Chlorobenzene → 1,4-Diphenyl-1,3-butadiyne

HRID 1834362

Reaktionsgleichung

Reaktionsgleichung von HRID 1834362
[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]#[CH:26])#C.Cl[C:28]1C=CC=C[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2].CO>[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]([C:20]1[CH:19]=[CH:24][C:23]([C:28]#[CH:29])=[CH:22][CH:21]=1)#[CH:26]

Komponenten

9

Edukt 4

HCID 7964ChlorobenzeneHCID 11776TriphenylphosphineHCID 701741,4-Diphenyl-1,3-butadiyneHCID 1408621,2-Diethynylbenzene4×

Produkt 2

HCID 701741,4-Diphenyl-1,3-butadiyneHCID 1204631,4-Diethynylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9834912Nickel(II) acetylacetonateKatalysatorHCID 241BenzeneLösungsmittel3×HCID 887MethanolLösungsmittel

Versuchsvorschrift

A copolymer prepolymer of diphenylbutadiyne and p-diethynylbenzene was prepared in refluxing benzene solvent. The polymerization vessel was charged with 63 parts of diphenylbutadiyne, 2 parts of diethynylbenzene, 600 parts of benzene, and 2 parts of chlorobenzene. After heating to reflux, 2 parts of a catalyst mixture prepared by mixing 2 parts of nickel acetylacetonate and 4 parts of triphenylphosphine in 20 parts of benzene were added. After 1 hour, an additional 10 parts of diethynylbenzene was added. After 2 hours, 10 parts of diethynylbenzene and 2 parts of catalyst solution were added. After 3 hours, 20 parts of diethynylbenzene and 4 parts of catalyst solution were added. After a total reaction period of 7 hours, gas-liquid chromatographic analysis of the reaction mixture showed that 10% of each of the monomeric components remained. The solution was added to 5 times its volume of methanol, and 77 parts of the copolymer was precipitated. It has an acetylene content of 8.4% and an aromatic to olefin hydrogen ratio of 8:1.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureto reflux
  3. custom2 parts of a catalyst mixture prepared
  4. additionwere added
  5. waitAfter 2 hours
  6. waitAfter 3 hours
  7. customAfter a total reaction period of 7 hours, gas-liquid chromatographic analysis of the reaction mixture
  8. customwas precipitated

Quellen und Nachweise

ORD-Eintrag
ord-3f51c561af8e4f85b216ac55c3c7a370
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04070333

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