SU37092A1 - The method of obtaining N-aryl-substituted phthalimides - Google Patents
The method of obtaining N-aryl-substituted phthalimidesInfo
- Publication number
- SU37092A1 SU37092A1 SU127333A SU127333A SU37092A1 SU 37092 A1 SU37092 A1 SU 37092A1 SU 127333 A SU127333 A SU 127333A SU 127333 A SU127333 A SU 127333A SU 37092 A1 SU37092 A1 SU 37092A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aryl
- aniline
- phthalic acid
- obtaining
- substituted
- Prior art date
Links
- 125000005543 phthalimide group Chemical class 0.000 title description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N Diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 1
- MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 1
- YTMSIVKCVBMPFF-UHFFFAOYSA-N 4-phenylisoindole-1,3-dione Chemical compound O=C1NC(=O)C2=C1C=CC=C2C1=CC=CC=C1 YTMSIVKCVBMPFF-UHFFFAOYSA-N 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N Anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N Mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N Phenylisocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 244000052616 bacterial pathogens Species 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines 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
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- DFLCZDIXTAAMLZ-UHFFFAOYSA-N phthalic acid;sodium Chemical compound [Na].OC(=O)C1=CC=CC=C1C(O)=O DFLCZDIXTAAMLZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
Description
в литературе описан р д способов получени N арил-замсщенныхфтальимидов общей формулы:The literature describes a number of methods for the preparation of N aryl-substituted phthalimide with the general formula:
х x
иand
N -RN -R
СО/CO /
где R-лгобой радикал ароматического р да. Способы эти можно разделить на ДОС группы.where R is a radical aromatic radical. These methods can be divided into DOS groups.
Способы пероой группы основаны на применении высокой температуры. Нппркм р , фталанил (фенилфтальимид)получаСгсл нзгреппинем фтальимида с гнилчисм (3. 16, 1323 перегонкой фталевой КИСЛОТЫ с анилином (А 210, 267,1847/43, 605), нагреалнисм фснольного эфира фталесой КИСЛОТЫ с анилином (Ж. 29, 195, В. 29. 1795) при быстром нагревании до 160-200 КИСЛОГО фгалеоого кислого анилинэ (3. 29, 280)), при плаокс виилснэ с фталеооП кислотой (R. Ch. (3) 24, 128; А: 65, 33), нагреванием до 200 фталево-кислого натри с сол нокислым анилином (Am. Soc. 25, 618) и т. д.The methods of the first group are based on the use of high temperature. Npprkm p, phthalanil (phenylphthalimide) obtained by nzgreppeem phthalimide with rotting (3. 16, 1323 by distilling phthalic ACID with aniline (A 210, 267.1847 / 43, 605), with green phthalate with phthalic acid and antamine;), I have also been treated with an aniline (A 210, 267.1847 / 43, 605), and I have received phthalic acid with phthalic acid with aniline (A 210, 267.1847 / 43, 605), phthalol with phthalic acid, and phthalic acid with aniline (A 210, 267.1847 / 43, 605), phthalol with phthalic acid and aniline (A. 210, 267.1847 / 43, 605), phthalol with phthalic acid, and phylamine; V. 29. 1795) with rapid heating to 160–200 ACID phgaleic acid aniline (3. 29, 280)), with plaox vilnesne with phthalic acid (R. Ch. (3) 24, 128; A: 65, 33) , heating to 200 phthalic acid sodium with aniline hydrochloride (Am. Soc. 25, 618), etc.
Способы второйгруппы.в оиду приГ1сне1 и ДОВОЛЬНО высоких температур от 160-200, пригзод т к продуктам, зиаг чительно осмоленным, выхода тпкже оставл ют желать лучшег.The methods of the second group are suitable for high temperatures from 160 to 200, they are suitable for products that are highly tarred, and leave much to be desired.
Способы второй группы основаны на примскени - в качестве исходных, материалов ДОВОЛЬНО дорогих и сраонительС 1 ).,.-.-;КО труднодоступных продуктов, кок, например , фенилизоцианта о-цианобензил-эмина (В. 31, 2884), изофталпнила fCh. Z. . 1924, I, 1784). гидразофталанила (Ch. Z. 1912, I, 333), фталилхлоридо (Am. Chem. J. 26, 454) и потому не могут иметь технического значени , тем более, что и выхода продуктов незначительны.The methods of the second group are based on priming the raw materials as PRATELY expensive and using 1)., .-.;; TO of hard-to-reach products, such as phenyl isocyanate o-cyanobenzyl-emine (V. 31, 2884), isophthalpyl fCh. Z. 1924, I, 1784). hydrazophthalanyl (Ch. Z. 1912, I, 333), phthalyl chloride (Am. Chem. J. 26, 454) and therefore cannot have a technical meaning, especially since the product yield is insignificant.
Обособленно стоит способ каталистического получени замещенных фтальимида из нафталина, кислорода и аминов (А. Р. Ка 1450678. Ch. Z. 1925 I 1804). но требует дорого стоющих катализаторов и применени высоких температур. О выходах продуктов по этому способу нет никаких указаний.Separately, there is a method for the catalytic production of substituted phthalimide from naphthalene, oxygen and amines (A. R. Ka 1450678. Ch. Z. 1925 I 1804). but requires costly catalysts and the use of high temperatures. On the outputs of the products in this way there is no indication.
Между тем арилфтальимиды получили в последнее врем большое значемка ДЛЯ производства красителей и других синтетических продуктов (ср. герм. пат. 2 551256). Автором , что получать М-арилзамещенные фтальимиды высокой степени чистоты, почти химически чистые, при обыкнопенкой температуре , путем пропускани хлористоводородного газа через суспензы или растворы соответствующих фталакикопых КИСЛОТ в органических растворител х, смешивающихс С водой, или плохо раствор ющих М - арилзамешенныо фтгльимида (спирты, диоксан, ацетон и пр.). Продукты при этом Еыаел ютс в пхда осадког), либoиx J J :iyr --crггг77::.ть разбавлениех:г- гСи;оро8 ,,.рс;;7.оД.Meanwhile, arylphthalimides have recently received a big meaning for the production of dyes and other synthetic products (cf. germ pat. 2 551256). The author has said that to obtain M-aryl-substituted phthalimides of high purity, almost chemically pure, at ordinary temperature, by passing hydrochloric gas through suspensions or solutions of the corresponding phthalic acid ACIDS in organic solvents that are mixed with water, or poorly dissolving M-aryl-substituted hydrolyzimyme , dioxane, acetone, etc.). Products in this case are in a state-of-the-art), or JJ: iyr - crgg777 ::. Dilution: r-gCi; oro8 ,,. Pc ;; 7.oD.
при этом N-арил-фтальими ы получаютс вполне чистые, даже еспи исходить из темных, технических фталаминосых кислот. Выход продуктоз, близких к теоретическому, и зависит только от большей или меньшей растпоримости иг. в илточлом растворе.at the same time, N-aryl-phthalimy s are completely pure, even if they come from dark, technical phthalamino acids. Output products close to theoretical, and depends only on more or less rastorimosti u. in a fine solution.
Пример. 25 т. фекилфталамннозой ккгпоты, получеииоГ из фталеоого ангидрида и анилина, например, по герм, пат. Х2 523503 простым смешением анилина с фгалеоым ангридриДом, растао. рпюг п 30 г. метилового спирта, и, при оОыччой температуре и размешиоанин, пропускают через этот рпстпор хлористо-оодорэдный газ D течение 3-х, 8-ми часоз, до тех пор, пока реакционна мзсса не будет сильно дымить. Во орсм пропускание хлористого водорода фтапа| ил выдел етс в виде красиоых белых игл. Фгаланил отфильтровывают и тщательно промывают холодной водой. Высушенный фгаланил имеет точку плавлени 204,5 и весит 22,5 г, что составл ет пыход 97/ теории.Example. 25 t. Fekylphthalamnnose cgppots, polucheioiG from phthalic anhydride and aniline, for example, according to germs, US Pat. X2 523503 by simple mixing of aniline with fgaley Angridrid, Rastao. Rugged 30 g of methyl alcohol, and, at a temperature of omechi and razmeshioanin, pass through this rspstor chloride-oodoreny gas D for 3, 8-th hour, until the reactionary process will not smoke much. In orsm transmission hydrogen chloride phtap | The sludge is excreted in the form of beautiful white needles. Phgalanyl is filtered off and washed thoroughly with cold water. Dried phgalanyl has a melting point of 204.5 and weighs 22.5 grams, which is 97% theory.
.Аналогичным образом могут быть получены и другие N замещенные фтальимида , если CSMCCTO анилина (при получении фснилфталаминовой кислоты) прин ть его гомологи и производные, а также производные и гомологи других первичных аминов, например, полуидиноо, ксилидимов, фенилендиаминов, н фтиламинов , п также их хлор-нитро-и др. производных н т. п.. Similarly, other N substituted phthalimide can be obtained, if CSMCCTO aniline (when preparing phnyl phthalamic acid) accept its homologues and derivatives, as well as derivatives and homologs of other primary amines, for example, semi-dino, xylidyms, phenylenediamines, n phylamines, p their chlorine-nitro and other derivatives n.
Предмет изобретени .The subject matter of the invention.
Способ получени N-ори л-за мешенных фтальимидов, отличающийс тем, что через растворы или суспензы орилфталаминовых кислот в органических растворител х, плохо раствор ющих N-. орил-замещенные фтальимиды или смешивающихс с водой, пропускают хлоpиcтo-вoдopoд iый газ.A method of producing N-ori-l due to intermixed phthalimides, characterized in that through solutions or suspensions of orylphthalamic acids in organic solvents that poorly dissolve N-. or substituted phthalimides or miscible with water, let chlorine water pass through the gas.
Publications (1)
Publication Number | Publication Date |
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SU37092A1 true SU37092A1 (en) | 1934-06-30 |
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