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Saturday 20 June 2015

L-Tartaric acid diethyl ester

L-Tartaric acid diethyl ester

L-Tartaric acid diethyl ester

Name L-Tartaric acid diethyl ester
Synonyms Diethyl L-tartrate
Name in Chemical Abstracts Butanedioic acid, 2,3-dihydroxy-, diethyl ester, (2R,3R)-
CAS No 87-91-2
EINECS No 201-783-3
Molecular formula C8H14O6
Molecular mass 206.20
SMILES code CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC
1H NMR 1H NMR
1H-NMR: L-Tartaric acid diethyl ester
250 MHz, CDCl3
delta [ppm] mult. atoms assignment
1.33 t 6 H CH3 ethyl
3.18 m 2 H OH
4.32 q 4 H CH2 ethyl
4.54 s 2 H 2-CHOH, 3-CHOH
7.26 CHCl3
 

13C-NMR

13C NMR
13C-NMR: L-Tartaric acid diethyl ester
250 MHz, CDCl3
delta [ppm] assignment
14.14 CH3 ethyl
62.48 CH2 ethyl
72.05 C2, C3 (CHOH)
171.59 C1, C4 (CO-O)
76.5-77.5 CDCl3
 

IR

IR
IR: L-Tartaric acid diethyl ester
[Film, T%, cm-1]
[cm-1] assignment
3500 O-H valence
2985, 2940 aliph. C-H valence
2910 aliph. C-H valence
1745 C=O valence, ester
L-(+)-Tartaric acid + Ethanol
Amberlyst 15
reacts to
L-Tartaric acid diethyl ester ; Side reactions
 

Acid catalyzed reaction of L-(+)-tartaric acid with ethanol to L-(+)-tartaric acid diethyl ester

 

Operating scheme

Operating scheme
 

Chromatogram

crude product chromatogram
HPLC: crude product
column Phenomenex Luna C18; particle diameter 3 µm, L= 150 mm, ID= 4.6 mm
column temperature 25 °C
injection 15 µL
mobile phase gradient: 3% methanol/water --> 98% methanol/water in 30 min, 10 min isocratic
flow 0.6 mL/min
detector (UV 220 nm) percent concentration calculated from relative peak area

pure product chromatogram
GC: pure product
column Zebron ZB-1, L=15 m, d=0.25 mm, film=0.25 µm
inlet injector: 250°C, split injection, 0.2 µl
carrier gas He, pre-column pressure 90 kPa
oven 30°C (4 min), 20°C/min --> 240°C (7 min)
detector FID, 230°C, H2 30.8 mL/min, synth. air 361 mL/min
integration percent concentration calculated from relative peak area



 

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