SU509578A1 - Способ получени пропилендиаминов - Google Patents
Способ получени пропилендиаминовInfo
- Publication number
- SU509578A1 SU509578A1 SU2060973A SU2060973A SU509578A1 SU 509578 A1 SU509578 A1 SU 509578A1 SU 2060973 A SU2060973 A SU 2060973A SU 2060973 A SU2060973 A SU 2060973A SU 509578 A1 SU509578 A1 SU 509578A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- ammonia
- propylenediamines
- polyamines
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 title claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 claims description 2
- -1 chloroalkane hydrocarbon Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 239000002594 sorbent Substances 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229920000768 polyamine Polymers 0.000 claims 3
- 238000004821 distillation Methods 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 238000004817 gas chromatography Methods 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002351 wastewater Substances 0.000 claims 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- PPKPKFIWDXDAGC-NSCUHMNNSA-N (e)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C/Cl PPKPKFIWDXDAGC-NSCUHMNNSA-N 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 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
(54) СНОСОВ г1а1Учь:ии ПРОПИЛКИЦИАМПНОВ
i
Изобретеаие отнскитс к усовершенство
Всцнному способу получений пропиле иди а минов , в частности 1,2- и 1,3-пропилендиам оь , которые могут найти применение в органическом с:-штезе дл получени сор- бентов, гербицидов, физиологически ак тиэнь х сое,аинений.
Известны различные способы получени проп лендиаминэв, В частности, известен способ получени 1,2 11ропилендиамина
аминироьаиием 1 2-дихлорпропана 25%- Еодьым . аммиаком под давлением, при 14Ос и мол |:ном соотношении между аммиаком и дихлорпропаном 50:1.
Предлагаетс способ получени пропилендиамиаов взаимодействием 1,2и 1.3-ди :лорпропанов, состо щей обычно из 1,2-.изомера, 1,3 изомера (10-20%), и 5% J.,2 Дихлорпропена, с аммиаком, ::Гз тым в виде вО -8О%- ного водного
раствора.
Процесс провод т при давлении 50- 100 гдтМ; пре51мущественно 75-85 атм, и тeмпep, i;,pe 50.200С, преимуществен к: Г 1оО°С,
Соотношение между аммиаком и ди- хлорпропанами поддерживаетс равным 7:1 или 8:1.
По предлагаемому способу можно попу«чить как 1,2-, так. и 1,3.-пропилендиамины , использу при этом дешевое исходное сырье, а именно отходы производства гли церина - смесь 1,2- и 1,3-дихлорпропанов и 1,2-дихлорпропена. Кроме того, использова«ие более концентрированного раствора аммиака позвол ет ускорить процесс и сократить расход реагентов. Врем реакции сокращаетс до 1-1,5 час.
Claims (2)
- Полученные пропилендиамины могу быть разделены ректификацией ( 1,2-про- пилендиамин, т. кип. 120-122 ; ; 1,3-изомер , т. кип. 134-13б С) Либо использованы без разделени в виде смеси Нар ду с пропилендиаминами образуютс полиамины, выход которых составл ет 30% от общего веса аминированньгх про-ч дуктов. Полиамины также представл ют ценное сырье дл получени сорбентов и комплексонов, которые могут быть использованы дл очистки сточных вод и извлечени металлов. П JJ ,.(ЛЦ&| автоклав емкостью эарру Й т 5О ге смеси дихлоридов (состав cwe Jft||,W 1д2.41ихлорпропэн 75; 1.,Знр|$р |Э8 «й 1 дихлорпропены и гфугив-хлориды 5) и 4ОО г 80%-ного водного раствора аммиька. Содержимое автоклава нагревают при 130°С 1,5 час, а затем охлаждают. Далееаммиак отгон ют и к смеси добавл ют 35%-ный раствор едкого натра до образовани двух . Верхний сдой, содержащий пропилендиамины , отделЕвют, высушивают твердым едким кьлй и перегон ют в вакууме. Получают 22,8 г смеси пропилендиаминов, т. к 12О.-135°С, содержащей по данным газохроматографического анализа 1,2-пропилен диамин (77%) и 1,3-пропилендиамин (23%). Неперегон юшийс остаток (9,9 г представл ет собой полиамины, которые не были идентифицированы. Пример
- 2. В ана огичных услови из 1ОО г смеси дихлоридов указанного вы ше состава и 60%-ного водного раствора аммиака получают 67 г смеси аминов. Ректификацией в вакууме на колонке 40 т выдел ют: 1,2-лиаминопропак, выход 3S г, т. кип. 120-122°С, 1,4460, 1 3-ш1 мино1тропан, выход 9,5 г. т. кип. 134-135 С, П„ 1,4410, 0,883. Остаток ( 19,5 г) представл ет собой полипропи-. ленполиамины. Формула изобретени 1.Способ получени пропипендиаминов аминированием хлоралкаковых углеводородов водным раствором аммиака при нагр&,« вакии и давлении, отличающийс тем, что, сцелью расширени сырье-э вой базы и упрощени технологического процесса, в качестве хлоралкановых углеводородов используют смесь 1,2. и 1,3 -дихлорпропанов и 1,2.-нихлорпропеиа - отходы производства глицерина и еминиро- вание провод т 60-8О% -ным Боднь.1м раст. вором аммиака при весовомсоотношении соответственно 7-8:1. 2,Способ по п. 1, о т л и ч а ющ и и с тем, что процесс провод т при 120-13О°С и давлении 75-85 атм.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2060973A SU509578A1 (ru) | 1974-09-19 | 1974-09-19 | Способ получени пропилендиаминов |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2060973A SU509578A1 (ru) | 1974-09-19 | 1974-09-19 | Способ получени пропилендиаминов |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509578A1 true SU509578A1 (ru) | 1976-04-05 |
Family
ID=20596343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2060973A SU509578A1 (ru) | 1974-09-19 | 1974-09-19 | Способ получени пропилендиаминов |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU509578A1 (ru) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8691849B2 (en) | 2008-09-02 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| US8691813B2 (en) | 2008-11-28 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| US8716480B2 (en) | 2009-05-12 | 2014-05-06 | Janssen Pharmaceuticals, Inc. | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| US8748621B2 (en) | 2007-09-14 | 2014-06-10 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
| US8785486B2 (en) | 2007-11-14 | 2014-07-22 | Janssen Pharmaceuticals, Inc. | Imidazo[1,2-A]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US8841323B2 (en) | 2006-03-15 | 2014-09-23 | Janssen Pharmaceuticals, Inc. | 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors |
| US8906939B2 (en) | 2007-03-07 | 2014-12-09 | Janssen Pharmaceuticals, Inc. | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| US8937060B2 (en) | 2009-05-12 | 2015-01-20 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders |
| US8946205B2 (en) | 2009-05-12 | 2015-02-03 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US8993591B2 (en) | 2010-11-08 | 2015-03-31 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| US9067891B2 (en) | 2007-03-07 | 2015-06-30 | Janssen Pharmaceuticals, Inc. | 1,4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of mGluR2-receptors |
| US9114138B2 (en) | 2007-09-14 | 2015-08-25 | Janssen Pharmaceuticals, Inc. | 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′] bipyridinyl-2′-ones |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US9708315B2 (en) | 2013-09-06 | 2017-07-18 | Janssen Pharmaceutica Nv | 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of MGLUR2 receptors |
| US10106542B2 (en) | 2013-06-04 | 2018-10-23 | Janssen Pharmaceutica Nv | Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors |
| US10537573B2 (en) | 2014-01-21 | 2020-01-21 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US11369606B2 (en) | 2014-01-21 | 2022-06-28 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
-
1974
- 1974-09-19 SU SU2060973A patent/SU509578A1/ru active
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9266834B2 (en) | 2006-03-15 | 2016-02-23 | Janssen Pharmaceuticals, Inc. | 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors |
| US8841323B2 (en) | 2006-03-15 | 2014-09-23 | Janssen Pharmaceuticals, Inc. | 1, 4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of MGLUR2-receptors |
| US9067891B2 (en) | 2007-03-07 | 2015-06-30 | Janssen Pharmaceuticals, Inc. | 1,4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of mGluR2-receptors |
| US8906939B2 (en) | 2007-03-07 | 2014-12-09 | Janssen Pharmaceuticals, Inc. | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| US8748621B2 (en) | 2007-09-14 | 2014-06-10 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
| US9132122B2 (en) | 2007-09-14 | 2015-09-15 | Janssen Pharmaceuticals, Inc. | 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-ones |
| US9114138B2 (en) | 2007-09-14 | 2015-08-25 | Janssen Pharmaceuticals, Inc. | 1′,3′-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′] bipyridinyl-2′-ones |
| US8785486B2 (en) | 2007-11-14 | 2014-07-22 | Janssen Pharmaceuticals, Inc. | Imidazo[1,2-A]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US8691849B2 (en) | 2008-09-02 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| US8691813B2 (en) | 2008-11-28 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| US9085577B2 (en) | 2009-05-12 | 2015-07-21 | Janssen Pharmaceuticals, Inc. | 7-aryl-1,2,4-triazolo[4,3-A]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US9737533B2 (en) | 2009-05-12 | 2017-08-22 | Janssen Pharmaceuticals. Inc. | 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders |
| US10071095B2 (en) | 2009-05-12 | 2018-09-11 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of neurological and psychiatric disorders |
| US8946205B2 (en) | 2009-05-12 | 2015-02-03 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US8937060B2 (en) | 2009-05-12 | 2015-01-20 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders |
| US9226930B2 (en) | 2009-05-12 | 2016-01-05 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment of prevention of neurological and psychiatric disorders |
| US8716480B2 (en) | 2009-05-12 | 2014-05-06 | Janssen Pharmaceuticals, Inc. | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| US9012448B2 (en) | 2010-11-08 | 2015-04-21 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| US8993591B2 (en) | 2010-11-08 | 2015-03-31 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| US10106542B2 (en) | 2013-06-04 | 2018-10-23 | Janssen Pharmaceutica Nv | Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors |
| US10584129B2 (en) | 2013-06-04 | 2020-03-10 | Janssen Pharmaceuticals Nv | Substituted 6,7-dihydropyrazolo[1,5-a]pyrazines as negative allosteric modulators of mGluR2 receptors |
| US9708315B2 (en) | 2013-09-06 | 2017-07-18 | Janssen Pharmaceutica Nv | 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of MGLUR2 receptors |
| US10537573B2 (en) | 2014-01-21 | 2020-01-21 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US11103506B2 (en) | 2014-01-21 | 2021-08-31 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US11369606B2 (en) | 2014-01-21 | 2022-06-28 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| US12048696B2 (en) | 2014-01-21 | 2024-07-30 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
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