IL117987A - Process for the preparation of tetrabromobisphenol-a - Google Patents

Process for the preparation of tetrabromobisphenol-a

Info

Publication number: IL117987A
Authority: IL; Israel
Prior art keywords: reaction mass; water; alcohol; bisphenol; hbr
Prior art date: 1995-04-24

Application number

IL11798796A

Other languages

English (en)

Other versions

IL117987A0 (en

Original Assignee

Albemarle 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.)

1995-04-24

Filing date

1996-04-21

Publication date

2004-05-12

1995-04-24 Priority claimed from US08/426,997 external-priority patent/US5527971A/en

1996-04-21 Application filed by Albemarle Corp filed Critical Albemarle Corp

1996-09-12 Publication of IL117987A0 publication Critical patent/IL117987A0/xx

2004-05-12 Publication of IL117987A publication Critical patent/IL117987A/en

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)

IL11798796A 1995-04-24 1996-04-21 Process for the preparation of tetrabromobisphenol-a IL117987A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US42699895A	1995-04-24	1995-04-24
US42699695A	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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 JP JP53261596A patent/JP3882201B2/ja not_active Expired - Lifetime
- 1996-04-18 WO PCT/US1996/005511 patent/WO1996033964A1/en not_active Ceased
- 1996-04-18 EP EP96916430A patent/EP0822927B1/de not_active Expired - Lifetime
- 1996-04-18 ES ES96916430T patent/ES2182980T3/es not_active Expired - Lifetime
- 1996-04-18 AT AT96916430T patent/ATE222885T1/de not_active IP Right Cessation
- 1996-04-18 DE DE69623273T patent/DE69623273T2/de not_active Expired - Lifetime
- 1996-04-21 IL IL11798796A patent/IL117987A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69623273T2 (de)	2003-05-28
JP3882201B2 (ja)	2007-02-14
EP0822927A1 (de)	1998-02-11
DE69623273D1 (de)	2002-10-02
ATE222885T1 (de)	2002-09-15
JPH11504333A (ja)	1999-04-20
EP0822927B1 (de)	2002-08-28
ES2182980T3 (es)	2003-03-16
WO1996033964A1 (en)	1996-10-31
IL117987A0 (en)	1996-09-12

Legal Events

Date	Code	Title
2004-09-27	FF	Patent granted
2006-08-01	KB	Patent renewed
2010-10-31	KB	Patent renewed
2014-04-30	KB	Patent renewed
2016-11-30	EXP	Patent expired

Publication	Publication Date	Title
JP4917059B2 (ja)	2012-04-18	テトラブロモビスフェノール−ａの製造方法
US5723690A (en)	1998-03-03	Process for the preparation of tetrabromobisphenol-A
EP0822927B1 (de)	2002-08-28	Verfahren zur herstellung von tetrabrombisphenol-a
US6002050A (en)	1999-12-14	Process for the preparation of tetrabromobisphenol-A
US6084137A (en)	2000-07-04	Process for the preparation of tetrabromobisphenol-A
US6084136A (en)	2000-07-04	Process for the preparation of tetrabromobisphenol-A
US5773668A (en)	1998-06-30	Method of making trichloromethoxybenzene
US6147264A (en)	2000-11-14	Process for producing tetrabromobisphenol-A
CN101258118B (zh)	2012-05-30	制备四溴双酚a的方法
US6300527B1 (en)	2001-10-09	Process for the preparation of tetrabromobisphenol-A
US6313355B1 (en)	2001-11-06	Process for the preparation of tetrabromobisphenol-A
IL136483A (en)	2006-12-10	Process for the preparation of tetrabromobiphenol-A
JP2003525863A (ja)	2003-09-02	ヘキサブロモシクロドデカンを製造するための改良された方法
CA2064864A1 (fr)	1991-12-23	Procede de preparation de 1,1-bis(chlorophenyl)-2,2,2 trichloroethanol
US6103926A (en)	2000-08-15	Benzylic halogenation of alkylbenzoic acid esters
FR2638159A1 (fr)	1990-04-27	Procede pour la fabrication de l'alcool 3-phenoxybenzylique
HATCH	1993	Bromination and Bromine Compounds