IL44080A - Preparation of brominated aromatic compounds - Google Patents
Preparation of brominated aromatic compoundsInfo
- Publication number
- IL44080A IL44080A IL44080A IL4408074A IL44080A IL 44080 A IL44080 A IL 44080A IL 44080 A IL44080 A IL 44080A IL 4408074 A IL4408074 A IL 4408074A IL 44080 A IL44080 A IL 44080A
- Authority
- IL
- Israel
- Prior art keywords
- bromine
- reaction
- bromination
- aromatic compounds
- product
- Prior art date
Links
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 13
- 238000005893 bromination reaction Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000031709 bromination Effects 0.000 claims description 9
- 239000004411 aluminium Substances 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
- 229920000742 Cotton Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000011552 falling film 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
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7325801A FR2236818B1 (enrdf_load_stackoverflow) | 1973-07-13 | 1973-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44080A0 IL44080A0 (en) | 1974-05-16 |
| IL44080A true IL44080A (en) | 1977-01-31 |
Family
ID=9122563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44080A IL44080A (en) | 1973-07-13 | 1974-01-25 | Preparation of brominated aromatic compounds |
Country Status (12)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS491868B1 (enrdf_load_stackoverflow) * | 1970-06-08 | 1974-01-17 | ||
| JPS5726493B2 (enrdf_load_stackoverflow) * | 1974-07-31 | 1982-06-04 | ||
| JPS581090B2 (ja) * | 1977-03-15 | 1983-01-10 | 三井東圧化学株式会社 | ヘキサブロムジフエニルエ−テルの製造法 |
| JPS5840933B2 (ja) * | 1977-04-12 | 1983-09-08 | 三井東圧化学株式会社 | ２，４，２′，４′−テトラブロムジフェニルエ−テルの製造法 |
| JPS5929175B2 (ja) * | 1977-05-16 | 1984-07-18 | 三井東圧化学株式会社 | ヘキサブロムジフエニルエ−テルの製造法 |
| US4287373A (en) | 1979-05-16 | 1981-09-01 | Great Lakes Chemical Corporation | Perbromination of phenol and diphenyl ether at elevated temperature using bromine as the reaction medium |
| GB2081253B (en) * | 1980-07-23 | 1985-05-30 | Great Lakes Chemical Corp | Process for producing purified brominated aromatic compounds |
| DE3117481A1 (de) * | 1981-05-02 | 1982-11-18 | Great Lakes Chemical Corp., 47906 West Lafayette, Ind. | Verfahren zum perbromieren von phenol und diphenylaether |
| FR2505821B1 (fr) * | 1981-05-12 | 1986-02-14 | Great Lakes Chemical Corp | Procede de perbromation du phenol et de l'ether diphenylique a temperature elevee, en utilisant du brome comme milieu reactionnel |
| JPS57200322A (en) * | 1981-05-27 | 1982-12-08 | Great Lakes Chemical Corp | Perbromination of phenol and diphenyl ether carrying out under rising temperature as reactive medium of bromine |
| US4521633A (en) * | 1983-05-19 | 1985-06-04 | The Dow Chemical Company | Bromination process |
| US4879353A (en) * | 1987-01-28 | 1989-11-07 | Great Lakes Chemical Corporation | Bromination of polystyrene using bromine as the reaction solvent |
| DE3779747T2 (de) * | 1987-01-28 | 1993-01-07 | Great Lakes Chemical Corp | Aromatische bromierung von polystyrol mit einer bromverbindung als reaktionsloesungsmittel. |
| US4814525A (en) * | 1987-03-25 | 1989-03-21 | Eastman Kodak Company | Vapor phase bromination of aromatic compounds |
| US4778933A (en) * | 1987-07-15 | 1988-10-18 | Ethyl Corporation | Process for making decabromodiphenyl oxide |
| US4835322A (en) * | 1987-10-19 | 1989-05-30 | Great Lakes Chemical Corporation | Process for producing 4,4'-dibromodiphenyl ether |
| CA1321213C (en) * | 1988-06-13 | 1993-08-10 | Saadat Hussain | Bromination process |
| US5003117A (en) * | 1989-08-03 | 1991-03-26 | Ethyl Corporation | Process for decabromodiphenyl methane |
| US5026932A (en) * | 1990-02-22 | 1991-06-25 | Amoco Corporation | Preparation of 4-bromo-o-xylene in liquid sulfur dioxide |
| US5008477A (en) * | 1990-03-14 | 1991-04-16 | Ethyl Corporation | Decabromodiphenyl alkane process |
| US5136107A (en) * | 1990-06-04 | 1992-08-04 | Ethyl Corporation | Process for halogenating aromatic compounds |
| US5030778A (en) * | 1990-06-04 | 1991-07-09 | Ethyl Corporation | Decabromodiphenyl alkane process |
| US5401890A (en) * | 1990-07-30 | 1995-03-28 | Albemarle Corporation | Process and apparatus for heat treating halogenated compounds |
| CA2047256C (en) * | 1990-07-30 | 2002-03-05 | Saadat Hussain | Process for decabromodiphenylalkane predominant product |
| US5124496A (en) * | 1990-11-01 | 1992-06-23 | Ethyl Corporation | Process for decabromodiphenylalkane predominant product |
| US5055235A (en) * | 1990-12-12 | 1991-10-08 | Ethyl Corporation | Bromination process |
| US5324874A (en) * | 1992-05-26 | 1994-06-28 | Ethyl Corporation | Process for a decarbromodiphenylethane predominate product having enhanced whiteness |
| US6518468B1 (en) | 1994-09-16 | 2003-02-11 | Albemarle Corporation | Bromination process |
| US6743825B1 (en) | 2001-08-03 | 2004-06-01 | Albemarle Corporation | Poly(bromoaryl)alkane additives and methods for their preparation and use |
| AU2002361780A1 (en) | 2001-12-21 | 2003-07-15 | Pabu Services, Inc. | Method and apparatus for producing decabromodiphenyl alkanes |
| WO2008027776A2 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of high assay decabromodiphenyl oxide |
| WO2008027779A1 (en) * | 2006-08-29 | 2008-03-06 | Albemarle Corporation | Preparation of decabromodiphenyl oxide |
| MX2009004565A (es) | 2006-11-09 | 2009-05-12 | Albemarle Corp | Procesamiento de compuestos sólidos organicos aromaticos bromados que contienen bromo bloqueado. |
| US7408088B1 (en) | 2007-02-08 | 2008-08-05 | Albemarle Corporation | Process for separation of bromine from gaseous hydrogen bromide and use of such process in production of decabromodiphenylethane |
| CA2680010C (en) | 2007-03-16 | 2015-05-05 | Albemarle Corporation | Preparation and provision of high assay decabromodiphenylethane |
| JP5537955B2 (ja) | 2007-03-16 | 2014-07-02 | アルベマール・コーポレーシヨン | 高含有率デカブロモジフェニルエタンの調製および提供 |
| EP2459506B1 (en) | 2009-07-27 | 2014-04-09 | Albemarle Corporation | Preparation of high assay decabromodiphenylalkane product with low occluded free bromine content |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2031649A5 (enrdf_load_stackoverflow) * | 1969-02-03 | 1970-11-20 | Ugine Kuhlmann |
-
1973
- 1973-07-13 FR FR7325801A patent/FR2236818B1/fr not_active Expired
-
1974
- 1974-01-05 DE DE2400455A patent/DE2400455C3/de not_active Expired
- 1974-01-07 GB GB72874A patent/GB1411524A/en not_active Expired
- 1974-01-08 SE SE7400222A patent/SE395882B/xx not_active IP Right Cessation
- 1974-01-09 IT IT67050/74A patent/IT1011516B/it active
- 1974-01-11 BR BR184/74A patent/BR7400184D0/pt unknown
- 1974-01-11 CH CH37374A patent/CH582116A5/xx not_active IP Right Cessation
- 1974-01-16 CA CA190,327A patent/CA1032556A/en not_active Expired
- 1974-01-21 JP JP863474A patent/JPS5640129B2/ja not_active Expired
- 1974-01-23 NL NL7400929A patent/NL7400929A/xx active Search and Examination
- 1974-01-25 BE BE140156A patent/BE810140A/xx not_active IP Right Cessation
- 1974-01-25 IL IL44080A patent/IL44080A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5640129B2 (enrdf_load_stackoverflow) | 1981-09-18 |
| IT1011516B (it) | 1977-02-10 |
| DE2400455B2 (de) | 1975-06-12 |
| FR2236818B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| BR7400184D0 (pt) | 1975-08-05 |
| CA1032556A (en) | 1978-06-06 |
| SE395882B (sv) | 1977-08-29 |
| NL7400929A (nl) | 1975-01-15 |
| JPS5037735A (enrdf_load_stackoverflow) | 1975-04-08 |
| IL44080A0 (en) | 1974-05-16 |
| CH582116A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| DE2400455A1 (de) | 1975-02-06 |
| DE2400455C3 (de) | 1984-03-22 |
| BE810140A (fr) | 1974-05-16 |
| FR2236818A1 (enrdf_load_stackoverflow) | 1975-02-07 |
| GB1411524A (en) | 1975-10-29 |
| AU6485174A (en) | 1975-07-24 |
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