JP5575668B2 - ブロノポールの製造方法 - Google Patents
ブロノポールの製造方法 Download PDFInfo
- Publication number
- JP5575668B2 JP5575668B2 JP2010548244A JP2010548244A JP5575668B2 JP 5575668 B2 JP5575668 B2 JP 5575668B2 JP 2010548244 A JP2010548244 A JP 2010548244A JP 2010548244 A JP2010548244 A JP 2010548244A JP 5575668 B2 JP5575668 B2 JP 5575668B2
- Authority
- JP
- Japan
- Prior art keywords
- base
- reaction
- bronopol
- reaction mixture
- bromopicrin
- 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
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 229960003168 bronopol Drugs 0.000 title claims abstract description 82
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 109
- 239000011541 reaction mixture Substances 0.000 claims abstract description 66
- QQZIUHOKWDFXEY-UHFFFAOYSA-N tribromo(nitro)methane Chemical compound [O-][N+](=O)C(Br)(Br)Br QQZIUHOKWDFXEY-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 21
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 102
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 13
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000011049 filling Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 abstract description 18
- 239000002585 base Substances 0.000 description 100
- 239000000203 mixture Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 230000002572 peristaltic effect Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 230000020169 heat generation Effects 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000003556 assay Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 4
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000013021 overheating Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 241000220317 Rosa Species 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000013094 purity test Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical compound OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6432808P | 2008-02-28 | 2008-02-28 | |
| US61/064,328 | 2008-02-28 | ||
| PCT/IL2009/000218 WO2009107133A1 (en) | 2008-02-28 | 2009-02-26 | A process for the preparation of bronopol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513297A JP2011513297A (ja) | 2011-04-28 |
| JP2011513297A5 JP2011513297A5 (https=) | 2014-04-17 |
| JP5575668B2 true JP5575668B2 (ja) | 2014-08-20 |
Family
ID=40707861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010548244A Expired - Fee Related JP5575668B2 (ja) | 2008-02-28 | 2009-02-26 | ブロノポールの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8546619B2 (https=) |
| EP (1) | EP2247568B1 (https=) |
| JP (1) | JP5575668B2 (https=) |
| CN (2) | CN103396317B (https=) |
| AT (1) | ATE555076T1 (https=) |
| WO (1) | WO2009107133A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108614044A (zh) * | 2018-04-25 | 2018-10-02 | 上海海洋大学 | 溴硝醇有关物质的测定方法 |
| US12557812B2 (en) | 2019-05-28 | 2026-02-24 | Bromine Compounds Ltd | Method and composition for water treatment |
| WO2022118312A1 (en) | 2020-12-02 | 2022-06-09 | Bromine Compounds Ltd. | Method and composition for water treatment |
| WO2022118313A1 (en) | 2020-12-02 | 2022-06-09 | Bromine Compounds Ltd. | Method and composition for water treatment |
| CN112679359B (zh) * | 2020-12-29 | 2022-11-22 | 苏州亚科科技股份有限公司 | 一种溴硝醇的制备方法 |
| US12076675B2 (en) * | 2021-01-27 | 2024-09-03 | John Ruszkowski | Air filter inactivation of viruses and micro-organisms |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR96391E (https=) * | 1968-10-19 | 1972-06-16 | ||
| BE757999A (fr) * | 1969-10-28 | 1971-04-26 | Henkel & Cie Gmbh | Procede de preparation de bromonitro-alcools. |
| BE758026A (fr) * | 1969-10-30 | 1971-04-01 | Lonza Ag | Procede de fabrication de dinitrile d'acide malonique |
| JPS4970911A (https=) * | 1972-11-09 | 1974-07-09 | ||
| JPS572242A (en) * | 1980-06-06 | 1982-01-07 | Kumiai Chem Ind Co Ltd | Preparation of 2-bromo-2-nitro-1,3-propanediol |
| JPS59199643A (ja) * | 1983-04-26 | 1984-11-12 | Nippon Shokubai Kagaku Kogyo Co Ltd | エチレングリコ−ルの製造方法 |
| JP3214904B2 (ja) * | 1992-06-18 | 2001-10-02 | ケイ・アイ化成株式会社 | １，３−プロパンジオール誘導体の製造法 |
| JP2928044B2 (ja) | 1993-04-09 | 1999-07-28 | 株式会社片山化学工業研究所 | ブロモニトロアルコール化合物の製造法 |
| JPH1087538A (ja) * | 1996-09-09 | 1998-04-07 | Arakawa Chem Ind Co Ltd | ポリヒドロキシ化合物、その製造法およびエポキシ樹脂組成物 |
| DE10137829A1 (de) * | 2001-08-02 | 2003-02-13 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von 2-Brom-2-nitro-1,3-propandiol |
| CN101243037B (zh) | 2005-08-26 | 2013-01-09 | 溴化合物有限公司 | 制备溴化苦的方法 |
| CN100522923C (zh) | 2006-08-11 | 2009-08-05 | 江苏联化科技有限公司 | 2-溴-2-硝基-1,3-丙二醇的制备方法 |
| IL183445A (en) | 2007-05-27 | 2013-02-28 | Bromine Compounds Ltd | Continuous process of preparing bromopicrin |
-
2009
- 2009-02-26 CN CN201310330322.8A patent/CN103396317B/zh not_active Expired - Fee Related
- 2009-02-26 JP JP2010548244A patent/JP5575668B2/ja not_active Expired - Fee Related
- 2009-02-26 AT AT09716009T patent/ATE555076T1/de active
- 2009-02-26 CN CN200980106944.4A patent/CN101959842B/zh not_active Expired - Fee Related
- 2009-02-26 WO PCT/IL2009/000218 patent/WO2009107133A1/en not_active Ceased
- 2009-02-26 EP EP09716009A patent/EP2247568B1/en not_active Not-in-force
- 2009-02-26 US US12/735,886 patent/US8546619B2/en not_active Expired - Fee Related
-
2013
- 2013-08-28 US US14/012,411 patent/US8729314B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8729314B2 (en) | 2014-05-20 |
| JP2011513297A (ja) | 2011-04-28 |
| EP2247568B1 (en) | 2012-04-25 |
| CN103396317B (zh) | 2016-04-27 |
| CN103396317A (zh) | 2013-11-20 |
| WO2009107133A1 (en) | 2009-09-03 |
| EP2247568A1 (en) | 2010-11-10 |
| CN101959842B (zh) | 2014-09-10 |
| CN101959842A (zh) | 2011-01-26 |
| US20110065964A1 (en) | 2011-03-17 |
| US8546619B2 (en) | 2013-10-01 |
| US20140066662A1 (en) | 2014-03-06 |
| ATE555076T1 (de) | 2012-05-15 |
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