Patent GB-439491-A (GB)
Title: Improvements in the recovery of valuable products from hydrocarbons
IPC: C07C7/148
Filed: 1934-05-30
Abstract: Diolefines are removed from crude hydrocarbons such as cracking products, benzine or benzol, by treatment with quinones, such as a -naphthoquinone, addition products being obtained. Cyclic dienes may be separately removed as similar addition products by effecting a first treatment at low temperatures, the acyclic dienes reacting usually above 50 DEG  C.; moreover methylcyclopentadiene reacts more readily than cyclopentadiene. The quinones may be added in separate portions, each followed by separation of the addition product.  The addition products are anthraquinone derivatives, and may be used as initial materials for the production of dyes.  In examples: (1) a fraction of a cracking product of brown coal low temperature tar is treated with a -naphthoquinone and distilled under reduced pressure, the addition product of the quinone with cyclic dienes may be crystallized from methanol or ligroin; (2) a fraction of a cracking product of Panhandle oil is fractionally treated with a -naphthoquinone, the mixture being distilled after the first treatment, and successive additions being made to the successive distillates; the residues contain addition products of methylcyclopentadiene, a mixture of addition products of methylcyclopentadiene and cyclopentadiene, and the addition product of cyclopentadiene respectively; (3) a -naphthoquinone is added to the distillate free from cyclic dienes as in example 2, the addition product of acyclic dienes being obtained; (4) a -naphthoquinone is added to the first runnings of crude benzene from gasworks; (5) a cracking product freed from cyclic dienes is heated at 100 DEG  C. under pressure with portions of a -naphthoquinone; (6) chloranil is added to the initial cracking product used in example 5, addition products of methylcyclopentadiene and cyclopentadiene being obtained; (7) benzoquinone is added to the initial cracking product used in example 5, biscyclopentadienequinone being obtained. Specification 320,375, [Class 2 (iii)], is referred to.ALSO:Diolefines are removed from crude hydrocarbons such as cracking products, benzine or benzol, by treatment with quinones, such as a -naphthoquinone, addition products being obtained. Cyclic diones may be separately removed as similar addition products by effecting a first treatment at low temperatures, the acyclic dienes reacting usually above 50 DEG  C.; moreover methylcyclopentadiene reacts more readily than cyclopentadiene. The quinones may be added in separate portions, each followed by a separation of the addition product.  In examples: (1) a fraction of a cracking-product of brown coal low temperature tar is treated with a -naphthoquinone and distilled under reduced pressure; (2) a fraction of a cracking product of Panhandle oil is fractionally treated with a -naphthoquinone, the mixture being distilled after the first treatment, and successive additions being made to the successive distillates.  The residues contain addition products of methylcyclopentadiene and cyclopentadiene; (3) a -naphthaquinone is added to the distillate free from cyclic dienes as in example 2, the addition product of acyclic dienes being obtained; (4) a -naphthoquinone is added to the first runnings of crude benzene from gas works; (5) a cracking product freed from cyclic dienes is heated at 100 DEG  C., under pressure with portions of a -naphthoquinone; (6) chloranil is added to the initial cracking product used in example 5; (7) benzoquinone is added to the initial cracking product used in example 5.  Specification 320,375, [Class 2 (iii)], is referred to.