CN101475510A - Method for using carvone production wastewater for recycling acetone oxime - Google Patents
Method for using carvone production wastewater for recycling acetone oxime Download PDFInfo
- Publication number
- CN101475510A CN101475510A CNA2009100291006A CN200910029100A CN101475510A CN 101475510 A CN101475510 A CN 101475510A CN A2009100291006 A CNA2009100291006 A CN A2009100291006A CN 200910029100 A CN200910029100 A CN 200910029100A CN 101475510 A CN101475510 A CN 101475510A
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- CN
- China
- Prior art keywords
- acetoxime
- acetone oxime
- karvon
- water
- wastewater
- 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.)
- Granted
Links
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 title claims abstract description 52
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000002351 wastewater Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 238000004064 recycling Methods 0.000 title claims abstract description 8
- 239000005973 Carvone Substances 0.000 title abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 10
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000001953 recrystallisation Methods 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000010413 mother solution Substances 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000003809 water extraction Methods 0.000 claims description 2
- 239000012071 phase Substances 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 1
- 230000032798 delamination Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- 239000010865 sewage Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
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- Heat Treatment Of Water, Waste Water Or Sewage (AREA)
Abstract
The invention discloses a method for reclaiming acetone oxime from carvone production wastewater. The method comprises the following steps: firstly, reclaiming of an extractant, namely collecting 120-150 DEG C/2mmHg after-cut under the condition of rectification during carvone production as the extractant, wherein the mass content of the carvone is less than 0.5 percent; secondly, extraction of the wastewater, namely mixing the wastewater containing the acetone oxime and the extractant according to the weight ratio of 3.4-3.8:1, raising the temperature to be between 40 and 50 DEG C, stirring for 30 to 45 minutes, cooling the mixture to the room temperature, performing standing and delamination, re-extracting a water phase until reaching the standards, introducing the water phase into a wastewater purification treatment system, and reclaiming the acetone oxime from an organic phase, wherein the mass content of the acetone oxime in the water phase is less than 1.5 percent; thirdly, rectification, namely performing vacuum rectification on the organic phase, and collecting 80-85 DEG C/300mmHg acetone oxime cut fractions; and fourthly, recrystallization, namely dissolving the acetone oxime cut fractions into water according to the mass ratio of 1.5:1, reducing the temperature to be between 3 and 5 DEG C for crystallization and centrifugal separation, recycling a mother liquor, drying solid under vacuum and obtaining the acetone oxime. The method has simple technique, is convenient to operate and easy in industrial implementation, and changes the prior mode of no products after environment-friendly investment, and has high economic efficiency and social efficiency.
Description
Technical field
The present invention relates to the wastewater treatment of flavor compounds and the method for recovery by product, specifically the Karvon factory effluent is used to reclaim the method for acetoxime.
Background technology
The Karvon factory effluent is a kind of typical high concentrated organic wastewater, and it has characteristics such as organic concentration height, colourity height, bio-refractory, component complexity.
General treatment process is directly to utilize biochemical method to handle, but shortcoming is that the composition in the waste water is very complicated, and contain a large amount of acetoximes, and acetoxime all has bigger restraining effect to most growth of biochemical treatment, be difficult to biochemical degradation, must reclaim acetoxime before the biochemical treatment, traditional distillation method recovery acetoxime energy consumption and facility investment are very big, and processing efficiency is low.
Extraction process is a kind of in the waste water physicochemical treatment method, and most of commercialization extraction agents have good extraction ability to water-soluble low fragrant type organic matter, but to containing the highly water-soluble organic substance extraction poor effect of a plurality of hydrophilic radicals in the molecular structure.
Summary of the invention
The objective of the invention is: provide a kind of Karvon factory effluent to be used to reclaim the method for acetoxime, easy to operate, be easy to suitability for industrialized production, the processing efficiency height.
Technical solution of the present invention is that these method concrete steps are as follows:
1) recovery of extraction agent: the after cut of 120～150 ℃/2mmHg is an extraction agent when collecting rectifying in the Karvon production process, and wherein the Karvon mass content is lower than 0.5%;
2) waste water extraction: contain acetoxime waste water and mix with extraction agent according to weight ratio 3.4-3.8:1, be warming up to 40～50 ℃, stir 30～45min, be chilled to the room temperature standing demix, water is extracted to the waste water purifying treatment system that enters up to standard again, and organic phase reclaims acetoxime; Wherein, aqueous phase acetoxime mass content is lower than 1.5%;
3) rectifying: above-mentioned organic phase rectification under vacuum, collect 80-85 ℃/300mmHg acetoxime fraction;
4) recrystallization: the acetoxime fraction is dissolved in water according to mass ratio 1.5:1, is cooled to 3-5 ℃ of crystallization, centrifugation, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime.
Advantage of the present invention is: 1, the after cut with rectifying in the Karvon production is an extraction agent, wherein is rich in higher-boiling compounds such as ketone, acetals, alcohols, hydrazone, polymeric oxime, unsaturated aliphatic hydrocarbon, and is strong to the acetoxime extracting power in the waste water.
2, the boiling point of the after cut of acetoxime and Karvon rectifying differs greatly, and adopts rectifying, recrystallization method to be easy to make high purity acetoxime product.
3, the acetoxime product of Hui Shouing can compensate for environmental protection operation input expense, and produce huge surplus, make enterprise can realize the waste water control purpose, reach the sewage drainage standard of national regulation, also can realize the byproduct resource industriesization, obtain certain economic benefits, change the pattern that the environmental protection input does not have output.
Description of drawings
Fig. 1 is a process flow sheet of the present invention
Embodiment
Below by embodiment the present invention is carried out concrete description; be necessary to be pointed out that at this embodiment only is used for the present invention is further specified; can not be interpreted as limiting the scope of the invention, the person skilled in art can make some nonessential improvement and adjustment according to foregoing.
Embodiment 1
With in the 165 gram Karvon production processes during rectifying after cut of 120-150 ℃/2mmHg and the waste water of 600 gram mass concentration, 19.5% acetoxime drop into the 1000ml there-necked flask, be warming up to 45 ℃, stir 37min, be chilled to room temperature, change the 1000ml separating funnel over to, standing demix, water are measured and are contained acetoxime 1.3%, change sewage plant over to and handle; 80～85 ℃/300mmHg fraction, 105 grams are collected in the organic phase rectification under vacuum, and stratographic analysis acetoxime content is 99.2%; 105 gram acetoxime fractions and 70 gram water dissolution, slowly being cooled to 5 ℃ has the mass crystallization thing to separate out, and crystal solution is centrifugal, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime product 100 grams, and it is 99.6% that GC analyzes content.
Embodiment 2
With in the 160 gram Karvon production processes during rectifying after cut of 120-150 ℃/2mmHg and the waste water of 550 gram mass concentration, 18.3% acetoxime drop into the 1000ml there-necked flask, be warming up to 50 ℃, stir 45min, be chilled to room temperature, change the 1000ml separating funnel over to, standing demix, water are measured and are contained acetoxime 1.1%, change sewage plant over to and handle; 80～85 ℃/300mmHg fraction, 90 grams are collected in the organic phase rectification under vacuum, and stratographic analysis acetoxime content is 99.3%; 90 gram acetoxime fractions and 60 gram water dissolution, slowly being cooled to 4 ℃ has the mass crystallization thing to separate out, and crystal solution is centrifugal, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime product 86 grams, and it is 99.7% that GC analyzes content.
Embodiment 3
With in the 175 gram Karvon production processes during rectifying after cut of 120-150 ℃/2mmHg and the waste water of 655 gram mass concentration, 17.5% acetoxime drop into the 1000ml there-necked flask, be warming up to 40 ℃, stir 30min, be chilled to room temperature, change the 1000ml separating funnel over to, standing demix, water are measured and are contained acetoxime 1.0%, change sewage plant over to and handle; 80～85 ℃/300mmHg fraction, 100 grams are collected in the organic phase rectification under vacuum, and stratographic analysis acetoxime content is 99.1%; 100 gram acetoxime fractions and 65 gram water dissolution, slowly being cooled to 3 ℃ has the mass crystallization thing to separate out, and crystal solution is centrifugal, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime product 94 grams, and it is 99.7% that GC analyzes content.
Embodiment 4
With in the 195 gram Karvon production processes during rectifying after cut of 120-150 ℃/2mmHg and the waste water of 700 gram mass concentration, 19.8% acetoxime drop into the 1000ml there-necked flask, be warming up to 50 ℃, stir 35min, be chilled to room temperature, change the 1000ml separating funnel over to, standing demix, water are measured and are contained acetoxime 1.5%, change sewage plant over to and handle; 80～85 ℃/300mmHg fraction, 123 grams are collected in the organic phase rectification under vacuum, and stratographic analysis acetoxime content is 99.2%; 123 gram acetoxime fractions and 82 gram water dissolution, slowly being cooled to 3 ℃ has the mass crystallization thing to separate out, and crystal solution is centrifugal, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime product 118 grams, and it is 99.8% that GC analyzes content.
Claims (1)
1. the Karvon factory effluent is used to reclaim the method for acetoxime, it is characterized in that these method concrete steps are as follows:
1) recovery of extraction agent: the after cut people extraction agent of 120～150 ℃/2mmHg when collecting rectifying in the Karvon production process, wherein the Karvon mass content is lower than 0.5%;
2) waste water extraction: contain acetoxime waste water and mix with extraction agent according to weight ratio 3.4-3.8:1, be warming up to 40～50 ℃, stir 30～45min, be chilled to the room temperature standing demix, water is extracted to the waste water purifying treatment system that enters up to standard again, and organic phase reclaims acetoxime; Wherein, aqueous phase acetoxime mass content is lower than 1.5%;
3) rectifying: above-mentioned organic phase rectification under vacuum, collect 80-85 ℃/300mmHg acetoxime fraction;
4) recrystallization: the acetoxime fraction is dissolved in water according to mass ratio 1.5:1, is cooled to 3-5 ℃ of crystallization, centrifugation, and Recycling Mother Solution is applied mechanically, and solids vacuum-drying gets acetoxime.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100291006A CN101475510B (en) | 2009-01-21 | 2009-01-21 | Method for using carvone production wastewater for recycling acetone oxime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100291006A CN101475510B (en) | 2009-01-21 | 2009-01-21 | Method for using carvone production wastewater for recycling acetone oxime |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101475510A true CN101475510A (en) | 2009-07-08 |
| CN101475510B CN101475510B (en) | 2012-05-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009100291006A Active CN101475510B (en) | 2009-01-21 | 2009-01-21 | Method for using carvone production wastewater for recycling acetone oxime |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193672A (en) * | 2013-03-11 | 2013-07-10 | 浙江圣安化工有限公司 | Distillation method of oxime |
| CN105924374A (en) * | 2016-05-03 | 2016-09-07 | 海利贵溪化工农药有限公司 | Method for recovering methomyl-oxime |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9907194D0 (en) * | 1999-03-30 | 1999-05-26 | Quest Int | Preparation of carvone |
-
2009
- 2009-01-21 CN CN2009100291006A patent/CN101475510B/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193672A (en) * | 2013-03-11 | 2013-07-10 | 浙江圣安化工有限公司 | Distillation method of oxime |
| CN103193672B (en) * | 2013-03-11 | 2014-09-17 | 浙江圣安化工有限公司 | Distillation method of oxime |
| CN105924374A (en) * | 2016-05-03 | 2016-09-07 | 海利贵溪化工农药有限公司 | Method for recovering methomyl-oxime |
| CN105924374B (en) * | 2016-05-03 | 2017-12-12 | 海利贵溪化工农药有限公司 | A kind of method for reclaiming MHTA |
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| Publication number | Publication date |
|---|---|
| CN101475510B (en) | 2012-05-23 |
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Address after: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee after: Wanxiang Technology Co.,Ltd. Address before: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee before: HUAIAN WAN BANG SPICE INDUSTRY Co.,Ltd. |
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Address after: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee after: Wanxiang Technology Group Co.,Ltd. Country or region after: China Address before: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee before: Wanxiang Technology Co.,Ltd. Country or region before: China |