498-21-5
Methylsuccinic acid
CAS: 498-21-5
Molecular Formula: C5H8O4
498-21-5 - Names and Identifiers
| Name | Methylsuccinic acid |
| Synonyms | Methylsuccinic acid 2-Methylsuccinic acid 2-Methylbutanedioic acid 2-Propanedicarboxylic acid 1,2-Propanedicarboxylic acid (plus-minus)-methylsuccinic acid Methyl-Butanedioic acid Methylsuccinic acid Pyrotartaric acid |
| CAS | 498-21-5 |
| EINECS | 207-857-1 |
| InChI | InChI=1/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9) |
498-21-5 - Physico-chemical Properties
| Molecular Formula | C5H8O4 |
| Molar Mass | 132.11 |
| Density | 1.311g/cm3 |
| Melting Point | 110-115℃ |
| Boling Point | 236.5°C at 760 mmHg |
| Flash Point | 111.1°C |
| Water Solubility | Soluble in water. |
| Vapor Presure | 0.0162mmHg at 25°C |
| Appearance | White to light brown crystals |
| BRN | 1722946 |
| pKa | 4.13(at 25℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents. |
| Refractive Index | 1.474 |
| MDL | MFCD00002659 |
| Physical and Chemical Properties | Melting Point: 110 - 112 water-soluble: *** = 10g/100 mL at 22 C Appearance: white or yellowish crystals |
| Use | Pharmaceutical Intermediates |
498-21-5 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - 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 | 3 |
| TSCA | Yes |
| HS Code | 29171900 |
498-21-5 - Upstream Downstream Industry
| Raw Materials | Carbon tetrachloride Sodium cyanide Barium hydroxide Crotonic acid Phenetole Ethyl crotonate |
498-21-5 - Uses and synthesis methods
overview
Methylsuccinic acid (methylene succinic acid) is a compound used for organic synthesis. It is prepared by fermentation under the liquid surface of Aspergillus terreus. It is a colorless, odorless, and moisture-absorbing crystal. Low toxicity, but its vapor is toxic. Easy to polymerize, can also be copolymerized with other monomers. This substance may be harmful to the environment, and special attention should be paid to water bodies.
physical and chemical properties
Appearance and properties: white to beige crystalline powder
Standard heat of combustion (enthalpy) of crystalline phase (kJ • mol-1):-2152.65
Crystal phase standard claimed heat (enthalpy)( kJ • mol-1):-958.22
Volatile: not volatile, can be decomposed by overheating
Solubility: Soluble in water, ethanol and acetone, slightly soluble in benzene, chloroform and ether
storage method
Keep the container closed. Store in a cool, dark place.
Molecular structure data
molar refractive index: 28.30
molar volume (cm3/mol):100.6
isometric ratio (90.2K):272.0
surface tension (dyne/cm):53.2
polarizability (10-24cm3):11.21
Calculated chemical data
1. Hydrophobic parameter calculation reference value (XlogP):-0.2
2. Number of hydrogen bond donors: 2
3. Number of hydrogen bond receptors: 4
4. Number of rotatable chemical bonds: 3
5. Number of tautomers: None
6. Topological molecular polar surface area 74.6
7. Number of heavy atoms: 9
8. Surface charge: 0
9. Complexity: 129
10. Number of isotope atoms: 0
11. Determine the number of atomic stereocenters: 0
12. Uncertain number of atomic stereocenters: 1
13. Determine the number of chemical bond structure centers: 0
14. Uncertain number of chemical bond structure centers: 0
15. Number of covalent bond units: 1
Preparation method
1. oxidation method. High temperature and high pressure are required, which takes a long time.
2. Ester hydrolysis method. The process is complicated, the operation steps are many, and the cost is high.
3. Catalytic hydrogenation method. Commonly used catalysts are: Cu catalyst, Pd catalyst, Ni catalyst, Pt, Rh catalyst
Main references
[1]http://baike.baidu.com/item/甲基丁二酸#7
[2] Wang Yingying, Gao Chuanhui, Wang Chuanxing, et al. Hydrogenation of itaconic acid to prepare methylsuccinic acid [J]. Journal of Qingdao University of Science and Technology (Natural Science Edition), 2014, 35(1):9-12.
chemical properties
White or yellowish crystals
use
for organic synthesis.
production method
using butenoic acid as raw material, it is prepared by the following steps. Butenoic acid and ethanol are mixed with carbon tetrachloride, sulfuric acid is added, reflux reaction is carried out for 12h, ethanol and carbon tetrachloride are recovered, and ethyl crotonate is obtained by salting out. Ethyl crotonate, ethanol and sodium cyanide aqueous solution were refluxed for 5h. Add barium hydroxide solution, concentrate to porridge under reduced pressure, and cool. Add nitric acid and react violently to release hydrogen cyanide gas. Concentrate to dry under reduced pressure, extract with benzene and ether to obtain crude product, and finally recrystallize with benzene and water once each to obtain the finished product.
Last Update：2024-04-09 21:21:28
498-21-5 - Nature
| storage conditions | Sealed in dry,Room Temperature |
| acidity coefficient (pKa) | 4.13(at 25℃) |
| water solubility | Soluble in water. |
| BRN | 1722946 |
| stability | Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents. |
| NIST chemical information | Butanedioic acid, methyl-(498-21-5) |
| EPA chemical information | Butanedioic acid, 2-methyl- (498-21-5) |
Last Update：2024-04-09 20:48:19
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Raw Materials for 498-21-5