Sodium methoxide

Sodium methoxide - Names and Identifiers

Name	Sodium methoxide
Synonyms	NA 1289 feldalatnm methoxysodium metilatosodico Sodiummethoxide Sodium methylate Sodium methoxide methylatedesodium sodium methanolate Methanol,sodiumsalt Methanol,sodium salt Methanol, sodium salt methylatedesodium(french) sodium methylate solution Sodium methylate-methanol solution Sodium methoxide, anhydrous powder, pure Sodium methoxide, titrant, (0.5 M in methanol), pure
CAS	124-41-4
EINECS	204-699-5
InChI	InChI=1/CH3NaO/c1-2;/h2H,1H3;/q;+1
InChIKey	WQDUMFSSJAZKTM-UHFFFAOYSA-N

Sodium methoxide - Physico-chemical Properties

Molecular Formula	CH3NaO
Molar Mass	54.02
Density	0.97g/mLat 20°C
Melting Point	-98 °C
Boling Point	65 °C
Flash Point	11 °C
Water Solubility	reacts
Solubility	Miscible with ethanol, methanol, fats and esters.Immiscible with hydrocarbons and organic solvents.
Vapor Presure	50 mm Hg ( 20 °C)
Vapor Density	1.1 (vs air)
Appearance	Powder
Specific Gravity	0.945
Color	, clarity of solution to pass
Exposure Limit	ACGIH: Ceiling 2 mg/m3OSHA: TWA 2 mg/m3NIOSH: IDLH 10 mg/m3; Ceiling 2 mg/m3
Merck	14,8643
BRN	3592982
pKa	15.17[at 20 ℃]
Storage Condition	Store at +5°C to +30°C.
Stability	Stability Highly flammable. Reacts violently with water. Keep container dry. Incompatible with water, acids, chlorinated solvents.
Sensitive	8: reacts rapidly with moisture, water, protic solvents
Explosive Limit	36%
Refractive Index	1.3700
Physical and Chemical Properties	Character: colorless amorphous fine powder. soluble in methanol and ethanol.
Use	Mainly used as raw materials of medicine and pesticide, also used in dye and chemical fiber industry

Sodium methoxide - Risk and Safety

Risk Codes	R11 - Highly Flammable R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R34 - Causes burns R39/23/24/25 - R36/38 - Irritating to eyes and skin. R14 - Reacts violently with water R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed R10 - Flammable
Safety Description	S8 - Keep container dry. S16 - Keep away from sources of ignition. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S7 - Keep container tightly closed. S36/37 - Wear suitable protective clothing and gloves. S7/8 - S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
UN IDs	UN 1431 4.2/PG 2
WGK Germany	1
RTECS	PC3570000
FLUKA BRAND F CODES	9-21
TSCA	Yes
HS Code	29051900
Hazard Class	4.2
Packing Group	II
Toxicity	LD50 orally in Rabbit: 2037 mg/kg LD50 dermal Rat > 2000 mg/kg

Sodium methoxide - Upstream Downstream Industry

Raw Materials	Benzene Methyl alcohol Sodium Sodium hydroxide Sodium hydroxide
Downstream Products	2,4,6-Trimethoxybenzaldehyde Formic acid N,N-Dimethylformamide 3,4,5-Trimethoxybenzaldehyde 4-Chloro-2,6-diaminopyrimidine 4,6-Dihydroxypyrimidine 1,1-Cyclobutanedicarboxylic acid Cyclopropylamine 2-Nitroanisole Diphacinone Sodium

Sodium methoxide - Nature

Open Data Verified Data

colorless amorphous fine powder, sensitive to oxygen, flammable. Soluble in methanol, ethanol, water decomposition into methanol and sodium hydroxide, decomposition in air above 126.6 ℃.

Last Update：2024-01-02 23:10:35

Sodium methoxide - Preparation Method

Open Data Verified Data

sodium hydroxide and methanol in 85~100 deg C continuous reaction dehydration obtained.

Last Update：2022-01-01 10:15:45

Sodium methoxide - Use

Open Data Verified Data

mainly used as condensation agent and strong basic catalyst, and methoxylating agent for the preparation of vitamin Bi and A, sulfadiazine and other drugs. Small amounts are used in the production of pesticides. It is also useful as a catalyst for the treatment of edible fats and edible oils, in particular lard. It can also be used as an analytical reagent.

Last Update：2022-01-01 10:15:45

Sodium methoxide - Safety

Open Data Verified Data

The methanol in the sodium methoxide solution is highly toxic. Sodium methoxide is highly corrosive and can irritate the eyes and nose. Inhalation of high concentrations of steam will cause strong stimulation, severe cases will affect breathing, resulting in dizziness, can be restored by the rescue. But prolonged inhalation of high concentrations of steam, can cause pulmonary edema and death. Inhalation of vapors and contact with the skin should be prevented. In addition, the production process should pay attention to safety measures, the equipment should be sealed, the operator should wear protective equipment.
sealed with iron drum, 200kg per barrel, stored in a cool, ventilated, dry place, fire, heat, sunscreen. According to the provisions of flammable chemicals storage and transportation.

Last Update：2022-01-01 10:15:45

Sodium methoxide - Reference Information

update date:	2022/11/11 19:50:47
LogP	-0.77 at 25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
Overview	Sodium methoxide is also called sodium methoxide. It is a kind of alkoxide produced by methanol, the chemical formula is CH3ONa, which is a strong base commonly used in organic synthesis. Sodium methoxide is usually stored in solutions of alcohol solvents such as methanol and ethanol. Dissolved in ether to generate suspension, sensitive to moisture, decomposed into methanol and sodium hydroxide when exposed to water: CH3ONa + H2O → CH3OH + NaOH sodium methoxide products have two forms: solid and liquid. The solid is pure sodium methoxide, the liquid is methanol solution of sodium methoxide, and the content of sodium methoxide is 27.5 ~ 31%. Liquid sodium methoxide is colorless or yellowish viscous liquid, sensitive to oxygen, flammable and explosive. Very easy to absorb moisture. Soluble in methanol and ethanol, decompose into methanol and sodium hydroxide in water, and decompose in air above 126.6 ℃. Insoluble in benzene and toluene. It is strongly irritating and extremely corrosive. Used as a condensing agent and strong basic catalyst, and methoxy agent for the preparation of vitamin B1 and A, sulfadiazine and other drugs. A small amount is used for pesticide production. It can also be used as a catalyst for the treatment of edible fats and edible oils (especially lard). It can also be used as an analytical reagent. Solid sodium methoxide is colorless amorphous powder, sensitive to oxygen, flammable, soluble in methanol and ethanol, decomposed into methanol and sodium hydroxide when exposed to water, and decomposed in air above 126.6 ℃. Mainly used in the production of sulfonamides, VB6 and VA, sodium methoxide is also a catalyst for organic synthesis, used in pesticide production and oil processing industry. Solid sodium methoxide and sodium methoxide methanol solution
sodium alkoxide	sodium alkoxide is made by adding metallic sodium to the corresponding alcohol. it is a white powder with strong hygroscopicity, which is decomposed into alcohol and sodium hydroxide when exposed to water. Widely used in organic synthesis reactions. In particular, sodium ethoxide is used as a condensing agent. Sodium methoxide is also a commonly used catalyst. Because its hygroscopicity is not as strong as sodium ethoxide and its properties are more stable, it is easy to control its quality during preparation. Sodium methoxide and sodium ethoxide are two kinds of sodium alkoxide commonly used in industry at present, both of which are used for condensation reactants and esterifying agents (such as condensation and esterification of ethyl acetate, acetylacetone, methyl formate, ethyl malonate, barbiturates, amino acid drugs, glycerides, etc.); pharmaceutical raw materials and reactants (barbituric acid and its derivatives, sulfonamides, vitamins, antipyrine, chloroquine, amino acids, adipine, butazone preparations, etc.); dyes (Hansa yellow, methyl violet, tartrazine, toluidine, etc.); spices (pseudoionone, cyclamen aldehyde, indole, etc.); oil modification, fatty acid ester preparation, non-ionic surfactant preparation, pesticide preparation, etc. Sodium methoxide is used as a catalyst for the transesterification reaction of oils and fats. The transesterification reaction can improve the physical properties of oils and fats, such as improving the shape retention and ductility of oils and fats. Sodium methoxide is prepared by the reaction of methanol and sodium metal in the laboratory, and sodium methoxide is prepared by the reaction of methanol and sodium hydroxide in industry. The relevant chemical reaction formula is as follows: Reference: Editor-in-Chief Gao Hongbin. Practical Dictionary of Organic Chemistry. Beijing: Higher Education Press. 1997. Page 710.
sodium methoxide produced by alkali process	sodium methoxide produced by alkali process is obtained by the action of methanol and sodium hydroxide. its reaction formula is as follows: ch3oh + naoh -- ch3ona + h2o (1) the configuration of methanol alkali solution breaks the solid sodium hydroxide, adds it to the alkali solution pot containing methanol (99.8%) in proportion, and starts the liquid alkali circulation pump, control the temperature below 70 ℃ to dissolve sodium hydroxide. when the content reaches 20% ~ 23%, cool down to 40 ℃, drive into the sedimentation tank and let stand for 1 2 h for standby. (2) preparation of sodium methoxide is heated by water vapor to the interlayer of the vaporization pot and the reaction tower, the temperature is controlled at 85~100 ℃, anhydrous methanol is added to the vaporization pot at a flow rate of 180L/h, and methanol lye is added from the top of the reaction tower at a flow rate of 25 kg/h, and the methanol gas containing 2% water generated by the reaction is steamed from the top of the reaction tower , enter the purification distillation tower to separate water and recycle anhydrous methanol. The temperature of the bottom of the reaction tower (I. e. vaporization pot) is controlled at 65~70 ℃, and the material containing sodium methoxide is 27% ~ 31%, and the free alkali is less than 1%, thus the product is obtained, and the yield is 86% (calculated by sodium hydroxide). the consumption quota of this process is as follows: methanol (95%)973 kg/t, sodium hydroxide (99.5%)209 kg/t.
sodium methoxide produced by sodium process	sodium methoxide methanol solution was produced by chemical reaction using batch production process with metal sodium and methanol as raw materials. The reaction formula is as follows: 2ch3oh 2na- -2ch3onah2 this production process is mainly divided into four parts: 1, feeding process, conveying industrial methanol to methanol metering tank by pump, putting 120kg of metal sodium into reaction kettle 2, nitrogen replacement process, closing feeding and releasing empty valve, introducing nitrogen into reaction kettle, making pressure gauge index reach 0.1MPa, open the vent valve to relieve pressure, repeat it for three times and then return back. the vent valve remains open continue to supply nitrogen 3. in the reaction process, pass the condenser into cooling water, immediately add methanol through the methanol metering tank (pay attention to the methanol addition speed), perform reverse and stop introducing nitrogen after 5~10min of reaction. Continue to add methanol, add 820kg of methanol within 2~3h, close the methanol feeding valve, continue to react 2~3h until no bubbles are generated in the reaction liquid 4. in the blending process, add the product to the blending storage tank, sample and analyze, reconcile to the required concentration, and pack into barrels.
comparison between alkali production process and sodium production process	sodium methoxide obtained by sodium method is higher and more stable and reliable than sodium methoxide obtained by alkali method, with low free alkali. sodium methoxide can remove a large amount of "alcohol" and other impurities in sodium during the reaction, and the content of Na2CO3 in sodium methoxide obtained by sodium method is lower than that in sodium methoxide obtained by alkali method, can improve the product quality and yield of users.
solution reference quality standard	project index colorless to pale yellow viscous liquid content (total alkali) 29.5% ~ 31.0% sodium methoxide (NaOCH3) 28.9-31.0% sodium hydroxide (NaOH) ≤ 0.5% sodium carbonate (Na2CO3) ≤ 0.1% moisture (H2O) ≤ 0.2% methanol 69.0-70.7%
How to separate sodium hydroxide and sodium methoxide solids	1. Dissolve in water (sodium alkoxide reacts violently with water, production of alcohol and sodium hydroxide) 2. Distillation (separation of alcohol) 3. Evaporation (separation of sodium hydroxide) 4. Try to make the alcohol into an anhydrous state (repeated distillation) 5. Add sodium to form sodium alcohol 6. Evaporate the alcohol to obtain the solid of sodium alcohol. (Avoid contact with air when steaming, if it is in contact with air or does not wait for evaporation to dry and cooling to take it off, the state of sodium alkoxide precipitated by is not good. if it is done well, it will be white. if it is not done well, it will be yellowish brown, but it will not have much effect. it is very easy to do)
production process	solid sodium hydroxide and methanol are prepared according to a certain proportion, stirred and dissolved, precipitated and clarified, solid impurities are removed, the clear liquid is pumped into the top of the reaction dehydration tower, refined methanol steam is added from the bottom of the tower to continuously react and dehydrate in the tower, and the product is obtained from the bottom of the tower. After the aqueous methanol vapor comes out from the top of the tower, it enters the rectification system for refining, and the anhydrous methanol is returned to use.
identification test	can react with oxygen and carbon dioxide. Decomposed in water, the sodium test (IT-28) of this solution was positive. Take 0.1ml of 5% dilute sulfuric acid and 0.2ml of potassium permanganate test solution (TS-193), add 1 drop of 1% sample aqueous solution, add 0.2ml of 25% sodium sulfite test solution and 3ml of sulfuric acid after 5min, and add 0.2ml of chromic acid test solution (TS-l66). The solution is purplish red to purple.
content analysis	in the following content analysis and quality index analysis, the sample should be exposed to air as much as possible, and it is best to carry out nitrogen sealing. Content analysis and sodium carbonate and sodium hydroxide analysis sample preparation select two weighing bottles with a diameter of about 30mm, a height of about 80mm and a constant weight, and after the samples are almost filled, carefully cover and weigh them, which should be 12~15g. Determination of alkalinity of sodium methoxide (CH3ONa), remove the cap of a sample bottle, and quickly slide the sample bottle into a 500ml conical flask along the edge wall. The bottle contains 200ml of decarbon dioxide ice water, which should prevent splashing. Immediately plug the flask with a rubber stopper and shake until the sample dissolves. The sample liquid was washed into a 250ml volumetric flask with decarbon dioxide water and diluted to a near scale. Let the solution reach room temperature, then add water to fix the volume and mix. Take 50.0ml of this solution and move it into a 500ml conical flask with glass plug, add 150ml of decarbon dioxide water and 5ml of barium chloride test solution (TS-37), add plug and mix, and let stand for 5min. Add 3 drops of phenolphthalein test solution (TS-167) and titrate with 1mol/L hydrochloric acid until pink disappears. The titrated solution is retained for the determination of sodium carbonate. The percentage content a of sodium methoxide alkalinity is calculated according to the following formula: A =(V1 × c × 5.403)/(W× 0.2) where V1 -- the volume of hydrochloric acid consumed, m1; C- concentration of hydrochloric acid consumed, mol/L; W-sample quality, g. Determination of Sodium Carbonate Add 2 drops of methyl orange test solution (TS-148) to the above-mentioned retained titrated solution, and then continue to titrate with 1mol/L hydrochloric acid to long-lasting pink. The percentage content of sodium carbonate (Na2CO3) is calculated according to the following formula: Na2CO3 content (%)=(V2 × cf× 5.30)/(W× 0.2) where V2 -- the volume of hydrochloric acid consumed for the second titration, ml; C and W-meaning the same as the alkalinity determination of sodium methoxide above.) For the determination of sodium hydroxide, please refer to Carl in GT-32. The Fischer titration method is carried out, or the following method is used for determination. Solution A takes 400ml of colorless pyridine with water content not exceeding 0.05%, adds it to a 500ml flat-bottomed flask, plugs a double-hole rubber stopper, plugs a 7mm glass tube in one hole, and extends down to the vicinity of the bottom of the flask. An exhaust pipe is installed in the other hole, which is equipped with a rubber tube and clamped with a clamp. Put the flask into a cooling tank with circulating water. Dry sulfur dioxide (80 s 0.5)g is passed from an upright steel cylinder. Before the air valve is closed, the exhaust pipe should be loosened. Move the solution into a dry bottle with glass stopper, add 400ml of anhydrous methanol, mix and store in a dark place. Solution B is added to a dry glass stopper bottle containing 900ml of anhydrous methanol, 75g of iodine is added, shaken until iodine is dissolved, and then transferred to an automatic burette protected by a drying tube. Calibration of solution B: Measure A15ml of solution with a dry measuring cylinder, move it into a dry 125ml iodine measuring flask, and titrate to brown with solution B. Immediately plug the iodine measuring bottle to prevent moisture absorption and disappearance of the end point. The amount of solution B added will not be calculated. Take 50ml of standard methanol/aqueous solution containing 1.0mg of water per ml of methanol, add to the iodine volumetric flask, and immediately titrate with solution B to the same brownish end point. Calculate the equivalent factor F: the mass of water in solution B per milliliter (mg). This calibration work needs to be carried out every day. Two 120ml wide-mouth bottles with only plastic screw caps are selected for operation. They are first washed with hydrochloric acid, then rinsed with water, and finally washed with isopropanol and dried by airflow. Another hole is drilled in a spare plastic screw cap so that it can be connected to the tip of the automatic burette. Put short magnetic stirring rods in each bottle and pass in dry nitrogen to repel carbon dioxide. Add A30ml of solution and 1,5ml of anhydrous methanol to each bottle, and screw on the lid. Take a spare cover instead of one, insert the tip of the burette and start stirring. Titrate with solution B to the above brownish yellow and maintain for at least 5min. Put on the original lid. Titrate another solution in the same way. Remove the caps of the two bottles, weigh 2g of the sample accurately from the above preparation sample by decrement method in one of the bottles, and add it. Re-close the lid on the two bottles. Titrate the sample solution (the first bottle) to brown with solution B, and then titrate the blank sample (the second bottle). The percentage content a of water in the sample is calculated according to the following formula: A(%)=(F × V × 100)/(w × 1000) where f-equivalent factor of solution B, mg/ml; Y-net volume of solution B consumed by the sample, ml; W-sample quality, g. The percentage content a of sodium hydroxide is calculated by the following formula: A(%)= 2.222 ×[%H2O-(%NaCO3 × 0.170)] finally, the percentage content (B) of sodium methoxide is calculated by the following formula: B(%)=%AO(%NaOH × 1.350) arsenic is taken from 1g of sample, carefully dissolved in 10ml of water, neutralized with dilute sulfuric acid test solution (TS-241) until litmus test paper is neutral, dilute with water to 35ml as sample solution, and then measure according to GT-3 method. Take 800mg of heavy metal sample, carefully dissolve it in 10ml of water, add 10ml of dilute hydrochloric acid test solution (TS-117), and heat it to boiling. Cool and dilute with water to 25ml, which is used as sample liquid and determined by GT-16 method. The amount of lead ion (Pb) in the control solution (solution A) was 20 μg. Take 1g of lead sample, carefully dissolve it in 10ml of water, add 10ml of dilute hydrochloric acid test solution (TS-117), and heat it to boiling. Cool and dilute with water to 25ml, which is used as sample liquid and determined by GT-18 method. The amount of lead ion (Pb) in the control solution was 10 μg. Take 2g of mercury sample, put it into a small beaker, carefully dissolve it in 10ml of water, add 2 drops of phenolphthalein test solution (TS-167), and slowly neutralize it with 20% dilute sulfuric acid solution under constant stirring. Add 1:5 dilute sulfuric acid solution 1ml and 1:25 potassium permanganate solution 1m1 and mix. This is used as sample liquid and then measured according to GT-22 method.
Use	Used as an alkaline condensing agent and catalyst in organic synthesis, used for the synthesis of fragrances, dyes, etc., and is the raw material of vitamin B1, A and sulfadiazine Used as a condensing agent in organic synthesis, used as a catalyst in the treatment of edible oils and fats, it is also an important raw material for the synthesis of sulfamidine, sulfamethoxazole, sulfamethoxazole synergist and other drugs It is mainly used as a raw material for medicines and pesticides, and is also used in the dye and chemical fiber industry Fat transesterification catalyst. In order to change the fat structure and make it suitable for margarine, etc. It must be removed from the final food. It is mainly used as a condensing agent, a strong basic catalyst and a methoxylating agent, used to produce vitamin B1, A, sulfadiazine and other drugs, and a small amount of it is used in pesticide production. It is also used as a catalyst for the treatment of edible fats and edible oils (especially for the treatment of lard). It is also used as an analytical reagent. Widely used in spices, dyes and other industries. It is mainly used as a condensing agent and a strong basic catalyst, and a methoxy agent for the preparation of vitamin B1 and A, sulfadiazine and other drugs. A small amount is used for pesticide production. It can also be used as a catalyst for the treatment of edible fats and edible oils (especially lard). It can also be used as an analytical reagent. Used as a condensing agent for organic synthesis
production method	add xylene (moisture <0.05) and metal sodium to the reaction pot, heat to 130-140 ℃, keep the temperature for 1h, stop heating, quickly stir for 1h, cool to 50 ℃ with cooling, start dropping anhydrous methanol (moisture <0.1%), and appropriately add anhydrous xylene, dropping acceleration depends on methanol reflux and hydrogen release. After dropping, heating and refluxing for 4 hours, cooling to room temperature to obtain slurry sodium methoxide, distillation under reduced pressure to recover xylene, vacuum drying for 4 hours, nitrogen filling and cooling to obtain finished sodium methoxide. The yield is over 90%. It can also be prepared by continuous reaction and dehydration of sodium hydroxide and methanol at 85-100°C. It is obtained by the reaction of sodium hydroxide and methanol in benzene.
category	corroded articles
explosive hazard characteristics	its hydrolysate caustic soda is corrosive to skin and cornea
flammability hazard characteristics	decomposes methanol and sodium hydroxide when exposed to water, flammable
storage and transportation characteristics	warehouse ventilation and low temperature drying; Store separately from acids and oxidants.
fire extinguishing agent	foam, carbon dioxide, sand
auto-ignition temperature	878 °F
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)