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Phosphoric Acid → L-Lysinol

HRID 592128
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 592128
[NH2:1][C@H:2]([C:8](O)=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].S(=O)(=O)(O)O.P(=O)(O)(O)O.[H][H].[OH-].[Na+]>O.[Pt].[Re].[Ru].[Pt].[Ru].[Re]>[NH2:1][C@H:2]([CH2:8][OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 5

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 5962L-Lysine5×HCID 14798Sodium HydroxideHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 11607920L-Lysinol

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23939PlatinumKatalysator2×
HCID 23950RutheniumKatalysator
HCID 57449507HCID 57449507, VerbindungKatalysator
HCID 60209655HCID 60209655, VerbindungKatalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

In particular, the process comprises charging a high pressure reactor with a solution of lysine in water, acid, and a hydrogenation catalyst. The high pressure reactor may be a batch, continuous, or semi-continuous reactor. The acid including, but not limited to sulfuric acid or phosphoric acid, is present in an amount of at least 0.5 molar equivalent of lysine or 1 molar equivalentor of lysine or 2 molar equivalent of lysine. Alternatively, the pH of the aqueous lysine solution can be adjusted with an acid to a pH in the range of 1-5 or 1.5-4 or 2-3. The catalyst is present in an amount in the range of 0.2-50% or 0.5-10% or 1-5% by weight of the total reaction mass. The hydrogenation catalyst can be chosen from those known in the art, for example ruthenium supported on carbon, platinum supported on carbon, platinum supported on titanium dioxide, or supported rhenium-ruthenium or rhenium-platinum catalysts. The process further comprises filling the reactor with hydrogen up to a pressure in the range of 0.7-14 MPa or 1.5-11 MPa or 2-9 MPa at a temperature in the range of 50-220° C. or 100-200° C. or 120-180° C. The process also comprises maintaining the pressure until ceasing of hydrogen uptake. The process further comprises cooling the reactor to room temperature and adding sodium hydroxide until pH is greater than 12. The process also comprises removing water and extracting the resulting residue, a mixture of lysinol and salt, with a solvent that will disolve lysinol but not the salts and then removing the solvent to obtain lysinol in the form of a colorless oil. In an embodiment, the lysinol is enantioenriched (S)-lysinol. In another embodiment, the ratio of (S)-lysinol to (R)-lysinol is in the range of 99.9:0.1 to 51:49 or 98:2 to 70:30 or 95:5 to 80:20.

Aufarbeitung

  1. customin the range of 50-220° C. or 100-200° C. or 120-180° C
  2. customThe process also comprises removing water
  3. extractionextracting the resulting residue
  4. additiona mixture of lysinol and salt
  5. customnot the salts and then removing the solvent

Quellen und Nachweise

ORD-Eintrag
ord-4f4a326648da4a47a46966a155b73ee3
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238714B2

Notizen zur Reaktion

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