Hydrogen Cyanide → Methacrylic Acid

HRID 2280039Notes

Reaction equation

HRID 2280039 reaction equation
C#N.[S:3](=[O:7])(=[O:6])([OH:5])[OH:4].[C:8]([NH2:13])(=[O:12])[C:9]([CH3:11])=[CH2:10]>CC(C)=O>[S:3](=[O:5])(=[O:4])([OH:7])[O-:6].[NH4+:13].[C:8]([OH:12])(=[O:4])[C:9]([CH3:11])=[CH2:10]

Participants

6

Reactant 3

HCID 768Hydrogen CyanideHCID 1118Sulfuric AcidHCID 6595Methacrylamide

Product 2

HCID 4093Methacrylic AcidHCID 24655Ammonium bisulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methacrylic acid (MAA), 3-hydroxybutyric acid and 2-hydroxyisobutyric acid are exemplary reduced products. The production of MAA through fermentation has a theoretical yield of 1.33 moles MAA per mole of glucose. It is most commonly produced from the acetone cyanohydrin (ACH) route using the raw materials acetone and hydrogen cyanide as raw materials. The intermediate cyanohydrin is converted with sulfuric acid to a sulfate ester of the methacrylamide, hydrolysis of which gives ammonium bisulfate and MAA. Other producers start with an isobutylene or, equivalently, tert-butanol, which is oxidized to methacrolein, and again oxidized to methacrylic acid. MAA is then esterified with methanol to MMA. Methacrylic acid is used industrially in the preparation of its esters, known collectively as methacrylates, such as methyl methacrylate. The methacrylates have numerous uses, most notably in the manufacture of polymers. C6H12O6→1.33C4H6O2+0.67CO2+2H2O

Sources & evidence

ORD record
ord-778a2ea434fc4a678a01841a9f20f1a7
Source dataset
uspto-grants-2015_09
Patent number
US09133487B2

Reaction notes

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