JPS61218536A - ハロゲン化アルキルベンゼンの製法 - Google Patents
ハロゲン化アルキルベンゼンの製法Info
- Publication number
- JPS61218536A JPS61218536A JP5917885A JP5917885A JPS61218536A JP S61218536 A JPS61218536 A JP S61218536A JP 5917885 A JP5917885 A JP 5917885A JP 5917885 A JP5917885 A JP 5917885A JP S61218536 A JPS61218536 A JP S61218536A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- halogen
- alkylbenzene
- light
- wavelength
- 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.)
- Granted
Links
- 150000004996 alkyl benzenes Chemical class 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 230000001427 coherent effect Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 7
- 239000008096 xylene Substances 0.000 abstract description 7
- 238000005658 halogenation reaction Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000026030 halogenation Effects 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 15
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- FEWANSQOXSIFOK-UHFFFAOYSA-N 1,2,3,4-tetraethylbenzene Chemical compound CCC1=CC=C(CC)C(CC)=C1CC FEWANSQOXSIFOK-UHFFFAOYSA-N 0.000 description 1
- DNACCRIUIKLKNZ-UHFFFAOYSA-N 1,2,3-tris(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1C(Cl)(Cl)Cl DNACCRIUIKLKNZ-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical group ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- FEWDXGMBVQULLN-UHFFFAOYSA-N 1-hydroxy-2-phenyl-1,5,6,7-tetrahydro-4H-benzimidazol-4-one Chemical compound ON1C=2CCCC(=O)C=2N=C1C1=CC=CC=C1 FEWDXGMBVQULLN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- -1 benzyl chloride Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5917885A JPS61218536A (ja) | 1985-03-23 | 1985-03-23 | ハロゲン化アルキルベンゼンの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5917885A JPS61218536A (ja) | 1985-03-23 | 1985-03-23 | ハロゲン化アルキルベンゼンの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61218536A true JPS61218536A (ja) | 1986-09-29 |
| JPH0246013B2 JPH0246013B2 (https=) | 1990-10-12 |
Family
ID=13105881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5917885A Granted JPS61218536A (ja) | 1985-03-23 | 1985-03-23 | ハロゲン化アルキルベンゼンの製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61218536A (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006290765A (ja) * | 2005-04-07 | 2006-10-26 | Shiratori Pharmaceutical Co Ltd | ７−アルキル−１０−ヒドロキシカンプトテシン類の製造法 |
| JP2015534978A (ja) * | 2012-10-18 | 2015-12-07 | リライアンス インダストリーズ リミテッドＲｅｌｉａｎｃｅ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ． | 炭化水素のハロゲン化 |
| JP2016536339A (ja) * | 2013-09-13 | 2016-11-24 | シャンハイ ファンルン ニュー マテリアル テクノロジー シーオー．， エルティーディー．Ｓｈａｎｇｈａｉ Ｆａｎｇｌｕｎ Ｎｅｗ Ｍａｔｅｒｉａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | トリクロロメチル置換ベンゼンを調製するための方法 |
| JP2017537953A (ja) * | 2014-12-22 | 2017-12-21 | シャンハイ ファンルン ニュー マテリアル テクノロジー シーオー．， エルティーディー．Ｓｈａｎｇｈａｉ Ｆａｎｇｌｕｎ Ｎｅｗ Ｍａｔｅｒｉａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | クロロホルミル置換ベンゼンを調製するクリーンなプロセス |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50129525A (https=) * | 1974-03-28 | 1975-10-13 |
-
1985
- 1985-03-23 JP JP5917885A patent/JPS61218536A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50129525A (https=) * | 1974-03-28 | 1975-10-13 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006290765A (ja) * | 2005-04-07 | 2006-10-26 | Shiratori Pharmaceutical Co Ltd | ７−アルキル−１０−ヒドロキシカンプトテシン類の製造法 |
| JP2015534978A (ja) * | 2012-10-18 | 2015-12-07 | リライアンス インダストリーズ リミテッドＲｅｌｉａｎｃｅ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ． | 炭化水素のハロゲン化 |
| JP2019011366A (ja) * | 2012-10-18 | 2019-01-24 | リライアンス インダストリーズ リミテッドＲｅｌｉａｎｃｅ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ． | 炭化水素のハロゲン化 |
| JP2016536339A (ja) * | 2013-09-13 | 2016-11-24 | シャンハイ ファンルン ニュー マテリアル テクノロジー シーオー．， エルティーディー．Ｓｈａｎｇｈａｉ Ｆａｎｇｌｕｎ Ｎｅｗ Ｍａｔｅｒｉａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | トリクロロメチル置換ベンゼンを調製するための方法 |
| US9556090B2 (en) | 2013-09-13 | 2017-01-31 | Shanghai Fanglun New Material Technology Co., Ltd. | Method for the preparation of trichloromethyl-group-substituted benzene |
| EP3045440A4 (en) * | 2013-09-13 | 2017-03-01 | Shanghai Fanglun New Material Technology Co. Ltd. | Method for the preparation of trichloromethyl-group-substituted benzene |
| JP2017537953A (ja) * | 2014-12-22 | 2017-12-21 | シャンハイ ファンルン ニュー マテリアル テクノロジー シーオー．， エルティーディー．Ｓｈａｎｇｈａｉ Ｆａｎｇｌｕｎ Ｎｅｗ Ｍａｔｅｒｉａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | クロロホルミル置換ベンゼンを調製するクリーンなプロセス |
| US10196340B2 (en) | 2014-12-22 | 2019-02-05 | Finings Co. Ltd. | Clean process for preparing chloroformyl-substituted benzene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0246013B2 (https=) | 1990-10-12 |
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