CS233475B1 - Production method of potassium or sodium salt of phthalimide - Google Patents
Production method of potassium or sodium salt of phthalimide Download PDFInfo
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- CS233475B1 CS233475B1 CS951682A CS951682A CS233475B1 CS 233475 B1 CS233475 B1 CS 233475B1 CS 951682 A CS951682 A CS 951682A CS 951682 A CS951682 A CS 951682A CS 233475 B1 CS233475 B1 CS 233475B1
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- Prior art keywords
- potassium
- phthalimide
- sodium
- alcohol
- sodium salt
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000011591 potassium Substances 0.000 title claims abstract description 33
- 229910052700 potassium Inorganic materials 0.000 title claims abstract description 30
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title claims description 29
- 159000000000 sodium salts Chemical class 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910000567 Amalgam (chemistry) Inorganic materials 0.000 claims description 4
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 4
- 229910001023 sodium amalgam Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 abstract description 9
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract description 7
- 229910052708 sodium Inorganic materials 0.000 abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 6
- DEGPIRUPAKWDBU-UHFFFAOYSA-N isoindole-1,3-dione;sodium Chemical compound [Na].C1=CC=C2C(=O)NC(=O)C2=C1 DEGPIRUPAKWDBU-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 239000003973 paint Substances 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 229910000497 Amalgam Inorganic materials 0.000 abstract 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 abstract 1
- 238000006053 organic reaction Methods 0.000 abstract 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 N-substituted phthalimides Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MWGKAIKWBCTKHF-UHFFFAOYSA-N C1(=O)OCC2=CC=CC=C12.[Na] Chemical compound C1(=O)OCC2=CC=CC=C12.[Na] MWGKAIKWBCTKHF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Indole Compounds (AREA)
Abstract
Vynález rieši spfisob výroby draselnej alebo sodnej soli ftalimidu, chemického N"Me kde Me Na priamou reakciou volného alebo v organickom rozpúšťadle suspendovaného ftalimidu s draselnou alebo sodnou soTou alkoholu C. až G., získanou rozkladom draselnej alebo sodnej amalgámy v přebytku alkoholu. Využitie draselnej alebo sodnej soli ftalimidu ako medziproduktu pre dalšie spraeovanie je vo farmaceutickom priemysle, pri výrobě organických farieb a při výrobě gumárenských a plastikářských chemikálií, napr. při výrobě N-cyklohexyltioftalimidu.The invention relates to a method of producing potassium or sodium phthalimide, chemical N 'Me where Me Na a direct free or organic reaction potassium phthalimide suspended solvent or sodium alcohol C to G., obtained by potassium decomposition or sodium amalgams in excess alcohol. Use of potassium or sodium salt phthalimide intermediate processing is in the pharmaceutical industry in the production of organic paints and in production rubber and plastic chemicals e.g. in the manufacture of N-cyclohexylthiophthalimide.
Description
Vynález a· týk· spfisobu výroby draselnej alebo sodnej soli ftalimidu chemického vzorcaThe invention relates to a process for the production of the potassium or sodium salt of a phthalimide of the chemical formula
kde Me+ .« K+, Na+ získaného priamou reakciou ftalimidu a draselnej alebo sodnej soli alkoholu pripravenej rozkladom draselnej alebo sodnej amalgámy ze přítomnosti příslušného bezvodého alkoholu.wherein Me + , K + , Na + is obtained by direct reaction of phthalimide and a potassium or sodium salt of an alcohol prepared by decomposing a potassium or sodium amalgam in the presence of the corresponding anhydrous alcohol.
Draselná alebo sodná soT ftalimidu je dfiležitá surovina pri výrobě N-substituovaných ftalimidov využívaných v oblasti spracovanie kaučukových zmesi, vo farmaceutickom priemyele a pri výrobě organických farieb a pigmentov.The potassium or sodium salt of phthalimide is an important raw material in the production of N-substituted phthalimides used in the processing of rubber mixtures, in the pharmaceutical industry and in the production of organic paints and pigments.
Zo známých spfisobov přípravy draselnej alebo sodnej soli ftalimidu možno uviesť spfisoby, v ktorých dochádža k priamej reakcii voTného, resp. roztoku ftalimidu s alkoholátmi sodíka alebo draslík·. Uvedená alkoholáty sú připravená rozpuštěním hydroxidu draselného alebo sodného v príslušnoa alkohole.Among the known methods for preparing the potassium or sodium salt of phthalimide, mention may be made of methods in which a direct or free reaction of the phthalimide takes place. Phthalimide solution with sodium or potassium alcoholates. Said alcoholates are prepared by dissolving potassium or sodium hydroxide in an appropriate alcohol.
Iný spfisob přípravy ftalimidu draselného vychádza z priamej dehydratácie amónnej soli kyseliny ftalovej.Another method of preparing potassium phthalimide is based on direct dehydration of the ammonium salt of phthalic acid.
Literatúre popisuje přípravu ftalimidu draselného ako medziproduktu pri príprave prokalnamidhydrochloridu alebo pri príprave 1,4-diaminobutánu. Uvedenými metodami přípravy .sodnej alebo draselnej soli ftalimidu sa nedajú připravit produkty s vyhovujúcimi kvalitatívnymi parametrami soli, resp. majú význam pre laboratórnu přípravu. Z iných známých spfisobov přípravy draselnej alebo sodnej soli možno uviesť spfisob podlá AO 200 126 /111/1980/. alebo spfisob přípravy ftalimidu draselného priamou reakciou suchého ftalimidu s bezvodým butanolátom draselným.The literature describes the preparation of potassium phthalimide as an intermediate in the preparation of procalnamide hydrochloride or in the preparation of 1,4-diaminobutane. By the above mentioned methods of preparation of the sodium or potassium salt of phthalimide, it is not possible to prepare products with satisfactory quality parameters of the salt or the salt. are relevant for laboratory preparation. Other known methods for the preparation of potassium or sodium salt include those disclosed in AO 200 126 (111) (1980). or a process for preparing potassium phthalimide by direct reaction of dry phthalimide with anhydrous potassium butanolate.
Nevýhodou uvedených spfisobov přípravy draselnej alebo sodnej soli ftalimidu je, že poskytujú nižšie výtažky v dfisledku přítomnosti i nepatrného množstva vody v roztokoch alkoholátov, ktorá spfisobuje hydrolýzu draselnej alebo sodnej soli ftalimidu, pričom vzniká jú deriváty kyseliny ftalovej. lnou nevýhodou sú technologické problémy súvisiace s přípravou bezvodých alkoholátov.A disadvantage of these methods of preparing the potassium or sodium salt of phthalimide is that they provide lower yields due to the presence of even a small amount of water in alcoholate solutions which cause hydrolysis of the potassium or sodium salt of phthalimide to form phthalic acid derivatives. Another disadvantage is the technological problems associated with the preparation of anhydrous alcoholates.
Podstatou spfisobu výroby draselnej alebo sodnej soli ftalimidu priamou reakciou draselné j alebo sodnej soli alkoholu s ftalimidom je, že draselná alebo sodná sol alkoholu a alkohole o koncentrácii 1 až 25 8 hmot. sa získá rozkladom draselnej alebo sodnej amalgámy V přebytku alkoholu s 1 až 4 atómami uhlíka. Takto získaný roztok draselnej alebo , sodnej soli alkoholu sa priamo použije na reakciu s volným, alebo v organickom rozpúštadle suspendovaným ftalimidom tak, aby lolárny poměr draselnej alebo sodnej soli alkoholu k předloženému ftalimidu bol 1 až 1,5 ku 1 a koncentrácia suspendovaného ftalimidu v organickom rozpúštadle, s výhodou v alkohole identickom s alkoholom použitým na přípravu dreselnej alebo sodnej soli alkoholu v alkohole, 5 až 25 8 hmot. Draselná alebo sodná sol alkoholu v alkohole reaguje s ftalimidom pri 0 °C až teplota bodu varu zmesi, pričom reakčný čas je 5 až 180 minút. Reakciou získaná draselná alebo sodná soT ftalimidu sa z reakčnej zmesi oddělí filtráéiou.The essence of the process for producing the potassium or sodium salt of phthalimide by direct reaction of the potassium or sodium salt of the alcohol with phthalimide is that the potassium or sodium salt of the alcohol and alcohol at a concentration of 1 to 25% by weight. is obtained by decomposition of potassium or sodium amalgam in an excess of C 1 -C 4 alcohol. The potassium or sodium salt solution thus obtained is used directly for the reaction with the free or organic solvent suspended with phthalimide such that the molar ratio of potassium or sodium salt of the present phthalimide is 1-1.5 to 1 and the concentration of suspended phthalimide in the organic % solvent, preferably in an alcohol identical to the alcohol used to prepare the alcoholic or alcoholic salt or the sodium salt of the alcohol; The potassium or sodium alcohol in alcohol is reacted with phthalimide at 0 ° C to the boiling point of the mixture, the reaction time being 5 to 180 minutes. The potassium or sodium salt of phthalimide obtained by the reaction is separated from the reaction mixture by filtration.
Spfisob výroby draselnej alebo sodnej soli ftalimidu podTa predmetu vynálezu má oproti doposial známým postupom přípravy draselnej alebo sodnej soli mnohé výhody. Na přípravu draselnej alebo sodnej soli alkoholu nie je potřebné použit hydroxid draselný, resp. sodný, ale>využije sa priamo surovina, ktorá sa používá k výrobě hydroxidov. Tým uvedený spfisob odstraňuje manipuláciu s hydroxidmi a pri príprave příslušného alkoholátu odstraňuje Sašovo i energeticky náročný spfisob dehydratácie roztokov alkoholátov. lnou výhodou v uvedenom postupe je fakt, že pre přípravu alkoholátov možno použiť akýkoTvek alkohol, s výhodou použitia alifatických Oj až alkoholov. Produkt - draselná alebo sodná soT ftalimidu - získaný týmto spfisobom je vysokej čistoty s obsahom zékladnej látky min.The process of producing the potassium or sodium salt of phthalimide according to the present invention has many advantages over the prior art processes for the preparation of the potassium or sodium salt. It is not necessary to use potassium hydroxide or sodium hydroxide to prepare the potassium or sodium salt of the alcohol. sodium, but the raw material used to produce the hydroxides is used directly. This method eliminates the manipulation of hydroxides and, in the preparation of the corresponding alcoholate, removes both the energy-intensive method of dehydration of the alcoholate solutions. Another advantage of the process is that any alcohol can be used to prepare alcoholates, preferably aliphatic O to alcohols. The product - potassium or sodium phthalimide - obtained by this method is of high purity with a basic substance content of min.
% Λαα./ · uvedený spfisob možno technologicky realizovat bez zvláštnych požiadaviek na Speciálně technická a technologické zariadenia. Přípravu draselnej alebo sodnej soli alkoholu možno uvedeným spfisobom realizovat v existujúcich zariadeniach pre elektrolýzu halogenidov draslíka alebo sodíka./ · The said method can be implemented technologically without special requirements for special technical and technological equipment. The preparation of the potassium or sodium salt of the alcohol may be carried out in existing facilities for the electrolysis of potassium or sodium halides.
iand
Vynález ilustruji} nasledujúcje příklady.The invention is illustrated by the following examples.
Příklad 1Example 1
Roztok metanolátu sodného v metanole o koncentrácii metanolátu 6,5 % hmot, získaného rozkladem sodnej amalgámy, sa přidal do miešanej suspenzie ftalimidu v metanole pri 55 až 60 °C a po přidaní za intentívneho miešania sa reakčná zmes nechala doreagovat při teplote 55 °C po dobu 50 min. Ftalimid sodný sa vylučoval z reakčnej zmesi už pri přidávání roztoku metanolátu sodného do suspenzie ftalimidu v metanolu. Fo ochladení reakčnej zmesi na laboratórnu teplotu sa ftalimid sodný oddělil filtráciou, na filtr! premyl čistým metanolom a vysušil. Získaný produkt obsahoval 98,2 % hmot. ftalinidu sodného.A 6.5% by weight solution of sodium methanolate in methanol, obtained by decomposition of sodium amalgam, was added to a stirred suspension of phthalimide in methanol at 55-60 ° C and after addition with vigorous stirring the reaction mixture was allowed to react at 55 ° C after 50 min. Sodium phthalimide was already precipitated from the reaction mixture when the sodium methoxide solution was added to a suspension of phthalimide in methanol. After cooling the reaction mixture to room temperature, sodium phthalimide was collected by filtration, to a filter. washed with pure methanol and dried. The product obtained contained 98.2 wt. sodium phthalide.
Příklad 2Example 2
Roztok butanolátu draselného v butanole o koncentrácii butanolátu 12,2 % hmot. získaného rozkladem draselnej amalgámy v přítomnosti bezvodého n-butanolu, sa přidal za miešania do roztoku ftalimidu v n-butanole ó koncentrácii 10 % hmot. ftalimidu při teplote tefluxu n-butanolu. Už počas přidáváni® sa z reakčnej zmesi vylučovala draselná sol ftalimidu. Po přidaní celého množstva roztoku butanolátu draselného v n-butanole do roztoku ftalimidu v n-butanole sa reakčná zmes za intenzívneho miešania udržiavala při teplote refluxu cca 40 min. Potom sa schladila na teplotu 20 až 25 °C a vylúčená draselná sol ftalimidu sa oddělila filtráciou. Na filtr! sa premyla čistým n-butanolom a vysušila. Získal sa produkt s obsahom ftalimidu draselného 99,1 % hmot.A solution of potassium butanolate in butanol at a butanolate concentration of 12.2% by weight. obtained by decomposition of potassium amalgam in the presence of anhydrous n-butanol, was added with stirring to a solution of phthalimide in n-butanol at a concentration of 10% by weight. of phthalimide at the teflux temperature of n-butanol. Already during the addition, the phthalimide potassium salt precipitated from the reaction mixture. After the entire amount of a solution of potassium butanolate in n-butanol was added to the solution of phthalimide in n-butanol, the reaction mixture was maintained at reflux temperature for about 40 minutes with vigorous stirring. It was then cooled to 20-25 ° C and the precipitated phthalimide potassium salt was collected by filtration. On the filter! was washed with pure n-butanol and dried. A product with a potassium phthalimide content of 99.1% by weight was obtained.
Oblasť využitia vynálezu je hlavně pri priemyselnej výrobě draselnej alebo sodnej soli ftalimidu ako medzlpro&iktu pře áalšie spracovanie vo farmaceutickom priemysle, pri výrobě organických farbív a pri výrobě gumárenských a plastikářských chemikálií.The field of application of the invention is mainly in the industrial production of potassium or sodium salt of phthalimide as intermediate process further processing in the pharmaceutical industry, in the production of organic dyes and in the manufacture of rubber and plastics chemicals.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS951682A CS233475B1 (en) | 1982-12-22 | 1982-12-22 | Production method of potassium or sodium salt of phthalimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS951682A CS233475B1 (en) | 1982-12-22 | 1982-12-22 | Production method of potassium or sodium salt of phthalimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS233475B1 true CS233475B1 (en) | 1985-03-14 |
Family
ID=5445142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS951682A CS233475B1 (en) | 1982-12-22 | 1982-12-22 | Production method of potassium or sodium salt of phthalimide |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS233475B1 (en) |
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1982
- 1982-12-22 CS CS951682A patent/CS233475B1/en unknown
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