contact, intraperitoneal, and intravenous routes. Human systemic effects by inhalation: change in motor activity, tremors, and convulsions. Experimental teratogenic and reproductive effects. A skin and eye irritant. Mutation data reported. When used under conditions that do not require the application of heat, thts material probably presents little hazard to health. However, in the manufacture of fused collars which require pressing with a hot iron, cases have been reported showing disturbance of the hemopoietic system with or without neurologcal signs and symptoms. The blood picture may resemble that produced by exposure to benzene. Two cases reported had severe aplastic anemia with tremors and marked mental dullness. The persons affected had been exposed to vapors of methyl "Cellosolve," ethanol, methanol, ethyl acetate, and petroleum naphtha. flame. A moderate explosion hazard. Can react with oxidizing materials to form explosive peroxides. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS. Flammable liquid when exposed to heat or
Potential Exposure
2-Methoxyethanol is used as a jet fuel additive; solvent for protective coating; and in chemical synthesis. Ethylene glycol ethers are used as solvents for resins used in the electronics industry, lacquers, paints, varnishes, gum, perfume; dyes and inks; and as a constituent of painting pastes, cleaning compounds; liquid soaps; cosmetics, nitrocellulose, and hydraulic fluids.
Carcinogenicity
There are no experimental carcinogenicity
or cancer epidemiology data relating to this
chemical , but some short-term test data are available
and are summarized in the section on genetic and related
cellular effects.
Environmental fate
Photolytic. Grosjean (1997) reported an atmospheric rate constant of 1.25 x 10-11
cm3/molecule?sec at 298 K for the reaction of methyl cellosolve and OH radicals. Based on an
atmospheric OH concentration of 1.0 x 106 molecule/cm3, the reported half-life of methyl
cellosolve is 0.64 d (Grosjean, 1997).
Chemical/Physical. At an influent concentration of 1,000 mg/L, treatment with GAC resulted in
an effluent concentration of 342 mg/L. The adsorbability of the carbon used was 132 mg/g carbon
(Guisti et al., 1974).
Shipping
UN1188 Ethylene glycol monomethyl ether,
Hazard Class: 3; Labels: 3-Flammable liquid
Purification Methods
Peroxides can be removed by refluxing with stannous chloride or by filtration under slight pressure through a column of activated alumina. 2-Methoxyethanol can be dried with K2CO3, CaSO4, MgSO4 or silica gel, then distilled from sodium. Aliphatic ketones (and water) can be removed by making the solvent 0.1% in 2,4-dinitrophenylhydrazine and allowing to stand overnight with silica gel before fractionally distilling. [Beilstein 1 IV 2375.]
Toxicity evaluation
High acute doses of methoxyethanol have a sedative and
hypnotic effect. Kidney and lung damages, accompanied by
hemoglobinuria, follow exposures to high doses. Toxicity is
attributed to the active metabolites: methoxyacetaldehyde and
methoxyacetate. In vitro studies with radiolabeled methoxyethanol
indicate that formation of methoxyacetyl-coenzyme A
may lead to the formation of methoxyacetyl derivatives of
Krebs cycle intermediates. Methoxyacetate produces the same
testicular lesions in rodents as does the parent compound,
although the immunosuppression elicited by methoxyethanol
exposure may depend on the putative metabolite, methoxyacetaldehyde.
In both the testicular lesion and the immune
suppression, some data suggest that the pattern of cell death
termed ‘apoptosis’ may be stimulated. Methoxyacetate stimulates
synthesis of progesterone by luteal cells in culture. This
disturbance of luteal function may be related to the prolongation
of gestation in rodents. Teratogenicity appears to be
related to interference by methoxyethanol, or its metabolites,
with one carbon metabolism in the synthesis of nucleotide
precursors, and can be relieved by administration of other
substrates, such as serine and glycine, which also provide
substrates for nucleotide synthesis. It has also been suggested
that toxicity is mediated through inhibition of flavoprotein
dehydrogenase-catalyzed reactions.
Incompatibilities
Vapors may form explosive mixture
with air. Heat or oxidizers may cause the formation of
unstable peroxides. Attacks many metals. Strong oxidizers
may cause fire and explosions. Strong bases cause decomposition and the formation of toxic gas. Attacks some plastics, rubber and coatings. May accumulate static electrical
charges, and may cause ignition of its vapors.
Waste Disposal
Concentrated waste containing no peroxides: discharge liquid at a controlled rate near
a pilot flame. Concentrated waste containing peroxides:
perforation of a container of the waste from a safe distance
followed by open burning.
Check Digit Verification of cas no
The CAS Registry Mumber 109-86-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 109-86:
(5*1)+(4*0)+(3*9)+(2*8)+(1*6)=54
54 % 10 = 4
So 109-86-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3
109-86-4Relevant articles and documents
Participation by Ether Oxygen (RO-3) in the Hydrolysis of Sulfonate Esters of 2-Methoxyethanol and 2-Methoxy-2-methyl-1-propanol. Implications Regarding the Nonlinear Ethanol-Trifluoroethanol Plot for Mustard Chlorohydrin
McManus, S. P.,Karman, R. M.,Sedaghat-Herati, R.,Neamati-Mazraeh, N.,Hovanes, B. A.,et al.
, p. 2518 - 2522 (1987)
The lack of scrambling with deuterium-labeled reactants, a nonlinear ethanol-trifluoroethanol plot, and rate acceleration by edded thiourea are used to show that sulfonate esters of methoxyethanol (MeOCH2CH2OH) undergo solvent-assisted displacement in a variety of solvents; neighboring group participation by ether oxygen (RO-3 participation) does not occur.This conclusion is in accord with predictions of rate based on the Taft treatment of substituent effects.On the other hand, the branched derivative MeOCMe2CH2OBs reacts with concerted RO-3 participation to give completely rearranged product.It solvolysis rate is insensitive to added thiourea, the Taft treatment predicts modest anchimeric assistance, and a linear ethanol-trifluoroethanol plot is observed.We discuss the implications of these results relative to the previously observed nonlinear plot for mustard chlorohydrin.
Fleming,Bolker
, p. 888,889, 892 (1974)
Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles
Chen, Xin,Brauman, John I.
, p. 15038 - 15046 (2008)
The relationship between nucleophilicity and the structure/environment of the nucleophile is of fundamental importance in organic chemistry. In this work, we have measured nucleophilicities of a series of substituted alkoxides in the gas phase. The functional group substitutions affect the nucleophiles through ion-dipole, ion-induced dipole interactions and through hydrogen bonding whenever structurally possible. This set of alkoxides serves as an ideal model system for studying nucleophiles under microsolvation settings. Marcus theory was applied to analyze the results. Using Marcus theory, we separate nucleophilicity into two independent components, an intrinsic nucleophilicity and a thermodynamic driving force determined solely by the overall reaction exothermicity. It is found that the apparent nucleophilicities of the substituted alkoxides are always much lower than those of the unsubstituted ones. However, ion-dipole, ion-induced dipole interactions, by themselves, do not significantly affect the intrinsic nucleophilicity; the decrease in the apparent nucleophilicity results from a weaker thermodynamic driving force. On the other hand, hydrogen bonding not only stabilizes the nucleophile but also increases the intrinsic barrier height by 3 to ～4 kcal mol-1. In this regard, the hydrogen bond is not acting as a perturbation in the sense of an external dipole but more directly affects the electronic structure and reactivity of the nucleophilic alkoxide. This finding offers a deeper insight into the solvation effect on nucleophilicity, such as the remarkably lower reactivities in nucleophilic substitution reactions in protic solvents than in aprotic solvents.
Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids
Saito, Susumu,Wen, Ke,Yoshioka, Shota
, p. 1510 - 1524 (2021/06/18)
Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.
Monomeric alkoxide and alkylcarbonate complexes of nickel and palladium stabilized with the iPrPCP pincer ligand: A model for the catalytic carboxylation of alcohols to alkyl carbonates
Martínez-Prieto, Luis M.,Palma, Pilar,Cámpora, Juan
, p. 1351 - 1366 (2019/01/30)
Monomeric alkoxo complexes of the type [(iPrPCP)M-OR] (M = Ni or Pd; R = Me, Et, CH2CH2OH; iPrPCP = 2,6-bis(diisopropylphosphino)phenyl) react rapidly with CO2 to afford the corresponding alkylcarbonates [(iPrPCP)M-OCOOR]. We have investigated the reactions of these compounds as models for key steps of catalytic synthesis of organic carbonates from alcohols and CO2. The MOCO-OR linkage is kinetically labile, and readily exchanges the OR group with water or other alcohols (R′OH), to afford equilibrium mixtures containing ROH and [(iPrPCP)M-OCOOH] (bicarbonate) or [(iPrPCP)M-OCOOR′], respectively. However, [(iPrPCP)M-OCOOR] complexes are thermally stable and remain indefinitely stable in solution when these are kept in sealed vessels. The constants for the exchange equilibria have been interpreted, showing that CO2 insertion into M-O bonds is thermodynamically more favorable for M-OR than for M-OH. Alkylcarbonate complexes [(iPrPCP)M-OCOOR] fail to undergo nucleophilic attack by ROH to yield organic carbonates ROCOOR, either intermolecularly (using neat ROH solvent) or in intramolecular fashion (e.g., [(iPrPCP)M-OCOOCH2CH2OH]). In contrast, [(iPrPCP)M-OCOOMe] complexes react with a variety of electrophilic methylating reagents (MeX) to afford dimethylcarbonate and [(iPrPCP)M-X]. The reaction rates increase in the order X = OTs IMe ? OTf and Ni Pd. These findings suggest that a suitable catalyst design should combine basic and electrophilic alcohol activation sites in order to perform alkyl carbonate syntheses via direct alcohol carboxylation.
Bipyridine ligand ruthenium complex is carried and its preparation method and application (by machine translation)
-
Paragraph 0098; 0099; 0100; 0102; 0104, (2017/04/28)
The invention relates to a novel bipyridine is carried ligand ruthenium complex and its preparation method and in the ester compound hydrogenation is the application of the alcohol compound in the reaction. The use of the bipyridine ligand ruthenium complex catalytic hydrogenation is carried ester compound alcohol compound method is characterized in that: in order to ester compound material in an amount of 0.001 - 0.3 μM % bipyridyl is carried ligand ruthenium complex as catalyst, adding esters compound material in an amount of 1 - 10mol % alkali, in the 25 - 100 °C and 1 - 10MPa hydrogen pressure catalytic hydrogenation under the conditions of ester compound corresponding alcohol compound. The invention of the bipyridine ligand ruthenium complex is carried is convenient to prepare, stable structure, in the ester compound in hydrogenation reaction exhibits excellent catalytic activity. This invention has overcome the ester compound or a non-homogeneous phase catalytic hydrogenation system requires high-temperature high-pressure reaction conditions and high defects of the catalyst amount, catalyst consumption is small, mild reaction conditions, the reaction selectivity is good, improves the economy and the safety of the production system. (by machine translation)
