Succinic Acid

Base Information

• Chemical Name: Succinic Acid
• CAS No.: 110-15-6
• Deprecated CAS: 623158-99-6,2087491-34-5
• Molecular Formula: C4H6O4
• Molecular Weight: 118.089
• Hs Code.: 2917190090
• European Community (EC) Number: 203-740-4
• NSC Number: 106449,25949
• UNII: AB6MNQ6J6L
• DSSTox Substance ID: DTXSID6023602
• Nikkaji Number: J2.879G
• Wikipedia: Succinic acid
• Wikidata: Q213050
• NCI Thesaurus Code: C61954
• RXCUI: 37255
• Metabolomics Workbench ID: 1966
• ChEMBL ID: CHEMBL576
• Mol file: 110-15-6.mol

Synonyms:1,2 Ethanedicarboxylic Acid;1,2-Ethanedicarboxylic Acid;1,4 Butanedioic Acid;1,4-Butanedioic Acid;Ammonium Succinate;Butanedioic Acid;Potassium Succinate;Succinate;Succinate, Ammonium;Succinate, Potassium;Succinic Acid

Chemical Property of Succinic Acid

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.0165mmHg at 25°C
• Melting Point: 185 °C
• Refractive Index: n20/D 1.4002(lit.)
• Boiling Point: 236.1 °C at 760 mmHg
• PKA: 4.24±0.17(Predicted)
• Flash Point: 110.9 °C
• PSA: 74.60000
• Density: 1.552 g/cm³
• LogP: -0.06420
• Water Solubility.: 80 g/L (20℃)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 118.02660867
• Heavy Atom Count: 8
• Complexity: 92.6

Purity/Quality:

99.5%MIN, ^*data from raw suppliers

Succinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(CC(=O)O)C(=O)O
• Recent ClinicalTrials: A Pooled Analysis of the Data From Two Studies of Ammonium Succinate for Menopausal Symptoms
• Chemical Properties and Production: Succinic acid, also known as amber acid or butanedioic acid, has the molecular formula C4H6O4. It was first purified from amber by Georgius Agricola in 1546 and has historically been produced through microbial fermentation. However, most commercially available succinic acid is currently produced via chemical processes using liquefied petroleum gas (LPG) or petroleum oil, predominantly from n-butane through maleic anhydride.
• Industrial Uses: Succinic acid is utilized as a precursor for many industrially important chemicals including adipic acid, 1,4-butanediol, tetrahydrofuran, N-methyl pyrrolidinone, succinate salts, and gamma-butyrolactone. Its demand is increasing as it finds applications in the synthesis of biodegradable polymers like polybutyrate succinate (PBS), polyamides (Nylon庐x,4), and green solvents.
• Historical and Traditional Applications: Traditionally, succinic acid has been used in various industries for applications such as food additives, detergents, cosmetics, pigments, toners, cement additives, soldering fluxes, and pharmaceutical intermediates. Its market size has expanded due to the potential of converting it into a range of industrial chemicals.
• Biological Production and Microbial Strains: Succinic acid is naturally produced by various microorganisms, serving as a metabolic co-product of ethanol fermentation. Anaerobiospirillum succiniciproducens is one of the microorganisms with commercial potential for succinic acid production. The development of microbial strains capable of accumulating succinic acid at high concentrations has been crucial for economically feasible recovery.
• Importance and Market Value: Succinic acid is identified as a top value-added chemical derived from biomass via fermentation by the US Department of Energy. It serves as a crucial platform molecule used in various industries such as agriculture, food, and pharmaceuticals, with a total immediate addressable market exceeding $7.2 billion.

Technology Process of Succinic Acid

There total 1251 articles about Succinic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

methanol (67-56-1) + succinamic acid (638-32-4) → Succinimide (123-56-8,89963-74-6) + N-methylsuccinimide (1121-07-9) + succinic acid (110-15-6) + succinic acid-mono-N-methylamide (56269-39-7)

Guidance literature:

With ammonia; In water; at 280 ℃; for 10h;

Reference yield: 0.08%

maleic acid (110-16-7,26099-09-2) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 4-butanolide (96-48-0) + Butane-1,4-diol (110-63-4) + 4-hydroxybutanoic acid (591-81-1) + malic acid (617-48-1,78644-42-5) + succinic acid (110-15-6) + acetic acid (64-19-7,77671-22-8)

Guidance literature:

With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO₂; at 110 ℃; Product distribution / selectivity;

Reference yield: 0.04%

maleic acid (110-16-7,26099-09-2) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 4-butanolide (96-48-0) + Butane-1,4-diol (110-63-4) + 4-hydroxybutanoic acid (591-81-1) + malic acid (617-48-1,78644-42-5) + succinic acid (110-15-6) + terephthalic acid (100-21-0) + acetic acid (64-19-7,77671-22-8) + propionic acid (802294-64-0,79-09-4) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO₂; at 110 ℃; for 170 - 1009h; Product distribution / selectivity;

upstream raw materials:

oxirane

tetrahydrofuran

2-methyltetrahydrofuran

2-methyloxane

Downstream raw materials:

bis(2-hydroxyethyl) butanedioate

dipropyl succinate

Succinimide

bis-(2-phenoxyethyl) succinate

Refernces

• 1、 Badovskaya,Latashko,Poskonin,Grunskaya,Tyukhteneva,Rudakova,Pestunova,Sarkisyan. "Catalytic oxidation of furan and hydrofuran compounds. 7. Production of 2(5H)-furanone by oxidation of furfural with hydrogen peroxide and some of its transformations in aqueous solutions". . p. 1040 - 1048. Retrieved 2002.
• 2、 Jian, Jian,You, Kuiyi,Duan, Xuezhi,Gao, Hongxu,Luo, Qing,Deng, Renjie,Liu, Pingle,Ai, Qiuhong,Luo, He'an. "Boosting one-step conversion of cyclohexane to adipic acid by NO2 and VPO composite catalysts". . p. 3320 - 3323. Retrieved 2016.
• 3、 Bruylants. "-". . . Retrieved 1923.
• 4、 Li, Jie,Tian, Wei-Ping,Shi, Li. "Highly active and selective nickel-platinum catalyst for the low temperature hydrogenation of maleic anhydride to succinic anhydride and synthesis of succinic acid at 40 °c". . p. 565 - 571. Retrieved 2011.
• 5、 Ruggiero, Emmanuel,Hernández-Gil, Javier,Mareque-Rivas, Juan C.,Salassa, Luca. "Near infrared activation of an anticancer PtIV complex by Tm-doped upconversion nanoparticles". . p. 2091 - 2094. Retrieved 2015.
• 6、 Khan, Amjad,Schofield, Christopher J.,Claridge, Timothy D. W.. "Reducing Agent-Mediated Nonenzymatic Conversion of 2-Oxoglutarate to Succinate: Implications for Oxygenase Assays". . p. 2898 - 2902. Retrieved 2020.
• 7、 Kirby, Anthony J.,Souza, Bruno S.,Medeiros, Michelle,Priebe, Jacks P.,Manfredi, Alex M.,Nome, Faruk. "Hydroxylamine as an oxygen nucleophile. Chemical evidence from its reaction with a phosphate triester". . p. 4428 - 4429. Retrieved 2008.
• 8、 Ts'ai. "-". . p. 1886. Retrieved 1951.
• 9、 Xing, Shengtao,Lu, Xiaoyang,Ren, Limei,Ma, Zichuan. "Characterization and reactivity of Mn-Ce-O composites for catalytic ozonation of antipyrine". . p. 60279 - 60285. Retrieved 2015.
• 10、 Cavani, Fabrizio,Raabova, Katerina,Bigi, Franca,Quarantelli, Carla. "A rationale of the BaeyerVilliger oxidation of cyclohexanone to ε-caprolactone with hydrogen peroxide: Unprecedented evidence for a radical mechanism controlling reactivity". . p. 12962 - 12969. Retrieved 2010.