JP2003520275A5 - - Google Patents
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- Publication number
- JP2003520275A5 JP2003520275A5 JP2001553272A JP2001553272A JP2003520275A5 JP 2003520275 A5 JP2003520275 A5 JP 2003520275A5 JP 2001553272 A JP2001553272 A JP 2001553272A JP 2001553272 A JP2001553272 A JP 2001553272A JP 2003520275 A5 JP2003520275 A5 JP 2003520275A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction mixture
- halogen
- imide
- bromine
- compound
- 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
- 238000000034 method Methods 0.000 description 197
- 239000011541 reaction mixture Substances 0.000 description 181
- 150000001875 compounds Chemical class 0.000 description 84
- 150000001408 amides Chemical class 0.000 description 78
- 150000007529 inorganic bases Chemical class 0.000 description 78
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 74
- 125000004433 nitrogen atom Chemical group N* 0.000 description 73
- 229910052794 bromium Inorganic materials 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 229910001868 water Inorganic materials 0.000 description 66
- 150000003949 imides Chemical class 0.000 description 65
- 229910052757 nitrogen Inorganic materials 0.000 description 63
- 239000002585 base Substances 0.000 description 57
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 54
- 239000007791 liquid phase Substances 0.000 description 54
- 239000012320 chlorinating reagent Substances 0.000 description 51
- 239000007864 aqueous solution Substances 0.000 description 41
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 38
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 38
- 239000002002 slurry Substances 0.000 description 38
- 229910052736 halogen Inorganic materials 0.000 description 36
- 229910052801 chlorine Inorganic materials 0.000 description 32
- 150000001768 cations Chemical class 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 19
- 150000001342 alkaline earth metals Chemical class 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052783 alkali metal Inorganic materials 0.000 description 18
- 150000001340 alkali metals Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 238000006467 substitution reaction Methods 0.000 description 18
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 17
- 229940091173 hydantoin Drugs 0.000 description 17
- 150000001447 alkali salts Chemical class 0.000 description 16
- 150000002367 halogens Chemical class 0.000 description 15
- 125000001246 bromo group Chemical group Br* 0.000 description 13
- 125000005462 imide group Chemical class 0.000 description 13
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 238000011065 in-situ storage Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 7
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 7
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 7
- 229910001950 potassium oxide Inorganic materials 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000003842 bromide salts Chemical class 0.000 description 6
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 6
- 239000000292 calcium oxide Substances 0.000 description 6
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 229910001503 inorganic bromide Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 235000012255 calcium oxide Nutrition 0.000 description 5
- 239000012527 feed solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 5
- 229910001948 sodium oxide Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 235000011116 calcium hydroxide Nutrition 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 150000003950 cyclic amides Chemical class 0.000 description 3
- -1 cyclic imide Chemical class 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chlorine chlorite Inorganic materials ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/484,844 | 2000-01-18 | ||
| US09/484,844 US6809205B1 (en) | 2000-01-18 | 2000-01-18 | Process for producing N-halogenated organic compounds |
| PCT/US2001/001544 WO2001053270A2 (en) | 2000-01-18 | 2001-01-17 | Process for producing n-halogenated organic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003520275A JP2003520275A (ja) | 2003-07-02 |
| JP2003520275A5 true JP2003520275A5 (enExample) | 2008-03-06 |
| JP5170927B2 JP5170927B2 (ja) | 2013-03-27 |
Family
ID=23925854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001553272A Expired - Lifetime JP5170927B2 (ja) | 2000-01-18 | 2001-01-17 | Ｎ−ハロゲン置換有機化合物の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6809205B1 (enExample) |
| EP (1) | EP1250327B1 (enExample) |
| JP (1) | JP5170927B2 (enExample) |
| AT (1) | ATE346048T1 (enExample) |
| CA (1) | CA2397423A1 (enExample) |
| DE (1) | DE60124668T2 (enExample) |
| ES (1) | ES2276765T3 (enExample) |
| PT (1) | PT1250327E (enExample) |
| WO (1) | WO2001053270A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7999118B2 (en) * | 2000-01-18 | 2011-08-16 | Albemarle Corporation | Process for producing N-halogenated hydantoins |
| US6565868B1 (en) * | 2000-01-18 | 2003-05-20 | Albemarle Corporation | Methods for microbiological control in aqueous systems |
| US20050049420A1 (en) * | 2000-01-18 | 2005-03-03 | Elnagar Hassan Y. | Process for producing N-halogenated organic compounds |
| US6986910B2 (en) | 2001-06-28 | 2006-01-17 | Albemarle Corporation | Microbiological control in poultry processing |
| US6908636B2 (en) | 2001-06-28 | 2005-06-21 | Albermarle Corporation | Microbiological control in poultry processing |
| US20040086463A1 (en) * | 2002-05-06 | 2004-05-06 | Hansen Richard L. | Nasal solution containing a broad spectrum microbicide and a method for its use |
| US7901276B2 (en) | 2003-06-24 | 2011-03-08 | Albemarle Corporation | Microbiocidal control in the processing of meat-producing four-legged animals |
| US9629376B2 (en) | 2007-01-12 | 2017-04-25 | Albemarle Corporation | Microbiocidal treatment of edible fruits and vegetables |
| AR064779A1 (es) * | 2007-01-12 | 2009-04-22 | Albemarle Corp | Tratamiento microbicida de frutas y verduras comestibles |
| AR064778A1 (es) * | 2007-01-12 | 2009-04-22 | Albemarle Corp | Biocidas a base de bromo adecuados para el procesamiento de alimentos |
| WO2011012279A1 (en) * | 2009-07-27 | 2011-02-03 | Lonza Inc | Stabilized active halogen solutions |
| CN102285922B (zh) * | 2011-08-22 | 2013-07-17 | 河北亚光精细化工有限公司 | 用作医药中间体合成的二氯海因的生产方法 |
| US9028807B2 (en) * | 2012-04-05 | 2015-05-12 | Ues, Inc. | Synthesis models for antimicrobial agents via the halogenation of organic/inorganic composites |
| PE20151419A1 (es) | 2013-01-11 | 2015-09-19 | Albemarle Corp | Tratamiento microbicida para frutas y verduras comestibles |
| US9656967B2 (en) | 2013-03-19 | 2017-05-23 | Nippoh Chemicals Co., Ltd. | Method for producing halohydantoin compound |
| CN110305065B (zh) * | 2019-07-26 | 2022-05-17 | 河北利仕化学科技有限公司 | 溴氯海因连续式生产设备及生产方法 |
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| US2795556A (en) | 1954-07-26 | 1957-06-11 | Theobald Ind | Composition providing available chlorine and process of making same |
| US2920997A (en) | 1955-02-14 | 1960-01-12 | Pittsburgh Coke And Chemical C | Fungicidal composition of a hydantoin selected from the group consisting of 5, 5 polymethylene and 5, 5 diaryl, and 5, 5 aryl, alky hydantion |
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-
2000
- 2000-01-18 US US09/484,844 patent/US6809205B1/en not_active Expired - Fee Related
-
2001
- 2001-01-17 EP EP01906581A patent/EP1250327B1/en not_active Revoked
- 2001-01-17 ES ES01906581T patent/ES2276765T3/es not_active Expired - Lifetime
- 2001-01-17 JP JP2001553272A patent/JP5170927B2/ja not_active Expired - Lifetime
- 2001-01-17 WO PCT/US2001/001544 patent/WO2001053270A2/en not_active Ceased
- 2001-01-17 PT PT01906581T patent/PT1250327E/pt unknown
- 2001-01-17 DE DE60124668T patent/DE60124668T2/de not_active Revoked
- 2001-01-17 CA CA002397423A patent/CA2397423A1/en not_active Abandoned
- 2001-01-17 AT AT01906581T patent/ATE346048T1/de not_active IP Right Cessation
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