CS200126B1 - Process for preparing potassium phthalimide - Google Patents
Process for preparing potassium phthalimide Download PDFInfo
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- CS200126B1 CS200126B1 CS839878A CS839878A CS200126B1 CS 200126 B1 CS200126 B1 CS 200126B1 CS 839878 A CS839878 A CS 839878A CS 839878 A CS839878 A CS 839878A CS 200126 B1 CS200126 B1 CS 200126B1
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- Czechoslovakia
- Prior art keywords
- phthalimide
- mol
- potassium phthalimide
- potassium
- koh
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- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 34
- 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
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 101150012195 PREB gene Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 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
- HVOCMPMAOLOKRK-UHFFFAOYSA-N potassium;pentan-1-olate Chemical class [K+].CCCCC[O-] HVOCMPMAOLOKRK-UHFFFAOYSA-N 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
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
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- Indole Compounds (AREA)
Description
Predmetom vynálezu je spdsob výroby ftalimidu draselného vzorcaThe present invention relates to a process for the preparation of potassium phthalimide of the formula
CO co' z ftalimidu a hydroxidu draselného vo vodno-aeetonovom prostředí priamou syntézou podTa reakčnej BohémyCO what from phthalimide and potassium hydroxide in aqueous-acetone medium by direct synthesis according to reaction Bohema
Ftalimid draselný je jednou zo základných surovin pri výrobě N-eubetituovaných tioftalimidov /napr. N-cyklohexyltioftalimid/ používaných ako retardérov navulkanizácie, ktoré nadobudli v poalednom čase značný priemyselný význam.Potassium phthalimide is one of the basic raw materials in the production of N-eubetitized thiophthalimides / e.g. N-cyclohexylthiophthalimide used as vulcanization retardants, which have gained considerable industrial importance in the recent years.
Zo starších apĎeobov přípravy ftalimidu draselného možno uviesť přípravu Gabrielovou reakciou /Gabriel. S.: Ber. 20. a 2224-5 /1887//, ked aa do horúceho roztoku ftalimidu v absolútnom alkohole přidá zodpovedájúce množstvo alkoholického roztoku KOH za vzniku krystalického ftalimidu draselného.Among the older and the processes for the preparation of potassium phthalimide may be mentioned the preparation by the Gabriel reaction / Gabriel. S .: Ber. 20 and 2224-5 (1887), when an appropriate amount of alcoholic KOH solution is added to a hot solution of phthalimide in absolute alcohol to form crystalline potassium phthalimide.
200 126200 126
200 120200 120
Možný spósob přípravy sodnej alebo draselnej soli ftalimidu uvádza /Landsberg: Liebiga Annalen d. Chemie, str. 215 /1882//, keď sa na ftalimid priamo pósobí etanolétom sodným alebo draselným. Podl’a Hammicka /Hammick D. L., Locket G. H.: Journal of Chem. aoc., 121, 2362 /1922// této metoda však nedává uspokojivé výtažky. Použitie etanolických roztokov hydroxidov uvedených kovov vedle v každom případe k velkým objemom rozpúáťadiel. Avšak takmer kvantitativné výtažky ftalimidu sodného alebo draselného dosiahol za použitia pentylalkoholátov sodíka alebo draslíka.A possible way of preparing the sodium or potassium salt of phthalimide is given by / Landsberg: Liebiga Annalen d. Chemie, p. 215/1882], when the phthalimide is directly treated with sodium or potassium ethanol. According to Hammick / Hammick D. L., Locket G. H., Journal of Chem. aoc., 121, 2362 (1922), however, does not give satisfactory yields. The use of ethanolic hydroxide solutions of said metals in addition to large volumes of solvents in each case. However, almost quantitative yields of sodium or potassium phthalimide were achieved using sodium or potassium pentylalcoholates.
Iný spósob přípravy ftalimidu draselného kvalitativně i kvantitativné v dobrých výťažkoch uvédza /Schoenheimer R.,, Ratner S.: J. Biol. Chem. 127. /1939// a /Mainmind V. I., Tokarev Β. V.: Žurnál Obšč. Chim., 26, 1962-67 /1956// dehydratáciou kyslého ftalátu amonného.Another method for the preparation of potassium phthalimide, both qualitatively and quantitatively, in good yields is given in Schoenheimer, R., Ratner, S .: J. Biol. Chem. 127. / 1939 // and / Mainmind V. I., Tokarev Β. V .: Journal Obšč. Chim., 26, 1962-67 / 1956 // by dehydration of ammonium acid phthalate.
Tiež je uvádzaný možný spósob získavania ftalimidu draselného ako medziproduktu pri príprave prokaínamidhydrochloridu /Tsu-hein Shen-lan Yu: Yao Heweh Pao 8, str. 319-321 /1960// alebo pri přípravě 1,4 diaminobutánu /Chambret F., Joly D.: Bul. aoc. chim. France s. 1023-6 /1974//.Also disclosed is a possible method of obtaining potassium phthalimide as an intermediate in the preparation of procainamide hydrochloride / Tsuin-Shen-lan Yu: Yao Heweh Pao 8, p. 319-321 (1960) or in the preparation of 1,4 diaminobutane (Chambret F., Joly D .: Bul. AOC. chim. France s. 1023-6 (1974).
Nevýhodou uvedených spósobov přípravy ftalimidu draselného eú vo všeobecnosti nízké výtažky, zvýšenie ktorých sa dosiahne len pri použiti absolútnych rozpúšťadiel.A disadvantage of the above processes for the preparation of potassium phthalimide eu is generally low yields, which are only increased by the use of absolute solvents.
Pri všetkých spósoboch přípravy ftalimidu draselného vo vysokých výťažkoch by v konečnom dósledku stažovala technologiu výroby právě příprava absolútnych rozpúšťadiel .vplyve obsahu vody v organických rozpúšťadléeh použitých pri príprave, na výťažok ftalimidu draselného a jeho možnej hydrolýze pojednává článok - Ježek a kol.; Meranie a výpočet kinetických veličin hydrolýzy ftalimidu draselného vo vodě a v organických rozpúšťadléeh s róznym obsahom vody /v tlači/.In all processes for the preparation of potassium phthalimide in high yields, ultimately the production technology would be precluded by the preparation of absolute solvents due to the water content of the organic solvents used in the preparation. Measurement and calculation of kinetic quantities of hydrolysis of potassium phthalimide in water and in organic solvents with different water content (in press).
Uvedené nevýhody a spóeob výroby ftalimidu draselného rieši vynález, ktorého podstata je v tom, že umožňuje výrobu ftalimidu draselného vo vysokých kvalitatívnych i kvantitativných výťažkoch vo vodno-aeetonovom prostředí s obsahom vody 3 až 20% hmot.The above-mentioned disadvantages and methods for the production of potassium phthalimide are solved by the invention, which is based on the fact that it enables the production of potassium phthalimide in high qualitative and quantitative yields in a water-acetone medium with a water content of 3 to 20% by weight.
Princip spósobu podTa predmetu vynélezu spočívá v tom, že k acetonovému roztoku ftalimidu o koncentrácii 2 až 5% hmot. za refluxu sa přidá za intenzívneho miešania vodný roztok hydroxidu draselného o koncentrácii 10 až 30% hmot. v molérnom přebytku 1,00 až 1,25 v priebehu 10 až 30 minút. Po přidaní vodného roztoku hydroxidu draselného sa reakčná zmee za miešania nechá doreagovať počas 10 až 20 minút, pričom dochádza k aamovoTnému pokleau teploty. Ftalimid draselný sa izoluje po ochladení reakčnej zMeei na teplotu nižšiu ako 25 °C.The principle of the method according to the invention is based on the fact that to an acetone solution of phthalimide at a concentration of 2 to 5% by weight. at reflux, an aqueous solution of potassium hydroxide at a concentration of 10 to 30% by weight is added under vigorous stirring. in a molar excess of 1.00 to 1.25 over 10 to 30 minutes. After addition of the aqueous potassium hydroxide solution, the reaction mixture is allowed to react with stirring for 10 to 20 minutes, resulting in an ammoniacal temperature drop. Potassium phthalimide is isolated after cooling the reaction mixture to a temperature below 25 ° C.
Výhodou vynélezu oproti dopoeial’ známým spósobom přípravy ftalimidu draselného je, že nevyžaduje použitie abaolútnych rozpúšťadiel a umožňuje pracovať v prostředí s obaahom vody 3 až 20% hmot. bez výrazného ovplyvnenia čistoty i výťažku získávaného ftalimidu draselného.The advantage of the invention over the known methods of preparing potassium phthalimide is that it does not require the use of abaolute solvents and allows to work in an environment with a water content of 3 to 20% by weight. without significantly affecting the purity and yield of the obtained potassium phthalimide.
Vynález ilustrujú nasledujúce příklady.The following examples illustrate the invention.
Příklad 1 g ftalimidu /0,068 mól/ aa rozpustí v 190 g vriaceho acetonu /3,276 mol/ a zaExample 1 g of phthalimide (0.068 mol) and dissolved in 190 g of boiling acetone (3.276 mol) and
200 120 intenzívneho miešania sa do reakčnej zmesi přidá v priebehu 12 minút roztok 4,38 g /0,078 mól/ KOH v 13,14 g /0,730 mol/ HgO /25% roztok KOH, 1,15 mol. preb./. Vzniknutá suspenzia sa mieSa po dobu 15 minút, pričom teplota klesne na 35 °C a ďalej sa ochladí na 20 °C. Izoléciou aa získá 12,55 g /99,6% výťažok/ ftalimidu draselného.A solution of 4.38 g (0.078 mol) / KOH in 13.14 g (0.730 mol) / HgO / 25% KOH solution (1.15 mol) was added to the reaction mixture over 12 minutes under vigorous stirring. preb./. The resulting suspension was stirred for 15 minutes while the temperature dropped to 35 ° C and further cooled to 20 ° C. Isolation of aa yields 12.55 g (99.6% yield) of potassium phthalimide.
Příklad 2 g ftalimidu /0,068 mól/ sa rozpustí v 190 g vriaceho acetonu /3,276 mol/ a za mieSania sa do reakčnej zmesi přidá v priebehu 15 minút roztok 4,19 g /0,075 mól/ KOH v 15,36 g /0,853 mól/ vody /22% roztok KOH, 1,1 mol. preb./. Ďalej sa reakčná zmes spracovala ako v příklade 1. Izoláciou sa získalo 12,25 g ftalimidu draselného, čo je 97,2% výťažok.Example 2 g of phthalimide (0.068 mol) was dissolved in 190 g of boiling acetone (3.276 mol) and a solution of 4.19 g (0.075 mol) of KOH in 15.36 g (0.853 mol) was added to the reaction mixture over 15 minutes. water / 22% KOH solution, 1.1 mol. preb./. Further, the reaction mixture was worked up as in Example 1. Isolation gave 12.25 g of potassium phthalimide, which is 97.2% yield.
Příklad 3 g ftalimidu /0,068 mol/ ea rozpustí v 190 g vriaceho acetonu /3,276 mol/ a za miešania ea do reakčnej zmesi přidá v priebehu, 10 minút roztok 4,19 g /0,075 mól/ KOH a 11,18 g /0,62 mól/ vody /28% roztok KOH, 1,1 mol. preb./. Spracovaním reakčnej zmesi rovnakým postupom ako v příklade 1 se získalo 12,35 g ftalimidu draselného, čo je 98,0% výťažok.Example 3 g of phthalimide (0.068 mol) e was dissolved in 190 g of boiling acetone (3.276 mol) and a solution of 4.19 g (0.075 mol) of KOH and 11.18 g (0.18 mol) was added to the reaction mixture over 10 minutes. 62 mol / water / 28% KOH solution, 1.1 mol. preb./. Working up the reaction mixture in the same manner as in Example 1 gave 12.35 g of potassium phthalimide, which is 98.0% yield.
Příklad 4 g ftalimidu /0,068 mól/ sa rozpustí v 190 g vriaceho acetonu /3,276 mol/ a za miešania sa přidá do reakčnej zmesi 4,38 g /0,078 mol/ KOH v 13,14 g /0,73 mol/ vody, čo představuje 25% roztok KOH, 1,15 molérny prebytok. Vzniknutá suspenzia sa ochladí na 40 °C a při tejto teplote ea udržuje po dobu 15 minút. Pri tejto teplote sa ftalimid draselný vyizoloval v množstve 12,4 g, čo je 98,4% výťažok.EXAMPLE 4 g of phthalimide (0.068 mol) were dissolved in 190 g of boiling acetone (3.276 mol) and added with stirring to the reaction mixture 4.38 g (0.078 mol) of KOH in 13.14 g (0.73 mol) of water. represents a 25% KOH solution, 1.15 molar excess. The resulting suspension was cooled to 40 ° C and held at that temperature for 15 minutes. At this temperature, potassium phthalimide was isolated in an amount of 12.4 g, 98.4% yield.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS839878A CS200126B1 (en) | 1978-12-15 | 1978-12-15 | Process for preparing potassium phthalimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS839878A CS200126B1 (en) | 1978-12-15 | 1978-12-15 | Process for preparing potassium phthalimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200126B1 true CS200126B1 (en) | 1980-08-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS839878A CS200126B1 (en) | 1978-12-15 | 1978-12-15 | Process for preparing potassium phthalimide |
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|---|---|
| CS (1) | CS200126B1 (en) |
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1978
- 1978-12-15 CS CS839878A patent/CS200126B1/en unknown
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