Tetrahydrothiophene → Hydrogen Sulfide

HRID 1873300Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[S:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:11][CH2:12][CH2:13][CH2:14]S>>[CH3:7][CH2:8][CH2:9][CH2:10][CH2:5][CH2:4][CH2:3][CH2:2][SH:1].[CH3:11][C:12]([CH2:13][C:14]([CH3:14])([CH3:13])[CH3:12])=[CH2:11].[SH2:6]

Participants

Reactant 3

HCID 1127Tetrahydrothiophene

HCID 8012Butanethiol

HCID 8030Thiophene2×

Product 3

HCID 402Hydrogen Sulfide

HCID 78682,4,4-Trimethyl-1-pentene

HCID 81441-Octanethiol

Procedure

Thiophene hydrodesulfurization proceeds in the first reactor. Because a catalyst with low hydrogenation activity was used, no thiacyclopentane or butylthiol production was found in the thiophene hydrogenation product. Octylthiol was also produced by reaction between diisobutylene and hydrogen sulfide generated by the hydrodesulfurization. In the second reactor, the octylthiol produced by the first reactor was hydrodesulfurized, yielding a model gasoline base with a total sulfur content of no greater than 10 ppm by weight.

Sources & evidence

ORD record: ord-e50dcea785a74c798fdc9732f3598bbf
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08303805B2

Reaction notes

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