CS239397B1 - Production method of potashium phthalimide - Google Patents
Production method of potashium phthalimide Download PDFInfo
- Publication number
- CS239397B1 CS239397B1 CS846430A CS643084A CS239397B1 CS 239397 B1 CS239397 B1 CS 239397B1 CS 846430 A CS846430 A CS 846430A CS 643084 A CS643084 A CS 643084A CS 239397 B1 CS239397 B1 CS 239397B1
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- CS
- Czechoslovakia
- Prior art keywords
- phthalimide
- potassium
- polar solvent
- solvent
- potassium phthalimide
- Prior art date
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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 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 30
- 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 20
- 239000002798 polar solvent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 abstract description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 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
- 238000002360 preparation method Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- IQEXVQXICRQRFK-UHFFFAOYSA-N C(CCCC)OCCCCC.[K] Chemical compound C(CCCC)OCCCCC.[K] IQEXVQXICRQRFK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 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
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 239000002244 precipitate Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002002 slurry 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
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- Indole Compounds (AREA)
Abstract
Predmetom vynálezu je sposob výroby ftalimidu draselného reakciou suspendovaného ftalimidu v horúcom polárnom rozpúšťadle pri teplote 60 °C a hydroxidu draselného, ktorý je rozpuštěný v polárnom rozpúšťadle pri teplote 50 až 60 °C a zrnes sa refluxuje, ochladl a ftalimid draselný sa izoluje od rozpúštadla.The present invention provides a process for producing potassium phthalimide by reacting suspended phthalimide in a hot polar solvent at 60 ° C and potassium hydroxide dissolved in a polar solvent at 50 to 60 ° C and refluxing, cooling and isolating potassium phthalimide from the solvent.
Description
(54) Sposob výroby ftalimidu draselného(54) Method of production of potassium phthalimide
Predmetom vynálezu je sposob výroby ftalimidu draselného reakciou suspendovaného ftalimidu v horúcom polárnom rozpúšťadle pri teplote 60 °C a hydroxidu draselného, ktorý je rozpuštěný v polárnom rozpúšťadle pri teplote 50 až 60 °C a zmes sa refluxuje, ochladl a ftalimid draselný sa izoluje od rozpúšťadlá.SUMMARY OF THE INVENTION The present invention provides a process for producing potassium phthalimide by reacting suspended phthalimide in a hot polar solvent at 60 ° C and potassium hydroxide dissolved in a polar solvent at 50-60 ° C and refluxing, cooling, and potassium phthalimide isolated from the solvent.
Jednou zo základných surovin pri různých organických syntézách je ftalimid draselný. Například sa používá ako medziprodukt pri výrobo N-substituovaných tioftalimidov, ktoré sa využívajú ako retardéri navulkanizácie.One of the basic raw materials in various organic syntheses is potassium phthalimide. For example, it is used as an intermediate in the production of N-substituted thiophthalimides which are used as vulcanization retarders.
Ftalimid draselný sa připravuje pósobením hydroxidu draselného na ftalimid alebo podta Gabrielovej reakcie. Gabrielovu reakciu možno použiť aj pri príprave 1,4-diaminobutánu, kde sa ftalimid draselný získá ako medziprodukt.Potassium phthalimide is prepared by reacting potassium hydroxide to phthalimide or to the Gabriel reaction. The Gabriel reaction can also be used in the preparation of 1,4-diaminobutane, where potassium phthalimide is obtained as an intermediate.
Ftalimid draselný je možno získat aj ako medziprodukt pri výrobě prokaínamidhydrochloridu, alebo ako kondenzačný produkt primárného aminu s anhydridom kyseliny fialověj.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 spósobov přípravy uvádza Landsberg přípravu sódnej a draselnej soli ftalimidu působením etanolátu sodného alebo draselného na ftalimid. Podía Hammicka dobré výtažky ftalimidu sodného a draselného sa dosiahli za použitia amyloxidu sodného alebo draselného v amylalkohole.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 amylalcohol.
Uvedené metódy 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.The above preparation methods 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 do suspenzie ftalimidu v polárnom rozpúšťadle pri 60 °C přidá ekvivalentně množstvo hydroxidu draselného vo formě roztoku v polárnom rozpúšťadle pri teplote 50— —60 °C a za miešania sa zmes udržuje za refluxu počas 5 až 120 minút a po ochladení sa ftalimid draselný izoluje filtráciou.It has now been found that the above disadvantages can be overcome by the present invention in that an equivalent amount of potassium hydroxide as a solution in a polar solvent at 50-60 ° C is added to a suspension of phthalimide in a polar solvent at 60 ° C. and with stirring, the mixture is maintained at reflux for 5 to 120 minutes and after cooling, potassium phthalimide is isolated by filtration.
Použité rozpúštadlo sa regeneruje destiláciou.The solvent is recovered by distillation.
Predmet vynálezu dokumentují! nasledujúce příklady prevedenia.The subject of the invention is documented. the following examples.
Příklad 1Example 1
Do 100 ml izobutanolu sa nadávkovalo 8 g ftalimidu, ktorý sa za miešania pri teplote 60 aC z časti rozpustil a z časti tvořil suspenziu v rozpúšťadle. Do takto pripravenej suspenzie sa přidalo 100 ml izobutanolu obsahujúceho 8,94 % hmot. KOH pri teplote 60 °C a zmes sa refluxovala 30 minút. Po ochladení sa získalo 8,8 g ftalimidu draselného, čo představuje 87,5 % výťažnosť. Analýzou ftalimidu draselného sa zistil obsah draslíka 20,1 a dusíka 7,18 %.To 100 ml of isobutanol were charged 8 g of phthalimide which was stirred at 60 C and partly dissolved and partly forms a suspension in the solvent. 100 ml of isobutanol containing 8.94 wt. KOH at 60 ° C and the mixture was refluxed for 30 minutes. After cooling 8.8 g of potassium phthalimide was obtained, which represents 87.5% yield. Analysis of potassium phthalimide revealed a potassium content of 20.1 and a nitrogen content of 7.18%.
Příklad 2Example 2
8,95 %-ná suspenzia ítalimidu v izobutanole pri teplote 60 °C sa zmiešala s alkoholickým roztokom KOH v izobutanole obsahujúci 9 % KOH pri teplote 55 °C. Po refluxovaní 10 minút sa zmes ochladila, izoloval sa ftalimid draselný, pričom jeho výtažok bol 90,2 %-ný.An 8.95% slurry of thalimide in isobutanol at 60 ° C was mixed with an alcoholic solution of KOH in isobutanol containing 9% KOH at 55 ° C. After refluxing for 10 minutes, the mixture was cooled, and potassium phthalimide was isolated, yielding 90.2%.
Přiklad 3Example 3
Pre rozpustenie ftalimidu a KOH sa použil filtrát z pokusu 1 a 2 získaný po izolácii ftalimidu draselného. Ostatně podmienky pokusu boli zhodné ako v příklade 1. Po odfiltrovaní ftalimidu draselného sa zrazenina premyla čistým alkoholom a vysušila sa. Výťažok pokusu bol 97 %-ný. Filtrát bol opakované použitý 4krát, pričom výtažky ftalimidu draselného boli následovně: 97,0 %, 100 %, 98,5 %, 97 %.The filtrate from Experiments 1 and 2 obtained after isolation of potassium phthalimide was used to dissolve the phthalimide and KOH. Moreover, the experimental conditions were the same as in Example 1. After the potassium phthalimide was filtered off, the precipitate was washed with pure alcohol and dried. The yield of the experiment was 97%. The filtrate was used 4 times, yielding potassium phthalimide as follows: 97.0%, 100%, 98.5%, 97%.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846430A CS239397B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846430A CS239397B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS643084A1 CS643084A1 (en) | 1985-05-15 |
| CS239397B1 true CS239397B1 (en) | 1986-01-16 |
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ID=5411304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS846430A CS239397B1 (en) | 1984-08-27 | 1984-08-27 | Production method of potashium phthalimide |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS239397B1 (en) |
-
1984
- 1984-08-27 CS CS846430A patent/CS239397B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS643084A1 (en) | 1985-05-15 |
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