NO130394B - - Google Patents
Download PDFInfo
- Publication number
- NO130394B NO130394B NO483371A NO483371A NO130394B NO 130394 B NO130394 B NO 130394B NO 483371 A NO483371 A NO 483371A NO 483371 A NO483371 A NO 483371A NO 130394 B NO130394 B NO 130394B
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- weight
- catalyst
- reactor
- hydrocarbons
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 79
- 238000006317 isomerization reaction Methods 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 55
- 229930195733 hydrocarbon Natural products 0.000 claims description 53
- 150000002430 hydrocarbons Chemical class 0.000 claims description 53
- 238000005984 hydrogenation reaction Methods 0.000 claims description 34
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- -1 alkyl radical Chemical class 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 235000012239 silicon dioxide Nutrition 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 3
- 239000000956 alloy Substances 0.000 claims description 3
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001260 Pt alloy Inorganic materials 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229930007927 cymene Natural products 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 238000004821 distillation Methods 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 19
- 239000010437 gem Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 12
- 150000001350 alkyl halides Chemical class 0.000 description 12
- GCYUJISWSVALJD-UHFFFAOYSA-N 1,1-diethylcyclohexane Chemical class CCC1(CC)CCCCC1 GCYUJISWSVALJD-UHFFFAOYSA-N 0.000 description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 229910000039 hydrogen halide Inorganic materials 0.000 description 9
- 239000012433 hydrogen halide Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- SEKSWDGNGZWLDU-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclohexane Chemical class CC1(C)CCCCC1(C)C SEKSWDGNGZWLDU-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- ZTHNOZQGTXKVNZ-UHFFFAOYSA-L dichloroaluminum Chemical compound Cl[Al]Cl ZTHNOZQGTXKVNZ-UHFFFAOYSA-L 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 150000005195 diethylbenzenes Chemical class 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000003738 xylenes Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001269524 Dura Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 3
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010517 secondary reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910021419 crystalline silicon Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WNHVGQQCXWXANA-UHFFFAOYSA-N 1,1,2-triethylcyclohexane Chemical class CCC1CCCCC1(CC)CC WNHVGQQCXWXANA-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- ZYMCVIZKLGUPBG-UHFFFAOYSA-N 1-propan-2-ylcyclohexene Chemical compound CC(C)C1=CCCCC1 ZYMCVIZKLGUPBG-UHFFFAOYSA-N 0.000 description 1
- GQVLBFQEABXQDC-UHFFFAOYSA-N 3,3,5-trimethylcyclohexene Chemical compound CC1CC=CC(C)(C)C1 GQVLBFQEABXQDC-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- YAIQCYZCSGLAAN-UHFFFAOYSA-N [Si+4].[O-2].[Al+3] Chemical compound [Si+4].[O-2].[Al+3] YAIQCYZCSGLAAN-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002395 hexacarboxylic acids Chemical class 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical class CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical class CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002932 p-cymene derivatives Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011027 prehnite Substances 0.000 description 1
- 229910001746 prehnite Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR717125590A FR2145396B1 (enExample) | 1971-07-13 | 1971-07-13 | |
| FR717125592A FR2145397B1 (enExample) | 1971-07-13 | 1971-07-13 | |
| FR7125591A FR2186961A5 (en) | 1971-07-13 | 1971-07-13 | Polymethyl benzenes prepn. - from alkyl aromatics by hydrogenating, ring isomerising and dehydrogenating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130394B true NO130394B (enExample) | 1974-08-26 |
Family
ID=27249619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO483371A NO130394B (enExample) | 1971-07-13 | 1971-12-27 |
Country Status (3)
| Country | Link |
|---|---|
| ES (1) | ES399567A1 (enExample) |
| IT (1) | IT946713B (enExample) |
| NO (1) | NO130394B (enExample) |
-
1971
- 1971-12-27 NO NO483371A patent/NO130394B/no unknown
-
1972
- 1972-01-19 IT IT1955072A patent/IT946713B/it active
- 1972-02-08 ES ES399567A patent/ES399567A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT946713B (it) | 1973-05-21 |
| ES399567A1 (es) | 1974-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101599491B1 (ko) | ｐ-자일렌의 제조를 위한 통합공정 | |
| US10071939B2 (en) | Combined heavy reformate dealkylation-transalkylation process for maximizing xylenes production | |
| KR101148565B1 (ko) | 파라-자일렌 제조 방법 및 장치 | |
| US3932542A (en) | Process for preparation of 2,5-dibromo-p-xylene | |
| US6448459B1 (en) | Process for the production of paraxylene that comprises an adsorption stage, a liquid phase isomerization stage and a gas phase isomerization stage with an euo-type zeolite | |
| WO2014058550A1 (en) | Purge streams in paraxylene production | |
| US5574198A (en) | Process for producing linear alkylbenzenes | |
| KR0146023B1 (ko) | 에틸벤젠의 제조방법 | |
| US3078318A (en) | Production of specific xylene isomers | |
| NO130394B (enExample) | ||
| CA2103116C (en) | Production of para-xylene by selective methylation of toluene with methyl halides | |
| CN110997602A (zh) | 改善对二甲苯生产的氢解方法 | |
| USRE30157E (en) | Xylene isomerization | |
| US2563826A (en) | Process for producing 3, 5-dimethyl 1-ethyl benzene | |
| US2950329A (en) | Production of chlorstyrenes | |
| US3651165A (en) | Method for recovery and purification of isobutylene | |
| US2855430A (en) | Process for the preparation of diisopropylbenzene | |
| US3597490A (en) | Process for converting toluent to benzene and xylenes | |
| US2864874A (en) | Preparation of m-and p-diisopropylbenzene | |
| US2803686A (en) | Process for producing ethylxylene and meta xylene | |
| CN114716291B (zh) | 一种由混合芳烃多产对二甲苯的工艺系统和工艺方法 | |
| US4314091A (en) | Preparation of 1-methyl-3,5-diisopropyl benzene from charge streams containing diisopropyl toluene | |
| JP3042366B2 (ja) | メタジイソプロピルベンゼンの製造方法 | |
| CN117126030A (zh) | 均四甲苯的生产方法和系统 | |
| JP2511264B2 (ja) | ｍ−エチルジフエニル類の製造方法 |