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Water → Sodium stearyl succinate

HRID 1606791
Notes
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Reaction equation

HRID 1606791 reaction equation
[CH2:1]([CH:19]([CH2:23][C:24]([OH:26])=O)C(O)=O)[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]CCC.[OH-:27].[Na+:28].[OH2:29]>CC(C)=O>[C:24]([O:26][CH2:24][CH2:23][CH2:19][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][CH3:15])(=[O:26])[CH2:23][CH2:19][C:1]([O-:29])=[O:27].[Na+:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 110691Octadecylsuccinic acid

Product 1

HCID 23673896Sodium stearyl succinateYield 98.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
40 °C

Procedure

In a 2000 ml. Erlenmeyer flask, there were placed 150 g. of monostearyl succinic acid (acid value, 156.7) and 1200 ml. of acetone. This mixture was first warmed and stirred to effect solution and then cooled to 40°C., at which point 17.3 g. of sodium hydroxide in 100 ml. of water were slowly added. The addition step was accomplished with vigorous agitation of the mixture, while the temperature of the acetone solution was always maintained at 40°-43°C. throughout said step. The resulting reaction mixture was then stirred for a further 15 minutes, cooled down to 10°-15°C. and filtered with suction. The filter cake so obtained was washed twice with separate 100 ml. portions of cold acetone and sucked dry on the filter funnel. After drying the product in a vacuum oven at 50°C., it was found that a yield of 157.5 g. (98.5%) of sodium stearyl succinate was obtained. This particular salt, which was obtained in the form of a white powder, gave a 0.1% (W/V) aqueous dispersion at 25°C. and a 1% dispersion at 50°C.

Workup

  1. temperatureThis mixture was first warmed
  2. additionThe addition step
  3. temperaturewas always maintained at 40°-43°C.
  4. customThe resulting reaction mixture
  5. stirringwas then stirred for a further 15 minutes
  6. temperaturecooled down to 10°-15°C.
  7. filtrationfiltered with suction
  8. customThe filter cake so obtained
  9. washwas washed twice
  10. customwith separate 100 ml
  11. dry with materialportions of cold acetone and sucked dry on the filter funnel
  12. customAfter drying the product in a vacuum oven at 50°C.

Sources & evidence

ORD record
ord-91b90ee236a54dec9a85c957e84bc2ef
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03953616

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes