CN1827576A - 邻苯二醛水溶液的制备方法 - Google Patents
邻苯二醛水溶液的制备方法 Download PDFInfo
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- CN1827576A CN1827576A CNA2006100578375A CN200610057837A CN1827576A CN 1827576 A CN1827576 A CN 1827576A CN A2006100578375 A CNA2006100578375 A CN A2006100578375A CN 200610057837 A CN200610057837 A CN 200610057837A CN 1827576 A CN1827576 A CN 1827576A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/544—Diformyl benzenes; Alkylated derivatives thereof
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Abstract
本发明涉及一种制备邻苯二醛水溶液的方法,所述方法包括将邻苯二醛的缩醛加到水中,随后,通过加酸,将pH调为小于7,接着,在10℃和90℃之间的温度下,通过消去相应的醇,将所述缩醛转化为邻苯二醛,本发明还涉及OPA缩醛用于制备其溶液的用途。
Description
技术领域
本发明涉及一种由邻苯二醛缩醛制备邻苯二醛水溶液的方法。
背景技术
邻苯二醛(OPA)水溶液用在杀虫剂领域中。具体的说,这种溶液用在内诊镜的高活性消毒领域中,也用于医疗器械的消毒。
迄今为止,OPA水溶液一直通过将适量OPA溶解在水中来制备。OPA是固体且以结晶形式存在,这种形式的OPA具有一些缺点,由于它有毒且刺激皮肤,因而处理OPA很困难且在配制OPA水溶液中需要相当的安全措施。另外,OPA有结块的趋势,结果是,第一在装料时出现问题,第二需要很长的溶解过程。
例如EP0839789中所描述的,通过将液体OPA缩醛皂化制备来OPA本身,该液态OPA缩醛作为OPA的储存化合物。根据以上文献,采用例如HCl、H2SO4、H3PO4的无机酸或例如乙酸、甲酸、对甲苯磺酸或甲磺酸的有机酸,在0到7之间的pH下通过水解进行皂化。
例如,EP0843966公开了OPA或OPA缩醛用于制备同样用在杀虫剂领域中的OPA-戊二醛水溶液的用途,根据该专利,通过在戊二醛水溶液中裂解OPA缩醛并除去消去的醇得到OPA-戊二醛水溶液。
发明内容
本发明的目的在于制备OPA水溶液,同时避免使用结晶OPA的缺点。
因此本发明涉及邻苯二醛水溶液的制备方法,该方法包括将邻苯二醛的缩醛加到水中,随后通过加酸,将pH调为小于7,接着,在10℃到90℃的温度下,通过消去相应的醇,该缩醛转化为邻苯二醛。
在本发明的方法中,将OPA缩醛加到或乳化到水中,并通过水解将其溶解。考虑烷基部分具有1到6个碳原子的二烷基缩醛(开链缩醛)或二烷氧基酞烷(dialkoxyphthalanes)(环状OPA缩醛)作为该OPA缩醛。优选的是,烷基部分具有1到4个碳原子的二烷氧基酞烷或二烷基缩醛,特别优选的是,烷基部分具有1到2个碳原子。
根据本发明,将足量的缩醛加到水中并将其溶解,酸化后,得到重量浓度为0.025%到9%的OPA水溶液。优选的是,溶液的重量浓度为0.05%到5%,特别优选的是,溶液的重量浓度为0.5%到2%。此处必须要注意到,根据1H-NMR,水溶液的平衡为25%的OPA和75%的半缩醛。
为了得到更高浓度的溶液,可以在溶液中加入增溶剂,例如聚乙二醇,或者加入选自例如N-甲基吡咯烷酮、丙酮等的酮和例如戊二醛等的醛的可与水混溶的溶剂,结果可以得到浓度达到50重量%的OPA。
为了将缩醛转化为OPA,将酸加到水溶液中使得pH调为小于7。考虑例如硫酸、HCl等无机酸,或例如甲酸、乙酸、二羟乙酸的有机酸作为酸。优选的是,使用硫酸、二羟乙酸或甲酸。
pH应小于7,优选的是等于5,特别优选的是至多为3。
在10℃到90℃的温度进行裂解,优选的是在20℃到50℃。优选的是,搅拌该溶液。
如果将缩醛置于水中,那么首先出现2相乳液,该乳液仅仅在pH调到小于7以后转化成均相溶液。
与使用OPA本身相比,本发明的方法中的有利之处是可以制备更高浓度的溶液(9%比5%),因为通过酸化消去乙醇有利于所形成的OPA的溶解。
如果适当的话,裂解以后,例如通过添加诸如NaHCO3、NaOH、KOH等的无机碱,可以中和得到的OPA水溶液,或者将pH调到4或10,优选的是调到8。另外,如果希望的话,可以通过蒸馏从溶液除去消去的醇,然而,结果是溶解度又降到5%。
而且,除了以上提及的增溶剂以外,可以将其它常用的助剂,例如稳定剂、抗氧化剂、香料、染料等加到根据本发明制备的溶液中。
根据本发明制备的OPA水溶液特别适于用在杀虫剂领域中,具体的是,其特点在于以下事实,首先,由于直接使用缩醛,所以省略了OPA的最后制备步骤,这节约了成本,第二,通过使用OPA缩醛提供了明显的可处理性优点。
然而,本发明OPA水溶液的制备方法还可以在自动消毒设备中进行。
本发明还涉及OPA缩醛作为原料用于制备用在杀虫剂领域中的OPA水溶液的用途。
实施例1:
由OPA缩二甲醇-水-酸混合物制备不同浓度的OPA溶液。
下表中,清楚地列出反应条件(使用的酸、pH、温度、重量%)和得到均相清液的时间(完全裂解)。
表1)pH:1.0使用硫酸
A | B | 25℃下得到清液的时间(min) | 35℃下得到清液的时间(min) | 45℃下得到清液的时间(min) |
0.7 | 0.5 | 15 | 7.5 | 3.75 |
1.3 | 1 | 15 | 7.5 | 3.75 |
2.7 | 2 | 30 | 15 | 7.5 |
4.0 | 3 | 40 | 20 | 10 |
5.4 | 4 | 45 | 22.5 | 11.25 |
6.7 | 5 | 60 | 30 | 15 |
8.1 | 6 | 80 | 40 | 20 |
9.4 | 7 | 90 | 45 | 22.5 |
10.7 | 8 | 150 | 75 | 37.5 |
13.4 | 9 | 330 | 165 | 82.5 |
A:使用的OPA-缩醛的浓度(以重量%计)
B:溶液中OPA的浓度(以重量%计)
表2)pH:2.0使用硫酸
A | B | 25℃下得到清液的时间(min) |
1.3 | 1 | 15 |
4.0 | 3 | 120 |
9.4 | 7 | 400 |
表3)pH:2.0使用二羟乙酸
A | B | 25℃下得到清液的时间(min) |
0.7 | 0.5 | 30 |
1.3 | 1 | 60 |
2.7 | 2 | 90 |
4.0 | 3 | 120 |
6.7 | 5 | 480 |
表4)pH:2.0使用乙酸
A | B | 25℃下得到清液的时间(min) |
0.7 | 0.5 | 15 |
1.3 | 1 | 20 |
2.7 | 2 | 60 |
4.0 | 3 | 120 |
5.4 | 4 | 240 |
表5)pH:2.0使用甲酸
A | B | 25℃下得到清液的时间(min) |
1.3 | 1 | 20 |
2.7 | 2 | 90 |
4.0 | 3 | 150 |
5.4 | 4 | 300 |
Claims (10)
1.用于制备邻苯二醛水溶液的方法,所述方法包括将邻苯二醛的缩醛加到水中,随后通过加酸将pH调为小于7,接着,在10℃到90℃的温度下,通过消去相应的醇将所述缩醛转化为邻苯二醛。
2.如权利要求1所述的方法,其中作为邻苯二醛的缩醛使用的是烷基部分具有1到6个碳原子的二烷基缩醛或二烷氧基酞烷。
3.如权利要求1所述的方法,其中作为酸使用的是选自硫酸或HCl的无机酸或选自甲酸、乙酸或二羟乙酸的有机酸。
4.如权利要求1所述的方法,其中所述pH值调到至多3。
5.如权利要求1所述的方法,其中制备重量浓度为0.025%到9%的邻苯二醛溶液。
6.如权利要求1到5中任意一项所述的方法,其中如果适当的话,选自聚乙二醇、N-甲基吡咯烷酮、丙酮或戊二醛的增溶剂被加到所述溶液中。
7.如权利要求1到6中任意一项所述的方法,其中如果适当的话,其他助剂被加到所述溶液中。
8.如权利要求1到7中任意一项所述的方法,其中如果适当的话,通过裂解后加碱,所述溶液的pH调到4到10。
9.如权利要求1到8中任意一项所述的方法,其中在自动消毒设备中进行所述制备操作。
10.邻苯二醛缩醛作为原料用于制备用在杀虫剂领域中的邻苯二醛水溶液的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ATA354/2005 | 2005-03-02 | ||
AT0035405A AT501448B1 (de) | 2005-03-02 | 2005-03-02 | Verfahren zur herstellung von wässrigen ortho-phthalaldehyd-lösungen |
Publications (1)
Publication Number | Publication Date |
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CN1827576A true CN1827576A (zh) | 2006-09-06 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2006100578375A Pending CN1827576A (zh) | 2005-03-02 | 2006-03-01 | 邻苯二醛水溶液的制备方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7402708B2 (zh) |
EP (1) | EP1698610A1 (zh) |
JP (1) | JP2006241160A (zh) |
CN (1) | CN1827576A (zh) |
AT (1) | AT501448B1 (zh) |
CA (1) | CA2538424C (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103079600A (zh) * | 2010-04-27 | 2013-05-01 | 怀特利集团控股有限公司 | 非平衡增效型醛类抗微生物剂 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6861053B1 (en) | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
JP5013583B2 (ja) * | 2006-06-27 | 2012-08-29 | ケイ・アイ化成株式会社 | 染色特性の低下された殺菌組成物及び染色特性の低下方法 |
US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4122314A1 (de) * | 1991-07-05 | 1993-01-07 | Basf Ag | O-phthaldialdehydtetraalkylacetale, ihre herstellung und ihre verwendung als depotverbindung |
DE4407986A1 (de) * | 1993-03-19 | 1994-09-22 | Basf Ag | Verfahren zur Herstellung von o-Phthalaldehydtetraalkylacetalen |
AT404938B (de) * | 1996-10-30 | 1999-03-25 | Chemie Linz Gmbh | Verfahren zur reinigung von o-phthaldialdehyd |
AT404592B (de) * | 1996-11-26 | 1998-12-28 | Chemie Linz Gmbh | Verfahren zur herstellung von wässrigen o-phthalaldehyd-glutaraldehydlösungen |
AT413537B (de) * | 2001-05-15 | 2006-03-15 | Dsm Fine Chem Austria Gmbh | Verbessertes verfahren zur reinigung und formulierung von o-phthalaldehyd |
-
2005
- 2005-03-02 AT AT0035405A patent/AT501448B1/de not_active IP Right Cessation
-
2006
- 2006-01-25 US US11/338,727 patent/US7402708B2/en active Active
- 2006-02-10 EP EP06002691A patent/EP1698610A1/de not_active Withdrawn
- 2006-03-01 CN CNA2006100578375A patent/CN1827576A/zh active Pending
- 2006-03-01 CA CA2538424A patent/CA2538424C/en active Active
- 2006-03-02 JP JP2006056864A patent/JP2006241160A/ja active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103079600A (zh) * | 2010-04-27 | 2013-05-01 | 怀特利集团控股有限公司 | 非平衡增效型醛类抗微生物剂 |
CN103079600B (zh) * | 2010-04-27 | 2015-09-09 | 怀特利集团控股有限公司 | 非平衡增效型醛类抗微生物剂 |
Also Published As
Publication number | Publication date |
---|---|
AT501448B1 (de) | 2006-11-15 |
CA2538424C (en) | 2014-04-22 |
CA2538424A1 (en) | 2006-09-02 |
US20060199870A1 (en) | 2006-09-07 |
US7402708B2 (en) | 2008-07-22 |
EP1698610A1 (de) | 2006-09-06 |
JP2006241160A (ja) | 2006-09-14 |
AT501448A1 (de) | 2006-09-15 |
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