Salicylic Acid → Calcium bis(5-hexadecyl-2-hydroxybenzoate)

HRID 1950691Notes

Reaction equation

HRID 1950691 reaction equation
[CH2:1]([C:17]1[CH:25]=[C:21]([C:22]([OH:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(O)(=O)C1C(=CC=CC=1)O.C(C1C=CC(O)=CC=1)CCCCCCCCCCCCCCC.[OH-].[Ca+2:61].[OH-]>C1(C)C(C)=CC=CC=1.O.CO>[CH2:1]([C:17]1[CH:25]=[C:21]([C:22]([O-:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Ca+2:61].[CH2:1]([C:17]1[CH:25]=[C:21]([C:22]([O-:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 338Salicylic Acid2×HCID 75768Phenol, 4-hexadecyl-HCID 110437Benzoic acid, 5-hexadecyl-2-hydroxy-HCID 6093208Calcium Hydroxide

Product 1

HCID 140546752Calcium bis(5-hexadecyl-2-hydroxybenzoate)

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Conditions

Temperature
40 °C

Procedure

The 5-(hexadec-1-yl)salicylic acid of Example 3 (3.16 g) was mixed with a commercial lower alkyl (i.e. less than C20) salicylic acid (Infineum M7103, obtainable from Infineum UK Limited, 3.89 g), and 4-(hexadec-1-yl)phenol of Example 2 (0.34 g). The salicylic acid mixture and xylene (100 g) were mixed together at room temperature. Calcium hydroxide (2.50 g), a promoter (methanol:water (97%:3%), 25.29 ml) and further xylene (120 g) were added, nitrogen passed through the mixture (60 ml.min−1) and the resulting mixture heated in an oil bath at 40° C. for 1 hour.

Sources & evidence

ORD record
ord-06f681b0e40b46c79595b0ef4547f532
Source dataset
uspto-grants-2013_03
Patent number
US08404627B2

Reaction notes

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