JPH01175946A - ２−メチルナフタレンの製造方法 - Google Patents

２−メチルナフタレンの製造方法

Info

Publication number: JPH01175946A
Authority: JP; Japan
Prior art keywords: catalyst; reaction; methylnaphthalene; isomerization; acid
Prior art date: 1987-12-28
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.): Granted

Application number

JP62330266A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0460588B2 (de

Inventor

Hitoshi Saima

等齋間

Tokio Iizuka

飯塚　時男

Yoshinori Takagi

嘉則高木

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.)

JFE Steel Corp

Original Assignee

Kawasaki Steel Corp

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.)

1987-12-28

Filing date

1987-12-28

Publication date

1989-07-12

1987-12-28 Application filed by Kawasaki Steel Corp filed Critical Kawasaki Steel Corp

1987-12-28 Priority to JP62330266A priority Critical patent/JPH01175946A/ja

1989-07-12 Publication of JPH01175946A publication Critical patent/JPH01175946A/ja

1992-09-28 Publication of JPH0460588B2 publication Critical patent/JPH0460588B2/ja

Status Granted legal-status Critical Current

Links

QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 7
239000003054 catalyst Substances 0.000 claims abstract description 26
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052742 iron Inorganic materials 0.000 claims abstract description 5
229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
229910052710 silicon Inorganic materials 0.000 claims abstract description 3
229910052718 tin Inorganic materials 0.000 claims abstract description 3
229910052719 titanium Inorganic materials 0.000 claims abstract description 3
229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 19
239000007787 solid Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
239000010703 silicon Substances 0.000 claims description 2
239000010936 titanium Substances 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 19
238000006317 isomerization reaction Methods 0.000 abstract description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
229910044991 metal oxide Inorganic materials 0.000 abstract description 4
150000004706 metal oxides Chemical class 0.000 abstract description 4
239000011973 solid acid Substances 0.000 abstract description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 3
235000011114 ammonium hydroxide Nutrition 0.000 abstract description 3
239000000975 dye Substances 0.000 abstract description 3
-1 sulfate radical Chemical class 0.000 abstract description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 2
229910052921 ammonium sulfate Inorganic materials 0.000 abstract description 2
235000011130 ammonium sulphate Nutrition 0.000 abstract description 2
238000001354 calcination Methods 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract description 2
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
238000001035 drying Methods 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 2
229910001510 metal chloride Inorganic materials 0.000 abstract description 2
229910000000 metal hydroxide Inorganic materials 0.000 abstract description 2
239000000126 substance Substances 0.000 abstract 2
RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 abstract 1
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
238000007323 disproportionation reaction Methods 0.000 description 11
QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 9
239000003930 superacid Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002638 heterogeneous catalyst Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
230000007423 decrease Effects 0.000 description 5
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
238000010304 firing Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
229910021536 Zeolite Inorganic materials 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 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000002994 raw material Substances 0.000 description 4
239000010457 zeolite Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229940037003 alum Drugs 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
LCPUDZUWZDSKMX-UHFFFAOYSA-K azane;hydrogen sulfate;iron(3+);sulfate;dodecahydrate Chemical compound [NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LCPUDZUWZDSKMX-UHFFFAOYSA-K 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
229920006015 heat resistant resin Polymers 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
238000011068 loading method Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000002341 toxic gas Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP62330266A 1987-12-28 1987-12-28 ２−メチルナフタレンの製造方法 Granted JPH01175946A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP62330266A JPH01175946A (ja)	1987-12-28	1987-12-28	２−メチルナフタレンの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62330266A JPH01175946A (ja)	1987-12-28	1987-12-28	２−メチルナフタレンの製造方法

Publications (2)

Publication Number	Publication Date
JPH01175946A true JPH01175946A (ja)	1989-07-12
JPH0460588B2 JPH0460588B2 (de)	1992-09-28

Family

ID=18230724

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62330266A Granted JPH01175946A (ja)	1987-12-28	1987-12-28	２−メチルナフタレンの製造方法

Country Status (1)

Country	Link
JP (1)	JPH01175946A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0578265A (ja) *	1990-12-12	1993-03-30	Kawasaki Steel Corp	２−メチルナフタレンの製造方法及びそれに用いる触媒の活性回復方法
MA63522A1 (fr) *	2023-12-18	2025-06-30	Université Ibn Tofail	Catalyseur hétérogène pour une production durable des dérivés du 1-(benzothiazolylamino) méthyl-2-naphtols

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5141037A (ja) *	1974-10-03	1976-04-06	Ota Toshuki	Aruminiumunotosoho
JPS5146435A (en) *	1974-10-18	1976-04-20	Matsushita Electric Industrial Co Ltd	Ekitainenryonenshosochi
JPS57123125A (en) *	1981-01-20	1982-07-31	Ugine Kuhlmann	Selective manufacture of beta-isopropylnaphthalene
JPS61263932A (ja) *	1985-05-17	1986-11-21	Res Assoc Util Of Light Oil	炭化水素類の異性化方法
JPS61280440A (ja) *	1985-06-05	1986-12-11	Res Assoc Util Of Light Oil	炭化水素類の異性化方法

1987
- 1987-12-28 JP JP62330266A patent/JPH01175946A/ja active Granted

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5141037A (ja) *	1974-10-03	1976-04-06	Ota Toshuki	Aruminiumunotosoho
JPS5146435A (en) *	1974-10-18	1976-04-20	Matsushita Electric Industrial Co Ltd	Ekitainenryonenshosochi
JPS57123125A (en) *	1981-01-20	1982-07-31	Ugine Kuhlmann	Selective manufacture of beta-isopropylnaphthalene
JPS61263932A (ja) *	1985-05-17	1986-11-21	Res Assoc Util Of Light Oil	炭化水素類の異性化方法
JPS61280440A (ja) *	1985-06-05	1986-12-11	Res Assoc Util Of Light Oil	炭化水素類の異性化方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0578265A (ja) *	1990-12-12	1993-03-30	Kawasaki Steel Corp	２−メチルナフタレンの製造方法及びそれに用いる触媒の活性回復方法
MA63522A1 (fr) *	2023-12-18	2025-06-30	Université Ibn Tofail	Catalyseur hétérogène pour une production durable des dérivés du 1-(benzothiazolylamino) méthyl-2-naphtols
MA63522B1 (fr) *	2023-12-18	2025-09-30	Université Ibn Tofail	Catalyseur hétérogène pour une production durable des dérivés du 1-(benzothiazolylamino) méthyl-2-naphtols

Also Published As

Publication number	Publication date
JPH0460588B2 (de)	1992-09-28

Publication	Publication Date	Title
RU2126782C1 (ru)	1999-02-27	Способ селективного получения диметилнафталинов
JPH01175946A (ja)	1989-07-12	２−メチルナフタレンの製造方法
JPH11158087A (ja)	1999-06-15	ジアルキルナフタレンの製造方法
JP2921541B2 (ja)	1999-07-19	ジメチルナフタレンの異性化方法
EP0402207B1 (de)	1994-04-27	Verfahren zur Erzeugung von Nitrobenzolen
JPH06287151A (ja)	1994-10-11	ジメチルナフタレンの異性化方法
JP4526606B2 (ja)	2010-08-18	高純度２，６−ジメチルナフタレンの製造方法
JP2741233B2 (ja)	1998-04-15	固体酸触媒およびその利用方法
US5659097A (en)	1997-08-19	Process for producing a monoalkenyl aromatic hydrocarbon compound
JPH07206722A (ja)	1995-08-08	ジメチルナフタレンの異性化方法
KR950001675B1 (ko)	1995-02-28	2-메틸 나프탈렌의 제조방법
JP2911263B2 (ja)	1999-06-23	２−メチルナフタレンの製造方法
JP2003508367A (ja)	2003-03-04	単一触媒系を使用して１工程で芳香族二塩基酸を製造するための方法
JPH04322743A (ja)	1992-11-12	アルキルアダマンタン類の製造用触媒およびこれを用いたアルキルアダマンタン類の製造方法
JPH0232031A (ja)	1990-02-01	イソプロピル化ｐ‐ターフェニル類の製造法
JPH069441A (ja)	1994-01-18	ジアルキルナフタレンの異性化方法
JP2008001717A (ja)	2008-01-10	高純度２，６−ジメチルナフタレンの製造方法
JPH01199917A (ja)	1989-08-11	２‐メチルナフタレンの製造方法
RU2126783C1 (ru)	1999-02-27	Способ получения диметилнафталина
JP2578540B2 (ja)	1997-02-05	２−メチルナフタレンの製造方法
EP0546266A1 (de)	1993-06-16	Verfahren zur Herstellung von 2,6-Dimethylnaphtalen
EP0659717B1 (de)	1999-04-14	Verfahren zur Alkylierung der Seitenkette alkylsubstituierter aromatischer Kohlenwasserstoffe
JPH05310609A (ja)	1993-11-22	２，６−ジアルキルナフタレンの製造方法
JPS585888B2 (ja)	1983-02-02	ジメチルナフタリンノイセイカホウホウ
JPH09291045A (ja)	1997-11-11	２，６−ジメチルナフタレンの製造方法