DE1957146A1 - Verfahren zur Herstellung von Styrol und verwandten Verbindungen - Google Patents
Verfahren zur Herstellung von Styrol und verwandten VerbindungenInfo
- Publication number
- DE1957146A1 DE1957146A1 DE19691957146 DE1957146A DE1957146A1 DE 1957146 A1 DE1957146 A1 DE 1957146A1 DE 19691957146 DE19691957146 DE 19691957146 DE 1957146 A DE1957146 A DE 1957146A DE 1957146 A1 DE1957146 A1 DE 1957146A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- benzene
- toluene
- styrene
- dehydrogenation
- 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.)
- Pending
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 84
- 238000000034 method Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 144
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 114
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 82
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 51
- 239000000047 product Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000005804 alkylation reaction Methods 0.000 claims description 21
- 230000029936 alkylation Effects 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 18
- 238000011084 recovery Methods 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- 239000006227 byproduct Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 238000006900 dealkylation reaction Methods 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000020335 dealkylation Effects 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- KHGSIITYVUGTTQ-UHFFFAOYSA-N methane;toluene Chemical compound C.CC1=CC=CC=C1 KHGSIITYVUGTTQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- ASCHNMXUWBEZDM-UHFFFAOYSA-N chloridodioxygen(.) Chemical compound [O]OCl ASCHNMXUWBEZDM-UHFFFAOYSA-N 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 2
- 229910001950 potassium oxide Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000282346 Meles meles Species 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 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
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77758968A | 1968-11-21 | 1968-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1957146A1 true DE1957146A1 (de) | 1970-07-02 |
Family
ID=25110670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691957146 Pending DE1957146A1 (de) | 1968-11-21 | 1969-11-13 | Verfahren zur Herstellung von Styrol und verwandten Verbindungen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE741784A (enrdf_load_stackoverflow) |
| BR (1) | BR6914360D0 (enrdf_load_stackoverflow) |
| DE (1) | DE1957146A1 (enrdf_load_stackoverflow) |
| ES (1) | ES373609A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2023805A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1238602A (enrdf_load_stackoverflow) |
| NL (1) | NL6917319A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2177470C1 (ru) * | 2000-07-27 | 2001-12-27 | Воронежское открытое акционерное общество "Синтезкаучукпроект" | Способ получения стирола |
| US8076527B2 (en) | 2008-03-13 | 2011-12-13 | Fina Technology, Inc. | Process for production of ethylbenzene from toluene and methane |
| US11179702B2 (en) * | 2019-11-19 | 2021-11-23 | Fina Technology, Inc. | Process to prepare insoluble polymer abatement additives in styrene process streams by catalytic oxidation |
-
1969
- 1969-10-27 GB GB1238602D patent/GB1238602A/en not_active Expired
- 1969-11-13 DE DE19691957146 patent/DE1957146A1/de active Pending
- 1969-11-17 BE BE741784D patent/BE741784A/xx unknown
- 1969-11-17 ES ES373609A patent/ES373609A1/es not_active Expired
- 1969-11-18 NL NL6917319A patent/NL6917319A/xx unknown
- 1969-11-20 BR BR21436069A patent/BR6914360D0/pt unknown
- 1969-11-20 FR FR6939989A patent/FR2023805A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE741784A (enrdf_load_stackoverflow) | 1970-05-19 |
| NL6917319A (enrdf_load_stackoverflow) | 1970-05-25 |
| GB1238602A (enrdf_load_stackoverflow) | 1971-07-07 |
| FR2023805A1 (enrdf_load_stackoverflow) | 1970-08-21 |
| ES373609A1 (es) | 1972-03-16 |
| BR6914360D0 (pt) | 1973-01-11 |
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