BE629485A - - Google Patents
Info
- Publication number
- BE629485A BE629485A BE629485DA BE629485A BE 629485 A BE629485 A BE 629485A BE 629485D A BE629485D A BE 629485DA BE 629485 A BE629485 A BE 629485A
- Authority
- BE
- Belgium
- Prior art keywords
- alkyl
- naphthalene
- naphthalenes
- fraction
- product
- Prior art date
Links
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 30
- 238000006900 dealkylation reaction Methods 0.000 claims description 15
- 230000020335 dealkylation Effects 0.000 claims description 14
- 238000006317 isomerization reaction Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- -1 alkyl naphthalenes Chemical class 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229940075566 naphthalene Drugs 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
- 230000003197 catalytic effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 238000006477 desulfuration reaction Methods 0.000 description 3
- 230000023556 desulfurization Effects 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- WWGUMAYGTYQSGA-UHFFFAOYSA-N 2,3-dimethylnaphthalene Chemical compound C1=CC=C2C=C(C)C(C)=CC2=C1 WWGUMAYGTYQSGA-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010011416 Croup infectious Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 201000010549 croup Diseases 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- LRQYSMQNJLZKPS-UHFFFAOYSA-N 2,7-dimethylnaphthalene Chemical compound C1=CC(C)=CC2=CC(C)=CC=C21 LRQYSMQNJLZKPS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 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
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE629485A true BE629485A (en:Method) |
Family
ID=198930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE629485D BE629485A (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE629485A (en:Method) |
-
0
- BE BE629485D patent/BE629485A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0393029B2 (en) | Processing nitrogen-rich, hydrogen-rich, and olefin-rich gases with physical solvents | |
| AU622199B2 (en) | Low pressure noncryogenic processing for ethylene recovery | |
| KR100937080B1 (ko) | 부텐의 이중 결합 수소이성화 | |
| KR910004941B1 (ko) | 파라핀 및 시클릭 탄화수소를 포함하는 원료 스트림의 이성질체화 및 고리개방을 위한 이중 작용성 공정 | |
| US2799627A (en) | Process for obtaining concentrated aromatic hydrocarbons | |
| EA032112B1 (ru) | Способ получения лёгких олефинов и ароматических соединений из углеводородного сырья | |
| US4042490A (en) | Hydrocarbon upgrading process | |
| US3145238A (en) | Hydrodealkylation of special feed stocks | |
| KR20060018252A (ko) | 묽은 에틸렌 스트림들로부터 프로필렌 및 에틸벤젠 제조방법 | |
| US3055956A (en) | Process for the separation of naphthalene | |
| CA1110666A (en) | Process for producing high purity benzene | |
| US3917705A (en) | Production of secondary alkyl primary amines | |
| BE629485A (en:Method) | ||
| US2951886A (en) | Recovery and purification of benzene | |
| AU624770B2 (en) | Process for removing impurities from an aromatic stream | |
| US3153675A (en) | Preparation of naphthalene and dimethylnaphthalenes | |
| US3271297A (en) | Recycle of monoolefines to a hydrocarbon pyrolysis process | |
| US3153676A (en) | Preparation of naphthalene and 2, 6-dimethylnaphthalene | |
| US3316318A (en) | Process for recovery of aromatics from cracked gasoline fractions | |
| US3993554A (en) | Method of producing n-paraffin oximes | |
| US3917706A (en) | Production of secondary alkyl primary amines | |
| US3920744A (en) | Production of amines from sulfur bearing paraffins | |
| US3317623A (en) | Polycyclic aromatics by two-stage hydrodealkylation | |
| US3660272A (en) | Gasoline production from wellhead natural gas | |
| EP4453141A1 (fr) | Unité de production et de séparation des aromatiques avec valorisation d'un extrait et/ou d'un raffinat provenant d'un procédé d'extraction liquide-liquide |