142-73-4 - Names and IdentifiersNameIminodiacetic AcidSynonymsIDAaminodiaceticAminodiaceticacid
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| Name | Iminodiacetic Acid |
| Synonyms | IDA aminodiacetic Aminodiaceticacid Aminodiacetic acid Iminodiacetic Acid iminodi-acetic acid Acetic acid, iminodi- 2,2'-iminodiaceticacid 2,2'-iminodiacetic acid 2,2'-iminobis-aceticaci 2,2'-Iminodiacetic acid N-(carboxymethyl)-Glycine Acetic acid, 2,2'-iminobis- |
| CAS | 142-73-4 |
| EINECS | 205-555-4 |
| InChI | InChI=1/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9) |
| InChIKey | NBZBKCUXIYYUSX-UHFFFAOYSA-N |
| Molecular Formula | C4H7NO4 |
| Molar Mass | 133.1 |
| Density | 1.5325 (rough estimate) |
| Melting Point | 243 °C (dec.) (lit.) |
| Boling Point | 245.59°C (rough estimate) |
| Flash Point | 177.9°C |
| Water Solubility | 2.43 g/100 mL (5 ºC) |
| Solubility | 42g/l |
| Vapor Presure | 1.65E-06mmHg at 25°C |
| Appearance | White crystal |
| Color | White or yellow |
| Merck | 14,4917 |
| BRN | 878499 |
| pKa | 2.98, 9.89(at 25℃) |
| PH | 2.2-2.3 (H2O, 20℃)(saturated solution) |
| Storage Condition | Store below +30°C. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.4540 (estimate) |
| MDL | MFCD00004280 |
| Physical and Chemical Properties | Melting point 243°C water-soluble 2.43g/100 mL (5°C) |
| Use | Used in pesticides, rubber and amino carboxylate complexes, a large number of raw materials for glyphosate |
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 1 |
| RTECS | AI2975000 |
| TSCA | Yes |
| HS Code | 29224995 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| Raw Materials | Diethanolamine Diethanolamine Formaldehyde Formaldehyde Sodium hydroxide |
| Downstream Products | Glyphosate |
| use | iminodiacetic acid is an intermediate of herbicide glyphosate. Used for pesticides, rubber and aminocarboxylic complexes, used in large quantities as raw materials for glyphosate used as complexing agent, also used in organic synthesis used in the synthesis of glyphosate, and also used as amino acid The synthetic raw material of chelating resin is also an important raw material and intermediate in the rubber and electroplating industries, and is also used as an intermediate of surfactant and complexing agent. Preparation of complexing agents and surfactants, organic synthesis. Bovine liver glutamate dehydrogenase inhibitor |
| Production method | 1. Sodium chloroacetate method is prepared from chloroacetic acid to sodium chloroacetate, and then reacts with hydrazine hydrate to generate hydrazine-holding diacetic acid, and then iminodiacetic acid is prepared under the action of sodium nitrite. (1) Preparation of Sodium Chloroacetate Dissolve chloroacetic acid in water, and slowly add sodium carbonate under stirring until the gas in the solution escapes to obtain sodium chloroacetate. (2) Preparation of hydrazine holding diacetic acid The solution of sodium chloroacetate is added dropwise to the 50% hydrazine hydrate under stirring, and the reaction temperature shall not exceed 25 ℃. After adding, keep the temperature for 10min, and the pH value of the reactant should be between 9-10. Then sodium carbonate was added and the temperature was controlled to be 20-25 ℃. After adding, raise the temperature to 65-70 ℃ and keep the temperature for 1h. Then cool to the chamber, acidify with hydrochloric acid to precipitate white solids, filter, wash with water, and dry at 60°C to obtain hydrazine-holding diacetic acid with a melting point of 166-167°C. Add hydrazine to water, slowly add 16% sodium nitrite solution under stirring, then add concentrated hydrochloric acid, and react at 25 ℃ for 1.5h. The reaction liquid is evaporated and concentrated to 1/3 of the original volume, placed to precipitate crystals, filtered, and dried at 60°C to obtain iminodiacetic acid. 2. Direct synthesis with hydrocyanic acid. A mixed aqueous solution of hydrocyanic acid, urotropine and formaldehyde was reacted in a tubular reactor to obtain iminodiacetonitrile. 3. Chloroacetic acid and aminoacetic acid method. 4. Aminoacetic acid and ethanolonitrile method. 5. Chloroacetic acid and ammonia reaction method. the preparation method is to add powdered calcium hydroxide and 25% ammonia water into the reaction kettle, slowly add chloroacetic acid solution under stirring, control the temperature at (50±5)℃, keep the reaction at the temperature for 3 hours after adding chloroacetic acid, then raise the temperature to 80 ℃, add hydrochloric acid dropwise, raise the temperature to 95~100 ℃ for reaction for 15min after adding, cool, move the reactant to the crystallization kettle, and crystallize the product. Reaction equation: ClCH2COOH + Ca(OH)2 + NH4OH → NH(CH2COO)2Ca + 3H2ONH(CH2COO)2Ca + 3HCl → NH(CH2CO()H)2 · HCl + CaCl2 can also be dehydrogenated with diethanolamine in the presence of a catalyst to prepare iminodiacetaldehyde, and then react with a base to form a part of sodium iminodiacetonate and a part to diacetamines. Such repeated reactions make all diacetamines generate imin. Now the more advanced method is the diethanolamine method. |
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