IL117987A - Process for the preparation of tetrabromobisphenol-a - Google Patents
Process for the preparation of tetrabromobisphenol-aInfo
- Publication number
- IL117987A IL117987A IL11798796A IL11798796A IL117987A IL 117987 A IL117987 A IL 117987A IL 11798796 A IL11798796 A IL 11798796A IL 11798796 A IL11798796 A IL 11798796A IL 117987 A IL117987 A IL 117987A
- Authority
- IL
- Israel
- Prior art keywords
- reaction mass
- water
- alcohol
- bisphenol
- hbr
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 174
- 230000008569 process Effects 0.000 title claims abstract description 155
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 238000002360 preparation method Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 254
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 243
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 136
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 133
- 229910001868 water Inorganic materials 0.000 claims abstract description 130
- 229940106691 bisphenol a Drugs 0.000 claims abstract description 119
- 239000002904 solvent Substances 0.000 claims abstract description 61
- 238000004519 manufacturing process Methods 0.000 claims abstract description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 141
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 87
- 239000002244 precipitate Substances 0.000 claims description 31
- 239000007791 liquid phase Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 17
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 150000001347 alkyl bromides Chemical class 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 238000012544 monitoring process Methods 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- -1 propahol Natural products 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 abstract description 17
- 230000031709 bromination Effects 0.000 abstract description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 196
- 239000000243 solution Substances 0.000 description 67
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 39
- 238000007792 addition Methods 0.000 description 31
- 239000012452 mother liquor Substances 0.000 description 30
- 239000007788 liquid Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 26
- 239000007800 oxidant agent Substances 0.000 description 24
- 238000001556 precipitation Methods 0.000 description 24
- MFXDXKKESRYMQV-UHFFFAOYSA-N 2,3,5-tribromo-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C=C(O)C(Br)=C(Br)C=1C(C)(C)C1=CC=C(O)C=C1 MFXDXKKESRYMQV-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- 229940102396 methyl bromide Drugs 0.000 description 23
- 230000001590 oxidative effect Effects 0.000 description 23
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000008901 benefit Effects 0.000 description 12
- 241000894007 species Species 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- 239000002245 particle Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- 150000001649 bromium compounds Chemical class 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000006200 vaporizer Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 230000002572 peristaltic effect Effects 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- APAODYYKOZMIFU-UHFFFAOYSA-N 2,3,5-tribromo-6-chloro-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C(Cl)=C(O)C(Br)=C(Br)C=1C(C)(C)C1=CC=C(O)C=C1 APAODYYKOZMIFU-UHFFFAOYSA-N 0.000 description 3
- 241001550224 Apha Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000002238 attenuated effect Effects 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000002316 fumigant Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000005007 materials handling Methods 0.000 description 2
- 230000003278 mimic effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000011417 postcuring Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000000306 recurrent effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- OVGWMODSIORDDT-UHFFFAOYSA-N 3-bromo-2-chloro-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical class C=1C=C(O)C(Cl)=C(Br)C=1C(C)(C)C1=CC=C(O)C=C1 OVGWMODSIORDDT-UHFFFAOYSA-N 0.000 description 1
- VENULINRALIKKV-UHFFFAOYSA-N 3-monobromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C=C1 VENULINRALIKKV-UHFFFAOYSA-N 0.000 description 1
- 241000590428 Panacea Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000004836 empirical method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42699695A | 1995-04-24 | 1995-04-24 | |
| US42699895A | 1995-04-24 | 1995-04-24 | |
| US08/426,997 US5527971A (en) | 1995-04-24 | 1995-04-24 | Process for the preparation of tetrabromobisphenol-A |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL117987A0 IL117987A0 (en) | 1996-09-12 |
| IL117987A true IL117987A (en) | 2004-05-12 |
Family
ID=27411531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11798796A IL117987A (en) | 1995-04-24 | 1996-04-21 | Process for the preparation of tetrabromobisphenol-a |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0822927B1 (de) |
| JP (1) | JP3882201B2 (de) |
| AT (1) | ATE222885T1 (de) |
| DE (1) | DE69623273T2 (de) |
| ES (1) | ES2182980T3 (de) |
| IL (1) | IL117987A (de) |
| WO (1) | WO1996033964A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446212A (en) * | 1994-09-08 | 1995-08-29 | Great Lakes Chemical Corp. | Reduced methyl bromide process for making tetrabromobisphenol-A |
| US6084137A (en) * | 1995-03-06 | 2000-07-04 | Albemarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US6084136A (en) * | 1995-03-06 | 2000-07-04 | Albmarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US6218584B1 (en) | 1995-03-06 | 2001-04-17 | Albemarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US6002050A (en) * | 1995-03-06 | 1999-12-14 | Albemarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US6235946B1 (en) | 1995-03-06 | 2001-05-22 | Albemarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US7999118B2 (en) | 2000-01-18 | 2011-08-16 | Albemarle Corporation | Process for producing N-halogenated hydantoins |
| IL169592A (en) | 2005-07-07 | 2013-11-28 | Bromine Compounds Ltd | Process for making tetrabromobisphenol a |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234289A (en) * | 1961-05-26 | 1966-02-08 | Dow Chemical Co | Method of making a tetrabromobisphenol |
| GB949306A (en) * | 1962-01-30 | 1964-02-12 | Dow Chemical Co | Method of making alkylidene bis-dibromo-phenols |
| RU2026280C1 (ru) * | 1991-07-30 | 1995-01-09 | Крымское научно-производственное объединение "Йодобром" | Способ получения 2,2-бис(3,5-дибром-4-гидроксифенил)пропана |
-
1996
- 1996-04-18 AT AT96916430T patent/ATE222885T1/de not_active IP Right Cessation
- 1996-04-18 EP EP96916430A patent/EP0822927B1/de not_active Expired - Lifetime
- 1996-04-18 DE DE69623273T patent/DE69623273T2/de not_active Expired - Lifetime
- 1996-04-18 WO PCT/US1996/005511 patent/WO1996033964A1/en not_active Ceased
- 1996-04-18 JP JP53261596A patent/JP3882201B2/ja not_active Expired - Lifetime
- 1996-04-18 ES ES96916430T patent/ES2182980T3/es not_active Expired - Lifetime
- 1996-04-21 IL IL11798796A patent/IL117987A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2182980T3 (es) | 2003-03-16 |
| WO1996033964A1 (en) | 1996-10-31 |
| EP0822927B1 (de) | 2002-08-28 |
| JPH11504333A (ja) | 1999-04-20 |
| EP0822927A1 (de) | 1998-02-11 |
| DE69623273T2 (de) | 2003-05-28 |
| DE69623273D1 (de) | 2002-10-02 |
| IL117987A0 (en) | 1996-09-12 |
| ATE222885T1 (de) | 2002-09-15 |
| JP3882201B2 (ja) | 2007-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |