Hydrochloric Acid → Alpha-Lipoic Acid Alpha Cyclodextrin

HRID 448519Notes

Reaction equation

HRID 448519 reaction equation
[OH-].[K+].[CH2:3]1[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[S:6][S:5][CH2:4]1.[CH2:15]([OH:80])[C@H:16]1[O:21][C@@H:20]2[O:22][C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@@H:26]([O:31][C@H:32]4[C@H:37]([OH:38])[C@@H:36]([OH:39])[C@@H:35]([O:40][C@H:41]5[C@H:46]([OH:47])[C@@H:45]([OH:48])[C@@H:44]([O:49][C@H:50]6[C@H:55]([OH:56])[C@@H:54]([OH:57])[C@@H:53]([O:58][C@H:59]7[C@H:65]([OH:66])[C@@H:64]([OH:67])[C@@H:62]([O:63][C@H:17]1[C@H:18]([OH:79])[C@H:19]2[OH:78])[O:61][C@@H:60]7[CH2:68][OH:69])[O:52][C@@H:51]6[CH2:70][OH:71])[O:43][C@@H:42]5[CH2:72][OH:73])[O:34][C@@H:33]4[CH2:74][OH:75])[O:25][C@@H:24]3[CH2:76][OH:77].Cl>O>[CH2:3]1[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[S:6][S:5][CH2:4]1.[CH2:70]([OH:71])[C@H:51]1[O:52][C@@H:53]2[O:58][C@H:59]3[C@H:65]([OH:66])[C@@H:64]([OH:67])[C@@H:62]([O:63][C@H:17]4[C@H:18]([OH:79])[C@@H:19]([OH:78])[C@@H:20]([O:22][C@H:23]5[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@@H:26]([O:31][C@H:32]6[C@H:37]([OH:38])[C@@H:36]([OH:39])[C@@H:35]([O:40][C@H:41]7[C@H:46]([OH:47])[C@@H:45]([OH:48])[C@@H:44]([O:49][C@H:50]1[C@H:55]([OH:56])[C@H:54]2[OH:57])[O:43][C@@H:42]7[CH2:72][OH:73])[O:34][C@@H:33]6[CH2:74][OH:75])[O:25][C@@H:24]5[CH2:76][OH:77])[O:21][C@@H:16]4[CH2:15][OH:80])[O:61][C@@H:60]3[CH2:68][OH:69]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 864alpha Lipoic acidHCID 14797Potassium Hydroxide2×HCID 444913Alpha-Cyclodextrin

Product 1

HCID 131728183Alpha-Lipoic Acid Alpha Cyclodextrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

29.95 kg of potassium hydroxide pellets (87.9%, 469.3 moles) were added to 1920.0 kg of water and mixed at room temperature until clear. The pH of this solution was at pH 14. 97.8 kg alpha-lipoic acid (98%, 464.5 moles) was added to the potassium hydroxide solution and mixed until clear (in case of the presence of amorphous silica as flowing agent the solution will be slightly cloudy). 555.1 kg alpha cyclodextrin (8.9% water content, 520.3 moles) was added and stirred 60 minutes at room temperature. 469.3 moles of 37.7% hydrochloric acid was added precipitating the complex. This mixture was stirred 55 minutes at room temperature. The final pH was at about pH 3. The final aqueous mixture was spray dried immediately at about 180° C. inlet and about 80° C. outlet temperature.

Workup

  1. additionmixed at room temperature until clear
  2. additionmixed until clear (in case of the presence of amorphous silica
  3. customprecipitating the complex
  4. stirringThis mixture was stirred 55 minutes at room temperature
  5. customdried immediately at about 180° C. inlet
  6. customabout 80° C. outlet temperature

Sources & evidence

ORD record
ord-7679845bc27e42e6abafff3daea2c41f
Source dataset
uspto-grants-2013_07
Patent number
US08481716B2

Reaction notes

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