JPH0558919A - 芳香族炭化水素の製法 - Google Patents

芳香族炭化水素の製法

Info

Publication number: JPH0558919A
Authority: JP; Japan
Prior art keywords: gas; reaction; separation; catalyst; hydrocarbon
Prior art date: 1990-12-20
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

Application number

JP35508491A

Other languages

English (en)

Japanese (ja)

Inventor

Koji Adachi

康二安達

Kazuo Hirabayashi

一男平林

Shunji Shibata

俊二柴田

Shunsuke Saito

俊輔斉藤

Tadami Kondo

忠美近藤

Tadaaki Iino

忠昭飯野

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Research Association for Utilization of Light Oil

Original Assignee

Research Association for Utilization of Light Oil

Priority date (The priority date 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 date listed.)

1990-12-20

Filing date

1991-12-20

Publication date

1993-03-09

1991-12-20 Application filed by Research Association for Utilization of Light Oil filed Critical Research Association for Utilization of Light Oil

1993-03-09 Publication of JPH0558919A publication Critical patent/JPH0558919A/ja

Status Pending legal-status Critical Current

Links

150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title claims description 7
239000007789 gas Substances 0.000 claims abstract description 88
238000006243 chemical reaction Methods 0.000 claims abstract description 65
239000003054 catalyst Substances 0.000 claims abstract description 54
238000000926 separation method Methods 0.000 claims abstract description 52
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 46
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 34
239000007788 liquid Substances 0.000 claims abstract description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 29
229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 27
239000002994 raw material Substances 0.000 claims abstract description 26
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 24
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 23
125000003118 aryl group Chemical group 0.000 claims abstract description 20
238000009835 boiling Methods 0.000 claims abstract description 15
239000002245 particle Substances 0.000 claims description 18
229910052733 gallium Inorganic materials 0.000 claims description 13
229910052782 aluminium Inorganic materials 0.000 claims description 12
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000007795 chemical reaction product Substances 0.000 claims description 7
238000002156 mixing Methods 0.000 claims description 6
230000000694 effects Effects 0.000 abstract description 19
150000002431 hydrogen Chemical class 0.000 abstract description 16
230000008569 process Effects 0.000 abstract description 8
230000000717 retained effect Effects 0.000 abstract 1
229910052751 metal Inorganic materials 0.000 description 15
239000002184 metal Substances 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
229910004298 SiO 2 Inorganic materials 0.000 description 10
238000002425 crystallisation Methods 0.000 description 10
239000003381 stabilizer Substances 0.000 description 10
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 9
239000012528 membrane Substances 0.000 description 9
229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000011230 binding agent Substances 0.000 description 8
239000000571 coke Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
230000007423 decrease Effects 0.000 description 8
238000001027 hydrothermal synthesis Methods 0.000 description 8
230000008929 regeneration Effects 0.000 description 8
238000011069 regeneration method Methods 0.000 description 8
229910005191 Ga 2 O 3 Inorganic materials 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000012188 paraffin wax Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
239000001273 butane Substances 0.000 description 6
230000008021 deposition Effects 0.000 description 6
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
150000001342 alkaline earth metals Chemical class 0.000 description 5
-1 for example Substances 0.000 description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
239000011148 porous material Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229910021536 Zeolite Inorganic materials 0.000 description 4
230000004913 activation Effects 0.000 description 4
238000005899 aromatization reaction Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
238000000465 moulding Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000006259 organic additive Substances 0.000 description 4
239000010457 zeolite Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910000323 aluminium silicate Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000001294 propane Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229910052684 Cerium Inorganic materials 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
229910004283 SiO 4 Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000003570 air Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
229940044658 gallium nitrate Drugs 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
229910052741 iridium Inorganic materials 0.000 description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
229910052746 lanthanum Inorganic materials 0.000 description 2
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920002492 poly(sulfone) Polymers 0.000 description 2
235000019353 potassium silicate Nutrition 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000004064 recycling Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
238000005004 MAS NMR spectroscopy Methods 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004111 Potassium silicate Substances 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000003795 desorption Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000005350 fused silica glass Substances 0.000 description 1
150000002258 gallium Chemical class 0.000 description 1
229910001195 gallium oxide Inorganic materials 0.000 description 1
UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
QZQVBEXLDFYHSR-UHFFFAOYSA-N gallium(III) oxide Inorganic materials O=[Ga]O[Ga]=O QZQVBEXLDFYHSR-UHFFFAOYSA-N 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
VFOJFWOVDZGATC-UHFFFAOYSA-N methyl(tripropyl)azanium Chemical class CCC[N+](C)(CCC)CCC VFOJFWOVDZGATC-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
229910052913 potassium silicate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011164 primary particle Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
102200118166 rs16951438 Human genes 0.000 description 1
239000011163 secondary particle Substances 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001388 sodium aluminate Inorganic materials 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000002336 sorption--desorption measurement Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical class CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G35/00—Reforming naphtha
- C10G35/04—Catalytic reforming
- C10G35/06—Catalytic reforming characterised by the catalyst used
- C10G35/065—Catalytic reforming characterised by the catalyst used containing crystalline zeolitic molecular sieves, other than aluminosilicates
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation

Landscapes

Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP35508491A 1990-12-20 1991-12-20 芳香族炭化水素の製法 Pending JPH0558919A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP41246790		1990-12-20
JP2-412467		1990-12-20

Publications (1)

Publication Number	Publication Date
JPH0558919A true JPH0558919A (ja)	1993-03-09

Family

ID=18521301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP35508491A Pending JPH0558919A (ja)	1990-12-20	1991-12-20	芳香族炭化水素の製法

Country Status (3)

Country	Link
EP (1)	EP0493040A3 (de)
JP (1)	JPH0558919A (de)
AU (1)	AU637539B2 (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004269398A (ja) *	2003-03-07	2004-09-30	Masaru Ichikawa	低級炭化水素の芳香族化触媒反応方法および芳香族化触媒反応装置ならびに芳香族化合物および水素の製造方法
JP2005529978A (ja) *	2002-06-19	2005-10-06	エクソンモービル・ケミカル・パテンツ・インク	改質油を用いるキシレンの製造
JP2008266245A (ja) *	2007-04-24	2008-11-06	Mitsubishi Chemicals Corp	芳香族炭化水素の製造方法
JP2010514784A (ja) *	2006-12-28	2010-05-06	ユーオーピーエルエルシー	パラキシレンの回収および生産のための低温プロセスならびにそのための熱交換ネットワーク
JP2010184893A (ja) *	2009-02-12	2010-08-26	Meidensha Corp	芳香族炭化水素製造方法及び芳香族炭化水素製造装置
JP2012206955A (ja) *	2011-03-29	2012-10-25	Chiyoda Kako Kensetsu Kk	芳香族炭化水素の製造方法および芳香族炭化水素の製造プラント
JP2017119267A (ja) *	2015-12-18	2017-07-06	東ソー株式会社	芳香族化合物製造触媒及び芳香族化合物の製造方法
JP2019059704A (ja) *	2017-09-28	2019-04-18	東ソー株式会社	芳香族化合物の製造方法
JP2020037551A (ja) *	2018-09-03	2020-03-12	Ｊｘｔｇエネルギー株式会社	キシレンの製造方法

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US8809608B2 (en)	2008-02-18	2014-08-19	Shell Oil Company	Process for the conversion of lower alkanes to aromatic hydrocarbons
EA024491B1 (ru)	2008-02-18	2016-09-30	Шелл Интернэшнл Рисерч Маатсхаппий Б.В.	Способ преобразования этана в ароматические углеводороды
US8871990B2 (en)	2008-02-18	2014-10-28	Shell Oil Company	Process for the conversion of ethane to aromatic hydrocarbons
WO2009105447A1 (en)	2008-02-20	2009-08-27	Shell Oil Company	Process for the conversion of ethane to aromatic hydrocarbons
WO2011053746A1 (en) *	2009-11-02	2011-05-05	Shell Oil Company	Process for the conversion of lower alkanes to aromatic hydrocarbons
AU2010313369B2 (en)	2009-11-02	2014-02-13	Shell Internationale Research Maatschappij B.V.	Process for the conversion of mixed lower alkanes to aromatic hydrocarbons
WO2011053745A1 (en) *	2009-11-02	2011-05-05	Shell Oil Company	Process for the conversion of propane and butane to aromatic hydrocarbons
SG185516A1 (en)	2010-05-12	2012-12-28	Shell Int Research	Process for the conversion of lower alkanes to aromatic hydrocarbons

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US3751229A (en) *	1971-09-03	1973-08-07	Universal Oil Prod Co	Control of reaction zone severity by response to octane number of effluent liquid at reaction pressure
US4973778A (en) *	1987-12-29	1990-11-27	Mobil Oil Corp.	Continuous swing tubular reactor-regenerator
US5073673A (en) *	1989-05-31	1991-12-17	Research Association For The Utilization Of Light Oil	Process for the production of high-octane gasoline blending stock

1991
- 1991-12-20 JP JP35508491A patent/JPH0558919A/ja active Pending
- 1991-12-20 AU AU89977/91A patent/AU637539B2/en not_active Ceased
- 1991-12-20 EP EP19910311902 patent/EP0493040A3/en not_active Withdrawn

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005529978A (ja) *	2002-06-19	2005-10-06	エクソンモービル・ケミカル・パテンツ・インク	改質油を用いるキシレンの製造
JP2004269398A (ja) *	2003-03-07	2004-09-30	Masaru Ichikawa	低級炭化水素の芳香族化触媒反応方法および芳香族化触媒反応装置ならびに芳香族化合物および水素の製造方法
JP2010514784A (ja) *	2006-12-28	2010-05-06	ユーオーピーエルエルシー	パラキシレンの回収および生産のための低温プロセスならびにそのための熱交換ネットワーク
JP2008266245A (ja) *	2007-04-24	2008-11-06	Mitsubishi Chemicals Corp	芳香族炭化水素の製造方法
JP2010184893A (ja) *	2009-02-12	2010-08-26	Meidensha Corp	芳香族炭化水素製造方法及び芳香族炭化水素製造装置
US9358536B2 (en)	2009-02-12	2016-06-07	Meidensha Corporation	Method for producing aromatic hydrocarbon and apparatus for producing aromatic hydrocarbon
JP2012206955A (ja) *	2011-03-29	2012-10-25	Chiyoda Kako Kensetsu Kk	芳香族炭化水素の製造方法および芳香族炭化水素の製造プラント
JP2017119267A (ja) *	2015-12-18	2017-07-06	東ソー株式会社	芳香族化合物製造触媒及び芳香族化合物の製造方法
JP2019059704A (ja) *	2017-09-28	2019-04-18	東ソー株式会社	芳香族化合物の製造方法
JP2020037551A (ja) *	2018-09-03	2020-03-12	Ｊｘｔｇエネルギー株式会社	キシレンの製造方法
WO2020050092A1 (ja) *	2018-09-03	2020-03-12	Ｊｘｔｇエネルギー株式会社	キシレンの製造方法
US11459283B2 (en)	2018-09-03	2022-10-04	Eneos Corporation	Method for producing xylene

Also Published As

Publication number	Publication date
AU8997791A (en)	1992-06-25
EP0493040A3 (en)	1992-08-12
EP0493040A2 (de)	1992-07-01
AU637539B2 (en)	1993-05-27

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