Chlorobenzene → Phenylacetylene

HRID 839775

Reaktionsgleichung

Reaktionsgleichung von HRID 839775
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:10]1C=CC=C[CH:11]=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]>[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:10]#[CH:11])#[CH:8].[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 7964ChlorobenzeneHCID 10821Phenylacetylene2×HCID 11776Triphenylphosphine

Produkt 2

HCID 10821PhenylacetyleneHCID 1408621,2-Diethynylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9834912Nickel(II) acetylacetonateKatalysatorHCID 241BenzeneLösungsmittel3×

Versuchsvorschrift

A copolymer prepolymer of diethynylbenzene and phenylacetylene was prepared in refluxing benzene solvent. The polymerization vessel was charged with 60 parts of a 90:10 mixture of m- and p-diethynylbenzenes, 60 parts of phenylacetylene, 600 parts of benzene and 2 parts of chlorobenzene. After heating to reflux, 5 parts of a catalyst solution prepared by adding 0.3 part of nickel acetylacetonate and 0.6 part of triphenylphosphine in 15 parts benzene were added. After 2 hours, an additional 10 parts of this catalyst solution was added. After 5 hours, gas-liquid chromatographic analysis showed that 74% of the diethynylbenzenes and 35% of the phenylacetylene had been converted to copolymer. The copolymer was precipitated by adding the solution to five times its volume of petroleum ether, 26 parts being recovered. This product had a number average molecular weight of about 3,000, an acetylene content of 8.9%, and an aromatic to olefin proton ratio of 5.5:1.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureto reflux
  3. custom5 parts of a catalyst solution prepared
  4. additionwere added
  5. additionan additional 10 parts of this catalyst solution was added
  6. waitAfter 5 hours
  7. customThe copolymer was precipitated
  8. additionby adding the solution to five times its volume of petroleum ether, 26 parts
  9. custombeing recovered

Quellen und Nachweise

ORD-Eintrag
ord-b21e28e6866d411dbc59459847c4c688
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04097460

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