IL99204A - Process for the production of tetrabromobisphenol - Google Patents
Process for the production of tetrabromobisphenolInfo
- Publication number
- IL99204A IL99204A IL9920491A IL9920491A IL99204A IL 99204 A IL99204 A IL 99204A IL 9920491 A IL9920491 A IL 9920491A IL 9920491 A IL9920491 A IL 9920491A IL 99204 A IL99204 A IL 99204A
- Authority
- IL
- Israel
- Prior art keywords
- tba
- reaction
- acid
- bromine
- high quality
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 44
- 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 description 4
- 238000006243 chemical reaction Methods 0.000 claims description 42
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 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 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011877 solvent mixture Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 229940102396 methyl bromide Drugs 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- -1 bromine ions Chemical class 0.000 description 4
- 239000012776 electronic material Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 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 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 2
- 238000003918 potentiometric titration Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL11175294A IL111752A0 (en) | 1990-08-20 | 1994-11-24 | Process for producing tetrabromobisphenol a of high quality |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21702790A JP2897372B2 (ja) | 1990-08-20 | 1990-08-20 | 高品質テトラブロモビスフェノールａの製法 |
| JP3132155A JP3008552B2 (ja) | 1991-05-09 | 1991-05-09 | 高品質テトラブロモビスフェノ−ルａの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL99204A0 IL99204A0 (en) | 1992-07-15 |
| IL99204A true IL99204A (en) | 1995-03-30 |
Family
ID=26466788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9920491A IL99204A (en) | 1990-08-20 | 1991-08-15 | Process for the production of tetrabromobisphenol |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5138103A (de) |
| EP (2) | EP0779262B1 (de) |
| DE (2) | DE69128009T2 (de) |
| IL (1) | IL99204A (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283375A (en) * | 1992-04-01 | 1994-02-01 | Ethyl Corporation | Process for high purity tetrabromobisphenol-A |
| IL105722A (en) * | 1992-05-19 | 1997-11-20 | Tosoh Corp | Single crystals of tetrabromobisphenol a, having a large particle size and process for their production |
| US5237112A (en) * | 1992-08-31 | 1993-08-17 | Ethyl Corporation | Process for tetrabromobisphenol-A |
| US5475153A (en) * | 1995-01-04 | 1995-12-12 | Great Lakes Chemical Corp. | Process to produce tetrabromobisphenol with the reduced formation of alkyl bromide by-products |
| JP4112000B2 (ja) * | 1995-03-06 | 2008-07-02 | アルベマール・コーポレーシヨン | テトラブロモビスフェノール−ａの製造方法 |
| US5527971A (en) * | 1995-04-24 | 1996-06-18 | 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 |
| US6084136A (en) * | 1995-03-06 | 2000-07-04 | Albmarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US6084137A (en) * | 1995-03-06 | 2000-07-04 | 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 |
| US6218584B1 (en) | 1995-03-06 | 2001-04-17 | Albemarle Corporation | Process for the preparation of tetrabromobisphenol-A |
| US5777007A (en) * | 1996-03-13 | 1998-07-07 | Tosoh Corporation | Brominated p-cumylphenol flame-retardants for resin composition |
| IL131408A0 (en) * | 1997-02-19 | 2001-01-28 | Great Lakes Chemical Corp | Process for the manufacture of tetrabromobisphenol-a with co-production of n-propyl bromide |
| US6147264A (en) * | 1999-04-08 | 2000-11-14 | Albemarle Corporation | Process for producing tetrabromobisphenol-A |
| CN1243703C (zh) * | 1999-12-20 | 2006-03-01 | 索勒瑞斯化学技术有限公司 | 高纯度4,4－异亚丙基－双－(2,6－二溴苯酚)和制备该高纯度4,4－异亚丙基－双－(2,6－二溴苯酚)的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3182088A (en) * | 1961-05-26 | 1965-05-04 | Dow Chemical Co | Method of making a tetrabromobisphenol |
| FR1313469A (fr) * | 1962-02-01 | 1962-12-28 | Dow Chemical Co | Procédé de préparation d'alcoylidène bis-dibromophénols |
| JPS525745A (en) * | 1975-07-04 | 1977-01-17 | Asahi Glass Co Ltd | Process for preparation of tetrabromobisphenols |
| JPS5242789A (en) * | 1975-10-01 | 1977-04-02 | Hitachi Ltd | Method of inspecting pinholes of insulating film |
| US4701568A (en) * | 1986-06-30 | 1987-10-20 | Ethyl Corporation | Process for preparing tetrabromobisphenol-A |
| US5008469A (en) * | 1989-01-26 | 1991-04-16 | Tosoh Corporation | Process for producing tetrabromobisphenol A |
| DE3935224A1 (de) * | 1989-10-23 | 1991-04-25 | Degussa | Verfahren zur herstellung von tetrabrom-4,4'-alkylidendiphenolen |
-
1991
- 1991-08-15 IL IL9920491A patent/IL99204A/en active IP Right Review Request
- 1991-08-16 US US07/745,888 patent/US5138103A/en not_active Expired - Lifetime
- 1991-08-19 DE DE69128009T patent/DE69128009T2/de not_active Expired - Fee Related
- 1991-08-19 EP EP97102263A patent/EP0779262B1/de not_active Expired - Lifetime
- 1991-08-19 DE DE69133291T patent/DE69133291T2/de not_active Expired - Fee Related
- 1991-08-19 EP EP91307632A patent/EP0472395B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0779262A2 (de) | 1997-06-18 |
| EP0779262A3 (de) | 1998-05-13 |
| IL99204A0 (en) | 1992-07-15 |
| DE69133291T2 (de) | 2004-05-13 |
| EP0779262B1 (de) | 2003-07-02 |
| DE69128009D1 (de) | 1997-11-27 |
| US5138103A (en) | 1992-08-11 |
| DE69128009T2 (de) | 1998-02-26 |
| EP0472395A1 (de) | 1992-02-26 |
| DE69133291D1 (de) | 2003-08-07 |
| EP0472395B1 (de) | 1997-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CB | Opposition filed against grant of patent |
Free format text: 19.06.95 |
|
| CE | Application withdrawn (oppos. filed against grant of patent) |
Free format text: APPLICANT WITHDREW APPLICATION ON 1.2.96 |