Succinic anhydride → Butanedioic acid, 1-octadecyl ester, calcium salt (2:1)

HRID 326946Notes

Reaction equation

HRID 326946 reaction equation
[CH2:1]([OH:19])[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][CH2:16][CH2:17][CH3:18].[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1.[OH-].[Ca+2:28].[OH-]>>[C:20]([O:19][CH2:1][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][CH2:16][CH2:17][CH3:18])(=[O:26])[CH2:21][CH2:22][C:23]([O-:25])=[O:24].[Ca+2:28].[CH2:1]([O:19][C:20](=[O:26])[CH2:21][CH2:22][C:23]([O-:25])=[O:24])[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][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 8221Stearyl AlcoholHCID 6093208Calcium Hydroxide

Product 1

HCID 73456732Butanedioic acid, 1-octadecyl ester, calcium salt (2:1)

Conditions

Temperature
80 °C

Procedure

696.4 g of a commercially available technical stearyl alcohol were introduced into a reaction vessel and heated to 80° C. 256.6 g succinic anhydride were then added; the reaction mixture was heated to 130° C. The reaction was mildly exothermic; the temperature rose to 140° C. The reaction mixture was then stirred for 30 minutes at 130 to 140° C.; the acid value of the reaction mixture was 151 to 152. 94.3 g plus 2.8 g (3% excess) calcium hydroxide Were then introduced in portions over a period of 30 minutes at temperatures of 145° to 150° C. The reaction mixture was kept at that temperature for 4 hours, a light vacuum being applied at the beginning of the reaction. The vacuum was increased to 500 hPa after 30 minutes, to 32 hPa after 1 h and 39 hPa after 2 h and was left at that value until the end of the 4-hour reaction time.

Workup

  1. temperaturethe reaction mixture was heated to 130° C
  2. customrose to 140° C
  3. waitThe reaction mixture was kept at that temperature for 4 hours
  4. customa light vacuum being applied at the beginning of the reaction
  5. temperatureThe vacuum was increased to 500 hPa after 30 minutes, to 32 hPa after 1 h
  6. wait39 hPa after 2 h
  7. waitwas left at that value until the end of the 4-hour reaction time

Sources & evidence

ORD record
ord-7dc2f97feb2149d09e5c6c01e8bc6f70
Source dataset
uspto-grants-1993_12
Patent number
US05271855

Reaction notes

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