CN101568504B - 通过转碘化反应制备一碘代苯的方法 - Google Patents
通过转碘化反应制备一碘代苯的方法 Download PDFInfo
- Publication number
- CN101568504B CN101568504B CN2007800481476A CN200780048147A CN101568504B CN 101568504 B CN101568504 B CN 101568504B CN 2007800481476 A CN2007800481476 A CN 2007800481476A CN 200780048147 A CN200780048147 A CN 200780048147A CN 101568504 B CN101568504 B CN 101568504B
- Authority
- CN
- China
- Prior art keywords
- benzene
- phenyl
- reaction
- monoiodide
- catalyzer
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 title claims abstract description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 239000010457 zeolite Substances 0.000 claims abstract description 31
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 30
- 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 30
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000376 reactant Substances 0.000 claims abstract description 21
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011630 iodine Substances 0.000 claims abstract description 14
- 238000006192 iodination reaction Methods 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 230000008859 change Effects 0.000 claims description 12
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 10
- -1 phenyl triiodide Chemical compound 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000001354 calcination Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 27
- 239000006227 byproduct Substances 0.000 abstract description 12
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical compound IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 abstract 2
- SFPQFQUXAJOWNF-UHFFFAOYSA-N 1,3-diiodobenzene Chemical compound IC1=CC=CC(I)=C1 SFPQFQUXAJOWNF-UHFFFAOYSA-N 0.000 abstract 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 9
- 230000002779 inactivation Effects 0.000 description 9
- 230000009849 deactivation Effects 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- 229910052728 basic metal Inorganic materials 0.000 description 4
- 150000003818 basic metals Chemical group 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
- 229910052761 rare earth metal Chemical group 0.000 description 3
- 150000002910 rare earth metals Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 230000002083 iodinating effect Effects 0.000 description 2
- 150000008424 iodobenzenes Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VDTFISGKJZGCTH-UHFFFAOYSA-N naphthalene hydroiodide Chemical compound I.C1=CC=CC2=CC=CC=C21 VDTFISGKJZGCTH-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 229910052946 acanthite Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- WINTXHPCODMMRI-UHFFFAOYSA-N benzene naphthalene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 WINTXHPCODMMRI-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000001457 metallic cations Chemical group 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/02—Monocyclic halogenated hydrocarbons
- C07C23/10—Monocyclic halogenated hydrocarbons with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/04—Benzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
反应物1 | 反应物2 | 反应物3 | 反应物4 | |
苯/进料(重量比) | 7∶3 | 5∶5 | 3∶7 | 1∶9 |
苯/进料(摩尔比) | 16.5∶1 | 3.3∶1 | 1.5∶1 | 0.6∶1 |
苯(mol%) | 94.29 | 76.50 | 59.68 | 37.71 |
MIB(mol%) | 0.26 | 0.62 | 0.90 | 1.36 |
p-DIB(mol%) | 0.67 | 2.82 | 4.44 | 2.55 |
m-DIB(mol%) | 3.19 | 12.86 | 21.64 | 37.33 |
o-DIB(mol%) | 1.05 | 4.38 | 7.18 | 10.91 |
TIB(mol%) | 0.54 | 2.82 | 6.16 | 10.12 |
Claims (6)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020060137806A KR101112173B1 (ko) | 2006-12-29 | 2006-12-29 | 트랜스요오드화 반응을 통한 모노-요오드화 벤젠의 제조방법 |
KR1020060137806 | 2006-12-29 | ||
KR10-2006-0137806 | 2006-12-29 | ||
PCT/KR2007/005959 WO2008082082A1 (en) | 2006-12-29 | 2007-11-23 | Method of preparing mono-iodo benzene through transiodination |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101568504A CN101568504A (zh) | 2009-10-28 |
CN101568504B true CN101568504B (zh) | 2012-05-30 |
Family
ID=39588719
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2007800481476A Expired - Fee Related CN101568504B (zh) | 2006-12-29 | 2007-11-23 | 通过转碘化反应制备一碘代苯的方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7906694B2 (zh) |
EP (1) | EP2099734B1 (zh) |
JP (1) | JP5255570B2 (zh) |
KR (1) | KR101112173B1 (zh) |
CN (1) | CN101568504B (zh) |
ES (1) | ES2390238T3 (zh) |
HK (1) | HK1136272A1 (zh) |
WO (1) | WO2008082082A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101123148B1 (ko) * | 2007-12-17 | 2012-03-19 | 에스케이케미칼주식회사 | 방향족 요오드화 화합물의 제조 방법 |
KR101519496B1 (ko) | 2008-12-31 | 2015-05-13 | 에스케이케미칼 주식회사 | 양이온 교환 제올라이트 촉매 및 이를 이용한 트랜스 요오드화 반응을 통한 모노-요오드 벤젠의 제조 방법 |
US8820686B2 (en) * | 2010-02-04 | 2014-09-02 | William E. Hickle | Apparatus and system to mount objects in proximity to ceiling structure |
KR101381190B1 (ko) * | 2012-08-10 | 2014-04-14 | 코아텍주식회사 | 연속적 촉매 순환에 의한 방향족 요오드화 화합물 및 모노 요오드화 벤젠 제조방법 및 장치 |
KR20190021710A (ko) * | 2017-08-23 | 2019-03-06 | 에스케이케미칼 주식회사 | 모노-요오드 벤젠의 제조 방법 및 이로부터 제조된 모노-요오드 벤젠 |
WO2019232056A1 (en) | 2018-05-29 | 2019-12-05 | Gentherm Medical, Llc | Integral inlet port assembly |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4806698A (en) * | 1987-03-25 | 1989-02-21 | Eastman Kodak Company | Liquid phase isomerization of iodoaromatic compounds |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US453392A (en) | 1891-06-02 | Automatic vending apparatus | ||
SU453392A1 (ru) | 1973-04-18 | 1974-12-15 | Г. К. Павлова, Р. А. Бринкманис , П. Эглитис | Способ получения иодбензола |
JPS5777631A (en) | 1980-10-31 | 1982-05-15 | Kureha Chem Ind Co Ltd | Vapor-phase halogenation process |
JPS5877830A (ja) | 1981-11-04 | 1983-05-11 | Nissan Chem Ind Ltd | ヨ−ドベンゼルの製造法 |
JPS59219241A (ja) * | 1983-05-30 | 1984-12-10 | Asahi Chem Ind Co Ltd | 芳香族化合物のオキシヨウ素化法 |
IT1176856B (it) | 1984-10-05 | 1987-08-18 | Montedipe Spa | Metodo per la sintesi di iodobenzene |
IT1176981B (it) | 1984-10-16 | 1987-08-26 | Montedipe Spa | Metodo per la sintesi di iodobenzene |
JPH0651647B2 (ja) * | 1985-11-21 | 1994-07-06 | 旭化成工業株式会社 | ブロモベンゼンの製法 |
IT1197861B (it) * | 1986-08-11 | 1988-12-21 | Montedipe Spa | Processo per la trans-alogenzaione catalitica di un poli-iodo benzene e in particolare di un di-iodo-benzene |
IT1197862B (it) * | 1986-08-11 | 1988-12-21 | Montedipe Spa | Processo per la trans-alogenazione catalitica di un poli-iodo benzene |
US4792641A (en) * | 1987-03-25 | 1988-12-20 | Eastman Kodak Company | Process for preparing iodinated aromatic compounds |
DE4101528A1 (de) * | 1991-01-19 | 1992-07-23 | Bayer Ag | Verfahren zur umsetzung von polyhalogenierten aromaten mit monohalogenierten oder nicht halogenierten aromaten |
JP2005002083A (ja) * | 2003-04-18 | 2005-01-06 | Tosoh Corp | クロロベンゼンの製造方法 |
-
2006
- 2006-12-29 KR KR1020060137806A patent/KR101112173B1/ko active IP Right Grant
-
2007
- 2007-11-23 ES ES07851146T patent/ES2390238T3/es active Active
- 2007-11-23 EP EP07851146A patent/EP2099734B1/en not_active Not-in-force
- 2007-11-23 JP JP2009543918A patent/JP5255570B2/ja active Active
- 2007-11-23 US US12/519,894 patent/US7906694B2/en active Active
- 2007-11-23 WO PCT/KR2007/005959 patent/WO2008082082A1/en active Application Filing
- 2007-11-23 CN CN2007800481476A patent/CN101568504B/zh not_active Expired - Fee Related
-
2010
- 2010-03-23 HK HK10103056.3A patent/HK1136272A1/xx not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4806698A (en) * | 1987-03-25 | 1989-02-21 | Eastman Kodak Company | Liquid phase isomerization of iodoaromatic compounds |
Also Published As
Publication number | Publication date |
---|---|
US7906694B2 (en) | 2011-03-15 |
EP2099734B1 (en) | 2012-06-27 |
US20100094067A1 (en) | 2010-04-15 |
CN101568504A (zh) | 2009-10-28 |
KR101112173B1 (ko) | 2012-02-24 |
EP2099734A4 (en) | 2010-02-10 |
ES2390238T3 (es) | 2012-11-07 |
EP2099734A1 (en) | 2009-09-16 |
WO2008082082A1 (en) | 2008-07-10 |
JP2010514754A (ja) | 2010-05-06 |
HK1136272A1 (en) | 2010-06-25 |
KR20080062251A (ko) | 2008-07-03 |
JP5255570B2 (ja) | 2013-08-07 |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120530 |