CN115417798A - Continuous liquid separation process for dicyclohexyl disulfide - Google Patents
Continuous liquid separation process for dicyclohexyl disulfide Download PDFInfo
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- CN115417798A CN115417798A CN202210973153.9A CN202210973153A CN115417798A CN 115417798 A CN115417798 A CN 115417798A CN 202210973153 A CN202210973153 A CN 202210973153A CN 115417798 A CN115417798 A CN 115417798A
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- CN
- China
- Prior art keywords
- dicyclohexyl disulfide
- liquid separation
- separation process
- dicyclohexyl
- disulfide
- 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.)
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- ODHAQPXNQDBHSH-UHFFFAOYSA-N Dicyclohexyl disulfide Chemical compound C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000007788 liquid Substances 0.000 title claims abstract description 63
- 238000000926 separation method Methods 0.000 title claims abstract description 40
- 239000012452 mother liquor Substances 0.000 claims abstract description 20
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 239000011259 mixed solution Substances 0.000 claims abstract description 10
- 239000006228 supernatant Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- -1 na 2 S Chemical compound 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 10
- 238000007599 discharging Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of synthetic post-treatment of dicyclohexyl disulfide, in particular to a continuous liquid separation process of dicyclohexyl disulfide. The continuous liquid separation process of dicyclohexyl disulfide comprises the following steps: s1, cooling a dicyclohexyl disulfide mixed solution by flowing through a heat exchanger; s2, adding the cooled dicyclohexyl disulfide mixed liquor into a liquid separating device, and after layering, respectively flowing out upper-layer liquid and lower-layer liquid; s3, overflowing the supernatant liquid step by step to obtain dicyclohexyl disulfide; collecting the subnatant as a mother liquor; wherein the dicyclohexyl disulfide mixed liquor comprises dicyclohexyl disulfide and mother liquor. The dicyclohexyl disulfide liquid separation process effectively improves the yield of dicyclohexyl disulfide, greatly shortens the separation time, realizes efficient separation and has a very good application prospect.
Description
Technical Field
The invention relates to the technical field of synthetic post-treatment of dicyclohexyl disulfide, in particular to a continuous liquid separation process of dicyclohexyl disulfide.
Background
Dicyclohexyl disulfide (hereinafter simply referred to as disulfide) is widely used in the fields of coloring agents, agricultural chemicals, medicines, food flavors, organic synthesis, and the like; in the rubber industry, dicyclohexyl disulfide is an important intermediate for preparing a scorch retarder CTP (N-cyclohexyl thiophthalimide). With the development of modern rubber processing technology towards high temperature and high speed, the use of scorch retarder is more and more common, and the status of dicyclohexyl disulfide as an intermediate product is more and more important.
Currently, the main methods for synthesizing disulfides are: with Na 2 S, S and chlorocyclohexane are used as raw materials, sodium sulfide is dissolved by water, sulfur is added, the chlorocyclohexane is added for reaction after uniform stirring, and after the reaction is finished, disulfide products and mother liquor are separated. The conventional industrial treatment method for the mother liquor comprises the following steps: and (3) standing and cooling the reacted materials for layering, discharging after standing, observing an oil-water layering interface through a discharging sight glass, and switching a pipeline valve in time to separate the materials. Thus, a large amount of time is needed for standing and cooling, and personnel are needed to observe the temperature at any time.
The current industry development focuses on efficiency more and more, so it is important to develop an efficient and continuous method for treating dicyclohexyl disulfide and mother liquor generated by the reaction. However, most of the reports on dicyclohexyl disulfide at present relate to the synthesis method thereof, and the reports on the post-reaction treatment process are rare.
In summary, there is a need to develop a novel dicyclohexyl disulfide continuous liquid separation process to solve the problems existing in the prior art and meet the requirements of the current industry.
Disclosure of Invention
Based on this, there is a need to provide a new type of dicyclohexyl disulfide continuous liquid separation process to overcome the deficiencies of the prior art.
One objective of the present invention is to provide a dicyclohexyl disulfide continuous liquid separation process, which comprises the following steps:
s1, cooling a dicyclohexyl disulfide mixed solution by flowing through a heat exchanger;
s2, adding the cooled dicyclohexyl disulfide mixed solution into a liquid separating device, and after layering, respectively flowing out upper layer liquid and lower layer liquid;
s3, overflowing the supernatant liquid step by step to obtain dicyclohexyl disulfide; collecting the subnatant as a mother liquor;
wherein,
the dicyclohexyl disulfide mixed liquor comprises dicyclohexyl disulfide and mother liquor.
The dicyclohexyl disulfide mixed solution prepared by the reaction contains incompletely reacted chlorocyclohexane and cyclohexene generated by side reaction, is in an oil phase, has a density smaller than that of mother liquor, is in a water phase, has a density larger than that of the mother liquor, has different densities, and forms oil-water stratification, so that the two materials can be separated.
Further, the mother liquor comprises chlorocyclohexane, cyclohexene and Na 2 S, naCl.
Further, in the step S1, the mass ratio of the dicyclohexyl disulfide to the mother liquor in the dicyclohexyl disulfide mixed liquor is (10-30) to (70-90).
Further, in step S1, the temperature of the mixed solution is reduced to 75 to 80 ℃.
Further, in the step S1, the temperature reduction method is to reduce the temperature of the circulating water, and the temperature of the circulating water is 23 to 27 ℃.
The temperature of the circulating water is not suitable to be too low so as to prevent the mother liquor from crystallizing.
Further, in step S1, after the temperature is reduced to 75-80 ℃, cyclohexene generated by side reaction does not boil, and evaporation concentration is carried out at the temperature.
Further, in step S2, the liquid separation device is a liquid separation storage tank with a grid plate inside.
Further, in step S2, the supernatant and the underflow flow out through different outlets.
Further, in step S2, the height of the mother liquor outlet is adjusted to make the outlet slightly higher than the layering interface, and the upper layer liquid is discharged from the upper opening of the tank body and the lower layer liquid is discharged from the lower opening.
Further, in step S3, the step-by-step overflow is that the upper layer liquid enters from the lower part of the storage tank, and the upper part flows out and enters the lower storage tank.
Further, in step S3, the time for the gradual overflow is 5-7 min.
The upper layer liquid is treated by adopting gradual overflow, so that impurities such as black slag and the like in the upper layer liquid can be settled, and the purity of dicyclohexyl disulfide is further improved.
The invention has the following beneficial effects:
1. the method adopts a pure physical mode to continuously and rapidly separate the dicyclohexyl disulfide from the mother liquor, does not need to add other exogenous chemical reagents, saves resources and cost, and is green, safe and environment-friendly.
2. The invention reduces the steps of cooling, standing and other separation operations in the traditional process, simplifies the operation flow, greatly saves time and personnel operation, ensures the yield of dicyclohexyl disulfide and realizes high-efficiency separation.
Detailed Description
In order to more clearly illustrate the technical solution of the present invention, the following examples are given. The starting materials, reactions and work-up procedures which are given in the examples are, unless otherwise stated, those which are customary on the market and are known to the person skilled in the art.
The words "preferred", "preferably", "more preferred", and the like, in the present invention, refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
It should be understood that other than in any operating examples, or where otherwise indicated, all numbers expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained by the present invention.
The meaning of "up and down" in the present invention means that when the reader is right facing, the upper side of the reader is the upper side, and the lower side of the reader is the lower side, and is not a specific limitation to the mechanism of the apparatus of the present invention.
When a component, element, or layer is referred to as being "on," "bonded to," "connected to," or "coupled to" another element or layer, it may be directly on, bonded to, connected to, or coupled to the other element, or layer, or intervening elements or layers may be present. In contrast, when an element is referred to as being "directly on," "directly coupled to," "directly connected to" or "directly coupled to" another element or layer, there may be no intervening elements or layers present. Other words used to describe the relationship between elements should be interpreted in a similar manner (e.g., "between.. Versus" directly between.. Versus, "" adjacent to "directly adjacent to," etc.). As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The dicyclohexyl disulfide mixed liquor used in the examples and comparative examples of the present invention contains: dicyclohexyl disulfide 15.0 wt%, mother liquor 84.8 wt%, wherein the mother liquor contains chlorocyclohexane, cyclohexene and Na 2 S、NaCl。
Example 1
A dicyclohexyl disulfide continuous liquid separation process comprises the following steps:
s1, 8000L of dicyclohexyl disulfide mixed liquor with the temperature of 105 ℃ flows through a heat exchanger, and circulating water with the temperature of 26 ℃ is used for cooling to 76 ℃;
s2, adding the cooled dicyclohexyl disulfide mixed solution into a liquid separation storage tank, standing for layering, adjusting an upper layer liquid outlet to be slightly higher than a layering interface, discharging the upper layer liquid from an upper opening of the tank body, and discharging a lower layer liquid from a lower opening;
s3, overflowing the supernatant liquid step by step (the parameter is 14.3%, and the time is 5min and 34S) to obtain pure dicyclohexyl disulfide, and collecting the dicyclohexyl disulfide in a temporary storage tank 1; collecting the lower layer liquid as mother liquid, and storing the mother liquid in a temporary storage tank 2.
Example 2
A dicyclohexyl disulfide continuous liquid separation process comprises the following steps:
s1, 8000L of dicyclohexyl disulfide mixed liquor with the temperature of 103 ℃ flows through a heat exchanger, and circulating water with the temperature of 23 ℃ is used for cooling to 75 ℃;
s2, adding the cooled dicyclohexyl disulfide mixed solution into a liquid separation storage tank, standing for layering, adjusting an upper layer liquid outlet to be slightly higher than a layering interface, discharging the upper layer liquid from an upper opening of the tank body, and discharging a lower layer liquid from a lower opening;
s3, overflowing the supernatant liquid step by step (the parameter is 14.7%, and the time is 6min and 10S) to obtain pure dicyclohexyl disulfide, and collecting the dicyclohexyl disulfide in a temporary storage tank 1; collecting the lower layer liquid as mother liquid, and storing the mother liquid in a temporary storage tank 2.
Comparative example 1
A dicyclohexyl disulfide separation process, the comparative example differs from example 1 in that: this comparative example is at first carried out artifical cooling to the dicyclohexyl disulfide mixed solution of equivalent: manually opening a circulating water valve, and cooling for 30 min by using circulating water at the temperature of 23-27 ℃; then standing for 60 min, and finally separating for 30 min to obtain dicyclohexyl disulfide.
Comparative example 2
A dicyclohexyl disulfide separation process, the comparative example differs from example 2 in that: in the comparative example, the same amount of dicyclohexyl disulfide mixed liquor is artificially cooled for 30 min, then is kept stand for 60 min, and is finally separated for 30 min to obtain dicyclohexyl disulfide.
Test example
The test method comprises the following steps:
the continuous liquid separation process of dicyclohexyl disulfide of examples 1-2 and comparative examples 1-2 was performed with performance analysis, and the mass percentage of separated dicyclohexyl disulfide in the initial mixed liquid was calculated as the yield and the total separation time was counted.
The test results are shown in table 1.
TABLE 1 dicyclohexyl disulfide continuous liquid separation process performance test results
| Item | Yield (%) | Total time of separation (min) |
| Example 1 | 15.1 | 39 |
| Example 2 | 14.9 | 42 |
| Comparative example 1 | 14.3 | 120 |
| Comparative example 2 | 14.1 | 120 |
According to the table 1, the dicyclohexyl disulfide mixed liquor is separated by the dicyclohexyl disulfide liquid separation process, the yield of dicyclohexyl disulfide can be effectively increased, the separation time is only about one third of that of the traditional separation process, the separation time is greatly shortened, efficient separation is realized, the process is remarkably improved, and the application prospect is very good.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. A continuous liquid separation process for dicyclohexyl disulfide is characterized by comprising the following steps:
s1, cooling a dicyclohexyl disulfide mixed solution by flowing through a heat exchanger;
s2, adding the cooled dicyclohexyl disulfide mixed solution into a liquid separating device, and after layering, respectively flowing out upper layer liquid and lower layer liquid;
s3, overflowing the supernatant liquid step by step to obtain dicyclohexyl disulfide; collecting the subnatant as a mother liquor;
wherein,
the dicyclohexyl disulfide mixed liquor comprises dicyclohexyl disulfide and mother liquor.
2. The continuous liquid separation process of dicyclohexyl disulfide according to claim 1, wherein the components of the mother liquor comprise chlorocyclohexane, cyclohexene, na 2 S, naCl.
3. The continuous liquid separation process of dicyclohexyl disulfide as claimed in claim 1, wherein in step S1, the mass ratio of dicyclohexyl disulfide to mother liquor in the dicyclohexyl disulfide mixed liquor is (10-30): (70-90).
4. The continuous liquid separation process of dicyclohexyl disulfide as claimed in claim 1, wherein in step S1, the temperature of the mixed liquid is reduced to 75-80 ℃.
5. The continuous liquid separation process of dicyclohexyl disulfide as claimed in claim 1, wherein in step S1, the temperature reduction method is cooling by circulating water, and the temperature of the circulating water is 23-27 ℃.
6. The continuous liquid separation process of dicyclohexyl disulfide as claimed in claim 1, wherein in step S2, the liquid separation device is a liquid separation storage tank with a grid plate inside.
7. The continuous liquid separation process of dicyclohexyl disulfide according to claim 1, wherein in step S2, the upper layer liquid and the lower layer liquid flow out through different outlets.
8. The continuous liquid separation process of dicyclohexyl disulfide according to claim 1, wherein in step S3, the time of the stepwise overflow is 5-7 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210973153.9A CN115417798A (en) | 2022-08-15 | 2022-08-15 | Continuous liquid separation process for dicyclohexyl disulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210973153.9A CN115417798A (en) | 2022-08-15 | 2022-08-15 | Continuous liquid separation process for dicyclohexyl disulfide |
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| CN115417798A true CN115417798A (en) | 2022-12-02 |
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| CN202210973153.9A Pending CN115417798A (en) | 2022-08-15 | 2022-08-15 | Continuous liquid separation process for dicyclohexyl disulfide |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0920751A (en) * | 1995-07-07 | 1997-01-21 | Toray Fine Chem Co Ltd | Production of disulfides |
| CN102219920A (en) * | 2011-05-09 | 2011-10-19 | 邸勇 | Recycling process of hydroxypropyl methyl cellulose (HPMC) production solvent |
| CN102906069A (en) * | 2010-08-26 | 2013-01-30 | 东丽精密化学株式会社 | Preparation method of dicyclohexyl disulfide |
| CN103709080A (en) * | 2012-10-09 | 2014-04-09 | 河南省汤阴县永新助剂厂 | A rapid manufacturing method of dicyclohexyl disulfide |
| CN108434786A (en) * | 2018-04-28 | 2018-08-24 | 苏州长城开发科技有限公司 | A kind of liquid distributing device |
| CN111807592A (en) * | 2020-07-17 | 2020-10-23 | 河北兰升生物科技有限公司 | Continuous liquid separation device and organic solvent separation method using same |
-
2022
- 2022-08-15 CN CN202210973153.9A patent/CN115417798A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0920751A (en) * | 1995-07-07 | 1997-01-21 | Toray Fine Chem Co Ltd | Production of disulfides |
| CN102906069A (en) * | 2010-08-26 | 2013-01-30 | 东丽精密化学株式会社 | Preparation method of dicyclohexyl disulfide |
| CN102219920A (en) * | 2011-05-09 | 2011-10-19 | 邸勇 | Recycling process of hydroxypropyl methyl cellulose (HPMC) production solvent |
| CN103709080A (en) * | 2012-10-09 | 2014-04-09 | 河南省汤阴县永新助剂厂 | A rapid manufacturing method of dicyclohexyl disulfide |
| CN108434786A (en) * | 2018-04-28 | 2018-08-24 | 苏州长城开发科技有限公司 | A kind of liquid distributing device |
| CN111807592A (en) * | 2020-07-17 | 2020-10-23 | 河北兰升生物科技有限公司 | Continuous liquid separation device and organic solvent separation method using same |
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Application publication date: 20221202 |