CN111978165B - A kind of method that improves the recovery rate of acetone in the condensation process of producing pseudoionone - Google Patents
A kind of method that improves the recovery rate of acetone in the condensation process of producing pseudoionone Download PDFInfo
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- CN111978165B CN111978165B CN202010781210.4A CN202010781210A CN111978165B CN 111978165 B CN111978165 B CN 111978165B CN 202010781210 A CN202010781210 A CN 202010781210A CN 111978165 B CN111978165 B CN 111978165B
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 45
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 title claims abstract description 21
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000011084 recovery Methods 0.000 title claims abstract description 20
- 238000009833 condensation Methods 0.000 title claims abstract description 10
- 230000005494 condensation Effects 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000012071 phase Substances 0.000 claims abstract description 38
- 239000012074 organic phase Substances 0.000 claims abstract description 24
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 13
- 238000004821 distillation Methods 0.000 claims abstract description 9
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 5
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 238000009835 boiling Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 20
- 239000008346 aqueous phase Substances 0.000 claims description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract description 10
- 239000012670 alkaline solution Substances 0.000 abstract description 5
- 238000005194 fractionation Methods 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000003068 static effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000013517 stratification Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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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
- C07C45/55—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 of oligo- or polymeric oxo-compounds
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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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
技术领域technical field
本发明属于化工技术领域，涉及一种在生产假性紫罗兰酮的缩合过程中提高丙酮回收率的方法。The invention belongs to the technical field of chemical industry and relates to a method for improving the recovery rate of acetone in the condensation process of producing pseudoionone.
背景技术Background technique
目前假性紫罗兰酮缩合过程中丙酮的回收方法主要包括：首先将反应产物静置分层并取上层有机相，之后在常压下加热蒸发，取沸程55-60℃馏分，再减压到真空度50％左右，取沸程45-50℃馏分，所得丙酮回收率约为65％(扣去反应消耗的丙酮)。其中，静置分层时位于下层的水相通常经过中和后直接排放，如此便导致水相中残留丙酮的浪费，使得丙酮回收率降低，不利于减少生产成本；此外，水相中还含有大量有机物，主要包括在碱性环境下丙酮与水反应生成的双丙酮醇，该物质具有较高的水溶性，直接排放则易造成较为严重的环境污染。At present, the recovery method of acetone in the pseudoionone condensation process mainly includes: firstly, the reaction product is left to stand for stratification and the upper organic phase is taken, then heated and evaporated under normal pressure, and the fraction with a boiling range of 55-60 ° C is taken, and then depressurized to The degree of vacuum is about 50%, and the fraction with a boiling range of 45-50°C is taken, and the recovery rate of the obtained acetone is about 65% (the acetone consumed by the reaction is deducted). Wherein, the water phase that is positioned at the lower layer is usually directly discharged after neutralization when standing for stratification, so that the waste of residual acetone in the water phase is caused, the recovery rate of acetone is reduced, and it is not conducive to reducing production costs; in addition, the water phase also contains A large amount of organic matter mainly includes diacetone alcohol produced by the reaction of acetone and water in an alkaline environment. This substance has high water solubility, and direct discharge will easily cause serious environmental pollution.
发明内容Contents of the invention
本发明的目的就是提供一种在生产假性紫罗兰酮的缩合过程中提高丙酮回收率的方法，用于解决Aldol缩合反应工艺制备假性紫罗兰酮过程中，丙酮回收率较低的技术问题。The object of the present invention provides a kind of method that improves acetone recovery rate in the condensation process of producing pseudo-ionone, is used to solve the technical problem that acetone recovery rate is lower in Aldol condensation reaction technique preparation pseudo-ionone process.
本发明的目的可以通过以下技术方案来实现：The purpose of the present invention can be achieved through the following technical solutions:
一种在生产假性紫罗兰酮的缩合过程中提高丙酮回收率的方法，该方法包括：将经过Aldol缩合反应工艺制备假性紫罗兰酮的产物混合液进行静置分层，其中所得有机相依次经过有机相常压蒸馏与有机相减压蒸馏后，得到有机相中的丙酮；所得水相中加入碱性溶液，并依次经过水相常压蒸馏与水相减压蒸馏后，即得到水相中的丙酮。A method for improving the recovery rate of acetone in the condensation process of producing pseudoionones, the method comprising: standing and stratifying the product mixed solution prepared by the Aldol condensation reaction process, wherein the obtained organic phase is sequentially passed through After atmospheric distillation of the organic phase and vacuum distillation of the organic phase, the acetone in the organic phase is obtained; alkaline solution is added to the obtained water phase, and after the water phase atmospheric distillation and the water phase vacuum distillation in turn, the acetone in the water phase is obtained. of acetone.
进一步地，所述的碱性溶液为NaOH溶液。Further, the alkaline solution is NaOH solution.
进一步地，所述的NaOH溶液通过逐滴滴加的方式加入至水相中。Further, the NaOH solution is added to the water phase in a dropwise manner.
进一步地，所述的NaOH溶液的浓度为30-40wt％。Further, the concentration of the NaOH solution is 30-40wt%.
进一步地，所述的NaOH溶液的浓度为30wt％。Further, the concentration of the NaOH solution is 30wt%.
进一步地，所述的NaOH溶液的加入量为水相体积的2-5％。Further, the added amount of the NaOH solution is 2-5% of the volume of the aqueous phase.
进一步地，所述的NaOH溶液的加入量为水相体积的5％。Further, the added amount of the NaOH solution is 5% of the volume of the aqueous phase.
进一步地，所述的水相常压蒸馏中，所取馏分的沸程为55-60℃。Further, in the atmospheric distillation of the aqueous phase, the boiling range of the fractions obtained is 55-60°C.
进一步地，所述的水相减压蒸馏中，真空度为40-60％，所取馏分的沸程为45-50℃。Further, in the vacuum distillation of the water phase, the degree of vacuum is 40-60%, and the boiling range of the obtained fraction is 45-50°C.
进一步地，所述的水相中的丙酮经无水硫酸镁干燥后，可直接用于Aldol缩合反应工艺制备假性紫罗兰酮。Further, after the acetone in the water phase is dried over anhydrous magnesium sulfate, it can be directly used in Aldol condensation reaction process to prepare pseudoionone.
与现有技术相比，本发明通过向经过Aldol缩合反应工艺制备假性紫罗兰酮的分层水相产物中加入碱性溶液并加热，使水相中的双丙酮醇分解为丙酮与水，一方面通过后续的常压分馏与减压分馏的方式，提高丙酮的回收率，另一方面避免因污染物双丙酮醇直接随水相排放所导致的环境污染问题，并具有操作方法简单、条件温和、原料利用率高、绿色环保等优点。Compared with the prior art, the present invention is by adding alkaline solution and heating to the layered water phase product prepared by Aldol condensation reaction process to make the diacetone alcohol in the water phase be decomposed into acetone and water. On the one hand, the recovery rate of acetone is improved through subsequent atmospheric fractionation and vacuum fractionation; on the other hand, the environmental pollution problem caused by the direct discharge of pollutant diacetone alcohol with the water phase is avoided, and the operation method is simple and the conditions are mild. , High raw material utilization rate, green environmental protection and other advantages.
具体实施方式Detailed ways
下面结合具体实施例对本发明进行详细说明。The present invention will be described in detail below in conjunction with specific embodiments.
一种在生产假性紫罗兰酮的缩合过程中提高丙酮回收率的方法，该方法包括：将经过Aldol缩合反应工艺制备假性紫罗兰酮的产物混合液进行静置分层，其中所得有机相先在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％左右，取沸程45-50℃馏分，得到有机相中的丙酮；所得水相中先逐滴加入30-40wt％NaOH溶液混合，其中NaOH溶液的加入量为水相体积的2-5％，之后再在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度40-60％，取沸程45-50℃馏分，得到水相中的丙酮。A method for improving the recovery rate of acetone in the condensation process of producing pseudo-ionone, the method comprises: the product mixture solution prepared by Aldol condensation reaction process to prepare pseudo-ionone is subjected to static stratification, wherein the organic phase obtained is first Heating and evaporating under normal pressure, take the fraction with a boiling range of 55-60°C, and then reduce the pressure to about 50% of vacuum, take the fraction with a boiling range of 45-50°C, and obtain acetone in the organic phase; add 30 - 40wt% NaOH solution is mixed, wherein the amount of NaOH solution added is 2-5% of the volume of the water phase, and then heated and evaporated under normal pressure, and the fraction with a boiling range of 55-60°C is taken, and then decompressed to a vacuum degree of 40-60 %, take the fraction with a boiling range of 45-50° C. to obtain acetone in the water phase.
所得有机相中的丙酮与水相中的丙酮经无水硫酸镁干燥后，可直接用于Aldol缩合反应工艺制备假性紫罗兰酮。The obtained acetone in the organic phase and the acetone in the water phase can be directly used in Aldol condensation reaction process to prepare pseudoionone after being dried by anhydrous magnesium sulfate.
以下实施例以本发明技术方案为前提进行实施，给出了详细的实施方式和具体的操作过程，但本发明的保护范围不限于下述的实施例。The following examples are carried out on the premise of the technical solutions of the present invention, and detailed implementation methods and specific operation processes are provided, but the protection scope of the present invention is not limited to the following examples.
对比例：Comparative example:
取同实施例1的产物混合液进行静置分层，所得有机相先在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％左右，取沸程45-50℃馏分，得到有机相中的丙酮；所得水相经中和后直接排放。总丙酮回收率为65％。Take the same product mixture as in Example 1 for static layering. The organic phase obtained is first heated and evaporated under normal pressure, and the fraction with a boiling range of 55-60°C is taken, and then decompressed to a vacuum of about 50%, and the fraction with a boiling range of 45-60°C is taken. 50°C distillate to obtain acetone in the organic phase; the obtained water phase is directly discharged after neutralization. The total acetone recovery was 65%.
实施例1：Example 1:
取某工厂经Aldol缩合反应工艺制备假性紫罗兰酮的产物混合液进行静置分层，所得有机相先在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％左右，取沸程45-50℃馏分，得到有机相中的丙酮；所得水相中先逐滴加入40wt％NaOH溶液混合，其中NaOH溶液的加入量为水相体积的2％，之后再在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％，取沸程45-50℃馏分，得到水相中的丙酮。Take the product mixture of pseudo-ionone prepared by the Aldol condensation reaction process in a certain factory for static layering, the obtained organic phase is first heated and evaporated under normal pressure, and the fraction with a boiling range of 55-60°C is taken, and then depressurized to a vacuum degree of 50 % or so, take the boiling range 45-50 ° C fraction to obtain acetone in the organic phase; first add 40wt% NaOH solution dropwise to the obtained water phase and mix, wherein the addition of NaOH solution is 2% of the volume of the water phase, and then add Heating and evaporating under normal pressure, taking a fraction with a boiling range of 55-60°C, and then reducing the pressure to a vacuum of 50%, taking a fraction with a boiling range of 45-50°C to obtain acetone in the water phase.
所得有机相中的丙酮与水相中的丙酮经无水硫酸镁干燥后，可直接用于Aldol缩合反应工艺制备假性紫罗兰酮。与对比例相比，通过回收水相中的丙酮使得总丙酮回收率提高20％，总丙酮回收率达到85％。The obtained acetone in the organic phase and the acetone in the water phase can be directly used in Aldol condensation reaction process to prepare pseudoionone after being dried by anhydrous magnesium sulfate. Compared with the comparative example, the total acetone recovery rate is increased by 20% by recovering the acetone in the water phase, and the total acetone recovery rate reaches 85%.
实施例2：Example 2:
取同实施例1的产物混合液进行静置分层，所得有机相先在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％左右，取沸程45-50℃馏分，得到有机相中的丙酮；所得水相中先逐滴加入30wt％NaOH溶液混合，其中NaOH溶液的加入量为水相体积的5％，之后再在常压下加热蒸发，取沸程55-60℃馏分，再减压至真空度50％，取沸程45-50℃馏分，得到水相中的丙酮。Take the same product mixture as in Example 1 for static layering. The organic phase obtained is first heated and evaporated under normal pressure, and the fraction with a boiling range of 55-60°C is taken, and then decompressed to a vacuum of about 50%, and the fraction with a boiling range of 45-60°C is taken. 50°C fraction to obtain acetone in the organic phase; add 30wt% NaOH solution dropwise to the obtained water phase and mix, wherein the amount of NaOH solution added is 5% of the volume of the water phase, and then heated and evaporated under normal pressure to obtain boiling water. The fraction with a range of 55-60°C is decompressed to a vacuum of 50%, and the fraction with a boiling range of 45-50°C is taken to obtain acetone in the water phase.
所得有机相中的丙酮与水相中的丙酮经无水硫酸镁干燥后，可直接用于Aldol缩合反应工艺制备假性紫罗兰酮。与对比例相比，通过回收水相中的丙酮使得总丙酮回收率提高25％，总回收率达到90％。The obtained acetone in the organic phase and the acetone in the water phase can be directly used in Aldol condensation reaction process to prepare pseudoionone after being dried by anhydrous magnesium sulfate. Compared with the comparative example, the total recovery rate of acetone is increased by 25% by recovering the acetone in the water phase, and the total recovery rate reaches 90%.
上述的对实施例的描述是为便于该技术领域的普通技术人员能理解和使用发明。熟悉本领域技术的人员显然可以容易地对这些实施例做出各种修改，并把在此说明的一般原理应用到其他实施例中而不必经过创造性的劳动。因此，本发明不限于上述实施例，本领域技术人员根据本发明的揭示，不脱离本发明范畴所做出的改进和修改都应该在本发明的保护范围之内。The above descriptions of the embodiments are for those of ordinary skill in the art to understand and use the invention. It is obvious that those skilled in the art can easily make various modifications to these embodiments, and apply the general principles described here to other embodiments without creative effort. Therefore, the present invention is not limited to the above-mentioned embodiments. Improvements and modifications made by those skilled in the art according to the disclosure of the present invention without departing from the scope of the present invention should fall within the protection scope of the present invention.
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