Methanesulfonic Acid → Terpinen-4-ol

HRID 2078531

Reaktionsgleichung

Reaktionsgleichung von HRID 2078531
[CH3:1][C:2]1[CH2:7][CH2:6][C:5]([OH:11])([CH:8]([CH3:10])[CH3:9])[CH2:4][CH:3]=1.CC1(C)C(O)C2(C)CC1CC2.[C:23]12([CH3:33])[C:29]([CH3:31])([CH3:30])[CH:26]([CH2:27][CH2:28]1)[CH2:25][CH:24]2O.CS(O)(=O)=O.CC1CCC(C(O)(C)C)CC=1>>[CH3:1][C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[CH2:4][CH:3]=1.[CH3:33][C:23]1[CH2:28][CH2:27][C:26](=[C:29]([CH3:31])[CH3:30])[CH2:25][CH:24]=1.[CH3:1][C:2]1[CH2:7][CH2:6][C:5]([OH:11])([CH:8]([CH3:9])[CH3:10])[CH2:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 6395Methanesulfonic AcidHCID 11230Terpinen-4-ol2×HCID 15406FencholHCID 17100alpha-TerpineolHCID 64685Borneol2×

Produkt 3

HCID 11230Terpinen-4-olHCID 11463TerpinoleneHCID 440917(+)-Limonene

Versuchsvorschrift

Crude pine oil (138.8 g; dehydrated by vacuum stripping and containing terpineol: 94.0%; fenchol: 0.29%; borneol: 3.66%) is heated with ME-810 (12.4 g; mixture of methyl fatty acid esters, available from Peter Cremer NA, LP) and methanesulfonic acid (1.0 g) at 100° C., 30-60 mm Hg for 10 h. GC of the reaction mixture shows: terpineol: 19.9%; borneol: 1.85%; terpene alcohol fatty esters: 2%. Limonene and terpinolene, formed by acid-catalyzed dehydration of terpineol, account for 65% of the reaction mixture. Distillation of the reaction mixture gives 108 g of material containing 1.85% of borneol and 18.5% of terpineol. This example shows that methanesulfonic acid is an unacceptable catalyst for the transesterification.

Quellen und Nachweise

ORD-Eintrag
ord-3a4fa04424ae4e49aa840a2d63d20b60
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928269B2

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