CN1060091A - 二羟乙二肟的合成 - Google Patents
二羟乙二肟的合成 Download PDFInfo
- Publication number
- CN1060091A CN1060091A CN 90107764 CN90107764A CN1060091A CN 1060091 A CN1060091 A CN 1060091A CN 90107764 CN90107764 CN 90107764 CN 90107764 A CN90107764 A CN 90107764A CN 1060091 A CN1060091 A CN 1060091A
- Authority
- CN
- China
- Prior art keywords
- glyoxime
- hydroxy
- water
- naoh
- ethanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000002194 synthesizing effect Effects 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 7
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000004484 Briquette Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003891 environmental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明是关于二羟乙二肟的合成。以草酸二乙
酯和羟氨为原料，在碱性醇水介质中反应生成二羟乙
二肟盐沉淀物。将沉淀物过滤，于80到90℃水中加
酸酸化，冷却至室温得精品。本发明大大节约了生产
设备，缩短了生产周期，降低了成本。
Description
本发明涉及化学物质合成。
二羟乙二肟为白色粉末，其结构式为： 
，可作推进剂的燃速抑制剂和降温剂，用于环境分析中SO2的固定剂，还可作为蚊香、煤球的助燃剂和农药烟剂等。
日本专利4739391的合成方法如下：
1、羟氨的合成：
2、草酸酯与NH2OH反应
3、加水水解：
4、粗品精制
考虑到金属Na操作危险、繁琐，价格昂贵;NH2OH·HCl在无水醇中溶解度小，溶解速度慢，成本高，本发明的任务是降低成本，缩短生产周期，提高效益。其特征在于使用碱性醇水混合溶剂;为了防止逆反应，首先合成二羟乙二肟盐，然后再酸性水解。其反应原理如下：
将羟氨盐于室温下溶于醇水混合溶剂得饱和溶液。向该溶液中加入Na2CO3或KOH或NaOH，最好为NaOH，振荡，冲水浴冷却至室温。过滤除去NaCl沉淀。使用的羟氨盐可为硫酸羟氨，也可为盐酸羟氨，最好为盐酸羟氨。使用的醇可为甲醇、乙醇、丙醇、异丁醇，最好为乙醇。醇水体积比为1～8，最好为1～2。向羟氨溶液中滴加草酸酯，同时滴加NaOH溶液，在20～40℃下搅拌数小时，将沉淀过滤。将沉淀物溶于水中，80℃下加酸水解。冷却至室温，过滤得精品白色针状晶体，产率75%。
实施例：
称取NH2OH·HCl 70g NH2OH·HCl溶于200ml蒸馏水和35ml乙醇的混合溶剂中，冰水浴冷却至40℃以下。称取NaOH 40g溶于100ml蒸馏水中。将NH2OH·HCl溶液和NaOH溶液同时加入四口瓶中，20至40℃下搅拌数小时。量取草酸二乙酯34ml与10ml乙醇混合均匀;称量NaOH 20g溶于50ml蒸馏水中。将草酸二乙酯和NaOH同时滴加到四口瓶中，20到40℃下搅拌70分钟，过滤得白色沉淀。将白色沉淀溶于80℃水中，再加20ml HOAC酸化。冷却至室温，抽滤得16.2g精品，产率58%。
Claims (5)
1、一种二羟乙二肟的合成方法。以羟氨盐、草酸酯为原料，其特征在于使用碱性醇水混合溶剂作反应介质。
2、根据权项1，使用的碱为NaOH。
3、根据权项1，使用的醇为乙醇。
4、根据权项1、2，NaOH用量除满足中和NH2OH·HCl外，还需另加草酸二乙酯重量的34～35%。
5、根据权项1、3，乙醇与水的体积比为2∶3。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 90107764 CN1060091A (zh) | 1990-09-21 | 1990-09-21 | 二羟乙二肟的合成 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 90107764 CN1060091A (zh) | 1990-09-21 | 1990-09-21 | 二羟乙二肟的合成 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1060091A true CN1060091A (zh) | 1992-04-08 |
Family
ID=4880707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 90107764 Pending CN1060091A (zh) | 1990-09-21 | 1990-09-21 | 二羟乙二肟的合成 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1060091A (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7342141B2 (en) | 2006-02-22 | 2008-03-11 | Shell Oil Company | Process for the preparation of alkanediol |
| US7456299B2 (en) | 2006-02-22 | 2008-11-25 | Shell Oil Company | Process for the production of alkylene carbonate and use of alkylene carbonate thus produced in the manufacture of an alkane diol and a dialkyl carbonate |
| US7563919B2 (en) | 2006-02-22 | 2009-07-21 | Shell Oil Company | Process for the preparation of an alkanediol and a dialkyl carbonate |
| US7763745B2 (en) | 2006-02-22 | 2010-07-27 | Shell Oil Company | Process for the production of dialkyl carbonate and alkanediol |
-
1990
- 1990-09-21 CN CN 90107764 patent/CN1060091A/zh active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7342141B2 (en) | 2006-02-22 | 2008-03-11 | Shell Oil Company | Process for the preparation of alkanediol |
| US7456299B2 (en) | 2006-02-22 | 2008-11-25 | Shell Oil Company | Process for the production of alkylene carbonate and use of alkylene carbonate thus produced in the manufacture of an alkane diol and a dialkyl carbonate |
| US7563919B2 (en) | 2006-02-22 | 2009-07-21 | Shell Oil Company | Process for the preparation of an alkanediol and a dialkyl carbonate |
| US7763745B2 (en) | 2006-02-22 | 2010-07-27 | Shell Oil Company | Process for the production of dialkyl carbonate and alkanediol |
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| PB01 | Publication | ||
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| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |