CS239398B1 - Production method of potashium phthalimide - Google Patents
Production method of potashium phthalimide Download PDFInfo
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- CS239398B1 CS239398B1 CS846431A CS643184A CS239398B1 CS 239398 B1 CS239398 B1 CS 239398B1 CS 846431 A CS846431 A CS 846431A CS 643184 A CS643184 A CS 643184A CS 239398 B1 CS239398 B1 CS 239398B1
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- Prior art keywords
- phthalimide
- potassium
- solvent
- polar solvent
- dissolved
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 31
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 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 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- IQEXVQXICRQRFK-UHFFFAOYSA-N C(CCCC)OCCCCC.[K] Chemical compound C(CCCC)OCCCCC.[K] IQEXVQXICRQRFK-UHFFFAOYSA-N 0.000 description 1
- -1 N-substituted thiophthalimides Chemical class 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LBEJUYDXKLDFRL-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].[K].C1=CC=C2C(=O)NC(=O)C2=C1 LBEJUYDXKLDFRL-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229960003253 procainamide hydrochloride Drugs 0.000 description 1
- ABTXGJFUQRCPNH-UHFFFAOYSA-N procainamide hydrochloride Chemical compound [H+].[Cl-].CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 ABTXGJFUQRCPNH-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Indole Compounds (AREA)
Abstract
Predmetom vynálezu je sposob výroby ftalimidu draselného reakciou rozpuštěného ftalimidu v polárnom rozpúšťadle pri teplote blízkej teplote varu rozpúštadla s hydroxidom draselným, ktorý je rozpuštěný v polárnom rozpúšťadle při 60 °C, pričom sa reakčná zmes udržuje pri vare počas 5 až 30 minút a ftalimid draselný se izoluje.The subject of the invention is a method of production potassium phthalimide by dissolving the reaction phthalimide in a polar solvent at at a temperature close to the boiling point of the solvent s potassium hydroxide, which is dissolved in a polar solvent at 60 ° C the reaction mixture is kept at boiling during 5 to 30 minutes and potassium phthalimide recovered.
Description
(54) Spdsob výroby ftalimidu draselného(54) Method of production of potassium phthalimide
Predmetom vynálezu je sposob výroby ftalimidu draselného reakciou rozpuštěného ftalimidu v polárnom rozpúšťadle pri teplote blízkej teplote varu rozpúštadla s hydroxidom draselným, ktorý je rozpuštěný v polárnom rozpúšťadle při 60 °C, pričom sa reakčná zmes udržuje pri vare počas 5 až 30 minút a ftalimid draselný se izoluje.SUMMARY OF THE INVENTION The present invention provides a process for producing potassium phthalimide by reacting dissolved phthalimide in a polar solvent at a temperature near the boiling point of the solvent with potassium hydroxide dissolved in a polar solvent at 60 ° C, maintaining the reaction mixture boiling for 5 to 30 minutes. recovered.
239396239396
Jednou zo základných surovin pri různých organických syntézách je ítalimid draselný. Například sa používá ako medziprodukt pri výrobě N-substituovaných tioftalimidov, ktoré sa využívajú na retardéri navulkanizácie.One of the basic raw materials in various organic syntheses is potassium thalimide. For example, it is used as an intermediate in the production of N-substituted thiophthalimides which are used in the vulcanization retarder.
Ftalimid draselný sa připravuje působením hydroxidu draselného na ftalimid, alebo podlá Gabrielovej reakcie, Gabrielovu reakciu možno použiť aj pri príprave 1,4-diaminobutánu, kde1 sa ítalimid draselný získá ako medziprodukt.The potassium phthalimide is prepared by treating the phthalimide with potassium hydroxide, or according to the Gabriel reaction. The Gabriel reaction can also be used in the preparation of 1,4-diaminobutane, where 1 is obtained by potassium thalimide as an intermediate.
Ftalimid draselný je možno získať aj ako medziprodukt pri výrobě prokaínamidhydrochloridu, alebo ako kondenzačný produkt primárného· aminu s anhydridom kyseliny ftalovej.Potassium phthalimide can also be obtained as an intermediate in the production of procainamide hydrochloride, or as a condensation product of a primary amine with phthalic anhydride.
Okrem už spomínaných sposobov přípravy uvádza Landsberg přípravu sódnej a draselnej soli ftalimidu působením etanolátu sodného alebo draselného na ftalimid. Podla Hammicka dobré výtažky ftalimidu sodného a draselného sa dosiahli za použitia amyloxidu sodného alebo draselného v arnylalkohole.In addition to the aforementioned methods of preparation, Landsberg discloses the preparation of the sodium and potassium salts of phthalimide by the action of sodium or potassium ethanolate on phthalimide. According to Hammick, good yields of sodium and potassium phthalimide were obtained using sodium or potassium amyloxide in arnyl alcohol.
Uvedené metody přípravy nedávajú uspokojivé výtažky. Použitie etanolických roztokov hydroxidov uvedených kovov vedie v každom případe k používaniu velkých objemov rozpúšťadiel, čo je značné energeticky náročné pri ich regenerácii.Said methods of preparation do not give satisfactory yields. The use of ethanolic hydroxide solutions of said metals leads in each case to the use of large volumes of solvents, which is a considerable energy-intensive process for their regeneration.
Teraz bolo zistené, že uvedené nevýhody možno odstrániť podlá předloženého vynálezu, ktorého podstata je v· tom, že sa ftalimid rozpustí za horúca v polárnom rozpúšťadle, ako například v metanole, etanole, propanole, izo-butanole, v amylalkohole, pričom teplota roztoku sa udržuje v blízkosti teploty varu rozpúšťadla.It has now been found that these disadvantages can be overcome according to the present invention, which consists in dissolving the phthalimide hot in a polar solvent such as methanol, ethanol, propanol, isobutanol, amylalcohol, the temperature of the solution being maintains near the boiling point of the solvent.
Do takto připraveného roztoku ftalimidu sa za horúca přidává roztok hydroxidu draselného, ktorý je rozpuštěný v polárnom rozpúšťadle pri teplote 60 °C. Po premiešaní oboch roztokov pri teplote blízkej teplote varu rozpúšťadla sa zmes udržuje počas 5 až 30 minút a po ochladení sa vyzrážaný ftalimid draselný izoluje, premyje malým množstvom, čistým rozpúšťadlom a vysuší sa. Použité rozpúšťadlo sa čistí regeneráciou.Potassium hydroxide solution, which is dissolved in a polar solvent at 60 ° C, is added hot to the phthalimide solution thus prepared. After mixing the two solutions at a temperature close to the boiling point of the solvent, the mixture is maintained for 5 to 30 minutes and after cooling, the precipitated potassium phthalimide is isolated, washed with a small amount of pure solvent and dried. The solvent used is purified by regeneration.
Predmet vynálezu dokumentujú nasledujúce příklady prevedenia.The following examples illustrate the invention.
Příklad 1Example 1
Do 500 ml metanolu sa nadávkovalo za miešania 8 g ftalimidu, postupné sa roztok z ftalimidu vyhirial na 50 °C a přidalo sa 250 ml metanolu obsahujúceho 4,5 g hydroxidu draselného. Teplota zmesi sa vyhnala na 60 °C. Po 20 minutách sa zmes ochladila na teplotu 25 °C a ftalimid draselný sa izoloval filtráciou. Po premytí metanolom a vysušení sa získalo 8,3 g ftalimidu draselného, čo· představuje 81,0 % výťažok. Obsah draslika vo ftaliniide draselnom bol 22,7 a dusíka 7,44 %.8 g of phthalimide were metered into 500 ml of methanol with stirring, gradually the phthalimide solution was heated to 50 ° C and 250 ml of methanol containing 4.5 g of potassium hydroxide was added. The temperature of the mixture was forced to 60 ° C. After 20 minutes, the mixture was cooled to 25 ° C and potassium phthalimide was isolated by filtration. After washing with methanol and drying, 8.3 g of potassium phthalimide was obtained, which represents an 81.0% yield. The potassium content of potassium phthaliniide was 22.7 and nitrogen was 7.44%.
Příklad 2Example 2
V pokuse sa postupovalo obdobné ako je uvedené v příklade 1, ako rozpúšťadlo sa použilo 270 ml etanolu pre rozpustenie 8 g ftalimidu a 120 ml etanolu pre KOH. Po izolácii sa získalo 8,95 g ftalimidu draselného, čo představuje výťažok 89,0 %. Obsah draslíka 21,5, dusíka 7,16 %.The experiment was carried out analogously to Example 1, using 270 ml of ethanol as solvent to dissolve 8 g of phthalimide and 120 ml of ethanol for KOH. After isolation, 8.95 g of potassium phthalimide was obtained, representing a yield of 89.0%. Potassium content 21.5, nitrogen 7.16%.
Příklad 3Example 3
Návažky ftalimidu a KOH boli zhodné ako v příklade 1. Na rozpustenie ftalimidu sa použilo 250 ml Izopropanolu a pre KOH 150 ml toho istého rozpúšťadla. Laboratórny postup přípravy ftalimidu draselného bol zhodný s príkladom 1. Po vysušení sa získalo 9,9 g produktu, čo představuje 97 % výťažok.The phthalimide and KOH weights were the same as in Example 1. 250 ml of isopropanol was used to dissolve the phthalimide and 150 ml of the same solvent was used for KOH. The laboratory procedure for the preparation of potassium phthalimide was as described in Example 1. After drying, 9.9 g of the product was obtained, which is 97% yield.
Příklad 4 g ftalimidu sa za horúca rozpustilo v 300 ml n-butanolu a pri teplote 60 °C sa přidalo 100 ml n-butanolu a 4,7 g KOH. Zmes sa udržiavala pri uvedenej teplote · 15 minút, po ochladení sa ftalimid draselný izoloval filtráciou, premyl sa malým množstvom butanolu, po vysušení sa získalo. 10 gramov produktu, čo představuje 98 % výťažok. Obsah draslika vo ftalimide.draselnom bol: 21,3, a dusíka 7,3 %.Example 4 g of phthalimide was dissolved in 300 ml of n-butanol while hot and 100 ml of n-butanol and 4.7 g of KOH were added at 60 ° C. The mixture was kept at this temperature for 15 minutes, after cooling, potassium phthalimide was isolated by filtration, washed with a small amount of butanol, dried after drying. 10 grams of product, representing 98% yield. The potassium content in potassium phthalimide potassium was: 21.3, and nitrogen 7.3%.
P r í k 1 a d 5Example 5
V pokuse sa postupovalo ako je uvedené v příklade 4, ako rozpúšťadlo sa použilo 150 mililitrov amylalkoholu pre rozpustenie ftalimidu a 80 ml pre KOH po zmiešaní, vyhriatí, ochladení a izolácii sa získalo 10,15 g ftalimidu draselného, čo představuje 99 % výťažnosť.The experiment was carried out as described in Example 4, using 150 ml of amyl alcohol to dissolve the phthalimide and 80 ml of KOH after mixing, heating, cooling and isolation, yielding 10.15 g of potassium phthalimide, representing 99% yield.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846431A CS239398B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846431A CS239398B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
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| Publication Number | Publication Date |
|---|---|
| CS643184A1 CS643184A1 (en) | 1985-05-15 |
| CS239398B1 true CS239398B1 (en) | 1986-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS846431A CS239398B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
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1984
- 1984-08-27 CS CS846431A patent/CS239398B1/en unknown
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| Publication number | Publication date |
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| CS643184A1 (en) | 1985-05-15 |
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