JP4759521B2 - 臭素化反応からのアンチモン触媒残渣の回収 - Google Patents
臭素化反応からのアンチモン触媒残渣の回収 Download PDFInfo
- Publication number
- JP4759521B2 JP4759521B2 JP2006546968A JP2006546968A JP4759521B2 JP 4759521 B2 JP4759521 B2 JP 4759521B2 JP 2006546968 A JP2006546968 A JP 2006546968A JP 2006546968 A JP2006546968 A JP 2006546968A JP 4759521 B2 JP4759521 B2 JP 4759521B2
- Authority
- JP
- Japan
- Prior art keywords
- antimony
- catalyst
- organic solvent
- trihalide
- aqueous phase
- 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
- 239000003054 catalyst Substances 0.000 title claims description 71
- 229910052787 antimony Inorganic materials 0.000 title claims description 62
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 title claims description 60
- 238000005893 bromination reaction Methods 0.000 title claims description 24
- 238000011084 recovery Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 53
- 239000003960 organic solvent Substances 0.000 claims description 48
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 230000002378 acidificating effect Effects 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 35
- 239000008346 aqueous phase Substances 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 230000031709 bromination Effects 0.000 claims description 16
- 150000003440 styrenes Chemical class 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 7
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 7
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- -1 antimony halide Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000011260 aqueous acid Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 101710134784 Agnoprotein Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- 229910014265 BrCl Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- TXTQARDVRPFFHL-UHFFFAOYSA-N [Sb].[H][H] Chemical compound [Sb].[H][H] TXTQARDVRPFFHL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/02—Neutralisation of the polymerisation mass, e.g. killing the catalyst also removal of catalyst residues
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/08—Removal of catalyst residues
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/751,060 US6992148B2 (en) | 2003-12-31 | 2003-12-31 | Recovery of antimony catalyst residues from bromination reaction mixtures |
| US10/751,060 | 2003-12-31 | ||
| PCT/US2004/031598 WO2005068513A1 (en) | 2003-12-31 | 2004-09-24 | Recovery of antimony catalyst residues from bromination reaction mixtures |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007517106A JP2007517106A (ja) | 2007-06-28 |
| JP2007517106A5 JP2007517106A5 (https=) | 2007-11-01 |
| JP4759521B2 true JP4759521B2 (ja) | 2011-08-31 |
Family
ID=34701263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006546968A Expired - Fee Related JP4759521B2 (ja) | 2003-12-31 | 2004-09-24 | 臭素化反応からのアンチモン触媒残渣の回収 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6992148B2 (https=) |
| EP (1) | EP1699831B1 (https=) |
| JP (1) | JP4759521B2 (https=) |
| KR (1) | KR101120974B1 (https=) |
| CN (1) | CN1902236A (https=) |
| AU (1) | AU2004313905A1 (https=) |
| BR (1) | BRPI0418443A (https=) |
| CA (1) | CA2549907A1 (https=) |
| DE (1) | DE602004010431T2 (https=) |
| ES (1) | ES2294547T3 (https=) |
| IL (1) | IL176589A0 (https=) |
| PL (1) | PL1699831T3 (https=) |
| RU (1) | RU2006127468A (https=) |
| WO (1) | WO2005068513A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0418907A (pt) * | 2004-05-20 | 2007-11-27 | Albemarle Corp | aglomerados de polìmeros estirênicos aniÈnicos bromatadas inalterados e método de preparação |
| US7432332B2 (en) * | 2005-03-31 | 2008-10-07 | Albermarle Corporation | Polymer halogenation process with catalyst recovery |
| US7632893B2 (en) * | 2005-06-30 | 2009-12-15 | Albemarle Corporation | Brominated styrenic polymers and their preparation |
| ES2602097T3 (es) * | 2005-12-21 | 2017-02-17 | Albemarle Corporation | Polímeros aniónicos estirénicos bromados y su preparación |
| EP2044133B1 (en) * | 2006-07-20 | 2015-01-28 | Albemarle Corporation | Process technology for recovering brominated styrenic polymers from reaction mixtures in which they are formed and/or converting such mixtures into pellets or into granules or pastilles |
| CN101490106B (zh) * | 2006-07-20 | 2013-04-17 | 雅宝公司 | 用于从形成溴化苯乙烯类聚合物的反应混合物中回收溴化苯乙烯类聚合物和/或将这种混合物转化为颗粒或者小粒或锭剂的加工技术 |
| WO2008066970A1 (en) * | 2006-11-28 | 2008-06-05 | Albemarle Corporation | Converting brominated anionic styrenic polymer into harder and larger form for storage, shipment, and use |
| CN102224122B (zh) * | 2008-12-02 | 2014-09-03 | 雅宝公司 | 甲苯和苯乙烯衍生的调聚物分布物及由其制备的溴化阻燃剂 |
| WO2010114637A1 (en) * | 2009-03-31 | 2010-10-07 | Dow Global Technologies Inc. | Process for brominating unsaturated organic compounds with removal of quaternary ammonium or quaternary phosphonium monochlorides |
| CN115308012B (zh) * | 2022-08-31 | 2024-12-10 | 中国科学院地球化学研究所 | 一种低锑含量水体中锑同位素测定的前处理方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS627764A (ja) * | 1985-05-03 | 1987-01-14 | ザ ダウ ケミカル カンパニ− | アルケニル芳香族化合物の臭素化ポリマ−およびそれの製造方法 |
| JPH0853511A (ja) * | 1994-08-12 | 1996-02-27 | Teijin Chem Ltd | 臭素化ポリスチレンの製造方法 |
| JPH10130325A (ja) * | 1996-10-31 | 1998-05-19 | Teijin Chem Ltd | ハロゲン化されたスチレン重合物の製法 |
| JP2000281800A (ja) * | 1999-03-30 | 2000-10-10 | Teijin Chem Ltd | 臭素化ポリスチレン粉粒体の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2545220A1 (de) * | 1975-10-09 | 1977-04-21 | Hoechst Ag | Verfahren zur aufarbeitung von inaktiven antimonhalogenidkatalysatoren zu waessrigen antimon-iii-halogenidloesungen |
| US4352909A (en) * | 1980-08-20 | 1982-10-05 | Ferro Corporation | Process for the bromination of polystyrenes |
| EP0520007B1 (en) * | 1990-03-16 | 1998-06-03 | Great Lakes Chemical Corporation | Process for purifying brominated polystyrene |
| AU5369496A (en) | 1995-04-06 | 1996-10-23 | Ferro Corporation | Brominated syndiotactic styrenic polymers and method for mak ing and using same |
| US5723549A (en) * | 1996-06-14 | 1998-03-03 | Ferro Corporation | Process for the preparation of brominated polystyrene having improved color characteristics |
-
2003
- 2003-12-31 US US10/751,060 patent/US6992148B2/en not_active Expired - Fee Related
-
2004
- 2004-09-24 WO PCT/US2004/031598 patent/WO2005068513A1/en not_active Ceased
- 2004-09-24 KR KR1020067013247A patent/KR101120974B1/ko not_active Expired - Fee Related
- 2004-09-24 CA CA002549907A patent/CA2549907A1/en not_active Abandoned
- 2004-09-24 CN CNA200480039679XA patent/CN1902236A/zh active Pending
- 2004-09-24 PL PL04785104T patent/PL1699831T3/pl unknown
- 2004-09-24 RU RU2006127468/04A patent/RU2006127468A/ru not_active Application Discontinuation
- 2004-09-24 AU AU2004313905A patent/AU2004313905A1/en not_active Abandoned
- 2004-09-24 DE DE602004010431T patent/DE602004010431T2/de not_active Expired - Lifetime
- 2004-09-24 EP EP04785104A patent/EP1699831B1/en not_active Expired - Lifetime
- 2004-09-24 ES ES04785104T patent/ES2294547T3/es not_active Expired - Lifetime
- 2004-09-24 BR BRPI0418443-2A patent/BRPI0418443A/pt not_active IP Right Cessation
- 2004-09-24 JP JP2006546968A patent/JP4759521B2/ja not_active Expired - Fee Related
-
2006
- 2006-06-27 IL IL176589A patent/IL176589A0/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS627764A (ja) * | 1985-05-03 | 1987-01-14 | ザ ダウ ケミカル カンパニ− | アルケニル芳香族化合物の臭素化ポリマ−およびそれの製造方法 |
| JPH0853511A (ja) * | 1994-08-12 | 1996-02-27 | Teijin Chem Ltd | 臭素化ポリスチレンの製造方法 |
| JPH10130325A (ja) * | 1996-10-31 | 1998-05-19 | Teijin Chem Ltd | ハロゲン化されたスチレン重合物の製法 |
| JP2000281800A (ja) * | 1999-03-30 | 2000-10-10 | Teijin Chem Ltd | 臭素化ポリスチレン粉粒体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0418443A (pt) | 2007-09-04 |
| US20050143528A1 (en) | 2005-06-30 |
| CN1902236A (zh) | 2007-01-24 |
| CA2549907A1 (en) | 2005-07-28 |
| AU2004313905A1 (en) | 2005-07-28 |
| EP1699831B1 (en) | 2007-11-28 |
| ES2294547T3 (es) | 2008-04-01 |
| DE602004010431T2 (de) | 2008-10-16 |
| RU2006127468A (ru) | 2008-02-10 |
| KR20060121265A (ko) | 2006-11-28 |
| US6992148B2 (en) | 2006-01-31 |
| WO2005068513A1 (en) | 2005-07-28 |
| PL1699831T3 (pl) | 2008-09-30 |
| EP1699831A1 (en) | 2006-09-13 |
| KR101120974B1 (ko) | 2012-03-05 |
| JP2007517106A (ja) | 2007-06-28 |
| IL176589A0 (en) | 2006-10-31 |
| DE602004010431D1 (de) | 2008-01-10 |
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Legal Events
| Date | Code | Title | Description |
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