CS224818B1 - Method of hexaisoindoline iron complex preparation - Google Patents
Method of hexaisoindoline iron complex preparation Download PDFInfo
- Publication number
- CS224818B1 CS224818B1 CS206882A CS206882A CS224818B1 CS 224818 B1 CS224818 B1 CS 224818B1 CS 206882 A CS206882 A CS 206882A CS 206882 A CS206882 A CS 206882A CS 224818 B1 CS224818 B1 CS 224818B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- parts
- hexaisoindoline
- weight
- ammonium
- complex
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 7
- 238000000034 method Methods 0.000 title description 5
- GGTVTZARMWZNJP-UHFFFAOYSA-N [Fe].C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12 Chemical compound [Fe].C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12.C1NCC2=CC=CC=C12 GGTVTZARMWZNJP-UHFFFAOYSA-N 0.000 title description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 4
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 4
- 239000011609 ammonium molybdate Substances 0.000 claims description 4
- 229940010552 ammonium molybdate Drugs 0.000 claims description 4
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 3
- ZLXPLDLEBORRPT-UHFFFAOYSA-M [NH4+].[Fe+].[O-]S([O-])(=O)=O Chemical compound [NH4+].[Fe+].[O-]S([O-])(=O)=O ZLXPLDLEBORRPT-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000004698 iron complex Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- FPFSGDXIBUDDKZ-UHFFFAOYSA-N 3-decyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCCCCC1=C(O)C(=O)CC1 FPFSGDXIBUDDKZ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005569 Iron sulphate Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- XGGLLRJQCZROSE-UHFFFAOYSA-K ammonium iron(iii) sulfate Chemical compound [NH4+].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGGLLRJQCZROSE-UHFFFAOYSA-K 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- CSGLCWIAEFNDIL-UHFFFAOYSA-O azanium;urea;nitrate Chemical compound [NH4+].NC(N)=O.[O-][N+]([O-])=O CSGLCWIAEFNDIL-UHFFFAOYSA-O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- -1 diiminophthalimide Chemical compound 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
Vynález se týká způsobu přípravy hexaisoindolinového komplexu železa reakcí síranu železitoamnnného, diiminoftalimidu, dusičnanu amonného a močoviny za přítomnosti oxidu molybdenového nebo molybdenanu amonného.The present invention relates to a process for the preparation of an iron hexaisoindoline complex by reaction of ammonium sulfate, diiminophthalimide, ammonium nitrate and urea in the presence of molybdenum oxide or ammonium molybdate.
Hexaisoindolinový komplex Pe(III), jehož příprava je předmětem tohoto vynálezu, má sumární'vzorec C^gH^N-^OgFe a podle literatury oc,jedná o Pe(III)-bis-(ansa-dioxy-diamino-isoindolino^p-dioxy-diamino-diaza-cyklo-tetraisoindolin (Kaufmann, Pleiter: Pet te, Seifen, Anstrichmittel 66, 819 (1964))· Technický význam komplexu spočívá v jeho vynikající katalytické účinnosti. Hexaisoindolinový komplex Pe(III) byl aplikován jako sikativum pro vysychavé oleje, jako urychlovač vytvrzování nenasycených polyesterů, při polymerací akrylonitrilu, styrenu, vinylacetatu atd* Přípravu této sloučeniny je možno provádět postupem spočívajícím v reakci ftalanhydridu a močoviny se síranem železnatým (Kaufmann, Pleiter - viz výše), avšak požadovaná sloučenina vzniká jen v nízkém výtěžku (5 až 10 % teorie) a její izolace z reakčního produktu je proto obtížná. Zvýšení výtěžku na 25 až 40 % teorie lze dosáhnout reakcí soli trojmocného železa, anhydridu nebo dinitrilu kyseliny ftalové, močoviny a dusičnanu amonného při teplotě 160 až 210 °CThe hexaisoindoline complex Pe (III), the preparation of which is the object of the present invention, has the overall formula C 18 H 16 N 2 O 6 Fe and according to the literature it is Pe (III) -bis- (anasadioxy-diamino-isoindolino). -dioxy-diamino-diaza-cyclo-tetraisoindoline (Kaufmann, Pleiter: Pet te, Seifen, Anstrichmittel 66, 819 (1964)) · The technical significance of the complex lies in its excellent catalytic activity.Hexaisoindoline complex Pe (III) has been applied as a desiccant for drying oils, such as the curing accelerator of unsaturated polyesters, in the polymerization of acrylonitrile, styrene, vinyl acetate, etc. * The preparation of this compound can be carried out by the reaction of phthalic anhydride and urea with ferrous sulfate (Kaufmann, Pleiter - see above). yield (5-10% of theory) and its isolation from the reaction product is therefore difficult. Iron, anhydride or phthalic dinitrile, urea ammonium nitrate solution at 160 to 210 ° C
Výzkumem bylo nyní zjištěno, že hexaisoindolinový komplex Pe(III) lze připravit ve výtěžku cca 95 % teorie reakcí 2,6 ažResearch has now shown that the hexaisoindoline complex Pe (III) can be prepared in a yield of about 95% of reaction theory 2.6 to
3,2 dílu bezvodého síranu železeatoamonného, 8,7 až 18 dílů diiminoftalimidu, 0,5 až 1,5 dílu dusičnanu amonného, 2 až 7 dílů močoviny a 0,05 až 0,3 dílu oxidu molybdenového nebo molybdenanu amonného v prostředí organického rozpouštědla při teplotě 100 až 180 °C, přičemž uvedené díly znamenají díly hmotnostní.3.2 parts of anhydrous iron (III) ammonium sulphate, 8.7 to 18 parts of diiminophthalimide, 0.5 to 1.5 parts of ammonium nitrate, 2 to 7 parts of urea and 0.05 to 0.3 parts of molybdenum or ammonium molybdate in an organic solvent medium at a temperature of 100 to 180 ° C, said parts being parts by weight.
Způsob přípravy hexaisoindolinového komplexu Pe(IIl) podle vynálezu se zásadně liší od dřívějších postupů v tom, že jakoThe process for the preparation of the hexaisoindoline complex Pe (IIl) according to the invention is fundamentally different from the prior art in that as
224 818 výchozí suroviny se nepoužívá anhydridu nebo dinitrilu kyseliny ftalové, ale diiminoftalimidů. Dosáhne se tak podstatně vyššího výtěžku požadované sloučeniny, a zároveň, se reakce může provádět při nižší teplotě než tomu bylo dosud. Oproti dosavadním postupům se rovněž zkrátí reakční doba.224 818 of the starting material is not phthalic anhydride or dinitrile but diiminophthalimides. Thus, a substantially higher yield of the desired compound is achieved, and at the same time, the reaction can be carried out at a lower temperature than hitherto. The reaction time is also shorter than in the prior art.
Příprava komplexu se podle vynálezu provádí tak, že se síran železitoamonný, diiminoftalimid, dusičnan amonný, močovina a oxid molybdenový nebo molyhdenan amonný smísí (zhomogenizují) v organickém rozpouštědle, reakční směs se vyhřeje na 100 až 180 °C, s výhodou na 120 až 160 °C, a do směsi se začne vhánět vzduch nebo kyslík. Pro reakci je možno použít pouze síran železitoamonný dokonale zbavený krystalové vody·The preparation of the complex according to the invention is carried out by mixing (homogenizing) in an organic solvent, ferric ammonium sulfate, diiminophthalimide, ammonium nitrate, urea and molybdenum trioxide or ammonium molybdate, the reaction mixture being heated to 100-180 ° C, preferably 120-160 ° C. ° C, and air or oxygen is blown into the mixture. Only ferric ammonium sulphate, completely free of crystal water, can be used for the reaction.
Reakce se provádí v organickém rozpouštědle, např, v dichlor benzenu, trichlorbenzenu, nitrobenzenu, 1-chlornaftalenu atd. Vzduch nebo kyslík se do reakční směsi vhánějí s výhodou přes porézní přepážku.The reaction is carried out in an organic solvent, e.g. dichlorobenzene, trichlorobenzene, nitrobenzene, 1-chloronaphthalene, etc. Air or oxygen are preferably introduced into the reaction mixture through a porous septum.
Způsob izolace hexaisoindolinového komplexu železa se musí provádět s ohledem na druh použitého organického rozpouštědla. Obvykle se však v reakční směsi nejprve odfiltrují nerozpuštěné sloučeniny a z filtrátu se rozpouštědlo oddestiluje např. za sníženého tlaku. Z odparku, tj. ze surového produktu, lze komplex vyextrahovat např. chloridem uhličitým, chloroformem aj.The method for the isolation of the iron hexaisoindoline complex must be carried out with respect to the type of organic solvent used. Usually, however, undissolved compounds are first filtered off in the reaction mixture and the solvent is distilled off, for example, under reduced pressure. From the residue, ie from the crude product, the complex can be extracted, for example, with carbon tetrachloride, chloroform and the like.
Způsob přípravy hexaisoindolinového komplexu Pe(III) je ukázán v příkladu, ve kterém díly značí díly hmotnostní*The process for the preparation of the hexaisoindoline complex Pe (III) is shown in the example in which the parts denote parts by weight.
Příklad provedeníExemplary embodiment
Do 250 dílů nitrobenzenu bylo postupně vneseno 18 dílů diiminoftalimidu, 3,2 dílu bezvodého síranu železíUtoamonného, 6,5 dílu močoviny, 1,0 dílu dusičnanu amonného a 0,2 dílu oxidu molybdenového. Do reakční směsi byl vháněn vzduch a směs byla vyhřátá na 160 °C. Reakce byla prováděna po dobu 1,5 h^. Po ochlazení na 25 °C byla směs zfiltrována a z filtrátu bylo rozpouštědlo oddestilováno za tlaku 2,6 kPa. Odparek byl vyextrahován chloroformem. Po odpaření chloroformu bylo získáno 12,2 g Pe(III) -bis-(ansa-dioxy-diamino-isoindolino(-))-dioxy-diamino-diaza-cyklo-tetraisoindolinu, což je 96 % teorie (počítáno na síran želez^a*toamonný)·18 parts of diiminophthalimide, 3.2 parts of anhydrous ammonium sulfate, 6.5 parts of urea, 1.0 parts of ammonium nitrate and 0.2 parts of molybdenum oxide were gradually introduced into 250 parts of nitrobenzene. Air was blown into the reaction mixture and heated to 160 ° C. The reaction was carried out for 1.5 h. After cooling to 25 ° C, the mixture was filtered and from the filtrate the solvent was distilled off at 20 mm Hg. The residue was extracted with chloroform. Evaporation of chloroform gave 12.2 g of Pe (III) -bis- (anasadioxy-diamino-isoindolino (-)) - dioxy-diamino-diaza-cyclo-tetraisoindoline, 96% of theory (calculated on iron sulphate). and * toammonous) ·
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS206882A CS224818B1 (en) | 1982-03-25 | 1982-03-25 | Method of hexaisoindoline iron complex preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS206882A CS224818B1 (en) | 1982-03-25 | 1982-03-25 | Method of hexaisoindoline iron complex preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224818B1 true CS224818B1 (en) | 1984-01-16 |
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ID=5356697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS206882A CS224818B1 (en) | 1982-03-25 | 1982-03-25 | Method of hexaisoindoline iron complex preparation |
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| Country | Link |
|---|---|
| CS (1) | CS224818B1 (en) |
-
1982
- 1982-03-25 CS CS206882A patent/CS224818B1/en unknown
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