CN1060091A - Synthesizing of 2-hydroxy-glyoxime - Google Patents
Synthesizing of 2-hydroxy-glyoxime 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
The invention relates to the synthetic of 2-hydroxy-glyoxime.With oxalic acid diethyl ester and oxyammonia is raw material, and reaction generates 2-hydroxy-glyoxime salt throw out in the alkaline alcohol water medium.Throw out is filtered, be acidified with acid in 80 to 90 ℃ of water, be cooled to room temperature and get elaboration.The present invention has saved production unit greatly, has shortened the production cycle, has reduced cost.
Description
It is synthetic to the present invention relates to chemical substance.
2-hydroxy-glyoxime is a white powder, and its structural formula is:
, can make the burningrate deterrent and the cooling agent of propelling agent, be used for environmental analysis SO
2Fixing agent, also can be used as the ignition dope of mosquito-repellent incense, coal briquette and pesticide smoke etc.
The synthetic method of Japanese Patent 4739391 is as follows:
1, oxyammonia is synthetic:
2, barkite and NH
2The OH reaction
3, add the water hydrolysis:
4, crude product refining
Consider metal Na operational hazards, loaded down with trivial details, cost an arm and a leg; NH
2OHHCl solubleness in absolute alcohol is little, and dissolution rate is slow, the cost height, and task of the present invention is to reduce cost, and shortens the production cycle, increases the benefit.It is characterized in that using the alkaline alcohol water mixed solvent; In order to prevent reversed reaction, at first synthetic 2-hydroxy-glyoxime salt, and then acidic hydrolysis.Its reaction principle is as follows:
Oxyammonia salt is dissolved in pure water mixed solvent gets saturated solution under room temperature.In this solution, add Na
2CO
3Or KOH or NaOH, being preferably NaOH, vibration, bath are bathed and are cooled to room temperature.Remove by filter the NaCl precipitation.The oxyammonia salt that uses can be oxyammonia sulfate, also can be oxammonium hydrochloride, is preferably oxammonium hydrochloride.The alcohol that uses can be methyl alcohol, ethanol, propyl alcohol, isopropylcarbinol, is preferably ethanol.Volume ratio of alcohol to water is 1～8, is preferably 1～2.In oxyammonia solution, drip barkite, drip NaOH solution simultaneously, in 20～40 ℃ of following stirred for several hour, with sedimentation and filtration.Throw out is soluble in water, 80 ℃ of following acid hydrolysiss.Be cooled to room temperature, filter the elaboration white needle-like crystals, productive rate 75%.
Embodiment:
Take by weighing NH
2OHHCl 70g NH
2OHHCl is dissolved in 200ml distilled water and the 35ml ethanol mixed solvent, and ice-water bath is cooled to below 40 ℃.Taking by weighing NaOH 40g is dissolved in the 100ml distilled water.With NH
2OHHCl solution and NaOH solution add in the four-hole bottle simultaneously, 20 to 40 ℃ of following stirred for several hour.Measure oxalic acid diethyl ester 34ml and 10ml ethanol mixes; Weighing NaOH 20g is dissolved in the 50ml distilled water.Oxalic acid diethyl ester and NaOH are added drop-wise in the four-hole bottle simultaneously, and 20 to 40 ℃ were stirred 70 minutes down, filter white precipitate.White precipitate is dissolved in 80 ℃ of water, adds 20ml HOAC acidifying again.Be cooled to room temperature, suction filtration gets the 16.2g elaboration, productive rate 58%.
Claims (5)
1, a kind of synthetic method of 2-hydroxy-glyoxime.With oxyammonia salt, barkite is raw material, it is characterized in that using the alkaline alcohol water mixed solvent to make reaction medium.
2, according to claim 1, the alkali that uses is NaOH.
3, according to claim 1, the alcohol that uses is ethanol.
4, according to claim 1,2, during the NaOH consumption remove to satisfy and NH
2Outside the OHHCl, also need add 34～35% of oxalic acid diethyl ester weight in addition.
5, according to claim 1,3, the volume ratio of ethanol and water is 2: 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 90107764 CN1060091A (en) | 1990-09-21 | 1990-09-21 | Synthesizing of 2-hydroxy-glyoxime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 90107764 CN1060091A (en) | 1990-09-21 | 1990-09-21 | Synthesizing of 2-hydroxy-glyoxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1060091A true CN1060091A (en) | 1992-04-08 |
Family
ID=4880707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 90107764 Pending CN1060091A (en) | 1990-09-21 | 1990-09-21 | Synthesizing of 2-hydroxy-glyoxime |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1060091A (en) |
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/en 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |