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Citric Acid → 2-Propanol, 1-methoxy-, 2-propanoate

HRID 1109639
Notes
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Reaction equation

HRID 1109639 reaction equation
S(=O)(=O)(O)O.Cl.P(=O)(O)(O)O.C(O)(=O)[C:13](O)=[O:14].C(O)(=O)C[C:20]([CH2:25][C:26]([OH:28])=[O:27])(C(O)=O)O.[C:31]1([CH3:41])C=CC(S(O)(=O)=O)=C[CH:32]=1.CS(O)(=O)=O>CC1C=CC=CC=1.C(O)(=O)C>[C:26]([O:28][CH:31]([CH3:41])[CH2:32][O:14][CH3:13])(=[O:27])[CH2:25][CH3:20]
ParticipantsProcedureSources & evidenceReaction notes

Participants

10

Reactant 7

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 1004Phosphoric AcidHCID 1118Sulfuric Acid2×HCID 6101p-Toluenesulfonic acidHCID 6395Methanesulfonic Acid2×

Product 1

HCID 110080492-Propanol, 1-methoxy-, 2-propanoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

The catalysts used in the present invention include inorganic acids, such as sulfuric acid, hydrochloric acid and phosphoric acid, and organic acids, such as acetic acid, oxalic acid, citric acid, p-toluene sulfonic acid and methane sulfonic acid, among which the strong acids including sulfuric acid, p-toluene, sulfonic acid or methane sulfonic acid are preferred. Propylene glycol monomethyl ether propionate obtained according to the present application has a boiling point of 160.5° C., while other reactants and products having respective boiling point of 120° C. for PGM, 140.8° C. for propionic acid and 100° C. for water. It is apparently easier to rectify this solution comparing the respective boiling point of 146° C. for propylene glycol monomethyl ether acetate, 118° C. for acetic acid and 120° C. for PGM as in the conventional case. This is one of the effects achieved by the process according to the present invention.

Sources & evidence

ORD record
ord-abe7778d927a48e2908e51c27f7f7fc3
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05321152

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes