Heptane → HCID 18924070, compound

HRID 2166219Notes

Reaction equation

HRID 2166219 reaction equation
O[S:2]([OH:5])(=[O:4])=[O:3].[O:6]=[S:7](=[O:9])=[O:8].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O>[CH2:12]([C:11]1[C:12]([CH2:11][CH2:10][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:13][CH2:14][CH3:15])=[C:13]([S:7]([OH:9])(=[O:8])=[O:6])[C:14]([S:2]([OH:5])(=[O:4])=[O:3])=[C:15]2[C:10]=1[CH:12]=[CH:11][CH:10]=[CH:16]2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 8900Heptane2×HCID 24681Fuming sulfuric acid2×

Product 1

HCID 18924070HCID 18924070, compound

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 7416NitrobenzeneSolvent

Procedure

This example shows the feasibility of producing a heavy-phase concentrate of didodecylnaphthalene disulfonic acid using the double-sulfonation and controlled washing technique described above. 211 grams of didodecylnaphthalene synthesized by the alkylation of naphthalene with tetrapropylene using aluminum chloride catalyst and nitrobenzene solvent was diluted with an equal weight of heptane. This solution of "DDN" in heptane was sulfonated in two treats with 122 grams of 20% oleum per treat. After each oleum treat, the spent acid was allowed to separate and was then drawn off. The sulfonation was carried out at a temperature of 40° C. The overall mole ratio of available SO3 to alkylate was approximately 2.0:1. 441 grams of crude sulfonic acid in heptane was recovered from the reaction. 110 milliliters of heptane and 270 milliliters of hot water were added to the crude sulfonic acid in a separatory funnel and mixed well. On standing, a dense heavy-phase settled to the bottom. It contained 56.1% didodecylnaphthalene sulfonic acid in a total weight of 34.3 grams. the upper organic layer was washed several times with water. All of the washes including the heavy-phase wash were combined and yielded an additional 20.4 grams of disulfonic acid for a total yield of 39.6 grams of didodecylnaphthalene disulfonic acid.

Workup

  1. customof producing a heavy-phase
  2. concentrationconcentrate of didodecylnaphthalene disulfonic acid using the double-sulfonation and
  3. washcontrolled washing technique
  4. custom211 grams of didodecylnaphthalene synthesized by the alkylation of naphthalene with tetrapropylene
  5. additionper treat
  6. customto separate
  7. customwas carried out at a temperature of 40° C
  8. custom441 grams of crude sulfonic acid in heptane was recovered from the reaction
  9. addition110 milliliters of heptane and 270 milliliters of hot water were added to the crude sulfonic acid in a separatory funnel
  10. additionmixed well
  11. washthe upper organic layer was washed several times with water
  12. washwash

Sources & evidence

ORD record
ord-c487ce98be10445a8798025848ff6c7a
Source dataset
uspto-grants-1990_07
Patent number
US04943656

Reaction notes

Loading…