CN100376524C - 对溴氟苯的制备方法 - Google Patents
对溴氟苯的制备方法 Download PDFInfo
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- CN100376524C CN100376524C CNB2005100382967A CN200510038296A CN100376524C CN 100376524 C CN100376524 C CN 100376524C CN B2005100382967 A CNB2005100382967 A CN B2005100382967A CN 200510038296 A CN200510038296 A CN 200510038296A CN 100376524 C CN100376524 C CN 100376524C
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- reaction
- bromofluorobenzene
- separatory
- bromination reaction
- bromination
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 81
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 title claims description 116
- 239000000463 material Substances 0.000 claims abstract description 207
- 238000005893 bromination reaction Methods 0.000 claims abstract description 167
- 238000006243 chemical reaction Methods 0.000 claims abstract description 111
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 claims abstract description 98
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 51
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 51
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 46
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 37
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 18
- 239000000126 substance Substances 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 8
- 239000000376 reactant Substances 0.000 claims abstract description 5
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 100
- 238000006277 sulfonation reaction Methods 0.000 claims description 78
- 239000003513 alkali Substances 0.000 claims description 66
- 239000012074 organic phase Substances 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 52
- ZCJAYDKWZAWMPR-UHFFFAOYSA-N 1-chloro-2-fluorobenzene Chemical compound FC1=CC=CC=C1Cl ZCJAYDKWZAWMPR-UHFFFAOYSA-N 0.000 claims description 51
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 50
- 238000004140 cleaning Methods 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 32
- 238000003756 stirring Methods 0.000 claims description 27
- 238000005406 washing Methods 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 25
- 238000006386 neutralization reaction Methods 0.000 claims description 24
- 238000013019 agitation Methods 0.000 claims description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 238000010992 reflux Methods 0.000 claims description 20
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 16
- 239000011707 mineral Substances 0.000 claims description 16
- 230000000977 initiatory effect Effects 0.000 claims description 13
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000012805 post-processing Methods 0.000 abstract description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 3
- RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 32
- 239000007789 gas Substances 0.000 description 31
- 238000005070 sampling Methods 0.000 description 19
- 238000004587 chromatography analysis Methods 0.000 description 16
- 230000035484 reaction time Effects 0.000 description 16
- 238000012545 processing Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- QMOUJMLYMVNRIA-UHFFFAOYSA-N 3-bromo-4-fluorobenzenesulfonic acid Chemical compound BrC=1C=C(C=CC=1F)S(=O)(=O)O QMOUJMLYMVNRIA-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 125000001246 bromo group Chemical class Br* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000006200 vaporizer Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910002530 Cu-Y Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- -1 halogenated aryl hydrocarbon Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例序号 | 反应温度 | 氟苯 | 液溴 | 成品中物质的质量含量 | ||
对溴氟苯 | 对氯氟苯 | 邻溴氟苯 | ||||
1 | 2±2℃ | 500克 | 440克 | 98.20% | 0.4% | 1.1% |
2 | 15±2℃ | 500克 | 440克 | 97.50% | 0.6% | 1.5% |
3 | 25±2℃ | 500克 | 440克 | 97.1% | 0.55% | 2.1% |
4 | 38±2℃ | 500克 | 440克 | 96.6.% | 0.76% | 2.2% |
峰号 | 保留时间(分钟) | 峰高 | 峰面积 | 质量含量 | 峰名 |
1 | 1.638 | 3126.234 | 6174.600 | 0.5034% | 对氯氟苯 |
2 | 2.397 | 253294.938 | 1202801.750 | 98.0573% | 对溴氟苯 |
3 | 2.588 | 6183.219 | 16933.336 | 1.3805% | 邻溴氟苯 |
4 | 3.568 | 22.125 | 34.100 | 0.0028% | 二溴氟苯 |
5 | 3.622 | 33.321 | 41.700 | 0.0034% | |
6 | 3.672 | 44.824 | 62.400 | 0.0051% | |
7 | 4.140 | 357.186 | 583.400 | 0.0476% | 杂质 |
实施例序号 | 温度 | 氯磺酸质量 | 反应时间 | 邻溴氟苯含量 | 成品对溴氟苯含量 | |
后处理前 | 后处理后 | |||||
21 | 22±2℃ | 35克 | 5小时 | 2.2% | 0% | 97.5% |
22 | 35±2℃ | 35克 | 4.5小时 | 2.2% | 0.5% | 99.0% |
23 | 55±2℃ | 35克 | 4小时 | 2.3% | 0.37% | 98.7% |
24 | 65±2℃ | 35克 | 3.5小时 | 2.3% | 0.16% | 98.7% |
25 | 75±2℃ | 35克 | 2.5小时 | 2.3% | 0.02% | 98.9% |
26 | 98±2℃ | 35克 | 2小时 | 2.2% | 0.02% | 98.5% |
峰号 | 保留时间(分钟) | 峰高 | 峰面积 | 质量含量 | 峰名 |
1 | 1.690 | 3360.083 | 5996.400 | 0.9171% | 对氯氟苯 |
2 | 2.440 | 168690.969 | 637417.313 | 97.4831% | 对溴氟苯 |
3 | 3.723 | 181.545 | 498.800 | 0.0763% | 杂质 |
4 | 4.165 | 1026.138 | 1705.660 | 0.2609% | 二溴氟苯 |
5 | 4.223 | 2544.276 | 3943.590 | 0.6031% | |
6 | 5.215 | 365.458 | 766.800 | 0.1173% | 杂质 |
7 | 5.865 | 1527.000 | 3546.200 | 0.5423% |
实施例序号 | 温度 | 发烟硫酸质量 | 反应时间 | 邻溴氟苯(质量比) | 成品对溴氟苯(质量比) | |
磺化前 | 磺化后 | |||||
29 | 22±2℃ | 200克 | 3小时 | 2.2% | 0.18% | 98.5% |
30 | 55±2℃ | 180克 | 2小时 | 2.4% | 0.03% | 98.6% |
31 | 98±2℃ | 190克 | 2小时 | 2.3% | 0.04% | 98.8% |
实施例序号 | 温度 | 三氧化硫质量 | 反应时间 | 邻溴氟苯(质量比) | 成品对溴氟苯(质量比) | |
磺化前 | 磺化后 | |||||
32 | 22±2℃ | 30克 | 5小时 | 2.2% | 0.5% | 98.5% |
33 | 55±2℃ | 30克 | 4小时 | 2.1% | 0.37% | 98.8% |
34 | 80±2℃ | 30克 | 3.5小时 | 2.0% | 0.16% | 98.7% |
35 | 98±2℃ | 30克 | 2小时 | 2.2% | 0.02% | 98.5% |
峰号 | 保留时间(分钟) | 峰高 | 峰面积 | 质量含量 | 峰名 |
1 | 5.165 | 49.000 | 79.000 | 0.0329% | 对氯氟苯 |
2 | 5.975 | 65611.750 | 240294.453 | 99.9671% | 对溴氟苯 |
Claims (14)
Priority Applications (1)
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CNB2005100382967A CN100376524C (zh) | 2005-01-26 | 2005-01-26 | 对溴氟苯的制备方法 |
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CNB2005100382967A CN100376524C (zh) | 2005-01-26 | 2005-01-26 | 对溴氟苯的制备方法 |
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CN1810745A CN1810745A (zh) | 2006-08-02 |
CN100376524C true CN100376524C (zh) | 2008-03-26 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008017197A1 (fr) * | 2006-07-26 | 2008-02-14 | Keng Zong | Procédé de préparation de p-bromofluorobenzène |
CN116063145B (zh) * | 2023-03-29 | 2023-07-28 | 山东新龙农化有限公司 | 一种高纯度高收率的4-溴氟苯合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62221640A (ja) * | 1986-03-24 | 1987-09-29 | Asahi Chem Ind Co Ltd | パラブロモフルオロベンゼンの製造法 |
JPH06314742A (ja) * | 1993-04-28 | 1994-11-08 | Nec Ic Microcomput Syst Ltd | 面積見積りの方法 |
US5847241A (en) * | 1995-08-28 | 1998-12-08 | Bromine Compounds Ltd. | Process for the preparation of p-bromofluorobenzene |
-
2005
- 2005-01-26 CN CNB2005100382967A patent/CN100376524C/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62221640A (ja) * | 1986-03-24 | 1987-09-29 | Asahi Chem Ind Co Ltd | パラブロモフルオロベンゼンの製造法 |
JPH06314742A (ja) * | 1993-04-28 | 1994-11-08 | Nec Ic Microcomput Syst Ltd | 面積見積りの方法 |
US5847241A (en) * | 1995-08-28 | 1998-12-08 | Bromine Compounds Ltd. | Process for the preparation of p-bromofluorobenzene |
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