GB397901A - Improvements in the reduction of aromatic hydroxy compounds - Google Patents
Improvements in the reduction of aromatic hydroxy compoundsInfo
- Publication number
- GB397901A GB397901A GB592132A GB592132A GB397901A GB 397901 A GB397901 A GB 397901A GB 592132 A GB592132 A GB 592132A GB 592132 A GB592132 A GB 592132A GB 397901 A GB397901 A GB 397901A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphide
- vanadium
- molybdenum
- tungsten
- sulphides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 aromatic hydroxy compounds Chemical class 0.000 title abstract 4
- 239000003054 catalyst Substances 0.000 abstract 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 4
- 229910052750 molybdenum Inorganic materials 0.000 abstract 4
- 239000011733 molybdenum Substances 0.000 abstract 4
- 150000003346 selenoethers Chemical class 0.000 abstract 4
- 229910052720 vanadium Inorganic materials 0.000 abstract 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910002804 graphite Inorganic materials 0.000 abstract 3
- 239000010439 graphite Substances 0.000 abstract 3
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 3
- XCUPBHGRVHYPQC-UHFFFAOYSA-N sulfanylidenetungsten Chemical class [W]=S XCUPBHGRVHYPQC-UHFFFAOYSA-N 0.000 abstract 3
- 239000005995 Aluminium silicate Substances 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000005083 Zinc sulfide Substances 0.000 abstract 2
- 235000012211 aluminium silicate Nutrition 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000004763 sulfides Chemical class 0.000 abstract 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052721 tungsten Inorganic materials 0.000 abstract 2
- 239000010937 tungsten Substances 0.000 abstract 2
- 239000011787 zinc oxide Substances 0.000 abstract 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000003763 carbonization Methods 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000003077 lignite Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 1
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 abstract 1
- ZFDNHUHPLXMMBR-UHFFFAOYSA-N sulfanylidenevanadium Chemical compound [V]=S ZFDNHUHPLXMMBR-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003739 xylenols Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Aromatic hydrocarbons are prepared by circulating aromatic hydroxy compounds in the vapour phase with hydrogen under pressure over the customary catalysts, the time of contact being so short that a substantial part, preferably from 10 to 40 per cent, of the hydroxy compound remains unconverted. The hydroxy compound is preferably passed over the catalyst in an amount per hour which, measured as a liquid, is at least equal to but not more than twice the volume of the catalyst. The product is isolated from the reaction gases and the remainder introduced with fresh hydroxy compound into the reaction chamber. As catalyst is preferably employed a metal of group 6 or of the iron group or vanadium or a compound thereof, particularly a sulphide or selenide of molybdenum, tungsten or vanadium. The said sulphides or selenides may be mixed with graphite, kaolin, zinc oxide or sulphide; whilst it is advantageous, in the case of molybdenum and tungsten sulphides to heat them temporarily to a high temperature, e.g. 750-850 DEG C., before use. Pressures of 20-300 atmospheres and temperatures of 350-550 DEG C. may be employed. Aromatic hydroxy compounds mentioned are phenol, cresols, xylenols, ethylphenols, dihydroxy- and trihydroxybenzenes, and naphthols. Examples are given of the conversion into the corresponding aromatic hydrocarbons of (1) phenol over molybdenum sulphide, (2) the crude phenolic oil mixture obtained by dephenolizing brown coal low temperature carbonization water over a pressed mixture of graphite and tungsten sulphide previously heated to 750 DEG C., and (3) crude cresol over vanadium sulphide.ALSO:Catalysts for the reduction of aromatic hydroxy compounds to aromatic hydrocarbons at elevated temperature and pressure preferably comprise a metal of group 6 or of the iron group or vanadium or a compound thereof, particularly sulphide or selenide of molybdenum, tungsten or vanadium. The said sulphides or selenides may be mixed with graphite, kaolin, zinc oxide or sulphide, whilst it is advantageous, in the case of molybdenum and tungsten sulphides, to heat them temporarily to a high temperature, e.g. 750-850 DEG C., before use.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB592132A GB397901A (en) | 1932-02-27 | 1932-02-27 | Improvements in the reduction of aromatic hydroxy compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB592132A GB397901A (en) | 1932-02-27 | 1932-02-27 | Improvements in the reduction of aromatic hydroxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB397901A true GB397901A (en) | 1933-08-28 |
Family
ID=9805130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB592132A Expired GB397901A (en) | 1932-02-27 | 1932-02-27 | Improvements in the reduction of aromatic hydroxy compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB397901A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097541A (en) * | 1973-06-21 | 1978-06-27 | Kogyo Kaihatsu Kenkyusho (Industrial Research Institut) | Process of producing mainly monocyclic aromatic compounds from unutilized carbon resources mainly composed of polycyclic aromatic compounds |
-
1932
- 1932-02-27 GB GB592132A patent/GB397901A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097541A (en) * | 1973-06-21 | 1978-06-27 | Kogyo Kaihatsu Kenkyusho (Industrial Research Institut) | Process of producing mainly monocyclic aromatic compounds from unutilized carbon resources mainly composed of polycyclic aromatic compounds |
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