CA1338353C - Procede de preparation d'imides halogenes - Google Patents
Procede de preparation d'imides halogenesInfo
- Publication number
- CA1338353C CA1338353C CA000567006A CA567006A CA1338353C CA 1338353 C CA1338353 C CA 1338353C CA 000567006 A CA000567006 A CA 000567006A CA 567006 A CA567006 A CA 567006A CA 1338353 C CA1338353 C CA 1338353C
- Authority
- CA
- Canada
- Prior art keywords
- hydrazine
- anhydride
- carried out
- halogenated
- halogenation
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 8
- -1 halogen imides Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 19
- 230000026030 halogenation Effects 0.000 claims abstract description 11
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 150000003949 imides Chemical class 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000012493 hydrazine sulfate Substances 0.000 claims description 2
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000232971 Passer domesticus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940030850 avar Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004079 fireproofing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8706904A FR2615510B1 (fr) | 1987-05-18 | 1987-05-18 | Procede de preparation d'imides halogenes |
| FR8706904 | 1987-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1338353C true CA1338353C (fr) | 1996-05-28 |
Family
ID=9351168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000567006A Expired - Fee Related CA1338353C (fr) | 1987-05-18 | 1988-05-17 | Procede de preparation d'imides halogenes |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5977379A (https=) |
| EP (1) | EP0292362B1 (https=) |
| JP (1) | JPH0674247B2 (https=) |
| KR (1) | KR960007079B1 (https=) |
| CN (1) | CN1023008C (https=) |
| AT (1) | ATE79867T1 (https=) |
| AU (1) | AU610590B2 (https=) |
| CA (1) | CA1338353C (https=) |
| DE (1) | DE3873983T2 (https=) |
| DK (1) | DK168435B1 (https=) |
| ES (1) | ES2034300T3 (https=) |
| FI (1) | FI91962C (https=) |
| FR (1) | FR2615510B1 (https=) |
| GR (1) | GR3006273T3 (https=) |
| IE (1) | IE63144B1 (https=) |
| IL (1) | IL85986A (https=) |
| NO (1) | NO173734C (https=) |
| NZ (1) | NZ224640A (https=) |
| PT (1) | PT87494B (https=) |
| ZA (1) | ZA882731B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4997953A (en) * | 1989-10-23 | 1991-03-05 | Ethyl Corporation | Process for preparing N,N'-bis(tetrabromophthalimide) |
| WO1994013638A1 (en) * | 1992-12-04 | 1994-06-23 | Albemarle Corporation | Process for preparing bisimide products |
| CN112079803B (zh) * | 2020-09-11 | 2023-01-31 | 山东润科化工股份有限公司 | 一种4-卤代苯酐及其衍生物的合成方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2420702A (en) * | 1944-06-28 | 1947-05-20 | British Celanese | Amino-aliphatic hydrazines and process for making same |
| CH410898A (de) * | 1961-12-01 | 1966-04-15 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Tetrabromphthalsäureanhydrid |
| DE1518647A1 (de) * | 1965-05-06 | 1969-02-13 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Tetrabromphthalsaeureanhydrid |
| US3873567A (en) * | 1968-09-05 | 1975-03-25 | Universal Oil Prod Co | N-substituted polybromoaromatic ortho-dicarboximides |
| US3705127A (en) * | 1970-12-21 | 1972-12-05 | Universal Oil Prod Co | Polymeric flame retardant compositions |
| US3734925A (en) * | 1971-02-08 | 1973-05-22 | Tenneco Chem | N-amino-3,4-dimethyl-6-isobutyl-phthalimides |
| US3798327A (en) * | 1971-02-08 | 1974-03-19 | Tenneco Chem | Fungicidal compositions and their use |
| JPS4945062A (https=) * | 1972-09-08 | 1974-04-27 | ||
| JPS5625955B2 (https=) * | 1973-12-27 | 1981-06-16 | ||
| US4003862A (en) * | 1975-10-23 | 1977-01-18 | Michigan Chemical Corporation | N-substituted tetrahalophthalimides as flame retardants |
| US4087441A (en) * | 1976-07-19 | 1978-05-02 | Cities Service Company | Process for preparing aromatic bisimides |
| DE2648970A1 (de) * | 1976-10-28 | 1978-05-11 | Dynamit Nobel Ag | Azomethinimide |
| FR2369261A1 (fr) * | 1976-10-28 | 1978-05-26 | Dynamit Nobel Ag | Derives de tetrabromophtalimide et leur application a titre d'agents d'ignifugation |
| GB1584203A (en) * | 1976-12-16 | 1981-02-11 | Dynamit Nobel Ag | Tetrabromophthalimide derivatives and their use as flameprroofing agents |
| JPS555958A (en) * | 1978-06-30 | 1980-01-17 | Dainippon Ink & Chem Inc | Flame-retardant resin composition |
| US4254011A (en) * | 1979-11-19 | 1981-03-03 | Bayer Aktiengesellschaft | Flame retarded polyethylene terephthalate compositions with improved drip suppression |
| CA1192559A (en) * | 1982-04-09 | 1985-08-27 | Ralph H. Hansen | Polymer parts and compound useful therein |
| US4464240A (en) * | 1982-11-08 | 1984-08-07 | Canusa Coating Systems Limited | Thiodipropionoyl bis (halo benzhydrazide) additives for polymers |
| US4465571A (en) * | 1982-11-08 | 1984-08-14 | Canusa Coating Systems Limited | Thiodipropionoyl bis(halo 5-norbornene 2,3-dicarboxylic acid hydrazide) additives for polymers |
| US4477523A (en) * | 1982-04-26 | 1984-10-16 | National Distillers And Chemical Corporation | Flame retardant crosslinked polyolefin insulation material |
| JPS60161974A (ja) * | 1984-01-31 | 1985-08-23 | Nippon Shokubai Kagaku Kogyo Co Ltd | テトラクロロ無水フタル酸の製造方法 |
| JPS61118378A (ja) * | 1984-11-14 | 1986-06-05 | Kanto Denka Kogyo Kk | テトラクロロフタル酸無水物の製造法 |
| FR2618430B1 (fr) * | 1987-07-24 | 1991-02-15 | Atochem | Procede de preparation d'imides halogenes et leur application comme agents d'ignifugation |
| US5137948A (en) * | 1986-02-12 | 1992-08-11 | Atochem | Preparation of flame-resistant halogenated imides |
-
1987
- 1987-05-18 FR FR8706904A patent/FR2615510B1/fr not_active Expired - Lifetime
-
1988
- 1988-04-05 IL IL85986A patent/IL85986A/xx not_active IP Right Cessation
- 1988-04-19 ZA ZA882731A patent/ZA882731B/xx unknown
- 1988-05-04 NO NO881944A patent/NO173734C/no not_active IP Right Cessation
- 1988-05-10 ES ES198888401140T patent/ES2034300T3/es not_active Expired - Lifetime
- 1988-05-10 EP EP88401140A patent/EP0292362B1/fr not_active Expired - Lifetime
- 1988-05-10 AT AT88401140T patent/ATE79867T1/de not_active IP Right Cessation
- 1988-05-10 DE DE8888401140T patent/DE3873983T2/de not_active Expired - Fee Related
- 1988-05-16 NZ NZ224640A patent/NZ224640A/xx unknown
- 1988-05-16 PT PT87494A patent/PT87494B/pt not_active IP Right Cessation
- 1988-05-17 AU AU16341/88A patent/AU610590B2/en not_active Ceased
- 1988-05-17 DK DK268188A patent/DK168435B1/da not_active IP Right Cessation
- 1988-05-17 IE IE147988A patent/IE63144B1/en not_active IP Right Cessation
- 1988-05-17 CA CA000567006A patent/CA1338353C/fr not_active Expired - Fee Related
- 1988-05-17 FI FI882314A patent/FI91962C/fi not_active IP Right Cessation
- 1988-05-18 CN CN88102947A patent/CN1023008C/zh not_active Expired - Fee Related
- 1988-05-18 KR KR1019880005781A patent/KR960007079B1/ko not_active Expired - Fee Related
- 1988-05-18 JP JP63121691A patent/JPH0674247B2/ja not_active Expired - Lifetime
-
1992
- 1992-03-19 US US07/854,744 patent/US5977379A/en not_active Expired - Fee Related
- 1992-11-18 GR GR920402631T patent/GR3006273T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR3084668A1 (fr) | Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol | |
| EP0008548B1 (fr) | Nouveau procédé de préparation du disulfure de benzothiazyle | |
| CA1338353C (fr) | Procede de preparation d'imides halogenes | |
| EP0238374B1 (fr) | Procédé de préparation d'imides halogénés, compositions les contenant et leur application comme agents d'ignifugation | |
| EP0398783B1 (fr) | Procédé de synthèse de cyanures d'acyle | |
| EP0398782B1 (fr) | Procédé de préparation de cyanures d'acyles en milieu anhydre | |
| EP0211775A1 (fr) | Procédé de nitration de composés phénoliques | |
| EP0069001A1 (fr) | Procédé de préparation de dérivés de la tétrahydro-5,6,7,7a 4H-thiéno (3,2-C) pyridinone-2 | |
| FR2503141A1 (fr) | Procede de fabrication de bis(ether-acide phtalique) aromatique ou de bis(ether-anhydride) aromatique par reaction d'echange avec l'acide ou l'anhydride phtalique | |
| EP0047205A2 (fr) | Procédé de préparation d'alpha-benzamido alpha'-halogéno dianthrimides-1,1', nouveaux alpha-benzamido halogéno-5' ou -8' dianthrimides-1,1' et leur application comme intermédiaires de colorants de cuve | |
| EP0326455A1 (fr) | Procédé de préparation de chloranil | |
| EP0193475A1 (fr) | Procédé d'acétoacétylation de composés aromatiques | |
| CH627148A5 (https=) | ||
| JPH04360878A (ja) | 芳香族トリアゾール類の製造方法 | |
| FR2543948A1 (fr) | Procede de preparation de l'acide 1-naphtol-4-sulfonique | |
| CH301959A (fr) | Procédé de préparation du chlorhydrate du chlorure de thiamine. | |
| BE505572A (https=) | ||
| BE477562A (https=) | ||
| BE824608A (fr) | Procede pour la preparation de 7-oxo-7h-dibenzo(d,e,h)-quinolin-2-ol | |
| BE823745A (fr) | Procede ameliore pour la preparation de penicillines substituees en position 6 par un groupe alcoxy | |
| EP0347283A1 (fr) | Procédé de préparation de dichloro-2,6 amino-4 phénol | |
| CH654570A5 (fr) | Procede de preparation de 3,3'- ou 3,4'-diaminobenzophenone. | |
| BE544296A (https=) | ||
| JPH09512811A (ja) | ペルオキシ酸の製造方法 | |
| BE534731A (https=) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |