IL97569A - Process for purifying bromine-converted polystyrene - Google Patents

Process for purifying bromine-converted polystyrene

Info

Publication number: IL97569A
Authority: IL; Israel
Prior art keywords: halogen; polymers; occluded; ionic; slurry
Prior art date: 1990-03-16

Application number

IL9756991A

Other languages

English (en)

Hebrew (he)

Other versions

IL97569A0 (en

Original Assignee

Great Lakes Chemical Corp

Priority date (The priority date 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 date listed.)

1990-03-16

Filing date

1991-03-15

Publication date

1994-07-31

1991-03-15 Application filed by Great Lakes Chemical Corp filed Critical Great Lakes Chemical Corp

1992-06-21 Publication of IL97569A0 publication Critical patent/IL97569A0/xx

1994-07-31 Publication of IL97569A publication Critical patent/IL97569A/en

Links

238000000034 method Methods 0.000 title claims description 96
239000004793 Polystyrene Substances 0.000 title description 72
229920002223 polystyrene Polymers 0.000 title description 72
229910052736 halogen Inorganic materials 0.000 claims description 105
150000002367 halogens Chemical class 0.000 claims description 74
229920000642 polymer Polymers 0.000 claims description 74
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 64
239000002002 slurry Substances 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
-1 aliphatic halogen compounds Chemical class 0.000 claims description 31
229910021529 ammonia Inorganic materials 0.000 claims description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
239000003638 chemical reducing agent Substances 0.000 claims description 19
239000012535 impurity Substances 0.000 claims description 16
150000001298 alcohols Chemical class 0.000 claims description 14
238000001914 filtration Methods 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 5
238000001035 drying Methods 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
239000000463 material Substances 0.000 claims 7
230000029087 digestion Effects 0.000 description 93
238000000746 purification Methods 0.000 description 44
239000007787 solid Substances 0.000 description 44
230000000694 effects Effects 0.000 description 31
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 19
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
239000000908 ammonium hydroxide Substances 0.000 description 13
239000012043 crude product Substances 0.000 description 13
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000012264 purified product Substances 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
230000008030 elimination Effects 0.000 description 8
238000003379 elimination reaction Methods 0.000 description 8
238000005893 bromination reaction Methods 0.000 description 7
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
230000031709 bromination Effects 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
230000001419 dependent effect Effects 0.000 description 5
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000003247 decreasing effect Effects 0.000 description 4
239000002245 particle Substances 0.000 description 4
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
125000001246 bromo group Chemical class Br* 0.000 description 3
230000007423 decrease Effects 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
230000008961 swelling Effects 0.000 description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910001507 metal halide Inorganic materials 0.000 description 2
150000005309 metal halides Chemical class 0.000 description 2
239000000178 monomer Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
229920005992 thermoplastic resin Polymers 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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 1
238000012935 Averaging Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
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 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
229920006249 styrenic copolymer Polymers 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension 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
- C08F6/24—Treatment of polymer suspensions
- 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

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)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

IL9756991A 1990-03-16 1991-03-15 Process for purifying bromine-converted polystyrene IL97569A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US49430290A	1990-03-16	1990-03-16

Publications (2)

Publication Number	Publication Date
IL97569A0 IL97569A0 (en)	1992-06-21
IL97569A true IL97569A (en)	1994-07-31

Family

ID=23963919

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9756991A IL97569A (en)	1990-03-16	1991-03-15	Process for purifying bromine-converted polystyrene

Country Status (5)

Country	Link
US (1)	US5328983A (de)
EP (1)	EP0520007B1 (de)
DE (1)	DE69129533T2 (de)
IL (1)	IL97569A (de)
WO (1)	WO1991013915A1 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH08510208A (ja) *	1993-04-07	1996-10-29	グレート・レークス・ケミカル・コーポレーション	臭素化ジフェニルアルカン生成物および製法
US6518368B2 (en)	1996-06-14	2003-02-11	Albemarle Corporation	Brominated polystyrene having improved thermal stability and color and process for the preparation thereof
US5637650A (en)	1996-06-14	1997-06-10	Ferro Corporation	Brominated polysytrene having improved thermal stability and color and process for the preparation thereof
US6235831B1 (en)	1996-09-26	2001-05-22	Albemarle Corporation	Polymer compositions containing brominated polystyrenic resins
US6133381A (en) *	1996-09-26	2000-10-17	Albelmarle Corporation	Brominated polystyrenic flame retardants
US6232408B1 (en)	1996-09-26	2001-05-15	Albemarle Corporation	Brominated polstyrenic resins
US6326439B1 (en)	1996-09-26	2001-12-04	Albemarle Corporation	Process for brominating polystyrenic resins
US5677390A (en) *	1996-09-26	1997-10-14	Albemarle Corporation	Process for brominating polystyrenic resins
US6232393B1 (en)	1996-09-26	2001-05-15	Albemarle Corporation	Polymers flame retarded with brominated polystyrenic resins
EP0928300B1 (de)	1996-09-26	2000-05-10	Albemarle Corporation	Verfahren zur bromierung von styrolpolymeren
US6521714B2 (en)	1996-09-26	2003-02-18	Albemarle Corporation	Brominated polystyrenic resins
US6235844B1 (en)	1996-09-26	2001-05-22	Albemarle Corporation	Brominated polystyrenic resins
US5686538A (en) *	1996-09-26	1997-11-11	Albemarle Corporation	Process for brominating polystyrenic resins
DE69832912T2 (de) *	1997-05-07	2006-09-21	Albemarle Corp.	Verfahren zur Bromierung von Polystyrolharzen
CN100448821C (zh)	2001-12-21	2009-01-07	帕布服务公司	生产十溴二苯基烷烃的方法与装置
US6992148B2 (en) *	2003-12-31	2006-01-31	Albemarle Corporation	Recovery of antimony catalyst residues from bromination reaction mixtures
US11786891B2 (en)	2021-05-24	2023-10-17	Ddp Specialty Electronic Materials Us, Llc	Process for recovering quaternary salt bromination catalyst

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE600142A (de) *	1960-02-11
FR2413409A1 (fr) *	1978-01-02	1979-07-27	Huels Chemische Werke Ag	Procede pour preparer des polystyrenes resistant a la chaleur, bromes sur le noyau
DE3215911A1 (de) *	1982-04-29	1983-11-03	Basf Ag, 6700 Ludwigshafen	Verfahren zur behandlung von (co)polymerisaten zur entfernung von restmonomeren
EP0124278B1 (de) *	1983-04-01	1989-11-02	Exxon Research And Engineering Company	Verfahren zur Herstellung von halogenierten Polymerisaten
US4879353A (en) *	1987-01-28	1989-11-07	Great Lakes Chemical Corporation	Bromination of polystyrene using bromine as the reaction solvent

1991
- 1991-03-12 DE DE69129533T patent/DE69129533T2/de not_active Expired - Fee Related
- 1991-03-12 WO PCT/US1991/001648 patent/WO1991013915A1/en not_active Ceased
- 1991-03-12 EP EP91906520A patent/EP0520007B1/de not_active Expired - Lifetime
- 1991-03-15 IL IL9756991A patent/IL97569A/en not_active IP Right Cessation
1992
- 1992-03-02 US US07/844,478 patent/US5328983A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1991013915A1 (en)	1991-09-19
US5328983A (en)	1994-07-12
DE69129533D1 (de)	1998-07-09
DE69129533T2 (de)	1998-10-29
EP0520007A1 (de)	1992-12-30
EP0520007B1 (de)	1998-06-03
IL97569A0 (en)	1992-06-21

Legal Events

Date	Code	Title	Description
1997-07-13	KB	Patent renewed
2002-02-10	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5328983A (en)	1994-07-12	Process for purifying brominated polystyrene
EP0872490B1 (de)	2006-05-17	Hochmolekulares Flockungsmittel, Verfahren zu dessen Herstellung und Verfahren zur Wasserbehandlung mit diesem Mittel
US4879353A (en)	1989-11-07	Bromination of polystyrene using bromine as the reaction solvent
US3454544A (en)	1969-07-08	Process for the chlorination of polyolefins
CA1297628C (en)	1992-03-17	Aromatic bromination of polystyrene using bromine as the reaction solvent
JP3385586B2 (ja)	2003-03-10	改良された性能を示す四級化されている第三級アミノメチルアクリルアミドポリマーのミクロエマルジヨン
US2642417A (en)	1953-06-16	Process for making anionexchange resins
Bikales	1973	Preparation of acrylamide polymers
US4356289A (en)	1982-10-26	Polymeric N-halogenoamides on the basis of acrylamide and methacrylamide
US3835046A (en)	1974-09-10	Dewatering of aqueous suspensions
US3342755A (en)	1967-09-19	Oxidation stable halogen containing cation exchange resins
US5359011A (en)	1994-10-25	Process for the complete neutralization of chlorinated polyvinyl chloride and product resulting therefrom
SU1271373A3 (ru)	1986-11-15	Способ получени частично гидролизованного полиакриламида
JPS5950684B2 (ja)	1984-12-10	エチレン−マレイン酸無水物相互重合体の製法
JP5658744B2 (ja)	2015-01-28	セベラマーの製造方法
US2944033A (en)	1960-07-05	Exchange resins from nu-halogenated copolymers
CA1241497A (en)	1988-08-30	Preparation of pulverulent polymers and their use
WO1995012625A2 (en)	1995-05-11	Removal of base residues from poly(vinyl alcohol) reaction-slurries
NO142627B (no)	1980-06-09	Fremgangsmaate for fremstilling av poly-alfa-hydroksyakrylsyrer eller av kopolymerer av poly-alfa-hydroksyakrylsyre
US4661263A (en)	1987-04-28	Water clarification
EP0171661B1 (de)	1989-03-29	Verfahren zur Herstellung von kationischen Terpolymerisaten und Derivat davon
EP0084254A2 (de)	1983-07-27	Chlorierung und Vernetzung von selektierten Polymerisaten mittels Cl2O oder HOCl
JPS6265926A (ja)	1987-03-25	アルミナの製法
EP0015345B1 (de)	1983-01-12	Verfahren zur Herstellung von N-Chlorimiden
NO753408L (de)	1976-04-27