CN101362705B - 一种制备间二氨基苯甲酸的方法 - Google Patents
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- 238000002360 preparation method Methods 0.000 title abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims abstract description 9
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 5
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- 238000006722 reduction reaction Methods 0.000 claims abstract description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 229910003310 Ni-Al Inorganic materials 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 5
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000002351 wastewater Substances 0.000 abstract description 2
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 abstract 3
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002912 waste gas Substances 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- FSDYDMVMHCQRFV-UHFFFAOYSA-N C(=O)O.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound C(=O)O.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] FSDYDMVMHCQRFV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910018605 Ni—Zn Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- RCTSWDDNGIBRQE-UHFFFAOYSA-N C(=O)O.[N+](=O)([O-])C1=C(C=CC=C1)[N+](=O)[O-] Chemical compound C(=O)O.[N+](=O)([O-])C1=C(C=CC=C1)[N+](=O)[O-] RCTSWDDNGIBRQE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
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Classifications
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
本发明为一种制备间二氨基苯甲酸的方法，其特征在于：以间二硝基苯甲酸为原料，甲醇或乙醇为溶剂，加入催化剂，在反应压力为0.1-5Mpa，反应温度为20-150℃下，以间二硝基苯甲酸和理论反应量的氢气发生还原反应2-10小时，得到粗产物；经分离、脱溶，得到间二氨基苯甲酸产物。其中用料比例为：以1摩尔间二硝基苯甲酸计，甲醇或乙醇用量为200-1000毫升，催化剂用量为间二硝基苯甲酸重量的0.5-10％；所述的催化剂是雷尼镍或活性碳载体。本发明方法工艺路线短，产品纯度高达95％，收率高达96％以上，催化剂可回收再用，无三废污染。
Description
技术领域
本发明涉及制备有机中间体的方法，特别是一种制备间二氨基苯甲酸的方法。
背景技术
间二氨基苯甲酸是一种重要的有机中间体，该间二氨基苯甲酸可用作合成医药和染料的中间体，如合成泛影酸、活性染料等，这些物资在生产生活中扮演着极其重要的角色，由于间二氨基苯甲酸具有如此广泛的用途，它的制品和生产方法受到人们的普遍关注，目前主要采用的合成路线制备间二氨基苯甲酸如下：
此合成路线为铁粉还原法路线，该方法产品质量差，收率低，而且有大量的废渣(铁渣)和废水污染环境。
发明内容
本发明的目的在于提供一种替代上述方法的新的制备方法，以提高质量、收率，避免环境污染，满足间二氨基苯甲酸产品的社会需要。
本发明是一种制备间二氨基苯甲酸的方法，其特征在于：以间二硝基苯甲酸为原料，甲醇或乙醇为溶剂，加入催化剂，在反应压力为0.1-5Mpa，反应温度为20-150℃下，以间二硝基苯甲酸和理论反应量的氢气发生还原反应2-10小时，得到粗产物；经分离、脱溶，得到间二氨基苯甲酸产物。
其中用料比例为：以1摩尔间二硝基苯甲酸计，甲醇或乙醇用量为200-1000毫升(蒸馏出来的甲醇或乙醇循环使用)，催化剂用量为间二硝基苯甲酸重量的0.5-10％；所述的催化剂是雷尼镍或活性碳载体。
所述的催化剂用量优选为间二硝基苯甲酸重量的0.5-3％。
所述的雷尼镍包括Ni-Al型或Ni-Zn型骨架镍。
所述的活性碳载体包括以下按重量计的物质：
活性碳55-80％，
钯、铂或铑中至少一种，含量为1-10％，
铁、钴、镍、铜或锌至少一种，含量为15-40％。
所述的反应压力优选为1-5Mpa。
本发明方法在催化剂和甲醇或乙醇溶剂存在下，使原料间二硝苯甲酸和氢气进行反应，粗产物经过分离、脱溶得到间二氨基苯甲酸。使用的催化剂以雷尼镍、活性碳为载体引入选自钯、铂、铑或其混合物。氢气为还原剂，在一定温度、压力条件下实现还原过程。采用镍系催化剂或活性炭载体催化剂替代现有的铁粉催化剂，本发明催化剂是关键物质之一，经一系列筛选试验，通过比较结果后确认以镍系催化剂，或者以活性炭载体，如钯、铑或铂催化剂作为间二氨基苯甲酸工业化生产的理想的催化剂。镍系催化剂主要有Ni-Al型或Ni-Zn型骨架镍，统称雷尼镍(rnney-Ni)。本催化剂不仅能满足工艺的需要，而且可以回收循环使用，本方法使用的催化剂由于含有贵金属，在相同反应条件并取得相同反应效果的前提下，其投入量越少，越有利于降低生产成本，催化剂用量优选范围以间二硝基苯甲酸重量计的0.5-3％为最佳。
使用的活性炭载体可为市售活性炭，具有一般活性炭的性质，孔体积为0.6-1.1cm3/g，平均孔半径10-20，比表面500-1500m2/g。活性炭载体在使用前不需做特殊处理，但为了使制备的催化剂具有理想的孔体积和活性，最好使用前用稀酸如10％的硝酸处理，除去活性炭表面的不洁物，然后过滤，水洗、干燥。催化剂制备中加入的钯、铑或铂或其混合物，镁、钴、镍、铜、锌或其混合物或氯化物、硝基盐或其它可溶性的形式引入，优选以氯化物或硝基盐形式引入，所用氯化物或硝基盐均为化学纯试剂。
本发明中使用的催化剂，可以通过诸如混合法、浸渍法或沉淀法。常用的催化剂制备方法制得催化剂前体，再通过诸如氧气等还原性气体活化来制得催化剂。
综上所述，本发明工艺路线短，产品纯度高达95％，收率高达96％以上，催化剂可回收再用，无三废污染。
具体实施方式
实施例1
于1升不锈钢高压反应釜中投入溶剂300毫升甲醇，50g原料3，5-二硝基甲酸，催化剂0.25gNi-Al型镍，升温20℃通入氢气，控制氢气压力2MPa，反应10小时，卸压后出料过滤，滤液脱出甲醇后得产物间二氨基苯甲酸，色谱分析含量95％，收 率96％。将催化剂用甲醇洗涤后备用。
实施例2
用300毫升乙醇作溶剂，取50g原料3，5-二硝基甲酸，Ni-Al型镍3.5g，控制氢气压力3MPa，150℃温度下反应3小时，操作同实施例1，得产物间二氨基苯甲酸，色谱分析含量95％，收率97％。
Claims (5)
1.一种制备间二氨基苯甲酸的方法，其特征在于：以间二硝基苯甲酸为原料，甲醇或乙醇为溶剂，加入催化剂，在反应压力为0.1-5Mpa，反应温度为20-150℃下，以间二硝基苯甲酸和理论反应量的氢气发生还原反应2-10小时，得到粗产物；经分离、脱溶，得到间二氨基苯甲酸产物；
所述的催化剂是Ni-Al型骨架镍。
2.根据权利要求1所述的制备间二氨基苯甲酸的方法，其特征在于：其中用料比例为：以1摩尔间二硝基苯甲酸计，甲醇或乙醇用量为200-1000毫升，催化剂用量为间二硝基苯甲酸重量的0.5-10％。
3.根据权利要求2所述的制备间二氨基苯甲酸的方法，其特征在于：所述的催化剂用量优选为间二硝基苯甲酸重量的0.5-3％。
4.根据权利要求1或2或3所述的制备间二氨基苯甲酸的方法，其特征在于：所述的反应压力为1-5Mpa。
5.根据权利要求1或2或3所述的制备间二氨基苯甲酸的方法，其特征在于：所述的反应温度为20-100℃。
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| CN102249942B (zh) * | 2011-05-20 | 2013-10-30 | 山东富原化工有限公司 | 一种工业化连续加氢合成3,5-二氨基苯甲酸的方法 |
| CN104003892A (zh) * | 2014-06-13 | 2014-08-27 | 江苏恒祥化工有限责任公司 | 3,5-二氨基苯甲酸的催化加氢制备方法 |
| CN105949076B (zh) * | 2016-05-10 | 2018-01-23 | 浙江今晖新材料股份有限公司 | 一种3,5‑二氨基苯甲酸的制备方法 |
| CN106905173B (zh) * | 2017-02-08 | 2020-03-03 | 河北科技大学 | 制备氨基苯甲酸或其酯的方法 |
| CN113563213B (zh) * | 2021-08-30 | 2024-03-22 | 淄博晟亿弘新材料科技有限公司 | 3,5-二氨基苯甲酸的制备方法 |
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| DD228807A1 (de) * | 1984-09-28 | 1985-10-23 | Fahlberg List Veb | Verfahren zur herstellung hochwertiger 3,5-diamino-2,4,6-triiodbenzosaeure aus roher 3,5-diaminobenzoesaeure |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DD228807A1 (de) * | 1984-09-28 | 1985-10-23 | Fahlberg List Veb | Verfahren zur herstellung hochwertiger 3,5-diamino-2,4,6-triiodbenzosaeure aus roher 3,5-diaminobenzoesaeure |
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| 倪明.3,5-二氨基苯甲酸-4’-己氧基苯酯的合成.《精细化工中间体》.2005,第35卷(第1期),全文. * |
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