CN111807989A - Method for treating ketoxime hydrochloride - Google Patents
Method for treating ketoxime hydrochloride Download PDFInfo
- Publication number
- CN111807989A CN111807989A CN202010682038.7A CN202010682038A CN111807989A CN 111807989 A CN111807989 A CN 111807989A CN 202010682038 A CN202010682038 A CN 202010682038A CN 111807989 A CN111807989 A CN 111807989A
- Authority
- CN
- China
- Prior art keywords
- ketoxime
- hydrochloride
- treating
- solvent
- oxime
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- 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.)
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 238000005119 centrifugation Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 239000002244 precipitate Substances 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- ZKALVNREMFLWAN-VOTSOKGWSA-N (ne)-n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)C\C(C)=N\O ZKALVNREMFLWAN-VOTSOKGWSA-N 0.000 claims description 4
- FWSXGNXGAJUIPS-WAYWQWQTSA-N (nz)-n-pentan-2-ylidenehydroxylamine Chemical compound CCC\C(C)=N/O FWSXGNXGAJUIPS-WAYWQWQTSA-N 0.000 claims description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical group ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 4
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 claims description 3
- ZVZUNLVAVHYXNI-FPLPWBNLSA-N (nz)-n-(5-methylhexan-2-ylidene)hydroxylamine Chemical compound CC(C)CC\C(C)=N/O ZVZUNLVAVHYXNI-FPLPWBNLSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 238000004064 recycling Methods 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FQMBUNHGXNVGMH-UHFFFAOYSA-N N-pentan-2-ylidenehydroxylamine hydrochloride Chemical compound Cl.CC(CCC)=NO FQMBUNHGXNVGMH-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JBMPIPFJJRPTOC-UHFFFAOYSA-N n-(4-methylpentan-2-ylidene)hydroxylamine;hydrochloride Chemical compound Cl.CC(C)CC(C)=NO JBMPIPFJJRPTOC-UHFFFAOYSA-N 0.000 description 2
- CDCMMFMDDMEKSC-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine;hydrochloride Chemical compound Cl.CCC(C)=NO CDCMMFMDDMEKSC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MZTSMUNNNLVGKC-UHFFFAOYSA-N 4,6-dimethylheptan-3-one Chemical compound CCC(=O)C(C)CC(C)C MZTSMUNNNLVGKC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VLVVDHDKRHWUSQ-UHFFFAOYSA-N n-heptan-4-ylidenehydroxylamine Chemical compound CCCC(=NO)CCC VLVVDHDKRHWUSQ-UHFFFAOYSA-N 0.000 description 1
- DFMZGZYTSBUWAH-UHFFFAOYSA-N n-nonan-5-ylidenehydroxylamine Chemical compound CCCCC(=NO)CCCC DFMZGZYTSBUWAH-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- -1 silicon oxime Chemical class 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/16—Halides of ammonium
- C01C1/164—Ammonium chloride
-
- 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
- C07C249/14—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for treating ketoxime hydrochloride, which comprises the following steps: s1, dispersing the ketoxime hydrochloride in an organic solvent, neutralizing by ammonia, forming a precipitate and centrifuging; s2, distilling the centrifuged clear liquid to recover the solvent and the ketoxime; s3: dispersing the centrifuged solid in a solvent, washing again, and centrifuging to obtain a clear liquid for recycling, wherein the clear liquid is used for dissolving the ketoxime hydrochloride; and drying the solid obtained after centrifugation to recover the solvent to obtain solid ammonium chloride. The method for treating the ketoxime hydrochloride provided by the invention has the advantages of low production process safety risk, low energy consumption and convenience in operation.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a method for treating ketoxime hydrochloride.
Background
A great amount of oxime-containing hydrochloride is generated in the synthesis of an organic silicon oxime-containing cross-linking agent, and an invention patent with the publication number of CN105315139B discloses a method for treating ketoxime salt serving as a byproduct of ketoxime type silane.
At present, the ketoxime hydrochloride is neutralized by liquid alkali to obtain salt and ketone, a large amount of water is brought in the neutralization process to ensure that oxime is easy to hydrolyze, and the method ensures that the subsequent ketoxime recovery and salt crystallization have high energy consumption and large sewage amount.
Disclosure of Invention
Aiming at the problems, the invention provides a method for treating ketoxime hydrochloride, which has the advantages of simple process, low energy consumption and environmental protection.
The technical scheme adopted by the invention is as follows: the invention provides a method for treating ketoxime hydrochloride, which comprises the following steps:
s1, dissolving and dispersing the ketoxime hydrochloride in an organic solvent, neutralizing by ammonia to form a precipitate and centrifuging;
s2, distilling the centrifuged clear liquid to recover the solvent and the ketoxime;
s3: dispersing the centrifuged solid in an organic solvent, washing again, and centrifuging to obtain clear liquid for recycling, wherein the clear liquid is used for dissolving ketoxime hydrochloride; and drying the solid obtained after centrifugation to recover the solvent to obtain solid ammonium chloride.
In the above method for treating ketoxime hydrochloride, the ketoxime hydrochloride has the formula R1(C ═ NOH) R2, wherein R1 and R2 represent hydrogen or alkyl groups of C1 to C7.
In the above method for treating ketoxime hydrochloride, the organic solvent is a ketone.
In the above method for treating ketoxime hydrochloride, the ketoxime is cyclohexanone oxime, propyl ketoxime, butyl ketoxime, methyl isobutyl ketoxime, methyl isoamyl ketoxime or 2-pentanone oxime.
The invention has the beneficial effects that: the invention provides a method for treating ketoxime hydrochloride, which is characterized in that ketoxime hydrochloride is dispersed in an organic solvent, ammonia is utilized for neutralization, and generated ammonium chloride has low solubility in the organic solvent and is precipitated in large quantity to obtain solid ammonium chloride, so that the problems of high separation energy consumption and large wastewater quantity caused by large solubility of the ammonium chloride in an aqueous solution are effectively solved; in addition, hydrolysis of oxime is inhibited in an organic solvent system and in the process, so that free hydroxylamine is difficult to generate, and the safety of the production process is greatly improved.
Detailed Description
The present invention will now be described more fully hereinafter with reference to specific examples.
The technical scheme adopted by the invention is as follows: the invention provides a method for treating ketoxime hydrochloride, which comprises the following steps:
s1, dissolving and dispersing the ketoxime hydrochloride in an organic solvent, neutralizing by ammonia to form a precipitate and centrifuging;
s2, distilling the centrifuged clear liquid to recover the solvent and the ketoxime;
s3: dispersing the centrifuged solid in an organic solvent, washing again, and centrifuging to obtain clear liquid for recycling, wherein the clear liquid is used for dissolving ketoxime hydrochloride; and drying the solid obtained after centrifugation to recover the solvent to obtain solid ammonium chloride.
Example 1
This example is a process for the treatment of butanone oxime hydrochloride.
123.5g of butanone oxime hydrochloride (1mol) is dispersed in 380g of butanone, ammonia gas is introduced at a certain speed for neutralization, the clear solution after centrifugal separation is distilled to recover butanone and butanone oxime, 80.6g of butanone oxime is obtained, the solid after centrifugation is washed and separated by butanone containing 11.2 percent of water to obtain clear solution for recycling, the obtained solid is dried to obtain 48.4g of ammonium chloride solid, and the single yield is 90 percent.
Example 2
This example is a process for the treatment of methyl isobutyl ketoxime hydrochloride.
151.5g of methyl isobutyl ketoxime hydrochloride (1mol) is dissolved in 390g of methyl isobutyl ketone, ammonia gas is introduced at a certain speed for neutralization, the clear solution after centrifugal separation is distilled to recover butyl ketone and methyl isobutyl ketoxime, 111.4g of methyl isobutyl ketoxime is obtained, the centrifuged solid is washed by methyl isobutyl butanone containing 2.6 percent of water and separated to obtain clear solution for recycling, and the obtained solid is dried to obtain 49.4g of ammonium chloride with the yield of 92 percent.
Example 3
This example is a method of treatment of 2-pentanone oxime hydrochloride.
137.5g 2-pentanone oxime hydrochloride (1mol) is dissolved in 435g 2-pentanone, ammonia gas is introduced at a certain speed for neutralization, the clear solution after centrifugal separation is distilled to recover 2-pentanone and 2-pentanone oxime to obtain 98.8g of 2-pentanone oxime, the centrifuged solid is washed by 2-pentanone containing 4.3% of water, the separated clear solution is recycled, and the obtained solid is dried to obtain 49.2g of ammonium chloride with the yield of 92%.
The above description is only a preferred embodiment of the present invention, and not intended to limit the scope of the present invention, and all changes that can be made by applying the above description to the equivalent structure directly or indirectly applied to other related technical fields are also included in the scope of the present invention.
Claims (4)
1. The method for treating the ketoxime hydrochloride is characterized by comprising the following steps of:
s1, dispersing the ketoxime hydrochloride in an organic solvent, neutralizing by ammonia, forming a precipitate and centrifuging;
s2, distilling the centrifuged clear solution to recover the solvent and the ketoxime;
s3: dispersing the centrifuged solid in an organic solvent, washing again, and centrifuging to obtain clear liquid for dissolving the ketoxime hydrochloride; and drying the solid obtained after centrifugation to recover the solvent to obtain solid ammonium chloride.
2. A method of handling a ketoxime hydrochloride according to claim 1 wherein the ketoxime in the ketoxime hydrochloride has the general formula R1(C ═ NOH) R2 wherein R1 and R2 represent hydrogen or C1-C7 alkyl.
3. The method of claim 1, wherein the organic solvent is a ketone.
4. The method for treating ketoxime hydrochloride according to claim 1, wherein the ketoxime is cyclohexanone oxime, acetone oxime, butanone oxime, methyl isobutyl ketoxime, methyl isoamyl ketoxime, or 2-pentanone oxime.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010682038.7A CN111807989A (en) | 2020-07-15 | 2020-07-15 | Method for treating ketoxime hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010682038.7A CN111807989A (en) | 2020-07-15 | 2020-07-15 | Method for treating ketoxime hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111807989A true CN111807989A (en) | 2020-10-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010682038.7A Pending CN111807989A (en) | 2020-07-15 | 2020-07-15 | Method for treating ketoxime hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111807989A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516599A (en) * | 2011-11-23 | 2012-06-27 | 湖北新蓝天新材料股份有限公司 | Method for synthesizing mixed ketoxime cross-linking agent |
| CN103450245A (en) * | 2013-08-22 | 2013-12-18 | 浙江衢州硅宝化工有限公司 | Method for preparing ketoxime silane |
| CN103467508A (en) * | 2013-08-22 | 2013-12-25 | 浙江衢州硅宝化工有限公司 | Preparation method of methyl ketone oxime methoxy silane |
-
2020
- 2020-07-15 CN CN202010682038.7A patent/CN111807989A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516599A (en) * | 2011-11-23 | 2012-06-27 | 湖北新蓝天新材料股份有限公司 | Method for synthesizing mixed ketoxime cross-linking agent |
| CN103450245A (en) * | 2013-08-22 | 2013-12-18 | 浙江衢州硅宝化工有限公司 | Method for preparing ketoxime silane |
| CN103467508A (en) * | 2013-08-22 | 2013-12-25 | 浙江衢州硅宝化工有限公司 | Preparation method of methyl ketone oxime methoxy silane |
Non-Patent Citations (2)
| Title |
|---|
| 李建颖: "《食品添加剂速查手册》", 30 November 2017, 南开大学出版社 * |
| 马世昌: "《化学物质词典》", 30 April 1999, 陕西科学技术出版社 * |
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Legal Events
| Date | Code | Title | Description |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20201023 |
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| RJ01 | Rejection of invention patent application after publication |