CN1660785A - 制备肟的方法 - Google Patents
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- 150000002923 oximes Chemical class 0.000 title claims abstract description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 50
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 34
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
Abstract
提供了一种制备肟的方法,其中,该方法包括在具有MWW结构的结晶硅酸钛的存在下,在反应混合物液体部分中的氨浓度为约1重量%或更高的条件下,使酮、过氧化氢和氨进行反应的步骤。通过该方法,可以以高的酮转化率和相应于酮的生成肟的高选择率进行酮的氨肟化反应,从而以高产率制备出肟。
Description
技术领域
本发明涉及通过酮的氨肟化(ammoximation)反应制备肟的方法。肟适用作酰胺和内酰胺等的原料。
背景技术
为了制备肟,建议的方法之一是,以硅酸钛(参见日本未审专利公开No.(JP-A-)62-59256、JP-A-6-49015和JP-A-6-92922),尤其是使用具有MFI结构的结晶硅酸钛(例如JP-A-56-96720中公开的硅酸钛TS-1)作为催化剂,以过氧化氢和氨使酮氨肟化的方法。将具有MWW结构的特定结晶的硅酸钛用作氨肟化反应的催化剂是已知的(参见国际公开No.03/074421)。
发明内容
然而,在一些情况下,上述常规方法未必获得足够的酮转化率和足够的生成肟的选择率。本发明的一个目标是提供一种以高产率制备肟的方法,其是以高的酮转化率和高的生成肟的选择率对酮进行氨肟化。
本发明者们进行了深入的研究后发现,该目标可以通过使用具有MWW结构的结晶硅酸钛作为催化剂,在反应混合物的液体部分中的氨的优选浓度下,对酮进行氨肟化反应来实现。基于上述发现,从而完成了本发明。
本发明提供了一种制备肟的方法,该方法包括在具有MWW结构的结晶硅酸钛的存在下,在反应混合物的液体部分中氨浓度为约1重量%或更高的条件下,使酮、过氧化氢和氨进行反应的步骤。
根据本发明,可以以高的酮转化率和相应于酮的生成肟的高选择率进行酮的氨肟化反应,从而以高产率制备出肟。
具体实施方式
本发明中用于氨肟化反应的催化剂包括具有MWW结构的结晶硅酸钛(以下,有时将具有MWW结构的结晶硅酸钛称作“Ti-MWW”。)。符号“MWW”与上述的符号“MFI”一样,是一个由国际沸石联合会(IZA)定义的沸石结构代码。此外,术语“硅酸钛”是一种包含作为构成其骨架要素的钛、硅和氧的沸石,并可以具有基本由钛、硅和氧构成的骨架结构,或可以具有除钛、硅和氧外,包含其它任选的元素,例如硼、铝、镓、铁和铬的骨架结构。
具有MWW结构的结构可以通过X-射线衍射分析确定(参加,例如,美国专利No.4954325;Chemical Communications,No.10,pp.897-898,2001,Britain;等)。硅酸钛可通过紫外可视吸收光谱分析确定。具有MWW结构化合物的具体例子包括MCM-32、SSZ-25、ITQ-1、ERB-1、PSH-3等。
适用于本发明的Ti-MWW可以含有约0.05重量%-约10重量%的钛,且硅和钛的原子比为10-1000。Ti-MWW的形状例如可以是细粉状或颗粒状。
可制备Ti-MWW的方法粗分为直接合成法和后合成法。直接合成法是一种包括如下步骤的方法:在第一阶段使用凝胶形式的钛化合物作为一种原料,然后加热并煅烧得到的混合物,从而得到其结晶。直接合成法的例子包括(i)使用硅化合物和钛化合物作为原料的水热合成法(参见,Chemistry Letters,No.7,pp.774-775,2000等);和(ii)使用硅化合物和钛化合物作为原料的干凝胶转化法(参见,Proceedings of the 88th Catalyst Symposium A,p.154,2001等)。后合成法是一种包括如下步骤的方法:首先制备出不含钛的具有MWW结构的结晶硅酸盐,然后向其中导入钛。后合成法的例子包括(iii)一种包括如下步骤的方法:制备具有MWW结构的结晶硅酸铝,从中移除铝并向其中导入钛(参见,US专利No.6114551等);和(iv)一种包括如下步骤的方法:制备具有MWW结构的结晶硅酸硼,从中移除硼,破坏结晶结构,向其中导入钛,然后再形成结晶(参见Catalyst,Vol.44,No.6,pp.468-470,2002;国际公开No.03/074421等)。在这些方法中,上述(i)、(ii)和(iv)的方法中的结晶是在钛存在下形成的,这是由于钛甚至可以稳定地导入结晶内部。
本发明中,在Ti-MWW的存在下,通过酮、过氧化氢和氨的反应制备肟,即,使用过氧化氢和氨进行酮的氨肟化。在氨肟化反应中,Ti-MWW优选以其的固态形式存在于得到的反应混合物中,并悬浮于混合物中。即,反应混合物优选由固态Ti-MWW和混合物的液体部分组成。基于液体部分,悬浮的Ti-MWW为约0.1重量%-约10重量%。
起始原料酮可以是脂肪族酮、或脂环族酮、或芳香族酮。根据需要,可以使用其两种或多种。酮的例子包括二烷基酮,例如丙酮、甲乙酮和异丁基甲基酮;烷基烯基酮,例如亚异丙基丙酮;烷基芳基酮,例如苯乙酮;二芳基酮,例如二苯甲酮;环烷酮,例如环戊酮、环己酮、环辛酮和环十二烷基酮等。环烯酮(cycloalkenones),例如环戊烯酮和环己烯酮等。在上述酮中,本发明优选环烷酮。
起始原料酮可以通过例如烷烃的氧化、仲醇的氧化(脱氢)、或烯烃的水合和氧化(脱氢)获得。
过氧化氢通常是通过所谓的蒽醌法制备的,浓度为10重量%-70重量%的市售含溶液可以用于本发明。基于1摩尔欲反应的酮,使用的过氧化氢可以是约0.5摩尔-约3摩尔,并优选为约0.5摩尔-约1.5摩尔。过氧化氢可以含有,例如,稳定剂,包括磷酸盐,如磷酸钠、多磷酸盐,如焦磷酸钠和三聚磷酸钠、焦磷酸、抗坏血酸、乙二胺四乙酸、硝基三乙酸、氨基三乙酸、二亚乙基三氨基五乙酸。
本发明中氨可以以气态、或液体、或以水或有机溶剂的溶液形式使用。氨的使用量根据反应混合物液体部分的量进行适当地确定,使得氨在反应混合物液体部分中的浓度为约1重量%或更高。该氨在反应混合物液体部分中的浓度优选可提高酮(即,原料)的转化率,以及生成肟(即目标产物)的选择率,从而提高目标产物肟的产率。氨在反应混合物液体部分中的浓度更优选为约1.5重量%或更高,且可以为约10重量%或更低,并优选为约5重量%或更低。基于1摩尔欲反应的酮,氨的量,作为一个估计值(粗略的标准),可以是约1摩尔或更多,并优选为约1.5摩尔或更多。
氨肟化反应可以在溶剂的存在下进行。优选的溶剂的例子包括醇,如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇和叔戊醇;和水。使用醇和水的混合物溶剂是特别优选的。
氨肟化反应可以通过间歇操作和连续操作进行。当向反应体系中供入酮、过氧化氢和氨,并将所得反应混合物的液体部分移出反应体系时,反应优选通过连续操作进行。该连续操作就产量和可操作性而言是优选的。
间歇反应可以按例如下述方法进行:在反应器中加入酮、氨、Ti-MWW和溶剂,并在向其中加入过氧化氢的同时进行搅拌;或按如下方法进行:向容器中加入酮、Ti-MWW和溶剂,并在向其中加入过氧化氢和氨的同时进行搅拌;或按如下方法进行:向容器中加入Ti-MWW和溶剂,并在向其中加入酮、过氧化氢和氨的同时进行搅拌。
连续操作可以按例如下述方法顺利进行,所述方法包括如下步骤:在反应器中制备Ti-MWW悬浮混合物,并向其中供入酮、过氧化氢和氨,同时通过过滤器从反应器中排放出反应混合物的液体部分。从防止过氧化氢分解的观点出发,反应器优选是玻璃衬里的反应器或不锈钢反应器。
氨肟化反应的反应温度可以是约50℃-约100℃,并优选为约70℃-约100℃。反应可以在常压或更高的压力下进行。为增加氨在反应混合物液体部分中的溶解,反应优选在加压条件下进行,该压力就绝对压力而言,为0.2MPa-约1MPa(在常压以上),并更优选为约0.2MPa-约0.5MPa。在该情况下,可用惰性气体,如氮气或氦气调节压力。
对得到的反应混合物的后处理操作进行适当选择。例如,后处理可以按如下方式进行:即通过过滤、倾析或类似的方法从反应混合物中分离出Ti-MWW,然后对液体部分进行蒸馏以得到肟。
上面已对本发明进行了描述,显而易见的是,本发明可以进行各种变化。这些变化应被认为属于本发明的精神和范围内,且所有这些修饰对于本领域技术人员而言都是显而易见的,因此应属于下面权利要求的范围内。
2003.12.22提交的日本专利申请No.2003-424582的全部公开内容,包括说明书、权利要求书和摘要一并作为参考。
实施例
通过如下的实施例对本发明做更详细的说明,但这些实施例不应构成对本
发明范围的限制。
在实施例和比较例中,通过气相色谱法分析环己酮和环己酮肟、在结果的基础上,分别计算出环己酮的转化率、生成环己酮肟的选择率和环己酮肟的产率。
实施例1
向作为反应器的1升高压釜中加入环己酮、含水叔丁醇(含12重量%水)和60重量%的过氧化氢,其加入速率分别为67克/小时、260克/小时、44.7克/小时,同时向反应器中加入氨,使氨浓度占反应混合物液体部分的2重量%,同时通过过滤器从反应器中排放出反应混合物的液体部分,以进行连续反应,该连续反应在85℃的温度下和加压的条件下进行,所加的压力为0.35MPa(就绝对压力而言),停留时间为72分钟。在反应过程中,基于反应器内反应混合物的液体部分而言,Ti-MWW(根据国际申请No.03/074421描述的方法制备)的浓度为1重量%。反应结束1.5小时后,分析液体部分。结果表明,环己酮的转化率为96.2%,生成环己酮肟的选择率为99.5%,且环己酮肟的产率为95.7%。
实施例2
按照与实施例1同样的方式进行类似的步骤,所不同的是使用另外的Ti-MWW,其通过Chemistry Letters,No.7,pp.774-775,2000中描述的方法制备。结果表明,环己酮的转化率为97.0%,生成环己酮肟的选择率为99.6%,且环己酮肟的产率为96.6%。
对比实施例1
按照与实施例1同样的方式进行类似的步骤,所不同的是使用TS-1(通过JP-A-56-96720中描述的方法制备)替代实施例1中使用的Ti-MWW。结果表明,环己酮的转化率为87.3%,生成环己酮肟的选择率为97.2%,且环己酮肟的产率为84.8%。
Claims (6)
1.一种制备肟的方法,该方法包括在具有MWW结构的结晶硅酸钛的存在下,在反应混合物液体部分中的氨浓度为约1重量%或更高的条件下,使酮、过氧化氢和氨进行反应的步骤。
2.根据权利要求1的方法,其中,在反应进行的同时,向反应体系中供入酮、过氧化氢和氨,同时向反应体系外排放反应混合物的液体部分。
3.根据权利要求1或2的方法,其中,使用溶剂进行反应。
4.根据权利要求3的方法,其中,溶剂是醇和水的混合物。
5.根据权利要求1或2的方法,其中,反应在加压的条件下进行,该压力就绝对压力而言,为约0.2MPa-约1MPa。
6.根据权利要求1或2的方法,其中,酮包括环烷酮。
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US4954325A (en) | 1986-07-29 | 1990-09-04 | Mobil Oil Corp. | Composition of synthetic porous crystalline material, its synthesis and use |
JPH0610181B2 (ja) * | 1986-11-14 | 1994-02-09 | モンテデイペ・ソチエタ・ペル・アツイオニ | オキシム製造のための接触方法 |
IT1244680B (it) * | 1991-01-23 | 1994-08-08 | Montedipe Srl | Processo a piu' stadi per l'ammossimazione in fase liquida dei composti carbonilici |
IT1255745B (it) * | 1992-04-01 | 1995-11-15 | Enichem Anic Srl | Processo in due stadi per la produzione in fase liquida di ossime |
WO1994012277A1 (de) * | 1992-12-03 | 1994-06-09 | Leuna-Katalysatoren Gmbh | Oxidationskatalysatoren |
IT1270196B (it) * | 1994-06-09 | 1997-04-29 | Enichem Spa | Procedimento catalitico per la produzione di ossime |
EP0958861B1 (en) * | 1998-05-19 | 2002-06-05 | Polimeri Europa S.r.l. | Activation method of titanium silicalite and its use in oxidation processes with hydrogen peroxide |
JP2000072737A (ja) | 1998-08-27 | 2000-03-07 | Mitsubishi Gas Chem Co Inc | オキシムの製造方法 |
JP2000072738A (ja) * | 1998-09-01 | 2000-03-07 | Mitsubishi Gas Chem Co Inc | オキシムの製造方法 |
US6114551A (en) | 1999-10-04 | 2000-09-05 | Mobil Oil Corporation | Olefin epoxidation catalysts |
DE10103581A1 (de) * | 2001-01-26 | 2002-08-01 | Degussa | Durch Ammoniumsalze oder substituierte Ammoniumsalze cokatalysiertes Verfahren zur Herstellung von Oximen |
DE10142620A1 (de) * | 2001-08-31 | 2003-03-20 | Degussa | Ammoximation von Ketonen und Aufarbeitung durch Pervaporation/Dampfpermeation |
JP4270901B2 (ja) * | 2002-03-07 | 2009-06-03 | 昭和電工株式会社 | チタノシリケート、その製造方法およびチタノシリケートを用いた酸化化合物の製造方法 |
ATE469864T1 (de) * | 2002-05-23 | 2010-06-15 | Consejo Superior Investigacion | Mikroporöses kristallines zeolithmaterial (zeolith itq-22), syntheseverfahren dafür und verwendung davon als katalysator |
-
2003
- 2003-12-22 JP JP2003424582A patent/JP4552435B2/ja not_active Expired - Fee Related
-
2004
- 2004-12-10 TW TW093138312A patent/TWI353971B/zh not_active IP Right Cessation
- 2004-12-15 KR KR1020040106193A patent/KR101147592B1/ko not_active IP Right Cessation
- 2004-12-20 US US11/014,812 patent/US7161036B2/en not_active Expired - Fee Related
- 2004-12-20 CN CN2004100104492A patent/CN1660785A/zh active Pending
- 2004-12-20 EP EP04030150A patent/EP1548000A1/en not_active Withdrawn
- 2004-12-20 CN CN200910008330A patent/CN101531615A/zh active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101544582B (zh) * | 2008-03-27 | 2012-06-27 | 中国石油化工股份有限公司 | 一种丁酮肟的合成方法 |
WO2013007054A1 (en) * | 2011-07-08 | 2013-01-17 | Ningbo Ocean Chemical New Materials Technology Co., Ltd. | Method for preparation of ketoxime compound and method for preparation of alkoxy-amine hydrochloride |
CN103282344A (zh) * | 2011-07-08 | 2013-09-04 | 宁波欧迅化学新材料技术有限公司 | 一种酮肟化合物的制备方法和烃氧基胺盐酸盐的制备方法 |
CN103282344B (zh) * | 2011-07-08 | 2015-02-18 | 宁波欧迅化学新材料技术有限公司 | 一种酮肟化合物的制备方法和烃氧基胺盐酸盐的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2005179295A (ja) | 2005-07-07 |
EP1548000A1 (en) | 2005-06-29 |
KR101147592B1 (ko) | 2012-05-21 |
US7161036B2 (en) | 2007-01-09 |
JP4552435B2 (ja) | 2010-09-29 |
CN101531615A (zh) | 2009-09-16 |
KR20050063684A (ko) | 2005-06-28 |
TWI353971B (en) | 2011-12-11 |
US20050137423A1 (en) | 2005-06-23 |
TW200528423A (en) | 2005-09-01 |
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