Itaconic acid
Itaconic Acid
CAS: 97-65-4
Molecular Formula: C5H6O4
Itaconic acid - Names and Identifiers
| Name | Itaconic Acid |
| Synonyms | ITA ITACONIC ACID Itaconic Acid methylene-succinicaci Methylenesuccinic acid METHYLENESUCCINIC ACID methylene-butanedioicaci 2-methylidenebutanedioate Succinic acid, methylene- 3-CARBOXY-3-BUTENOIC ACID Methylenebutanedioic acid PROPYLENEDICARBOXYLIC ACID 2-PROPENE-1,2-DICARBOXYLIC ACID |
| CAS | 97-65-4 |
| EINECS | 202-599-6 |
| InChI | InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)/p-2 |
| InChIKey | LVHBHZANLOWSRM-UHFFFAOYSA-N |
Itaconic acid - Physico-chemical Properties
| Molecular Formula | C5H6O4 |
| Molar Mass | 130.1 |
| Density | 1.573 g/mL at 25 °C (lit.) |
| Melting Point | 165-168 °C (lit.) |
| Boling Point | 268°C |
| Flash Point | 268°C |
| Water Solubility | Soluble in water, acetone, methanol, hexane and ethanol. Slightly soluble in benzene, chloroform, carbon disulfide and petroleum ether. |
| Solubility | Soluble in water, ethanol and acetone, slightly soluble in chloroform, benzene and ether. |
| Vapor Presure | 0.0000115 Pa (20 °C) |
| Appearance | Colorless crystal |
| Specific Gravity | 1.573 |
| Color | White to light beige |
| Merck | 14,5242 |
| BRN | 1759501 |
| pKa | 3.85(at 25℃) |
| PH | 3.5(1 mM solution);2.95(10 mM solution);2.43(100 mM solution); |
| Storage Condition | Store below +30°C. |
| Stability | Light Sensitive |
| Sensitive | Hygroscopic |
| Refractive Index | 1.4980 (estimate) |
| MDL | MFCD00004260 |
| Physical and Chemical Properties | Character: colorless crystals. melting point 167~168 ℃ relative density 1.6320 solubility: soluble in water, ethanol and acetone, slightly soluble in chloroform, benzene and ether. |
| Use | As a comonomer of polyacrylonitrile fiber, can also be used for the preparation of plasticizers, lubricating oil additives |
Itaconic acid - Risk and Safety
| 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. |
| WGK Germany | 1 |
| TSCA | Yes |
| HS Code | 29171990 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
Itaconic acid - Reference
| Reference Show more | 1. Zhang Peng, Yang Ziteng, Wang Wenzhe, et al. Preparation of water-soluble polyrotaxane cross-linking agent and its potential application in hydrogel particle type profile control agent [J]. Oilfield chemistry, 2019, 29 (1). |
Itaconic acid - Nature
Open Data Verified Data
This product is a colorless crystal. Melting point 167 ~ relative density 1. 6320. Sublimation under vacuum. Soluble in water, ethanol and acetone, chloroform-soluble, benzene and ether. Easy polymerization, can also be copolymerized with other monomers. It is not easy to volatilize and can be decomposed by overheating.
Last Update：2024-01-02 23:10:35
Itaconic acid - Preparation Method
Open Data Verified Data
- the fermentation method is prepared by the biochemical action of Aspergillus terreus by adding an appropriate amount of nitrogen source and inorganic salt to carbohydrates (glucose, starch, etc.).
- chemical synthesis can be divided into the following two types according to different sources of raw materials:(1) taking agricultural products as raw materials, such raw materials include limonic acid, isocitric acid, aconitic acid or its anhydride, etc. Using citric acid as raw material and supported phosphate as Catalyst, the reaction was carried out at 290~340 ℃ to obtain citraconic acid, which was heated to 220 ℃ to get itaconic acid. (2) to petrochemical products as raw materials with succinic anhydride or succinic acid Diester as raw materials, thorium salt as catalyst, and formaldehyde reaction, the formation of citraconic acid, and then heated isomerization of itaconic acid.
- The new chemical synthesis method uses maleic anhydride as the main raw material to synthesize itaconic acid through four steps of esterification, addition, methylene and hydrolysis.
Last Update：2022-01-01 10:32:05
Itaconic acid - Introduction
Iconic acid is an unsaturated binary organic acid. Chemical properties are more active, easy to polymerize, and can also be copolymerized with other monomers, such as acrylic, succinic acid, and styrene. Soluble in water, ethanol and acetone, slightly soluble in chloroform, benzene and ether. It has a special smell and can sublimate under vacuum. It can also be copolymerized with other monomers. It is not easy to volatilize and can be decomposed by overheating.
Last Update：2022-10-16 17:30:25
Itaconic acid - Use
Open Data Verified Data
An important monomer for the preparation of synthetic fibers, synthetic resins and plastics, ion exchange resins; Also used as carpet mounting agent, paper coating agent, adhesive, coating dispersion emulsifier, plasticizers for polymers, etc.
Last Update：2022-01-01 10:32:05
Itaconic acid - Safety
Open Data Verified Data
The product is less toxic and less harmful to health, but its vapor is toxic. The equipment should be closed during production, and the operator should wear protective equipment.
It should be filled in a paper drum lined with plastic bags, and stored closely, and attention should be paid to moisture, heat and oxidant prevention. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:32:06
Itaconic acid - Reference Information
| LogP | -0.301 at 20℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Main use | 1. Itaconic acid and its polymer add a small amount of natural substances can be made into efficient deodorant, with ammonia, amine alkaline odor and hydrogen sulfide and other acidic odor reaction, can also be made with deodorant function of paper, plastic film and other products. 2, itaconic acid and styrene and butadiene copolymerization can be made into S.B.R latex, can be used for paper coating, so that the paper is strong and strong and the printing pattern is bright; Used for metal, concrete coating, easy to color and not affected by natural conditions; For paint additives can improve the quality of paint; For carpet sizing can make the synthetic fiber carpet durable. 3, itaconic acid and acrylic acid or methacrylic acid or its ester polymerization resin, can be used for surface coating and emulsion paint. As a leather coating can increase the plasticity of leather; Used for automobile, electrical appliances, cold storage coatings with strong adhesion, color and appearance and resistance to adverse weather and other advantages; Used as electrophoretic coating with excellent adhesion; the addition of polyvalent metal oxide can be made into a dental adhesive with good extrusion performance, strong adhesion and good physiological adaptability. The addition of chloroalkyl dimethyl benzyl ammonium chloride can be made into a water-soluble coating for food packaging materials, bacterial contamination of the packaging surface can be reduced. 4, itaconic acid esters can be used in paint, weak acid ion exchange resin, lubricating oil additives, binders and plasticizers, powder pressure plastic and sealant. 5, itaconic acid to form other derivatives can be used as pharmaceuticals, cosmetics reagents, lubricants, thickeners, herbicides and improve the performance of silk and wool fabrics. 6. Itaconate is a raw material for the production of citraconic acid, mesaconic acid, itaconic anhydride, etc. |
| Application | used as comonomer of polyacrylonitrile fiber, can also be used in the preparation of plasticizers, lubricant additives, etc. Preparation of synthetic fiber, an important monomer of synthetic resin and plastic, ion exchange resin; Can also be used as a carpet mounting agent, paper coating agent, binder, paint dispersion latex. Ester Derivatives of itaconic acid can be used for Copolymerization of styrene and the like or plasticizers of polyvinyl chloride. |
| production method | 1. The fermentation method is prepared by the biochemical action of Aspergillus terreus by adding appropriate amount of nitrogen source and inorganic salt to carbohydrate (glucose, starch, etc.). 2. Chemical synthesis according to different sources of raw materials, can be divided into the following two types:(1) to agricultural products as raw materials such raw materials are citric acid, isocitric acid, aconitic acid or its anhydride and so on. With citric acid as raw material, supported phosphate as catalyst, reaction at 290-340 ℃ to obtain citraconic acid, and then heated to 220 ℃ to get itaconic acid. (2) to petrochemical products as raw materials with succinic anhydride or succinic acid Diester as raw materials, thorium salt as catalyst, and formaldehyde reaction, the formation of citraconic acid, and then heated isomerization of itaconic acid. Itaconic acid was synthesized from maleic anhydride by four steps of esterification, addition, methylene and hydrolysis. |
| spontaneous combustion temperature | 430°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:12
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