Naphthalene → Naphthalene sodium

HRID 1944767Notes

Reaction equation

HRID 1944767 reaction equation
[Na][Na].C(#N)C=C.[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[Na:17]>O1CCCC1.C1C=CC=CC=1>[CH:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][CH:14]=1.[Na:17]

Participants

7

Reactant 4

HCID 931NaphthaleneHCID 7855AcrylonitrileHCID 141233DisodiumHCID 5360545Sodium

Product 1

HCID 66588811Naphthalene sodium

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In this example, a triblock copolymer (PAN-PEO-PAN) consisting of polyethylene oxide (PEO) chain and polyacrylonitrile (PAN) chains is synthesized by living anion polymerization. Using a polyethylene oxide macromer (disodium salt of polyethylene oxide) as a reaction initiator, acrylonitrile is polymerized. Tetrahydrofuran and benzene used as solvents are distilled twice using lithium aluminum hydride as a desiccating agent under an argon gas flow, to which molecular sieves 4A is charged. The acrylonitrile employed as a monomer is washed successively with a saturated aqueous solution of NaHSO3, a saturated aqueous solution of NaCl containing 1% of NaOH, and a saturated aqueous solution of NaCl, and then vacuum-distilled using calcium chloride as a desiccating agent, and further vacuum-distilled using calcium hydride as a desiccating agent under an argon gas flow, to which molecular sieves 4A is charged. Sodium naphthalene is prepared by reacting naphthalene with metallic sodium in THF. Crown ether (dicyclohexyl-18-crown-6) is freeze-dried from a solution in benzene, and then is dissolved in benzene. Polyethylene oxide, which has OH groups at both ends, is freeze-dried from a solution in benzene immediately before use. As for the polymerization apparatus, a pressure reactor (Taiatsu Glass Co., Ltd.) is employed. The reaction is carefully performed in an argon atmosphere under pressure of 4 atm so as to prevent an external air from entering the interior of the reaction system.

Workup

  1. customis synthesized
  2. customanion polymerization
  3. customis polymerized
  4. distillationare distilled twice using lithium aluminum hydride as a desiccating agent under an argon gas flow
  5. additionto which molecular sieves 4A is charged
  6. washis washed successively with a saturated aqueous solution of NaHSO3
  7. distillationa saturated aqueous solution of NaCl containing 1% of NaOH, and a saturated aqueous solution of NaCl, and then vacuum-distilled
  8. distillationfurther vacuum-distilled
  9. additionto which molecular sieves 4A is charged
  10. dry with materialCrown ether (dicyclohexyl-18-crown-6) is freeze-dried from a solution in benzene
  11. dissolutionis dissolved in benzene
  12. dry with materialis freeze-dried from a solution in benzene immediately before use

Sources & evidence

ORD record
ord-412b678d25e040ec9054b87ea3bf8761
Source dataset
uspto-grants-2013_03
Patent number
US08394877B2

Reaction notes

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