CN1318386C - 无色二苄胺的制备 - Google Patents
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- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims 2
- 238000011105 stabilization Methods 0.000 claims 2
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical class C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- BTDHNWBIBZPIDZ-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH+](CC=1C=CC=CC=1)CC1=CC=CC=C1 BTDHNWBIBZPIDZ-UHFFFAOYSA-N 0.000 description 1
- MIYKHJXFICMPOJ-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1CN=CC1=CC=CC=C1 MIYKHJXFICMPOJ-UHFFFAOYSA-N 0.000 description 1
- -1 phenyl aldehyde Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
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- 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及制备无色二苄胺的方法，包括在工业获得的二苄胺中加入氯化铵或胺并随后蒸馏。
Description
发明背景
发明领域
本发明涉及通过在工业生产的二苄胺中加入氯化铵和/或胺随后蒸馏制备无色二苄胺的新颖方法。
背景技术
已知，制备二苄胺的方法在技术质量已成熟。二苄胺工业上可以由苄腈或苯甲酰胺通过催化剂加氢来制备。也可以由苄腈或苯甲酰胺或由苄胺或氨和苯甲醛通过还原胺化来制备(EP-A-644177)。二苄胺还可以作为苄基氯与氨反应得到苄胺的副产物得到(Ullmann，苄胺；Itsuno S，Koizumi T，Okumonia C，Ito K，Synthesis，(2)，p.150-152，1995)。这些方法一般使用在掺混溶剂或稀释剂的反应混合物中的反应物。
为获得要求的产物，通常必须蒸馏除去副产物、溶剂和其它次要组分。然而，这种方式获得的二苄胺为有色的。通过现有技术毫无问题地制备Hazen色数大于100的二苄胺。然而，当寻求制备无色二苄胺时，即二苄的色数小于100，需要重复蒸馏。现有方法制备的二苄胺稳定性低且易于分解同时变色。
如认识到的，使用二苄胺时的变色对于制备用于塑料的稳定剂是不利的。
发明概述
本发明的目的是提供制备无色二苄胺的方法，因此而避免重复蒸馏。获得的二苄胺具有高稳定性。
根据前面所述，本发明包括一种制备色数小于100 Hazen的无色二苄胺的方法，其特征是在需提纯的二苄胺中加入选自氯化铵和/或胺的添加剂并随后蒸馏该混合物。按照这种方式获得的无色二苄胺具有高稳定性。
发明详细描述
下面参考较好实施方案详细地描述本发明。
用于本发明方法的氯化铵对应于下面通式：
R1R2R3N-HCl
其中，R1、R2和R3各自独立地是H或有机基团。
有机基团是C1-C6脂族基团或苄基。较好是苄基或H。
由上式表示的氯化铵类中，较好是氯化铵(NH4Cl)或苄基-二苄胺盐酸盐的混合物。例子包括氯化铵如盐酸盐、氯化铵(NH4Cl)或其相关化合物、或含水的或无水的氢氯酸和苄基氯。优选为苄基-二苄基铵盐酸盐。最好是氯化铵(NH4Cl)。
在此使用的胺是挥发性较低，能几乎全部留在蒸馏残余物中的那些胺。用于本发明方法的胺的例子包括高沸点胺如四亚乙基五胺(TEPA)或其蒸馏残余物、六亚乙基七胺(HEPA)或其蒸馏残余物、五亚乙基六胺(PEHA)或其蒸馏残余物、它们的混合物或与更高或较低沸点同型物的混合物。
对本发明目的，“高沸点胺”是指在相关条件具有高于二苄胺沸点的那些胺。
就其化学组成和可获得的市售产品，所述的氯化铵和胺类物质本身为已知。较好是使用五亚乙基六胺(PEHA)和四亚乙基五胺(TEPA)的蒸馏残余物，最好是五亚乙基六胺(PEHA)。
胺也包括多胺，由具有端胺官能团的饱和烃链组成，中间插有不同数量的仲胺和/或叔胺和/或季胺官能团。
本发明方法宜使用选自下列的多胺；二氯乙烷与氮和/或来自吖丙啶聚合的其它胺的反应产物、或环氧乙烷与氨或胺的反应产物。这些产物一般是水可溶的/水可混溶的液体或固体水合物。
最好是具有对应于下式(I)或(II)之一的多胺：
Hp-N(CH2-CH2)q-[NHr-(CH2-CH2)s]n-NHt (I)
NH2-CH2-CH2-CH2-[NHr-(CH2-CH2-CH2)s]n-NHt (II)
其中，“n”是0或0-300的整数，
p、q、s和t各自独立地是1和/或2，
r是0或1，使氮在各种情况下为三键合(triply)，偶尔为四键合(quadruply)(铵盐)。
这些胺可以游离胺或盐，较好是以氯化物存在。也可以通过进一步反应试剂例如随后与二氯乙烷、吖丙啶或丙烯腈反应，任选接着进行还原，交联或分支。
按照本发明，可以使用选自氯化铵或胺的化合物作为添加剂。
以二苄胺为基准，添加剂在需提纯的二苄胺中的加入浓度为0.01-15重量％，较好为0.1-3重量％。
宜控制二苄胺的蒸馏，使底部温度为120-220℃，较好为160-200℃。压力设定为使混合物的在上述温度条件下沸腾。压力一般设定在100-0.1mbar，较好为50-5mbar。在首次脱色操作后，产物为色数＜100 Hazen的纯的二苄胺。
这种方法能够可靠地得到小于100 Hazen的色数。观察到产物的色数一般＜30Hazen(无色)，更多的色数＜10 Hazen。
对本发明目的，色数是对透明物质的颜色在标准条件下测定的特征值，可由肉眼比较决定。用标准色表比较获得这种特征值，例如按照DIN EN 1557(1997年3月)或与标准溶液进行比较。
为使纯的二苄胺稳定，可将其储存在氮气中。除了氮气，加入肼(含水或无水)或羟胺(含水或无水)可以明显增加储存时间且色数没有变化或仅有很小变化。添加剂肼和羟胺可以单独使用或以混合物使用，以纯二苄胺为基准，添加剂浓度为0.01-10.0重量％。
下面以实施例说明本发明的方法，实施例中，百分数为重量百分数。
实施例
591克来自制备二苄胺的侧线流与2.2克氯化铵和7.5克五亚乙基六胺混合并加热至200℃，该侧线流包含0.1％水、18％苄胺、0.5％苄醇、77.9％二苄胺以及0.7％亚苄基苄胺和约3％的其它组分。
分馏后，获得423克(理论值的92％)的二苄胺，其色数为11Hazen，纯度为99.74％。按照DIN EN 1557用Dr.Lange in Dusseldorf的仪器纯度色数。
该产物在氮气中与羟胺(0.04％)混合且是储存稳定的。在60℃储存28天色数增大至30 Hazen。没有羟胺作为稳定性，28天色数增至90 Hazen。
尽管以说明的目的详细描述了本发明，但是，应理解这些详细描述近用于此说明目的，本领域技术人员在不偏离由权利要求限定的本发明精神和范围内，可以对其进行各种变动。
Claims (11)
1.制备色数小于100 Hazen的二苄胺的方法，该方法包括在需提纯的二苄胺中加入选自氯化铵盐和胺的添加剂并蒸馏该混合物。
2.如权利要求1所述的方法，其特征在于所述氯化铵盐对应于下式：
R1R2R3N-HCl
其中，R1、R2和R3各自独立地是H或有机基团，
该有机基团是C1-C6脂族基团或苄基。
3.如权利要求1所述的方法，其特征在于所述胺的沸点高于二苄胺的沸点。
4.如权利要求1所述的方法，其特征在于所述胺是四亚乙基五胺或其蒸馏残余物、六亚乙基七胺或其蒸馏残余物、或五亚乙基六胺或其蒸馏残余物。
5.如权利要求1所述的方法，其特征在于所述胺是多胺，该多胺选自二氯乙烷与氨和/或来自吖丙啶聚合的其它胺的反应产物或环氧乙烷与氨或胺的反应产物。
6.如权利要求1所述的方法，其特征在于所述胺是对应于下式(I)或(II)之一的多胺：
Hp-N(CH2-CH2)q-[NHr-(CH2-CH2)s]n-NHt (I)
NH2-CH2-CH2-CH2-[NHr-(CH2-CH2-CH2)s]n-NHt (II)
其中，“n”为0-300的整数，
p、q、s和t各自独立地是1和/或2，
r是0或1，使氮在各种情况下为三键合，或四键合铵盐，
其中，所述胺可以游离胺存在或以其盐存在。
7.如权利要求1所述的方法，其特征在于在需提纯的二苄胺中加入所述添加剂，以二苄胺为基准，该添加剂浓度为0.01-15重量％。
8.如权利要求1所述的方法，其特征在于在需提纯的二苄胺蒸馏中，底部温度为120-220℃，压力设定为在该温度条件下能使该混合物能有效沸腾的压力。
9.如权利要求1所述的方法，其特征在于制得的纯二苄胺储存在氮气中使其稳定化。
10.如权利要求9所述的方法，其特征在于加入含水或无水肼或含水或无水羟胺使纯的二苄胺稳定化。
11.如权利要求10所述的方法，其特征在于所述肼或羟胺单独或以混合物加入纯的淡颜色的二苄胺中，加入浓度为0.01-10重量％。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10228594A DE10228594B4 (de) | 2002-06-26 | 2002-06-26 | Herstellung von farblosem Dibenzylamin |
| DE10228594.2 | 2002-06-26 |
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| Publication Number | Publication Date |
|---|---|
| CN1470495A CN1470495A (zh) | 2004-01-28 |
| CN1318386C true CN1318386C (zh) | 2007-05-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB031452302A Expired - Fee Related CN1318386C (zh) | 2002-06-26 | 2003-06-25 | 无色二苄胺的制备 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7019174B2 (zh) |
| EP (1) | EP1375470B1 (zh) |
| JP (1) | JP4537021B2 (zh) |
| CN (1) | CN1318386C (zh) |
| DE (1) | DE10228594B4 (zh) |
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| US7049471B2 (en) * | 2003-10-10 | 2006-05-23 | E. I. Du Pont De Nemours And Company | Separation of amine from a phenolic compound |
| US7928258B2 (en) * | 2004-08-20 | 2011-04-19 | Momentive Performance Materials Inc. | Cyclic diol-derived blocked mercaptofunctional silane compositions |
| US7718819B2 (en) * | 2006-02-21 | 2010-05-18 | Momentive Performance Materials Inc. | Process for making organofunctional silanes and mixtures thereof |
| US7510670B2 (en) * | 2006-02-21 | 2009-03-31 | Momentive Performance Materials Inc. | Free flowing filler composition based on organofunctional silane |
| US7504456B2 (en) * | 2006-02-21 | 2009-03-17 | Momentive Performance Materials Inc. | Rubber composition containing organofunctional silane |
| US8097744B2 (en) * | 2006-08-14 | 2012-01-17 | Momentive Performance Materials Inc. | Free flowing filler composition comprising mercapto-functional silane |
| US7550540B2 (en) * | 2006-08-14 | 2009-06-23 | Momentive Performance Materials Inc. | Rubber composition and articles therefrom both comprising mercapto-functional silane |
| US8008519B2 (en) | 2006-08-14 | 2011-08-30 | Momentive Performance Materials Inc. | Process for making mercapto-functional silane |
| US7816435B2 (en) * | 2007-10-31 | 2010-10-19 | Momentive Performance Materials Inc. | Halo-functional silane, process for its preparation, rubber composition containing same and articles manufactured therefrom |
| JP6039392B2 (ja) * | 2012-12-10 | 2016-12-07 | シャープ株式会社 | 感光体の製造方法、感光体及び感光体を備えた画像形成装置 |
| PT3512830T (pt) * | 2016-09-14 | 2025-03-21 | Basf Se | Processo de hidrogenação de uma mistura na presença de uma amina incolor |
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| US5107024A (en) * | 1990-03-27 | 1992-04-21 | Atochem Agri, S.A. | Diphenylamine purification |
| JP2771011B2 (ja) | 1990-04-03 | 1998-07-02 | 三井化学株式会社 | 芳香族アミンの安定化方法 |
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2002
- 2002-06-26 DE DE10228594A patent/DE10228594B4/de not_active Expired - Fee Related
-
2003
- 2003-06-13 EP EP03013535.4A patent/EP1375470B1/de not_active Expired - Lifetime
- 2003-06-24 US US10/602,929 patent/US7019174B2/en not_active Expired - Fee Related
- 2003-06-24 JP JP2003179580A patent/JP4537021B2/ja not_active Expired - Fee Related
- 2003-06-25 CN CNB031452302A patent/CN1318386C/zh not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1351050A (en) * | 1970-12-28 | 1974-04-24 | Toyo Soda Mfg Co Ltd | Process for decolourizing polyethylene polyamines |
| US5616804A (en) * | 1993-09-20 | 1997-04-01 | Dsm N.V. | Process for the preparation of dibenzylamine |
| US5874619A (en) * | 1998-04-07 | 1999-02-23 | Albemarle Corporation | Reducing the coloration of aromatic diamines |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004026830A (ja) | 2004-01-29 |
| US7019174B2 (en) | 2006-03-28 |
| CN1470495A (zh) | 2004-01-28 |
| DE10228594B4 (de) | 2006-06-08 |
| JP4537021B2 (ja) | 2010-09-01 |
| US20040026226A1 (en) | 2004-02-12 |
| EP1375470A2 (de) | 2004-01-02 |
| EP1375470B1 (de) | 2015-09-23 |
| HK1060874A1 (zh) | 2004-08-27 |
| EP1375470A3 (de) | 2004-09-29 |
| DE10228594A1 (de) | 2004-01-22 |
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