Difference between revisions of "Succinic acid"

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| ExternalMSDS = [https://www.fishersci.com/shop/msdsproxy?productName=A294500 FisherSci]
 
| ExternalMSDS = [https://www.fishersci.com/shop/msdsproxy?productName=A294500 FisherSci]
 
| FlashPt = 160 °C (open cup)<br>206 °C  
 
| FlashPt = 160 °C (open cup)<br>206 °C  
| LD50 =  2260 mg/kg (oral, rat)
+
| LD50 =  2,260 mg/kg (oral, rat)
 
| LC50 =  
 
| LC50 =  
 
| MainHazards = Irritant
 
| MainHazards = Irritant

Latest revision as of 07:27, 31 August 2019

Succinic acid
Succinic acid bottle sample.jpg
Succinic acid sample and original bottle.
Names
IUPAC name
Butanedioic acid
Preferred IUPAC name
Butanedioic acid
Other names
Amber acid
Asuccin
Ethane-1,2-dicarboxylic acid
Katasuccin
Spirit of amber
Properties
C4H6O4
Molar mass 118.09 g/mol
Odor Odorless
Density 1.572 g/cm3 (at 20 °C)
Melting point 184 °C (363 °F; 457 K)
Boiling point 235 °C (455 °F; 508 K)
8.32 g/100 ml (25 °C)
Solubility Soluble in acetone, diethyl ether, ethanol, methanol
Slightly soluble in dimethylformamide
Insoluble in benzene, carbon disulfide, carbon tetrachloride, petroleum ether, toluene
Solubility in acetone 2.7 g 100/ml
Solubility in chloroform 0.02 g/100 ml
Solubility in diethyl ether 0.88 g/100 ml
Solubility in ethanol 5.4 g/100 ml
Solubility in glycerol 5 g/100 ml
Vapor pressure 1.91·10-7 mmHg (25 °C)
Acidity (pKa) pKa1 = 4.2
pKa2 = 5.6
Hazards
Safety data sheet FisherSci
Flash point 160 °C (open cup)
206 °C
Lethal dose or concentration (LD, LC):
2,260 mg/kg (oral, rat)
Related compounds
Related compounds
Tartaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Succinic acid is an organic compound, a dicarboxylic acid with chemical formula (CH2)2(COOH)2. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

Properties

Chemical

Succinic acid will react with sodium carbonate in aqueous solution to give sodium succinate.

Physical

Succinic acid is an odorless white crystalline solid, soluble in water, methanol, but less soluble in diethyl ether.

Availability

Succinic acid can be bought from various wine-making suppliers. It is also sold as plant growth stimulator, though in this form it's very expensive.[1]

Lastly it can be bought from chemical suppliers and online.

Preparation

Succinic acid was historically obtained from the distillation of amber.[2]

Succinic acid can be obtained from the fermentation of wines, along with acetic acid.

A more convenient route involves the partial hydrogenation of maleic acid.

Oxidation of 1,4-butanediol will yield succinic acid.

Carbonylation of ethylene glycol will also yield succinic acid.

Projects

  • Make polyesters
  • Make fumaric acid
  • Make succinic anhydride
  • Synthesis of 1,4-butanediol

Handling

Safety

Succinic acid may be irritant and should be handled with care.

Storage

Succinic acid should be kept in closed bottles, away from volatile compounds.

Disposal

No special disposal is required.

References

  1. https://www.amazon.com/Fertilizer-Amber-Plant-growth-stimulator/dp/B079BT7H4G
  2. http://digicoll.library.wisc.edu/cgi-bin/HistSciTech/HistSciTech-idx?type=turn&id=HistSciTech.Cyclopaedia01&entity=HistSciTech.Cyclopaedia01.p0122&q1=Spirit%20of%20Amber

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