CN1230170A - 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 - Google Patents
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 Download PDFInfo
- Publication number
- CN1230170A CN1230170A CN97197770A CN97197770A CN1230170A CN 1230170 A CN1230170 A CN 1230170A CN 97197770 A CN97197770 A CN 97197770A CN 97197770 A CN97197770 A CN 97197770A CN 1230170 A CN1230170 A CN 1230170A
- Authority
- CN
- China
- Prior art keywords
- tower
- diamine
- hexamethylene
- millibar
- pressure
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 238000000926 separation method Methods 0.000 title claims abstract description 12
- 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 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 50
- -1 2-aminomethyl cyclopentyl Chemical group 0.000 claims description 9
- 241000282326 Felis catus Species 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QLNNMIUPRPKARZ-UHFFFAOYSA-N n'-cyclopentylmethanediamine Chemical compound NCNC1CCCC1 QLNNMIUPRPKARZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 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 4
- 239000003054 catalyst Substances 0.000 description 4
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 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
- 239000000945 filler Substances 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
- 239000006227 byproduct Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002349 favourable effect Effects 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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition 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
- C07C209/86—Separation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/11—Batch distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种从含有六亚甲基二胺和2-氨甲基环戊基胺的混合物分离2-氨甲基环戊基胺的方法,该方法特征在于1—300毫巴的压力下通过蒸馏进行分离。
Description
本发明涉及从含有六亚甲基二胺和2-氨甲基环戊基胺(AMCPA)的一种混合物分离2-氨甲基环戊基胺的方法。
在基于金属如镍、钴、铁、铑或钌的催化剂存在下己二腈向六亚甲基二胺的完全氢化以及得到六亚甲基二胺和6-氨基己腈的部分氢化一般在例如下列文献中被公知:K.weissermel,H.-J.Arpe,Industrielle Organische Chemie,第三版,VCH VerlagsgesellschaftmbH,Weinheim,1988,第266页,US-A-4601859,US-A-2762835,US-A-2208598,DE-A-848654,DE-A-954416,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)和氨甲基环戊基胺(AMCPA)。
US-A-3696153揭示通过这种氢化得到六亚甲基二胺,其含有非常困难从混合物中分离的AMCPA副产物。
本发明的任务是提供了一种用简单的技术和经济的方式从主要含有六亚甲基二胺和AMCPA的混合物中分离AMCPA的方法。
我们已经发现本发明的目的通过从含有六亚甲基二胺和2-氨甲基环戊基胺的混合物分离2-氨甲基环戊基胺的方法实现,该方法包括在1-300毫巴压力下通过蒸馏进行分离。
己二腈的部分或者完全氢化可以根据任何一种已知方法进行,例如根据一种前面提到的描述在US-A-4601859,US-A-2762835,US-A-2208598,DE-A-848654,DE-A-954416,DE-A-4235466,US-A-3696153,DE-A-9500222或WO92/21650中的方法,通常是,在含镍、钴、铁或钌催化剂存在下进行氢化。使用的催化剂可以是载体催化剂或者非载体催化剂。作为催化剂的载体包括有,例如,氧化铝,二氧化硅,二氧化钛,氧化镁,活性炭和尖晶石。非载体催化剂的实例是拉尼镍和拉尼钴。
氢化获得一种混合物,该混合物含有六亚甲基二胺和AMCPA以及含有或者不合6-氨基己腈和己二腈。
从含有六亚甲基二胺和AMCPA的混合物的分离可以用常规方法进行,优选进行蒸馏,例如按照DE-A-19500222或德国专利申请19548289.1,同时或者连续地进行蒸馏,例如在蒸馏塔中或者在有间壁的支流取出塔(petlyuk塔)中进行,以使除去AMCPA时的下流物流提纯塔的冷凝温度通常较高,冷凝容易进行。如果存在低沸点的DACH,其可以有利地与AMCPA同时分离除去,但是除去DACH也可以在分离塔的塔顶进行。
如果存在的话,进行六亚甲基二胺的提纯之前,将有利地根据本发明的方法完全或者部分除去低沸点次要成份,如HMI。
在含六亚甲基二胺和AMCPA的混合物中,基于六亚甲基二胺的AMCPA的分离前重量比的范围通常是10-10000ppm,尤其是100-1000ppm,在此本发明的方法并不受这些限制。
根据本发明从混合物中分离AMCPA蒸馏的压力为1-300毫巴,优选1-200毫巴的压力下通过蒸馏进行,该压力范围导致底部温度范围是40-160℃。
蒸馏可以考虑在常规的装置中进行,如描述在例如:Kirk-other,《化工技术百科全书》,第三版,第7卷,Johm Wiley &S ons,New York,1979,第870-881页中的装置,如筛板塔,泡罩塔或填充塔。
优选给定的蒸馏装置从塔底至塔顶的压力降范围是0-200毫巴,优选0-50毫巴,有利的压力范围在塔底是3-300毫巴,尤其是3-200毫巴,在塔顶是1-300毫巴,尤其是1-200毫巴。
特别有利的是使用具有低的压力损失,优选每个理论塔板不超过1毫巴,尤其是0.5毫巴的蒸馏塔。
尤其适合的塔是填充塔,优选用排列填料如金属薄片填料,尤其是编织金属丝填料的填充塔。
本发明的方法得到作为塔顶产物的AMCPA,通常是,如果存在的话,则在混合物中含六亚甲基二胺和AMCPA,在混合物中含有DACH和低沸点组分。
蒸馏可以在多个塔中,如2或3个塔中进行,但是优选在一个塔中进行。
六亚甲基二胺可以用二元羧酸如己二酸处理成工业上重要的聚合物。
实施例
实施例1
将具有300ppm AMCPA含量的10千克/小时的HMD注入具有低的压力损失的相应于100理论塔板的编织丝填料塔中。调节塔顶至压力100毫巴,测定塔底的压力为140毫巴。在塔顶,固定将6克/小时产物转移,将50千克/小时作为物流循环至塔中回流。
作为塔底产物得到的六亚甲基二胺中的AMCPA的含量低于1ppm的检测限度,塔顶产物的六亚甲基二胺的含量是50.2%(重量)。
实施例2
除了将塔顶压力调节至250毫巴和塔底压力测定为305毫巴之外,重复发明实施例1。
作为塔底产物得到的六亚甲基二胺中的AMCPA的含量是11ppm,塔顶产物的六亚甲基二胺的含量是51.9%(重量)。
实施例3
除了将塔顶压力调节至500毫巴和塔底压力测定为545毫巴之外,重复发明实施例1。
作为塔底产物得到的六亚甲基二胺中的AMCPA的含量是48ppm,塔顶产物的六亚甲基二胺的含量是58.2%(重量)。
实施例4
将具有300ppm AMCPA含量的10千克/小时的HMD注入具有140块筛板的筛板塔中。调节塔顶至压力100毫巴,测定塔底的压力为900毫巴。在塔顶,固定将6克/小时产物转移,将50千克/小时物流循环至塔中回流。
作为塔底产物得到的六亚甲基二胺中的AMCPA的含量低于22ppm的检测限度,塔顶产物的六亚甲基二胺的含量是53.7%(重量)。
Claims (9)
1.一种从含有六亚甲基二胺和2氨甲基环戊基胺的混合物分离2-氨甲基环戊基胺的方法,该方法的特征在于,1-300毫巴的压力下通过蒸馏进行分离。
2.根据权利要求1的方法,其中蒸馏装置中塔顶与塔底之间的压力损失范围是0-200毫巴。
3.根据权利要求1或2的方法,其中蒸馏装置的塔底压力范围是3-300毫巴。
4.根据权利要求1-3之一的方法,其中蒸馏装置的塔顶压力范围是1-300毫巴。
5.根据权利要求1-4之一的方法,其中使用的蒸馏装置是蒸馏塔。
6.根据权利要求1-5之一的方法,其中使用的蒸馏装置是填充塔。
7.根据权利要求1-6之一的方法,其中使用的蒸馏装置是每个理论塔板具有的压力损失不超过1毫巴的蒸馏塔。
8.根据权利要求1-7之一的方法,其中基于六亚甲基二胺的分离前的2-氨甲基环戊基胺的重量比范围是1-10000ppm。
9.根据权利要求1-8之一的方法,其中基于六亚甲基二胺的分离后的2-氨甲基环戊基胺的重量比范围是0-100ppm。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19636764.6 | 1996-09-10 | ||
DE1996136764 DE19636764A1 (de) | 1996-09-10 | 1996-09-10 | Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend im wesentlichen Hexamethylendiamin und 2-Aminomethylcyclopentylamin |
DE19704617.7 | 1997-02-07 | ||
DE19704617A DE19704617A1 (de) | 1997-02-07 | 1997-02-07 | Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminomethylcyclopentylamin |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1230170A true CN1230170A (zh) | 1999-09-29 |
CN1085199C CN1085199C (zh) | 2002-05-22 |
Family
ID=26029224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97197770A Ceased CN1085199C (zh) | 1996-09-10 | 1997-08-28 | 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 |
Country Status (16)
Country | Link |
---|---|
US (1) | US6251229B1 (zh) |
EP (1) | EP0931054B2 (zh) |
JP (1) | JP2001500139A (zh) |
KR (1) | KR100480409B1 (zh) |
CN (1) | CN1085199C (zh) |
AU (1) | AU4456397A (zh) |
BR (1) | BR9711729A (zh) |
CA (1) | CA2265436C (zh) |
CZ (1) | CZ79699A3 (zh) |
DE (1) | DE59710180D1 (zh) |
ES (1) | ES2200196T3 (zh) |
ID (1) | ID18460A (zh) |
MY (1) | MY118008A (zh) |
TR (1) | TR199900517T2 (zh) |
TW (1) | TW375603B (zh) |
WO (1) | WO1998011052A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111788175A (zh) * | 2018-02-27 | 2020-10-16 | 巴斯夫欧洲公司 | 用于从含脂族伯二胺的混合物中分离链烷醇胺的方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2465811A1 (en) * | 2001-11-16 | 2003-05-22 | Basf Aktiengesellschaft | Method for isolating amines from aqueous solutions |
US6599398B1 (en) * | 2002-07-17 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Recovery of adiponitrile from a mixture of adiponitrile, aminocapronitrile and hexamethylenediamine |
US6924394B2 (en) * | 2003-06-05 | 2005-08-02 | Invista North America S.R.L. | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
EP2137122A1 (en) * | 2007-04-12 | 2009-12-30 | Dow Global Technologies Inc. | Process and apparatus for reducing heavy byproduct formation during recovery of dichlorohydrins |
EP2484421A1 (de) * | 2011-02-07 | 2012-08-08 | Basf Se | Verfahren zur Abtrennung von leichtsiedenden Komponenten aus einem Hexamethylendiamin enthaltenden Gemisch |
Family Cites Families (9)
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 |
CA915707A (en) * | 1969-07-11 | 1972-11-28 | J. Kershaw Bernard | Hydrogenation of adiponitrile |
US3775258A (en) * | 1972-04-27 | 1973-11-27 | Du Pont Canada | Purification of adiponitrile |
SU810669A1 (ru) * | 1978-12-06 | 1981-03-07 | Предприятие П/Я В-2609 | Способ очистки гексаметилендиа-МиНА |
FR2623801B1 (fr) * | 1987-11-30 | 1990-04-20 | Rhone Poulenc Chimie | Procede de purification de l'hexamethylenediamine |
US5192399A (en) * | 1991-01-30 | 1993-03-09 | E. I. Du Pont De Nemours And Company | Purification of aminonitriles or diamines |
US5133838A (en) * | 1991-02-28 | 1992-07-28 | E. I. Du Pont De Nemours And Company | Purification of 6-aminocapronitrile |
DE19704612A1 (de) * | 1997-02-07 | 1998-08-13 | Basf Ag | Verfahren zur Gewinnung von Hexamethylendiamin aus Hexamethylendiamin enthaltenden Mischungen |
US5961788A (en) * | 1998-10-09 | 1999-10-05 | E. I. Du Pont De Nemours And Company | Sequential distillation process for removing tetrahydroazepine from aminocapronitrile and/or hexamethylenediamine |
-
1997
- 1997-08-28 TR TR1999/00517T patent/TR199900517T2/xx unknown
- 1997-08-28 WO PCT/EP1997/004687 patent/WO1998011052A1/de active IP Right Grant
- 1997-08-28 AU AU44563/97A patent/AU4456397A/en not_active Abandoned
- 1997-08-28 EP EP97942889A patent/EP0931054B2/de not_active Expired - Lifetime
- 1997-08-28 CZ CZ99796A patent/CZ79699A3/cs unknown
- 1997-08-28 US US09/254,560 patent/US6251229B1/en not_active Expired - Lifetime
- 1997-08-28 DE DE59710180T patent/DE59710180D1/de not_active Expired - Lifetime
- 1997-08-28 CN CN97197770A patent/CN1085199C/zh not_active Ceased
- 1997-08-28 BR BR9711729A patent/BR9711729A/pt not_active IP Right Cessation
- 1997-08-28 JP JP10513197A patent/JP2001500139A/ja not_active Withdrawn
- 1997-08-28 KR KR10-1999-7001941A patent/KR100480409B1/ko not_active IP Right Cessation
- 1997-08-28 ES ES97942889T patent/ES2200196T3/es not_active Expired - Lifetime
- 1997-08-28 CA CA002265436A patent/CA2265436C/en not_active Expired - Fee Related
- 1997-09-09 TW TW086113037A patent/TW375603B/zh active
- 1997-09-09 MY MYPI97004168A patent/MY118008A/en unknown
- 1997-09-10 ID IDP973144A patent/ID18460A/id unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111788175A (zh) * | 2018-02-27 | 2020-10-16 | 巴斯夫欧洲公司 | 用于从含脂族伯二胺的混合物中分离链烷醇胺的方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100480409B1 (ko) | 2005-04-06 |
MY118008A (en) | 2004-08-30 |
US6251229B1 (en) | 2001-06-26 |
TR199900517T2 (xx) | 1999-07-21 |
EP0931054A1 (de) | 1999-07-28 |
ID18460A (id) | 1998-04-09 |
BR9711729A (pt) | 1999-08-24 |
TW375603B (en) | 1999-12-01 |
CA2265436C (en) | 2006-03-28 |
DE59710180D1 (de) | 2003-07-03 |
EP0931054B1 (de) | 2003-05-28 |
CN1085199C (zh) | 2002-05-22 |
JP2001500139A (ja) | 2001-01-09 |
AU4456397A (en) | 1998-04-02 |
EP0931054B2 (de) | 2012-07-11 |
KR20000035989A (ko) | 2000-06-26 |
CA2265436A1 (en) | 1998-03-19 |
WO1998011052A1 (de) | 1998-03-19 |
CZ79699A3 (cs) | 1999-06-16 |
ES2200196T3 (es) | 2004-03-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100351227C (zh) | 制备并分离二腈化合物的方法 | |
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 | |
EP1261580B1 (de) | Verfahren zur abtrennung eines azepin-derivats aus einer mischung enthaltend ein amin und ein azepin-derivat | |
CN1461295A (zh) | 分离戊烯腈异构体的方法 | |
EP1786760B1 (en) | Separation of 6-aminocapronitrile and hexamethylenediamine from a mixture comprising hexamethylenediamine, 6-aminocapronitrle and tetrahydroazepine | |
TW512139B (en) | Process for recovery of hexamethylendiamine from mixtures containing same | |
EP2581364B1 (en) | Separation of 6-aminocapronitrile and hexamethylenediamine from a mixture comprising hexamethylenediamine, 6-aminocapronitrile and tetrahydroazepinne | |
US6300497B1 (en) | Method for separating an azepine derivative from a mixture containing an amine and an azepine derivative | |
US6252115B1 (en) | Method for separating an imine from a mixture containing an amine and an imine | |
US7939691B2 (en) | Preparation of primary diamines | |
TW200418760A (en) | Distillative method for separating hexamethylenediamine from a mixture comprising hexamethylenediamine, -aminocapronitrile and tetrahydroazepine | |
CN1211354C (zh) | 从含有6-氨基己腈、己二腈和六亚甲基二胺的混合物中分离6-氨基己腈的方法 | |
CN1152856C (zh) | 从含6-氨基己腈和亚胺的混合物中分离6-氨基己腈的方法 | |
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 | |
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 | |
CN1215058C (zh) | 一种从酰胺中分离酮肟或醛肟的方法 | |
US20100292511A1 (en) | Purification of impure hexamethylenediamines | |
MXPA99007273A (en) | Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine | |
MXPA00008163A (en) | Method for separating an azepine derivative from a mixture containing an amine and an azepine derivative | |
CN104203894A (zh) | 高纯度非黄变(甲基)丙烯酸的制备方法 | |
MXPA99006740A (en) | Method for separating an imine from a mixture containing an amine and an imine | |
EP0320879A1 (en) | Separating toluenediamine from N-tertiarybutyl toluenediamine | |
MXPA99006690A (en) | Method for separating 6-aminocapronitrile from mixtures containing 6-aminocapronitrile and an imine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: BASF SE Free format text: FORMER NAME: BASF AG |
|
CP01 | Change in the name or title of a patent holder |
Address after: Ludwigshafen, Germany Patentee after: BASF SE Address before: Ludwigshafen, Germany Patentee before: BASF AG |
|
C35 | Partial or whole invalidation of patent or utility model | ||
IW01 | Full invalidation of patent right |
Decision date of declaring invalidation: 20141114 Decision number of declaring invalidation: 24323 Granted publication date: 20020522 |