CN1251567A - 由含有六亚甲基二胺和2－氨甲基环戊胺的混合物分离2－氨甲基环戊胺的方法 - Google Patents
由含有六亚甲基二胺和2－氨甲基环戊胺的混合物分离2－氨甲基环戊胺的方法 Download PDFInfo
- Publication number
- CN1251567A CN1251567A CN98803807A CN98803807A CN1251567A CN 1251567 A CN1251567 A CN 1251567A CN 98803807 A CN98803807 A CN 98803807A CN 98803807 A CN98803807 A CN 98803807A CN 1251567 A CN1251567 A CN 1251567A
- Authority
- CN
- China
- Prior art keywords
- diamine
- aminomethyl
- hexamethylene
- separating
- aminomethylcyclopentylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004821 distillation Methods 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960003263 cyclopentamine Drugs 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- -1 hexanodioic acid Chemical compound 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种由含六亚甲基二胺和2－氨甲基环戊胺的混合物分离2－氨甲基环戊胺的方法,该法包括利用在水存在下蒸馏进行分离。
Description
本发明涉及一种由含六亚甲基二胺和2-氨甲基环戊胺(AMCPA)的混合物分离AMCPA的方法。
在基于金属如镍、钴、铁、铑或钌的催化剂在下，己二腈完全氢化成六亚甲基二胺以及部分氢化同时生成六亚甲基二胺和6-氨基己腈是普通已知的，例如见：K.Weissermel，H.J.Arpe，工业有机化学(Industrille Organische Chemie)，第三版，VCHVerlagsgesellschaft mbH，Weinheim，1988，p.266；US-A4601859，US-A 2762835，US-A 2208598，DE-A 848654，DE-A954416，DE-A 4235466，US-A 3696153，DE-A 19500222，WO92/21650和德国专利申请19548289.1。
副产物包括六亚甲基亚胺(HMI)，1，2-二氨基环己烷(DACH)和AMCPA。
US-A 3696153提到，用这种氢化法得到的六亚甲基二胺含有副产物AMCPA，它很难从混合物中分离。
本发明的一个目的是提供一种以技术上简单而经济的方式由主要含六亚甲基二胺和AMCPA的混合物中分离AMCPA的方法。
我们发现利用一种由含六亚甲基二胺和AMCPA的混合物中分离AMCPA的方法可以实现这一目的，该方法包括通过在水存在下蒸馏来进行分离。
己二腈的部分氢化或完全氢化可以根据任何已知方法进行，例如根据在US 4601859、US 2762835、US 2208598、DE-A 848654、DE-A 954416、DE-A 4235466、US-A 3696153、DE-A 9500222或WO92/21650中所述的上述方法之一进行，通常是在含镍、钴、铁或钌的催化剂存在下进行氢化。所用的催化剂可以是有载体或无载体的催化剂。可能的载体包括例如氧化铝、二氧化硅、二氧化钛、氧化镁、活性炭和尖晶石。无载体的催化剂的实例是Raney镍和Raney钴。
氢化生成了含有六亚甲基二胺和AMCPA的混合物，其中含或不含6-氨基己腈和己二腈。
由含六亚甲基二胺和AMCPA的混合物的分离可以以常规方式进行，优选以蒸馏方式进行，例如在DE-A 19500222或德国专利申请19548289.1中所述，在蒸馏塔中或在带有间壁的侧流接取塔(Petlyuk塔)中同时或逐级蒸馏，以便使在AMCPA去除时下游纯化塔的冷凝温度通常较高，减轻冷凝的困难。若存在低沸点的DACH，它可以方便地与AMCPA一起分离，但DACH的去除也可以在另一分馏塔的塔顶进行。
完全或部分去除可能存在的低沸点物，例如HMI，有利于本发明方法进行六亚甲基二胺的纯化。
在含六亚甲基二胺和AMCPA的混合物中，分离前AMCPA的重量比，按六亚甲基二胺计，一般为10-10000ppm，尤其是100-1000ppm，但本发明方法不受这些限制的约束。
AMCPA自混合物中的分离宜在1-1100毫巴、优选1-500毫巴的压力下用蒸馏法进行，这造成塔底温度为40-250℃。
蒸馏可以在例如Kirk-Othmer“化学工业百科全书”第3版第7卷，John Wiley & Sons，New York，1979 870-881页中所述的常用装置中进行，例如筛板塔、泡罩塔或填充塔。
使用低压降的蒸馏塔特别有利，优选每个理论塔板的压降不超过1毫巴，尤其是0.5毫巴。
特别合适的蒸馏是填充塔，优选带有排列好的填料，例如金属片填料，尤其是金属丝网填料。
根据本发明，向蒸馏混合物中加水，优选水量为蒸馏混合物重量的0.01-10％，尤其是0.1-5％。
水可以在蒸馏之前或在例如塔中蒸馏期间加到混合物中，优选加到进料口之下的区域，尤其是塔底区。
如果在含有六亚甲基二胺和AMCPA的混合物中存在，本发明一般是以与DACH和低沸点组分的混合物的形式得到为作为塔顶产物的AMCPA和水。
蒸馏可以在多个蒸馏塔如2或3个塔中进行，但最好在单塔中进行。
六亚甲基二胺可以用二羧酸如己二酸处理，形成工业上重要的聚合物。
Claims (6)
1.一种由含六亚甲基二胺和2-氨甲基环戊胺的混合物分离2-氨甲基环戊胺的方法，该方法包括利用在水存在下蒸馏进行分离。
2.权利要求1的方法，其中使用的蒸馏装置是蒸馏塔。
3.权利要求1或2的方法，其中使用的蒸馏装置是填料塔。
4.权利要求1至3中任一项的方法，其中使用的蒸馏装置是压降不超过每理论塔板1毫巴的蒸馏塔。
5.权利要求1至4中任一项的方法，其中以六亚甲基二胺为基础计的2-氨甲基环戊胺的分离前重量比为1-10000ppm。
6.权利要求1至5中任一项的方法，其中以六亚甲基二胺为基础计的2-氨甲基环戊胺的分离后重量比为0-100ppm。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19704618.5 | 1997-02-07 | ||
| DE19704618A DE19704618A1 (de) | 1997-02-07 | 1997-02-07 | Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminomethylcyclopentylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1251567A true CN1251567A (zh) | 2000-04-26 |
Family
ID=7819570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98803807A Pending CN1251567A (zh) | 1997-02-07 | 1998-01-17 | 由含有六亚甲基二胺和2－氨甲基环戊胺的混合物分离2－氨甲基环戊胺的方法 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0960094A1 (zh) |
| JP (1) | JP2001511163A (zh) |
| KR (1) | KR20000070888A (zh) |
| CN (1) | CN1251567A (zh) |
| AR (1) | AR011636A1 (zh) |
| AU (1) | AU6094798A (zh) |
| BR (1) | BR9807188A (zh) |
| CA (1) | CA2280830A1 (zh) |
| DE (1) | DE19704618A1 (zh) |
| WO (1) | WO1998034901A1 (zh) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB731819A (en) * | 1951-04-11 | 1955-06-15 | Du Pont | Improvements in or relating to the production of hexamethylene diamine and salts thereof |
| GB1125706A (en) * | 1965-01-20 | 1968-08-28 | Ici Ltd | Process for the production of hexamethylene diamine |
| DE1543973A1 (de) * | 1966-06-08 | 1970-02-05 | Vickers Zimmer Ag | Verfahren zur Reinigung von Hexamethylendiamin |
| CA915707A (en) * | 1969-07-11 | 1972-11-28 | J. Kershaw Bernard | Hydrogenation of adiponitrile |
| SU810669A1 (ru) * | 1978-12-06 | 1981-03-07 | Предприятие П/Я В-2609 | Способ очистки гексаметилендиа-МиНА |
-
1997
- 1997-02-07 DE DE19704618A patent/DE19704618A1/de not_active Withdrawn
-
1998
- 1998-01-17 CN CN98803807A patent/CN1251567A/zh active Pending
- 1998-01-17 AU AU60947/98A patent/AU6094798A/en not_active Abandoned
- 1998-01-17 JP JP53367398A patent/JP2001511163A/ja active Pending
- 1998-01-17 BR BR9807188-2A patent/BR9807188A/pt not_active Application Discontinuation
- 1998-01-17 CA CA002280830A patent/CA2280830A1/en not_active Abandoned
- 1998-01-17 KR KR1019997007153A patent/KR20000070888A/ko not_active Application Discontinuation
- 1998-01-17 WO PCT/EP1998/000241 patent/WO1998034901A1/de not_active Application Discontinuation
- 1998-01-17 EP EP98905307A patent/EP0960094A1/de not_active Withdrawn
- 1998-02-05 AR ARP980100510A patent/AR011636A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2280830A1 (en) | 1998-08-13 |
| EP0960094A1 (de) | 1999-12-01 |
| AR011636A1 (es) | 2000-08-30 |
| JP2001511163A (ja) | 2001-08-07 |
| AU6094798A (en) | 1998-08-26 |
| WO1998034901A1 (de) | 1998-08-13 |
| BR9807188A (pt) | 2000-01-25 |
| KR20000070888A (ko) | 2000-11-25 |
| DE19704618A1 (de) | 1998-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1315935A (zh) | 同时制备6－氨基己腈与六亚甲基二胺的改良方法 | |
| CN1171781A (zh) | 6－氨基己腈制备的粗己内酰胺的连续纯化方法 | |
| US6139693A (en) | Method for obtaining hexamethylene diamine from mixtures containing hexamethylene diamine | |
| US7141668B2 (en) | Process for recovering caprolactam | |
| US6300497B1 (en) | Method for separating an azepine derivative from a mixture containing an amine and an azepine derivative | |
| US7939691B2 (en) | Preparation of primary diamines | |
| CN1085199C (zh) | 从含有六亚甲基二胺和2－氨甲基环戊基胺的一种混合物分离2－氨甲基环戊基胺的方法 | |
| CN1251567A (zh) | 由含有六亚甲基二胺和2－氨甲基环戊胺的混合物分离2－氨甲基环戊胺的方法 | |
| US6252115B1 (en) | Method for separating an imine from a mixture containing an amine and an imine | |
| US6169199B1 (en) | Method for separating 6-aminocaproic acid nitrile from mixtures containing 6-aminocaproic acid nitrile and an imine | |
| CN1140501C (zh) | 从包含6-氨基己腈和亚胺的混合物中分离6-氨基己腈的方法 | |
| US8436212B2 (en) | Purification of impure hexamethylenediamines | |
| MXPA99007273A (en) | Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine | |
| MXPA99006690A (en) | Method for separating 6-aminocapronitrile from mixtures containing 6-aminocapronitrile and an imine | |
| MXPA99006740A (en) | Method for separating an imine from a mixture containing an amine and an imine | |
| MXPA99007272A (en) | Method for separating 6-aminocaproic acid nitrile from mixtures containing 6-aminocaproic acid nitrile and an imine | |
| MXPA00008163A (en) | Method for separating an azepine derivative from a mixture containing an amine and an azepine derivative | |
| JP2003221390A (ja) | ガンマブチロラクトンの精製方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |