DE3419555A1 - Verfahren zur isomerisierung halogenierter thiophene - Google Patents
Verfahren zur isomerisierung halogenierter thiopheneInfo
- Publication number
- DE3419555A1 DE3419555A1 DE19843419555 DE3419555A DE3419555A1 DE 3419555 A1 DE3419555 A1 DE 3419555A1 DE 19843419555 DE19843419555 DE 19843419555 DE 3419555 A DE3419555 A DE 3419555A DE 3419555 A1 DE3419555 A1 DE 3419555A1
- Authority
- DE
- Germany
- Prior art keywords
- bromothiophene
- zeolite
- thiophenes
- halogenated
- catalyst
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 17
- 229930192474 thiophene Natural products 0.000 title claims description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000010457 zeolite Substances 0.000 claims abstract description 24
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 20
- 150000003577 thiophenes Chemical class 0.000 claims abstract description 19
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 14
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 claims abstract description 11
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims abstract description 9
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 claims abstract description 9
- QUBJDMPBDURTJT-UHFFFAOYSA-N 3-chlorothiophene Chemical compound ClC=1C=CSC=1 QUBJDMPBDURTJT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052680 mordenite Inorganic materials 0.000 claims abstract description 5
- 239000012013 faujasite Substances 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- -1 steam Substances 0.000 claims description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- 229910052786 argon Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OVXHWSNIIKNEQD-UHFFFAOYSA-N 2,3,4-trichlorothiophene Chemical class ClC1=CSC(Cl)=C1Cl OVXHWSNIIKNEQD-UHFFFAOYSA-N 0.000 description 1
- SKDNDSLDRLEELJ-UHFFFAOYSA-N 2,3,5-tribromothiophene Chemical compound BrC1=CC(Br)=C(Br)S1 SKDNDSLDRLEELJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843419555 DE3419555A1 (de) | 1984-05-25 | 1984-05-25 | Verfahren zur isomerisierung halogenierter thiophene |
| AT85106115T ATE47852T1 (de) | 1984-05-25 | 1985-05-18 | Verfahren zur isomerisierung halogenierter thiophene. |
| DE8585106115T DE3574140D1 (en) | 1984-05-25 | 1985-05-18 | Process for the isomerization of halogenated thiophenes |
| EP85106115A EP0166182B1 (de) | 1984-05-25 | 1985-05-18 | Verfahren zur Isomerisierung halogenierter Thiophene |
| HU851891A HU202223B (en) | 1984-05-25 | 1985-05-20 | Process for producing 3-halogenthiophene derivatives by isomerization of 2-halogenthiophene derivatives |
| US06/737,179 US4604470A (en) | 1984-05-25 | 1985-05-23 | Process for the isomerization of halogenated thiophenes |
| JP60110591A JPS60258178A (ja) | 1984-05-25 | 1985-05-24 | ハロゲン化チオフエンの異性化法 |
| BR8502437A BR8502437A (pt) | 1984-05-25 | 1985-05-24 | Processo para a isomerizacao de tiofenos halogenados |
| ZA853944A ZA853944B (en) | 1984-05-25 | 1985-05-24 | Process for the isomerization of halogenated thiophenes |
| AU42881/85A AU578290B2 (en) | 1984-05-25 | 1985-05-24 | Isomerization of halogenated thiophenes |
| CA000482383A CA1240684A (en) | 1984-05-25 | 1985-05-24 | Process for the isomerization of halogenated thiophenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843419555 DE3419555A1 (de) | 1984-05-25 | 1984-05-25 | Verfahren zur isomerisierung halogenierter thiophene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3419555A1 true DE3419555A1 (de) | 1985-11-28 |
Family
ID=6236857
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843419555 Withdrawn DE3419555A1 (de) | 1984-05-25 | 1984-05-25 | Verfahren zur isomerisierung halogenierter thiophene |
| DE8585106115T Expired DE3574140D1 (en) | 1984-05-25 | 1985-05-18 | Process for the isomerization of halogenated thiophenes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585106115T Expired DE3574140D1 (en) | 1984-05-25 | 1985-05-18 | Process for the isomerization of halogenated thiophenes |
Country Status (10)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0613027B2 (ja) * | 1985-06-26 | 1994-02-23 | 富士通株式会社 | 超音波媒体特性値測定装置 |
| DE3537288A1 (de) * | 1985-10-19 | 1987-04-23 | Hoechst Ag | Verfahren zur herstellung von 2.3-dichlorthiophen |
| GB8716587D0 (en) * | 1987-07-14 | 1987-08-19 | Shell Int Research | Preparing thiophene derivatives |
| US5096965A (en) * | 1988-06-27 | 1992-03-17 | Shell Oil Company | Polymeric compositions |
| US4981239A (en) * | 1989-01-03 | 1991-01-01 | The Procter & Gamble Company | Container having a drain-back spout |
| US7208610B2 (en) * | 2005-01-12 | 2007-04-24 | Honeywell International Inc. | Process for isomerization of 2-halothiophene to 3-halothiophene |
| CN108929306B (zh) * | 2018-07-16 | 2020-08-25 | 青岛科技大学 | 一种3-溴噻吩的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2492622A (en) * | 1947-01-24 | 1949-12-27 | Socony Vacuum Oil Co Inc | Continuous process for preparing halothiophenes |
| GB1334243A (en) * | 1969-10-10 | 1973-10-17 | Mobil Oil Corp | Crystalline zeolite and method of preparing the same |
-
1984
- 1984-05-25 DE DE19843419555 patent/DE3419555A1/de not_active Withdrawn
-
1985
- 1985-05-18 DE DE8585106115T patent/DE3574140D1/de not_active Expired
- 1985-05-18 AT AT85106115T patent/ATE47852T1/de not_active IP Right Cessation
- 1985-05-18 EP EP85106115A patent/EP0166182B1/de not_active Expired
- 1985-05-20 HU HU851891A patent/HU202223B/hu not_active IP Right Cessation
- 1985-05-23 US US06/737,179 patent/US4604470A/en not_active Expired - Lifetime
- 1985-05-24 CA CA000482383A patent/CA1240684A/en not_active Expired
- 1985-05-24 ZA ZA853944A patent/ZA853944B/xx unknown
- 1985-05-24 BR BR8502437A patent/BR8502437A/pt unknown
- 1985-05-24 JP JP60110591A patent/JPS60258178A/ja active Granted
- 1985-05-24 AU AU42881/85A patent/AU578290B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU578290B2 (en) | 1988-10-20 |
| EP0166182B1 (de) | 1989-11-08 |
| AU4288185A (en) | 1985-11-28 |
| CA1240684A (en) | 1988-08-16 |
| HU202223B (en) | 1991-02-28 |
| US4604470A (en) | 1986-08-05 |
| HUT39740A (en) | 1986-10-29 |
| ZA853944B (en) | 1986-01-29 |
| JPH0576476B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-10-22 |
| JPS60258178A (ja) | 1985-12-20 |
| EP0166182A1 (de) | 1986-01-02 |
| ATE47852T1 (de) | 1989-11-15 |
| BR8502437A (pt) | 1986-01-28 |
| DE3574140D1 (en) | 1989-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |