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Sodium N-(hydroxymethyl)glycinate(SHMG) is a chemical substance with the molecular formula C3H8NNaO3 and CAS 70161-44-3. Its physical state is manifested as a 50% sodium hydroxymethylglycinate aqueous solution with an appropriate pH value, which is due to the intermolecular interactions and crystal structure that give it this liquid characteristic. In addition, due to the presence of hydroxyl and amino groups in its molecules, it has strong hygroscopicity and can absorb moisture from the air. Therefore, it is necessary to pay attention to humidity conditions during storage and use. It has good water solubility and can dissolve in water at room temperature, forming a transparent solution. At the same time, it can also dissolve in organic solvents such as alcohols and ethers, showing good solubility. This provides convenience for its widespread use in practical applications. Conductivity is the ability of a substance to transfer electric current. This compound is an ionic compound with good conductivity.
Its conductivity is related to the concentration, temperature, and applied voltage of the solution. In practical applications, its conductivity can be utilized for electrochemical reactions and electroplating operations. It can also be applied in fields such as agriculture, environmental protection, and water treatment. For example, it can serve as a synergist for pesticides, enhancing their efficacy; It can also be used for sewage treatment and exhaust gas treatment in environmental engineering; In addition, due to its good water solubility and stability, it can also be used as a water treatment agent for the treatment of industrial circulating water and boiler water. Can be used for hair, skincare products, and other parts. It can also be used in alkaline cosmetics and detergents such as shampoo, perm, dye, conditioner, soap, shampoo, etc. The general addition amount is 0.2-0.6%. Features: This product remains stable in solutions with a pH of 3-12, making it suitable for use in highly alkaline cosmetics and laundry products.
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C.F |
C3H6NNaO3 |
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E.M |
293 |
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M.W |
293 |
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m/z |
127 (100.0%), 128 (3.2%) |
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E.A |
C, 28.36; H, 4.76; N, 11.02; Na, 18.09; O, 37.77 |
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Stability |
incompatible with strong oxidizing agents |
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Dangerous goods sign |
Xn |
|
Hazard category code |
22-36 |
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Safety instructions |
26 |
|
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Sodium N-(hydroxymethyl)glycinate (chemical formula: C3H6NNaO3, CAS number: 70161-44-3) is a hydroxymethylated derivative with glycine as the backbone. The hydroxymethyl (-CH₂OH) and sodium carboxylate groups (- COONa) in its molecular structure endow it with unique chemical activity. As a broad-spectrum preservative, metal chelating agent, and functional intermediate, this compound has demonstrated extensive application value in various fields such as daily chemical, food, medicine, papermaking, textile, and water treatment.
1. Alkaline cosmetics anti-corrosion system
Sodium N-hydroxymethylglycinate is a widely used preservative in alkaline cosmetics (pH 3-12), with a recommended dosage of 0.2% -0.6% (based on a 50% aqueous solution). In strong alkaline products such as shampoo, perm, hair dye, conditioner, soap, and shampoo, this compound can effectively inhibit the growth of Gram positive bacteria, Gram negative bacteria, yeast, and mold, extending the shelf life of the product. For example, in shampoo containing surfactants, 0.5% sodium hydroxymethylglycinate can significantly reduce the risk of microbial contamination while maintaining formula stability.
Mechanism of action: Hydroxymethyl groups inhibit protein synthesis by disrupting the structure of microbial cell membranes; The sodium carboxylate group enhances its compatibility with alkaline components, avoiding precipitation or stratification. Experiments have shown that the preservative has a 99.7% inhibition rate on Escherichia coli within 28 days in a shampoo system with a pH of 10.
2. Formula neutralization and compatibility optimization
Can be used as a neutralizing agent to adjust the acidic substances (such as citric acid and lactic acid) in the formula and balance the pH value. Its advantage is that it is compatible with most cosmetic raw materials (such as surfactants, oils, essence), and does not produce flocculation or discoloration. For example, in cleansers containing amino acid surfactants, adding 0.3% of this compound can neutralize residual acidity and enhance product mildness.
Application limitation: avoid mixing with yellow acid/sulfonic acid surfactants, soap based systems and products containing iron ion/aldehyde based essence, otherwise it may cause color change or activity reduction.
Food industry: safe and efficient anti-corrosion solutions
1. Food preservation standards and dosage
According to the Chinese "Hygienic Standards for the Use of Food Additives" (GB 2760-1996) and FAO/WHO regulations, the maximum allowable dosage of sodium N-(hydroxymethyl)glycinate in food is as follows:
Ice cream: 0.3 g/kg
Jelly: 2.5 g/kg
Instant noodles/noodles: 0.2 g/kg
Solid beverage: 0.5 g/kg
Jam: 1.0 g/kg
Canned sardine: 20 g/kg
Frozen fish strips/chunks: limited to GMP (Good Manufacturing Practice)
Mechanism of action: By disrupting the permeability of microbial cell membranes, inhibiting enzyme activity and DNA replication, broad-spectrum antibacterial effects are achieved.
Experiments have shown that in jam with a pH of 4.5, a 1.0% addition can reduce the germination rate of fungal spores by 98%.
2. Safety and Alternative Advantages
Compared to traditional preservatives such as sodium benzoate and potassium sorbate, sodium hydroxymethylglycinate has the following advantages:
Low toxicity: LD ₅₀ (oral administration to rats)>5000 mg/kg, which belongs to the actual non-toxic level;
Stability: Maintain activity under high temperature (121 ℃) and acidic/alkaline conditions;
Odorless: does not affect the flavor of food, especially suitable for sensitive products such as yogurt and seasoning sauce.
The dual role of intermediates and formulation stability in the pharmaceutical field
1. Synthesis of pharmaceutical intermediates
It is an important intermediate for synthesizing bioactive compounds. For example:
Chiral drugs: key intermediates for antiviral drugs (such as oseltamivir) are generated by reacting with chiral amines;
Metal complex: A stable complex formed with zinc and copper ions, used as an auxiliary ingredient in the preparation of anti ulcer drugs (such as magnesium aluminum carbonate).
Synthesis case: In the preparation of an intermediate for the antidepressant drug fluoxetine, sodium N-methylglycinate can act as a hydroxymethyl donor and undergo condensation reaction with aromatic amines, with a yield of 92%.
2. External anti-corrosion preparations
In cream, gel and other topical drugs, 0.1% -0.3% sodium N-hydroxymethylglycine can replace traditional preservatives (such as paraben) to reduce skin irritation. For example, in hormone containing anti-inflammatory creams, this compound can maintain formulation stability while reducing the risk of allergic reactions.
Paper Industry: Wet Strength Agents and Environmental Efficiency Enhancers
1. Improvement of wet strength of paper
As a wet strength agent, it can significantly improve the wet strength of paper by forming covalent bonds with hydroxyl groups in cellulose molecules through hydroxymethyl groups. For example, in the production of toilet paper, adding 1.5% of this compound can increase the wet tensile strength by 40%, meeting the needs of use in humid environments.
Process optimization: When used in combination with polyamide epichlorohydrin (PAE) wet strength agent, the amount of PAE can be reduced by 30%, while reducing the risk of formaldehyde release.
2. Environmental protection and cost advantages
Compared to traditional wet strength agents such as melamine formaldehyde resin, sodium N-(hydroxymethyl)glycinate has the following advantages:
Formaldehyde free: avoids VOCs emissions and complies with environmental regulations;
Low corrosiveness: No significant corrosion to papermaking equipment, extending equipment life;
Cost effectiveness: The unit price is about 60% of PAE, and the addition amount is lower.
Textile Industry: Post finishing and Functional Modification
1. Wrinkle resistance and hand feel improvement of fabrics
It can be used for post finishing of natural fibers such as cotton and linen. By reacting with hydroxyl groups in the fibers, a cross-linked structure is formed to enhance the wrinkle resistance and dimensional stability of the fabric. For example, in shirt fabric processing, adding 2% of this compound can increase the crease recovery angle by 30 ° while maintaining fabric softness.
Process conditions: After immersion rolling method (concentration 50 g/L, temperature 80 ℃, time 3 minutes), the best effect is achieved by baking at 160 ℃ for 1 minute.
2. Environmentally friendly dyeing auxiliaries
As a dyeing assistant, it can promote the binding of dyes and fibers, and improve the dye uptake rate. For example, in the process of dyeing cotton with reactive dyes, adding 1% of this compound can increase the dye utilization rate by 15% and reduce the COD value of wastewater.
1. Metal corrosion inhibitors
A protective film can be formed on the metal surface through hydroxymethyl groups to inhibit corrosion. For example, in a circulating cooling water system, adding 50 mg/L of this compound can reduce the corrosion rate of carbon steel by 80%, which is more effective than traditional corrosion inhibitors such as zinc salts.
Mechanism of action: The sodium carboxylate group enhances its dispersibility in water, while the hydroxymethyl group forms a stable complex with Fe ² ⁺/Fe ³ ⁺ to prevent oxidation reactions.
2. Metal chelating agents
This compound can form soluble complexes with metal ions such as Ca ² ⁺ and Mg ² ⁺ to prevent the formation of scale. For example, in boiler water treatment, adding 10 mg/L sodium hydroxymethylglycinate can reduce the calcium hardness (calculated as CaCO3) from 300 mg/L to below 50 mg/L, significantly reducing the risk of scaling.
1. Energy supplements
As a derivative of glycine, it can participate in human amino acid metabolism and supplement energy expenditure after exercise. For example, adding 0.5% of this compound to sports drinks can increase muscle glycogen synthesis rate by 20% and delay fatigue.
2. Agricultural synergists
Adding 0.1% -0.3% sodium hydroxymethylglycinate to fertilizers can improve fertilizer utilization by chelating trace elements (such as Zn and Fe) in the soil. Experiments have shown that compounding this compound in foliar fertilizers can increase rice yield by 8% -12%.
Sodium N-(hydroxymethyl)glycinate is a commonly used preservative and fungicide, widely used in cosmetics, personal care products, and pharmaceutical formulations. There are two main methods for its synthesis, namely the chloroform method and the sodium glycine method.
1. Chloroformaldehyde method
CH2(NH2)COOH + CH2O + NaOH → C3H8NNaO3 + NH3 ↑+H2O
Chloroformaldehyde method is one of the traditional synthesis methods for Sodium hydroxide glycinate, with the following steps:
Step 1: Prepare glycine
Add an appropriate amount of glycine to water, stir until it is completely dissolved, then slowly add sodium hydroxide solution dropwise to raise the pH value of the solution to 9.0-10.0, while continuously stirring. After the reaction is complete, filter the obtained glycine solution and remove impurities.
CH2(NH2)COOH + NaOH → CH2(NaO2)COOH + NH3 ↑
Step 2: Preparation of N-hydroxymethylglycine
Slowly add chloroform dropwise to the glycine solution while stirring continuously, and control the reaction temperature at 0-5 ℃. After the reaction is complete, filter the obtained N-hydroxymethylglycine and remove impurities.
CH2O + CH2(NaO2)COOH → CH2(OH)CH2(NaO2)COOH
Step 3: Prepare Sodium hydroxide glycinate
Add N-hydroxymethylglycine solution into an appropriate amount of sodium hydroxide solution, adjust the pH value to 10.0-11.0, and then heat the reaction for 2 hours. After the reaction is complete, filter and remove impurities from the obtained Sodium hydroxide glycinate solution.
CH2(OH)CH2(NaO2)COOH + NaOH → C3H8NNaO3 + H2O
2. Sodium glycine method
CH2(NaO2)COOH + 2 NaOH + CH3I → C3H8NNaO3 + CH3NH2 ↑+ CO2 ↑+ H2O
The sodium glycine method is another synthesis method of Sodium hydroxide glycinate, with the following steps:
Step 1: Prepare N, N-dimethylglycine disodium
Add sodium glycine, methyl iodine, and an appropriate amount of sodium hydroxide solution to the reaction vessel, control the reaction temperature at 70-80 ℃, and continuously stir. After the reaction is complete, filter the obtained N, N-dimethylglycine disodium and remove impurities.
CH2(NaO2)COOH + 2 NaOH + CH3I → NaO2CCH2N(CH3)2COONa + H2O
Step 2: Prepare Sodium hydroxide glycinate
Add N, N-dimethylglycine disodium solution to an appropriate amount of sodium hydroxide solution, control the pH value between 10.0-11.0, and then heat the reaction for 1 hour. After the reaction is complete, filter and remove impurities from the obtained Sodium hydroxide glycinate solution.
NaO2CCH2N(CH3)2COONa + NaOH → C3H8NNaO3 + CH3NH2 ↑
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