SU40983A1 - The method of purification of diethylaminoalkylamines - Google Patents
The method of purification of diethylaminoalkylaminesInfo
- Publication number
- SU40983A1 SU40983A1 SU153972A SU153972A SU40983A1 SU 40983 A1 SU40983 A1 SU 40983A1 SU 153972 A SU153972 A SU 153972A SU 153972 A SU153972 A SU 153972A SU 40983 A1 SU40983 A1 SU 40983A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diamine
- diethylaminoalkylamines
- purification
- impurities
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 238000000746 purification Methods 0.000 title description 2
- 150000004985 diamines Chemical class 0.000 description 11
- 239000012535 impurity Substances 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- BAFRTLDDFBNAIW-UHFFFAOYSA-N 1,1-diethyl-2-(3-methylbutyl)hydrazine Chemical compound CCN(CC)NCCC(C)C BAFRTLDDFBNAIW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- -1 phthalamide compound Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Первичные диэтиламиноалкиламины общей формулы:Primary diethylaminoalkylamines of the general formula:
QHsvQHsv
М(СН,)„ CH,NH,, CzH/M (CH,) „CH, NH ,, CzH /
CjHsvСН,CjHsvCH,
)N-(CH,X,-CH -Н,,) N- (CH, X, -CH -H ,,
QH/QH /
))N-(CH,)-CH(NH,)-(CH2),-CH3 )) N- (CH,) - CH (NH,) - (CH2), - CH3
благодар их высокой температуре кипени трудно отдел ютс от сопровождающих примесей как исходных полупродуктов , так и продуктов побочных процессов, протекающих при получении диаминов. Эти примеси часто кип т близко к температуре кипени диамина, пары их ассоциируют и разделение обычными физическими способами не удаетс .due to their high boiling point, it is difficult to separate from the accompanying impurities of both the initial intermediates and the products of the side processes occurring in the preparation of diamines. These impurities often boil close to the boiling point of the diamine, their vapors are associated, and separation by ordinary physical methods is not possible.
Мы нашли, что, примен способы химического св зывани диамина, удаетс очистить его даже от близких по строению органических оснований. Способ основан на св зывании первично аминной группы фт 1левым ангидридом во фталамидо-соединение:We have found that, by applying the methods of chemical bonding of a diamine, it is possible to purify it even from similar in structure organic bases. The method is based on the binding of a primary amine group of ft with 1 left anhydride to the phthalamido compound:
/СО.ЛгН-,/CO.LgN-,
С„Н, М-(СН,)„КС „Н, М- (СН,)„ К
QH,QH,
- со-или- co-or
/QH:,/ Qh :,
СН-(СНД,-N: SN- (SND, -N:
QH, IQH, I
сн.sn.
; Обычные примеси оказываютс при ; этом не св занными, так как только первично аминна группа способна ; давать фталамидо-соединение.; Common impurities occur at; this is unrelated, since only the primary amine group is capable; give a phthalamide compound.
I Пример. 450 г диэтиламиноизопентиламинаI Example. 450 g diethylaminoisopentylamine
N-СНо СН, СН,-СН (NH.,)-CHs, N-CHO CH, CH, -CH (NH.,) - CHs,
QH/ - имеющего по анализу только 70,- со , держани диамина при наличии в остальном других оснований, наливаютс в колбу. В нее при помешивании постепенно вноситс 300 о фталевого ангидрида. При этом происходит сильное разогревание. Когда весь фталевый ангидрид внесен, ко-тоу помещают в масл ную баню, где е нагревают 2 часа при температуре 175-190° в бане . После этого отгон ют в вакууме изQH / - having only 70, according to the analysis, - with, holding the diamine in the presence of other bases for the rest, is poured into the flask. With stirring, 300 o phthalic anhydride is gradually added. When this happens a strong warming up. When all the phthalic anhydride is added, the koe is placed in an oil bath, where it is heated for 2 hours at a temperature of 175-190 ° in a bath. Thereafter, distilled off in vacuum.
крпбы не св занные основани , причем, ртгон етс 140 г, не содержащих диамина . Остаток в колбе обливаетс 500 см сол ной кислоты технической (уд. в. 1,14 - 1,15), кип титс под обратным холодильником в течение 4 часов, остаетс на ночь. Выкристаллизовавша с фталева кислота отфильтровываетс , промываетс небольшим количеством воды. Соединенные фильтраты обрабатываютс измельченным твердым едким кали и выделившийс диамин обычным путем индивидуализируетс . Получаетс 250-270 г диамина, кип щего при 190-195° и дающего при титровании кислотою 96-97% содержани диамина. Особенно хорошо очищаетс диамин, возвращенный из реакции конденсации с соединени ми, имеющими галоид в гетероцикле.Cribs are not bound bases, and 140 g, not containing diamine, is PTH. The residue in the flask is doused with 500 cm of technical hydrochloric acid (sp. In. 1.14 - 1.15), boiled under reflux for 4 hours, left overnight. The crystallized phthalic acid is filtered off, washed with a small amount of water. The combined filtrates are treated with crushed solid potassium hydroxide and the precipitated diamine is individualized in the usual way. 250-270 g of diamine are obtained, boiling at 190-195 ° and giving 96% to 97% diamine content during titration with acid. The diamine recovered from the condensation reaction with compounds having a halogen in the heterocycle is especially well purified.
Диалогично описанному удаетс очистить 3 - N - диэтиламин и другие диамины указанных структур.Dialogically described, it is possible to purify 3-N-diethylamine and other diamines of the indicated structures.
iПредмет изобретени .The subject matter of the invention.
Способ очистки N-диэтиламикиламинов строени :The method of purification of N-diethylamylamines structure:
QH,. QH ,.
N-(CH,)NH,, СаН/N- (CH,) NH ,, CaH /
CgHoxCghox
N-(CHJ,,-CH-CH,,N- (CHJ ,, - CH-CH ,,
NH,NH,
CaHgx Cahgx
N-(CH,X -CH-NH, -(СН2)„QHN- (CH, X-CH-NH, - (CH2) „QH
отличающийс тем, что означенные амины дл отделени от примесей обрабатывают фталевым ангидридом, после чего примеси отгон ют и фталамидное I соединение разлага от обычными при: емами дл выделени свободного диамина .characterized in that the said amines are treated with phthalic anhydride for separation from impurities, after which the impurities are distilled off and the phthalamide I decomposition compound is taken from the usual ones in order to liberate free diamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU153972A SU40983A1 (en) | 1934-09-14 | 1934-09-14 | The method of purification of diethylaminoalkylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU153972A SU40983A1 (en) | 1934-09-14 | 1934-09-14 | The method of purification of diethylaminoalkylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU40983A1 true SU40983A1 (en) | 1935-01-31 |
Family
ID=48355902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU153972A SU40983A1 (en) | 1934-09-14 | 1934-09-14 | The method of purification of diethylaminoalkylamines |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU40983A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2382027C2 (en) * | 2008-03-24 | 2010-02-20 | ИНСТИТУТ НЕФТЕХИМИИ И КАТАЛИЗА Российской Академиия Наук | Method of producing symmetrical gem-diamines |
-
1934
- 1934-09-14 SU SU153972A patent/SU40983A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2382027C2 (en) * | 2008-03-24 | 2010-02-20 | ИНСТИТУТ НЕФТЕХИМИИ И КАТАЛИЗА Российской Академиия Наук | Method of producing symmetrical gem-diamines |
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