CN103396317B - 制备拌棉醇的方法 - Google Patents
制备拌棉醇的方法 Download PDFInfo
- Publication number
- CN103396317B CN103396317B CN201310330322.8A CN201310330322A CN103396317B CN 103396317 B CN103396317 B CN 103396317B CN 201310330322 A CN201310330322 A CN 201310330322A CN 103396317 B CN103396317 B CN 103396317B
- Authority
- CN
- China
- Prior art keywords
- base
- reaction
- bronopol
- reaction mixture
- reactor
- 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 85
- 229960003168 bronopol Drugs 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 85
- 239000011541 reaction mixture Substances 0.000 claims abstract description 70
- QQZIUHOKWDFXEY-UHFFFAOYSA-N tribromo(nitro)methane Chemical compound [O-][N+](=O)C(Br)(Br)Br QQZIUHOKWDFXEY-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000003513 alkali Substances 0.000 claims abstract description 19
- 239000002585 base Substances 0.000 claims description 107
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 25
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 10
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract description 20
- 229920002866 paraformaldehyde Polymers 0.000 abstract description 18
- 238000013019 agitation Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 99
- 239000000203 mixture Substances 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 239000002002 slurry Substances 0.000 description 9
- 230000002572 peristaltic effect Effects 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000020169 heat generation Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002994 raw material Substances 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
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000008859 change Effects 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
- 238000003306 harvesting Methods 0.000 description 3
- 238000013021 overheating Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- -1 Polyoxymethylene Polymers 0.000 description 2
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 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
- 230000008034 disappearance Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007031 hydroxymethylation reaction 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
- 229920000642 polymer Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 238000013094 purity test Methods 0.000 description 2
- 239000000376 reactant Substances 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
- 238000010268 HPLC based assay Methods 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
- 229910052783 alkali metal Inorganic materials 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 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
- 238000012546 transfer Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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 | ||
| CN200980106944.4A CN101959842B (zh) | 2008-02-28 | 2009-02-26 | 制备拌棉醇的方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980106944.4A Division CN101959842B (zh) | 2008-02-28 | 2009-02-26 | 制备拌棉醇的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103396317A CN103396317A (zh) | 2013-11-20 |
| CN103396317B true CN103396317B (zh) | 2016-04-27 |
Family
ID=40707861
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310330322.8A Expired - Fee Related CN103396317B (zh) | 2008-02-28 | 2009-02-26 | 制备拌棉醇的方法 |
| CN200980106944.4A Expired - Fee Related CN101959842B (zh) | 2008-02-28 | 2009-02-26 | 制备拌棉醇的方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980106944.4A Expired - Fee Related CN101959842B (zh) | 2008-02-28 | 2009-02-26 | 制备拌棉醇的方法 |
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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPH06293710A (ja) * | 1993-04-09 | 1994-10-21 | Katayama Chem Works Co Ltd | ブロモニトロアルコール化合物の製造法 |
| WO2003011811A1 (de) * | 2001-08-02 | 2003-02-13 | Basf Aktiengesellschaft | Verfahren zur kontinuierlichen herstellung von 2-brom-2-nitro-1, 3-propandiol |
| CN1903830A (zh) * | 2006-08-11 | 2007-01-31 | 南京苏研科创农化有限公司 | 2－溴－2－硝基－1,3－丙二醇的制备方法 |
Family Cites Families (8)
| 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 |
| 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 |
| 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 |
| CN101243037B (zh) | 2005-08-26 | 2013-01-09 | 溴化合物有限公司 | 制备溴化苦的方法 |
| 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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPH06293710A (ja) * | 1993-04-09 | 1994-10-21 | Katayama Chem Works Co Ltd | ブロモニトロアルコール化合物の製造法 |
| WO2003011811A1 (de) * | 2001-08-02 | 2003-02-13 | Basf Aktiengesellschaft | Verfahren zur kontinuierlichen herstellung von 2-brom-2-nitro-1, 3-propandiol |
| CN1903830A (zh) * | 2006-08-11 | 2007-01-31 | 南京苏研科创农化有限公司 | 2－溴－2－硝基－1,3－丙二醇的制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| 2-溴-2-硝基-1,3-二丙二醇的合成;巫民建;《江西化工》;20070930(第3期);第63-64页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US8729314B2 (en) | 2014-05-20 |
| JP2011513297A (ja) | 2011-04-28 |
| JP5575668B2 (ja) | 2014-08-20 |
| EP2247568B1 (en) | 2012-04-25 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160427 |
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| CF01 | Termination of patent right due to non-payment of annual fee |