Phenol → 2-Phenyloctadecanoic acid

HRID 1578425

Reaktionsgleichung

Reaktionsgleichung von HRID 1578425
C(O)(=[O:19])CCCCCCC/C=C\CCCCCCCC.C(O)(=O)CCCCCCC/C=C\CCCCCC.[Cl-].[Al+3].[Cl-].[Cl-].C1(O)C=CC=CC=1.[C:50]1([CH:56]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C:57]([OH:59])=[O:58])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1C=CC=CC=1>[C:50]1([CH:56]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C:57]([OH:59])=[O:58])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.[OH:19][C:56]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C:57]([OH:59])=[O:58]

Komponenten

8

Edukt 5

HCID 996PhenolHCID 445638Palmitoleic AcidHCID 445639Oleic AcidHCID 6451240Aluminum(III) ChlorideHCID 220152372-Phenyloctadecanoic acid

Produkt 2

HCID 220152372-Phenyloctadecanoic acidHCID 67710449Hydroxyphenylstearic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Phenylstearic acid and hydroxyphenylstearic acid were prepared from commercial grade oleic acid which contained a few percent of palmitoleic acid by a Friedel-Crafts reaction using aluminum chloride as the catalyst, and benzene and phenol; respectively, as the arylating agents. Thereafter, phenyloctadecylnitrile was prepared on a continuous nitrile unit over bauxite catalyst at 280°-300°C from 1127 grams phenylstearic acid. A crude yield of 833.5 grams of phenyloctadecylnitrile was obtained. The product was a mixture of isomers, predominately the C8 to C14 and the C17 isomers with lesser proportions of other isomers. Similarly, hydroxyphenyloctadecylnitrile was obtained in 62 percent crude yield from the crude acid.

Aufarbeitung

  1. customby a Friedel-Crafts reaction

Quellen und Nachweise

ORD-Eintrag
ord-faf30f356e664fa7b7dd9306029e4971
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03936503

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