CN1246108A - 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 - Google Patents
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 Download PDFInfo
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- CN1246108A CN1246108A CN98802139A CN98802139A CN1246108A CN 1246108 A CN1246108 A CN 1246108A CN 98802139 A CN98802139 A CN 98802139A CN 98802139 A CN98802139 A CN 98802139A CN 1246108 A CN1246108 A CN 1246108A
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- Prior art keywords
- aminocapronitrile
- mixture
- imines
- distillation
- desired method
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- 150000002466 imines Chemical class 0.000 title claims abstract description 32
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 14
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 8
- 235000011089 carbon dioxide Nutrition 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- -1 cyclic imide Chemical class 0.000 claims description 3
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 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
- 230000000052 comparative effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- JJNZXLAFIPKXIG-UHFFFAOYSA-N 2-Chlorobenzylidenemalononitrile Chemical compound ClC1=CC=CC=C1C=C(C#N)C#N JJNZXLAFIPKXIG-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GCNLQHANGFOQKY-UHFFFAOYSA-N [C+4].[O-2].[O-2].[Ti+4] Chemical compound [C+4].[O-2].[O-2].[Ti+4] GCNLQHANGFOQKY-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910010276 inorganic hydride Inorganic materials 0.000 description 1
- 150000002576 ketones 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- ICMWWNHDUZJFDW-DHODBPELSA-N oxymetholone Chemical compound C([C@@H]1CC2)C(=O)\C(=C/O)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 ICMWWNHDUZJFDW-DHODBPELSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 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
- 239000007787 solid Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Abstract
本发明公开了一种从包含6－氨基己腈和亚胺(Ⅱ)的混合物(Ⅰ)中蒸馏分离6－氨基己腈的方法,该方法包括在二氧化碳的存在下进行蒸馏。
Description
本发明涉及一种从包含6-氨基己腈和亚胺(II)的混合物(I)中蒸馏分离6-氨基己腈的方法。
在基于镍、钴、铁、铑或钌之类金属的催化剂的存在下，己二腈可部分氢化成6-氨基己腈，这通常可，例如从EP-A-161419、EP-A-77911、US-A-4389348、US-A-4601859、WO 93/1207、DE-A-4235466、DE-A-19500222和德国专利申请19548289.1中得知。
副产物包括亚胺，尤其是具有以下结构式的四氢吖庚因(THA)。
6-氨基己腈通过己内酰胺作为中间体或通过直接聚合反应成尼龙-6而主要用于制造纤维。为此，6-氨基己腈必须特别纯，在这一点上，已知去除THA存在问题。
US-A-5162567披露了在高温下，将包含6-氨基己腈和THA的混合物与有机羰基化合物，如酮或醛进行反应；然后从反应混合物中分离6-氨基己腈。US-A-5153351披露了将包含6-氨基己腈和THA的混合物与有机活性-CH亚甲基化合物，如丙二腈、环戊二烯、硝基甲烷或硝基乙烷进行反应；然后从混合物中分离6-氨基己腈。这些方法的缺点在于，向混合物中加入其它的有机化合物将难以制备出纯6-氨基己腈。
在US-A-5133838中，包含6-氨基己腈和THA的混合物与无机氢化物，如硼氢化锂进行反应。在该方法中，不利的是，必须使用超过化学计量所需量的大量氢化物。此外，在随后的蒸馏过程中，必须小心以防将有价值产品6-氨基己腈氢化。
EP-A-497333描述了一种方法，其中将包含6-氨基己腈和THA的混合物与碱性化合物进行反应。不利的是，必须使用超过化学计量所需量的碱性化合物，而且必须在极低的压力下从所得反应混合物中蒸馏出6-氨基己腈。
本发明的一个目的是提供一种技术上简单且经济的从主要包含6-氨基己腈和THA的混合物中分离6-氨基己腈的方法，该方法克服了前述的缺点。
已经发现，该目的可通过一种从包含6-氨基己腈和亚胺(II)的混合物(I)中蒸馏分离6-氨基己腈的方法而实现，该方法包括在二氧化碳的存在下进行蒸馏。
混合物(I)可按照常规方式，通过ADN的部分氢化，例如按照EP-A-161419、EP-A-77911、US-A-4389348、US-A-4601859、WO 93/1207、DE-A-4235466、DE-A-19500222和德国专利申请19548289.1中所描述的方法，一般在含镍、钴、铁、铑或钌的催化剂的存在下，通过氢化反应而得到。所用催化剂可以是载体上的催化剂或非载体催化剂。催化剂载体包括，例如氧化铝、二氧化硅、二氧化钛、氧化镁、活性炭和尖晶石。非载体催化剂例子为阮内镍和阮内钴。
通过氢化可得到包含6-氨基己腈、HMD和亚胺(II)的混合物，其中有或没有ADN。可例如，通过蒸馏从该混合物中得到主要包含6-氨基己腈和亚胺(II)的混合物(I)。
合适的亚胺(II)选自芳族，优选脂族，如无环的或尤其环状的亚胺、及其混合物，特别优选THA。
亚胺(II)可作为单独的化合物或作为，例如与6-氨基己腈之类胺的加成物存在于混合物(I)中，这时本文中的亚胺(II)也包括这些加成物。
二氧化碳可在蒸馏之前，优选在蒸馏时加入蒸馏混合物中，其形式为可在蒸馏条件下释放出二氧化碳的化合物，如碳酸铵、氨基甲酸铵或尿素、或其混合物，这时这些化合物的加入形式可以纯净态；或在液体稀释剂中作为混合物(I)的一种或多种组分；或固体、液体、或优选气态二氧化碳，例如包含二氧化碳的气体，或尤其是仅包含常规杂质的纯气态二氧化碳。
有利的是，蒸馏混合物中的二氧化碳含量应该为每摩尔的亚胺(II)的亚胺官能度，从0.1-1摩尔二氧化碳。
一般来说，为此可以考虑0.022-0.22标准立方米/千克亚胺。
合适的蒸馏装置包括以下所描述的任何常规装置：Kirk-Othmer，化学技术百科全书，第3版，第7卷，John Willey&Sons，New York，1979，第870-881页，如阀片柱、筛板柱、或填充有散装填料或排列填料的柱。
蒸馏有利地在10-100毫巴，优选20-50毫巴下进行。
实施例
在蒸馏柱(直径43毫米，高2.4米，Sulzer CY Fabric packing，22个理论板)中，以5∶1的回流比，将具有表所示THA含量(％重量，基于混合物)的6-氨基已腈进行间歇分馏。得到作为馏出物的纯化6-氨基已腈。结果示于表1。
| 本发明实施例1 | 本发明实施例2 | 本发明实施例3 | 对比例1 | 对比例2 | |
| 6-氨基已腈的THA含量，％ | 1.97 | 0.87 | 0.86 | 1.8 | 1.81 |
| 粗6-氨基已腈的加入量，克 | 1502 | 1487 | 1503 | 1440 | 1494 |
| 压力[毫巴] | 20 | 20 | 20 | 50 | 20 |
| 底部温度[℃] | 136 | 135 | 136 | 148 | 137 |
| 二氧化碳加料速率，标准升/小时 | 5 | 8 | 10 | 0 | 0 |
| THA的含量馏出物，％减少百分数，％底部产物，％ | 0.76618 | 0.27698.7 | 0.247211.7 | 1.3289.5 | 1.4226.3 |
| 馏出物，克 | 1389 | 1454 | 1434 | 1246 | 1351 |
| 底部产物，克 | 111 | 33 | 33 | 100 | 136 |
Claims (8)
1.一种从包含6-氨基己腈和亚胺(II)的混合物(I)中蒸馏分离6-氨基己腈的方法，该方法包括在二氧化碳的存在下进行蒸馏。
2.根据权利要求1所要求的方法，其中所述亚胺(II)为环状亚胺。
3.根据权利要求1或2所要求的方法，其中所述亚胺(II)为四氢吖庚因。
4.根据权利要求1-3中任何一项所要求的方法，其中所述蒸馏混合物中的二氧化碳含量为每摩尔亚胺(II)的亚胺官能度，从0.1-1摩尔二氧化碳。
5.根据权利要求1-4中任何一项所要求的方法，其中将包含二氧化碳的气体加入蒸馏柱的底部。
6.根据权利要求1-5中任何一项所要求的方法，其中所述蒸馏在10-100毫巴，优选20-50毫巴下进行。
7.根据权利要求1-6中任何一项所要求的方法，其中所述蒸馏混合物中已加入了一种能够在蒸馏条件下释放二氧化碳的化合物(III)。
8.根据权利要求1-7中任何一项所要求的方法，其中所述化合物(III)为尿素、碳酸铵、氨基甲酸铵、或其混合物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19704620.7 | 1997-02-07 | ||
| DE19704620A DE19704620A1 (de) | 1997-02-07 | 1997-02-07 | Verfahren zur Abtrennung von 6-Aminocapronitril aus Mischungen, die 6-Aminocapronitril und ein Imin enthalten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1246108A true CN1246108A (zh) | 2000-03-01 |
| CN1140501C CN1140501C (zh) | 2004-03-03 |
Family
ID=7819572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB988021390A Expired - Fee Related CN1140501C (zh) | 1997-02-07 | 1998-01-17 | 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 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6204408B1 (zh) |
| EP (1) | EP0963369B1 (zh) |
| JP (1) | JP2001510476A (zh) |
| KR (1) | KR100515226B1 (zh) |
| CN (1) | CN1140501C (zh) |
| AU (1) | AU6210898A (zh) |
| CA (1) | CA2279172A1 (zh) |
| CZ (1) | CZ275099A3 (zh) |
| DE (2) | DE19704620A1 (zh) |
| ES (1) | ES2163251T3 (zh) |
| ID (1) | ID22685A (zh) |
| MY (1) | MY120723A (zh) |
| TR (1) | TR199901895T2 (zh) |
| TW (1) | TW490453B (zh) |
| WO (1) | WO1998034911A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2353506A1 (en) * | 1998-11-02 | 2000-05-11 | 3M Innovative Properties Company | Transparent conductive oxides for plastic flat panel displays |
| DE10010825A1 (de) * | 2000-03-08 | 2001-09-13 | Basf Ag | Verfahren zur Abtrennung eines Azepin-Derivats aus einer Mischung enthaltend ein Amin und ein Azepin-Derivat |
| EP2125361B1 (en) * | 2006-12-28 | 2019-01-23 | 3M Innovative Properties Company | Nucleation layer for thin film metal layer formation |
| US8350451B2 (en) * | 2008-06-05 | 2013-01-08 | 3M Innovative Properties Company | Ultrathin transparent EMI shielding film comprising a polymer basecoat and crosslinked polymer transparent dielectric layer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4389348A (en) | 1981-10-26 | 1983-06-21 | Allied Corporation | Selective hydrogenation of dinitrile to omega-aminonitrile and supported rhodium-containing catalyst therefor |
| US4601859A (en) | 1984-05-04 | 1986-07-22 | Allied Corporation | Selective hydrogenation of aliphatic dinitriles to omega-aminonitriles in ammonia with supported, finely dispersed rhodium-containing catalyst |
| 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 |
| WO1993001207A1 (en) | 1991-07-12 | 1993-01-21 | Gist-Brocades N.V. | Process for the purification of serum albumin |
| US5153351A (en) | 1992-01-06 | 1992-10-06 | E. I. Du Pont De Nemours And Company | Removal of tetrahydroazepine (tha) from 6-aminocapronitrile by reaction with reactive methylene compounds |
| US5162567A (en) | 1992-02-27 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Purification of 6-aminocapronitrile |
| DE4235466A1 (de) | 1992-10-21 | 1994-04-28 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Aminonitrilen |
| DE19500222A1 (de) | 1995-01-05 | 1996-07-11 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von Caprolactam und Hexamethylendiamin |
| DE19548289A1 (de) | 1995-12-22 | 1997-06-26 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von Caprolactam und Hexamethylendiamin |
-
1997
- 1997-02-07 DE DE19704620A patent/DE19704620A1/de not_active Withdrawn
-
1998
- 1998-01-17 DE DE59801387T patent/DE59801387D1/de not_active Expired - Lifetime
- 1998-01-17 CN CNB988021390A patent/CN1140501C/zh not_active Expired - Fee Related
- 1998-01-17 CZ CZ992750A patent/CZ275099A3/cs unknown
- 1998-01-17 ES ES98904088T patent/ES2163251T3/es not_active Expired - Lifetime
- 1998-01-17 WO PCT/EP1998/000243 patent/WO1998034911A1/de active IP Right Grant
- 1998-01-17 AU AU62108/98A patent/AU6210898A/en not_active Abandoned
- 1998-01-17 CA CA002279172A patent/CA2279172A1/en not_active Abandoned
- 1998-01-17 JP JP53367598A patent/JP2001510476A/ja not_active Withdrawn
- 1998-01-17 EP EP98904088A patent/EP0963369B1/de not_active Expired - Lifetime
- 1998-01-17 KR KR10-1999-7007096A patent/KR100515226B1/ko not_active IP Right Cessation
- 1998-01-17 TR TR1999/01895T patent/TR199901895T2/xx unknown
- 1998-01-17 US US09/341,946 patent/US6204408B1/en not_active Expired - Lifetime
- 1998-01-17 ID IDW990802A patent/ID22685A/id unknown
- 1998-02-06 MY MYPI98000472A patent/MY120723A/en unknown
- 1998-02-07 TW TW087101637A patent/TW490453B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001510476A (ja) | 2001-07-31 |
| ES2163251T3 (es) | 2002-01-16 |
| CN1140501C (zh) | 2004-03-03 |
| DE19704620A1 (de) | 1998-08-13 |
| EP0963369B1 (de) | 2001-09-05 |
| TW490453B (en) | 2002-06-11 |
| EP0963369A1 (de) | 1999-12-15 |
| ID22685A (id) | 1999-12-09 |
| CA2279172A1 (en) | 1998-08-13 |
| KR20000070833A (ko) | 2000-11-25 |
| WO1998034911A1 (de) | 1998-08-13 |
| KR100515226B1 (ko) | 2005-09-16 |
| CZ275099A3 (cs) | 1999-12-15 |
| US6204408B1 (en) | 2001-03-20 |
| DE59801387D1 (de) | 2001-10-11 |
| MY120723A (en) | 2005-11-30 |
| TR199901895T2 (xx) | 2000-04-21 |
| AU6210898A (en) | 1998-08-26 |
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