SU172753A1 - METHOD OF OBTAINING Y '- (| 3-OXYETHYL) -DIETHYLENETRIAMIN- N, N, N ", N" -TETPAyKCyCHOH ACIDS - Google Patents
METHOD OF OBTAINING Y '- (| 3-OXYETHYL) -DIETHYLENETRIAMIN- N, N, N ", N" -TETPAyKCyCHOH ACIDSInfo
- Publication number
- SU172753A1 SU172753A1 SU928603A SU928603A SU172753A1 SU 172753 A1 SU172753 A1 SU 172753A1 SU 928603 A SU928603 A SU 928603A SU 928603 A SU928603 A SU 928603A SU 172753 A1 SU172753 A1 SU 172753A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acids
- oxyethyl
- tetpaykcychoh
- diethylenetriamin
- obtaining
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 8
- 150000007513 acids Chemical class 0.000 title description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229940106681 chloroacetic acid Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 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
- 239000000203 mixture Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JMHRGKDWGWORNU-UHFFFAOYSA-M sodium;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound [Na+].CC1=C(CC([O-])=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 JMHRGKDWGWORNU-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Description
Предлагаема кислота может найти применение дл тонкого разделени редкоземельных элементов, в сельском хоз йстве, в текстильной промышленности, а также в качестве лекарственного средства, ускор ющего выведение из организма инкорпорированных металлов.The proposed acid can be used for fine separation of rare-earth elements, in agriculture, in the textile industry, and also as a drug that accelerates the elimination of incorporated metals from the body.
Предложено получение Ы-(р-оксиэтил)-диэт1Илентриамин-Ы ,М,М,Ы -тетрауксусной кислоты . Способ заключаетс в том, что диарилидендиэтилентриамин раствор ют в метаноле и подвергают взанмодействию с окисью этилена . Реакционную смесь обрабатывают сол ной кислотой. Образующийс (|3-оксиэтил)диэтилентриамин конденсируют с хлоруксусной кислотой в присутствии щелочи. N-(P-OKсиэтил )- диэтилентр.иамин - N,N,N,N -TeTpayKсусную кислоту выдел ют на колонках с катионитом КУ-2.The preparation of N- (p-hydroxyethyl) -dieth1 Ilentriamine-S, M, M, and S-tetraacetic acid is proposed. The method involves dissolving diaryl diene diethylenetriamine in methanol and reacting with ethylene oxide. The reaction mixture is treated with hydrochloric acid. The resulting (| 3-hydroxyethyl) diethylenetriamine is condensed with chloroacetic acid in the presence of alkali. N- (P-Oxyethyl) - diethylenether. Amine - N, N, N, N -TeTpayKacetic acid was isolated on columns with cation exchange resin KU-2.
ПрИмер. 120 г (0,386 г моль) дисалицилидендиэтилентриамина раствор ют в 150 мл метилового спирта и через полученный раствор .пропускают струю окиси этилена, при этом наблюдаетс незначительное разогревание . Окись этилена прекращают пропускать, когда привес достигает 1,5-2-кратного избытка , смесь нагревают на вод ной бане (температура 40°С) еще 2 час. Реакционную массу упаривают в вакууме, добавл ют рассчитанное количество концентрированной сол нойExample. 120 g (0.386 g mol) of disalicylidene diethylenetriamine is dissolved in 150 ml of methyl alcohol and a stream of ethylene oxide is passed through the resulting solution, while a slight warming is observed. Ethylene oxide is stopped to pass, when the weight gain reaches 1.5-2 times excess, the mixture is heated in a water bath (temperature 40 ° C) for another 2 hours. The reaction mass is evaporated in vacuo, the calculated amount of concentrated hydrochloric acid is added.
кислоты (65 мл, 0,772 г-моль), салициловый альдегид отдел ют, сол нокислый слой промывают эфиром и упаривают в вакууме, отгон по возможности всю воду. К остатку прибавл ют 31 г (0,772 г-моль) NaOH в 300 мл абс. спирта, перемешивают до полного растворени щелочи и отфильтровывают NaCl. Спиртовой раствор сущат над MgSOi, упаривают и дважды перегон ют в вакууме, получают 22,6 г (400/0 от теоретического) N-(|3-OKсиэтил )-диэтилентриамина с т. кип. 134- 135°С при 0,5 мм рт. ст.acids (65 ml, 0.772 g-mol), salicylic aldehyde is separated, the hydrochloric acid layer is washed with ether and evaporated in a vacuum, the water is distilled off if possible. 31 g (0.772 g-mol) of NaOH in 300 ml of abs are added to the residue. alcohol, stirred until complete dissolution of the alkali and filtered off NaCl. The alcoholic solution is dissolved over MgSOi, evaporated and distilled twice in vacuo to obtain 22.6 g (400/0 of theoretical) of N- (| 3-Oxy ethyl) -diethylenetriamine from m.p. 134 - 135 ° C at 0.5 mm Hg. Art.
К Na-соли хлоруксусной кислоты, приготовленной из 55,5 г (0,585 г-моль) хлоруксуснойTo the Na-salt of chloroacetic acid prepared from 55.5 g (0.585 g-mol) of chloroacetic acid
кислоты и 23,5 г (0,585 г моль) NaOH в 50мл воды, прибавл ют по капл м 17,2 г (0,117 г-моль) М-(р-оксиэтил)-диэт1илентриамина, не допуска повыщени температуры реакционной массы более чем до 40°С. По окончании прибавлени амина приливают по капл м раствор , содержащий 23,5 г (0,585 г-моль) NaOH в 50 мл воды, поддержива температуру реакционной массы около 40°С и рН около 9. На второй день подкисл ют концентрированную ПС1 до .кислой реакции по конго , обрабатывают углем и пропускают через колОНку с катионитом КУ-2. Элюируют 0,5Voиым раствором аммиака. Элюат упаривают в вакууме, сущат в вакуум-эксикаторе на., N- (p- оксиэтил)-диэтилентриаминтетрауксусной кислоты с т. пл. 81°С (разложбиие). Предмет изобретени Споооб получени Ы-(|3-оксиэтил)-диэтилентр ,иамин-Ы,М,|К,Ы -тетрауксусной кислоты, отличающийс тем, что диарилидендиэтилент.р.и5 4 амин подвергают взаимодействию с окисью этилена в среде растворител , полученную при этом реакдионную массу обрабатывают сол ной кислотой, образующийс (р-оксиэтил)диэтилентриамин коиденсируют с хлоруксусной кислотой в присутствии щелочи с последующим выделением конечного продукта с помощью катионита.acids and 23.5 g (0.585 g mol) of NaOH in 50 ml of water, add 17.2 g (0.117 g-mol) of M- (p-hydroxyethyl) -diethyleneriamine dropwise, without allowing the temperature of the reaction mass to rise to more than 40 ° C. At the end of the addition of the amine, a solution containing 23.5 g (0.585 g-mol) of NaOH is added dropwise to 50 ml of water, maintaining the temperature of the reaction mass at about 40 ° C and pH of about 9. On the second day, the concentrated PS1 is acidified to acidic Congo reactions, treated with coal and passed through a column with cation exchanger KU-2. Elute with 0.5 V ammonia solution. The eluate is evaporated in vacuo, in a vacuum desiccator, in., N- (p-hydroxyethyl) -diethylenetriamine tetraacetic acid with m.p. 81 ° C (decompression). SUMMARY OF THE INVENTION The preparation of L- ((3-hydroxyethyl) diethyl, iamine-S, M, | K, L-tetraacetic acid, characterized in that the diarylidene diethyl ether and 4 amine are reacted with ethylene oxide in a solvent medium obtained the reactionary mass is treated with hydrochloric acid, the resulting (p-hydroxyethyl) diethylenetriamine is co-oxidized with chloroacetic acid in the presence of alkali, followed by isolation of the final product with the aid of a cation exchanger.
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843702435A Addition SU1251284A2 (en) | 1984-02-16 | 1984-02-16 | Device for controlling triac converter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU172753A1 true SU172753A1 (en) |
Family
ID=
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0299795A2 (en) * | 1987-07-16 | 1989-01-18 | Nycomed As | Aminopolycarboxylic acids and derivatives thereof |
| US5531978A (en) * | 1987-07-16 | 1996-07-02 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0299795A2 (en) * | 1987-07-16 | 1989-01-18 | Nycomed As | Aminopolycarboxylic acids and derivatives thereof |
| WO1989000557A1 (en) * | 1987-07-16 | 1989-01-26 | Cockbain, Julian, Roderick, Michaelson | Aminopolycarboxylic acids and derivatives thereof |
| US5198208A (en) * | 1987-07-16 | 1993-03-30 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
| US5419893A (en) * | 1987-07-16 | 1995-05-30 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof for magnetic resonance imaging |
| US5531978A (en) * | 1987-07-16 | 1996-07-02 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI440635B (en) | Process for the manufacture of an intermediate in the synthesis of dabigatran etexilate | |
| US20230339840A1 (en) | Preparation method for water-soluble magnolol derivatives and honokiol derivatives and intermediates thereof, and related monohydroxy protection intermediates | |
| KR101339046B1 (en) | Process for producing monopentaerythritol of high purity and monopentaerythritol produced by the process | |
| EP0363994B1 (en) | (2r,3s,4s)-alpha-(carboxycyclopropyl)glycine | |
| KR100434991B1 (en) | Preparation method of N-methyl-N'-nitroguanidine | |
| SU172753A1 (en) | METHOD OF OBTAINING Y '- (| 3-OXYETHYL) -DIETHYLENETRIAMIN- N, N, N ", N" -TETPAyKCyCHOH ACIDS | |
| CN114262278B (en) | Method for preparing oseltamivir phosphate | |
| SU1581220A3 (en) | Method of obtaining 4-oxypyrrolidine-2-on-1-yl-acetamide | |
| US3131210A (en) | Process for methionine nitrile synthesis | |
| KR100772815B1 (en) | Process for Making 3-Hydroxyalkanelnitriles and Conversion of the 3-Hydroxyalkanelnitrile to an Hydroxyaminoalkane | |
| EP0748813B1 (en) | Process for preparing an N-substituted aldonamide | |
| SU592823A1 (en) | Method of preparing 5-amino-2,3-dimethylquinoxaline | |
| SU160274A1 (en) | ||
| JPS603299B2 (en) | Method for producing 1,3-dimethyl-2-imidazolidinone | |
| JPH02142758A (en) | Production of carpeting methyl ester halide | |
| US5741897A (en) | Process for preparing an N-substitued aldonamide | |
| SU244337A1 (en) | METHOD OF OBTAINING 1-ARYL-3-ALKILTETRAHYDROIMIM- | |
| SU536168A1 (en) | The method of obtaining-alkyl-alanines or their salts on the amino group | |
| JPS62164656A (en) | Production of cyanoisophorone | |
| CN117903045A (en) | Synthesis method of (2S) -2-N-fluorenylmethoxycarbonyl amino-3- [4- (2-pyridine) phenyl ] propionic acid | |
| SU878763A1 (en) | Method of preparing 3-aminocyclopentane derivatives | |
| US2517496A (en) | Preparation of symmetrical monoaminodihydroxytoluene | |
| KR20150095970A (en) | Improved process for preparing Oseltamivir | |
| SU1337385A1 (en) | Method of producing optically active s-phenyl l-cycteine or s-benzyl-l-cycteine | |
| JPH03170453A (en) | Production of omega-amino-alpha-hydroxycarboxylic acid |