KR101988508B1 - Method for reduction of impurity in solvent using during a solution polymerization of styrene-butadiene - Google Patents

Method for reduction of impurity in solvent using during a solution polymerization of styrene-butadiene Download PDF

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KR101988508B1
KR101988508B1 KR1020150150994A KR20150150994A KR101988508B1 KR 101988508 B1 KR101988508 B1 KR 101988508B1 KR 1020150150994 A KR1020150150994 A KR 1020150150994A KR 20150150994 A KR20150150994 A KR 20150150994A KR 101988508 B1 KR101988508 B1 KR 101988508B1
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solvent
styrene
distillation column
butadiene
impurities
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KR1020150150994A
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Korean (ko)
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KR20170050004A (en
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정회인
고준석
황우성
이종구
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F6/00—Post-polymerisation treatments
    • C08F6/04—Fractionation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/04—Polymerisation in solution
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F6/00—Post-polymerisation treatments
    • C08F6/06—Treatment of polymer solutions
    • C08F6/12—Separation of polymers from solutions

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

In the process for producing a styrene-butadiene copolymer by solution polymerization, a method for reducing impurities in a solvent during polymerization of a styrene-butadiene solution, which can recover a solvent and reduce impurities in the solvent, is disclosed. In the method of reducing impurities in a solvent during polymerization of the styrene-butadiene solution, a solution polymerization reaction of a raw material including styrene and butadiene is carried out in a polymerization reactor, and then a polymer is discharged from a stripper, and the remaining unreacted monomer and solvent are supplied to a decanter to supply water. The components are removed; By transferring and supplying the unreacted monomer and the solvent to the first distillation column, the C4 fraction or the light impurities and the residual water component containing the unreacted butadiene having a lower boiling point than the solvent are discharged through the upper portion and flushed in the solvent. Recovering the solvent used in the low purity through a stage located below the feed stage of the first distillation column is supplied with the unreacted monomer and the solvent; And a solvent used for the polymerization reaction in the solvent is supplied to the second distillation column, and then the unreacted monomer and heavy impurities including unreacted styrene having a higher boiling point than the solvent are removed and recovered in high purity. .

Description

METHOD FOR REDUCTION OF IMPURITY IN SOLVENT USING DURING A SOLUTION POLYMERIZATION OF STYRENE-BUTADIENE}

The present invention relates to a method for reducing impurities in a solvent during polymerization of a styrene-butadiene solution, and more particularly, in a process of preparing a styrene-butadiene copolymer by solution polymerization, it is possible to reduce the impurities in the solvent by recovering the solvent. The present invention relates to a method for reducing impurities in a solvent during styrene-butadiene solution polymerization.

Generally, styrene-butadiene rubber (SBR) is prepared by solution polymerization or emulsion polymerization, and in the case of solution polymerization, it is easier to change the microstructure in the polymer chain or to arrange monomers than emulsion polymerization. It is also possible to bond the chain ends with tin or silicone compounds, or to modify them with compounds containing amines or hydroxyl groups, thereby reducing the number of chain ends or reducing the movement of the chain ends, as well as carbon. By improving the binding force with the black, it is possible to reduce the fuel consumption when used as a tire tread rubber, there is an advantage that it is easy to adjust the tire properties required, such as braking and wear resistance.

However, when styrene-butadiene (rubber) is manufactured by using the solution polymerization method, the regeneration cycle of the adsorption column is shortened due to the impurities in the solvent used for the polymerization, and the moisture in the solvent introduced into the polymerization reactor even after the adsorption column. As the content of is increased, the amount of the catalyst reacting with the water increases, so that the amount of the catalyst must be increased to maintain the activity.

Therefore, research to solve such a problem is continuously made. 1 is a flowchart illustrating a method for recovering a solvent in the polymerization of a conventional styrene-butadiene solution, and FIG. 2 illustrates a detailed process of a distillation column in a method for recovering a solvent in the polymerization of a conventional styrene-butadiene solution. It is a process chart. Referring to FIGS. 1 and 2, a method for recovering a solvent during polymerization of a conventional styrene-butadiene solution is described below. First, raw materials such as styrene and butadiene are supplied to and reacted with the reactor 2. , The unreacted monomer, polymer and solvent discharged are supplied to the mixer (4) and mixed with the reaction additives such as stabilizer and oil, and the remaining material after removing impurities using a filter is a stripper in which a stripping process is performed. to (stripper, 6). On the other hand, some solvent is used for lubrication when passing through a transfer pump, a mixer and a filter for transferring materials after the reaction. Subsequently, in the stripping process, unreacted monomers and solvents are transferred to the upper side together with steam using steam, and the polymers and water are discharged downwards together, and only the polymer except the water is sent to the process of production. Lose. The unreacted monomer and solvent transferred to the top of the stripper are subjected to a decanting process in a decanter (8), separated from most water, and then subjected to a distillation process (or monomer separation column, 10). In the first column 10, C4 and water containing unreacted monomer (butadiene) having a low boiling point are azeotropically (azeotropically distilled) and removed through the upper portion, and the solvent is removed through the lower portion. 2 columns (or solvent separation column, 12). Subsequently, in the second column, the solvent is recovered through the top, and the heavy boiling heavies containing the high boiling unreacted monomer (styrene) are separated out through the bottom. At this time, some of the solvent recovered to the upper portion of the second column 12 is removed by the adsorption of a small amount of the remaining catalyst poison (moisture, etc.) and then re-supplied to the reactor 2 (22) Is used for lubrication in a transfer pump, mixer and filter which transfers the material after the reaction (24).

On the other hand, the styrene-butadiene polymer produced by solution polymerization exhibits high reactivity to polar substances such as water because lithium (Li) -based catalysts are usually used in the polymerization reaction, and therefore, water contained in the solvent to be recovered. It is preferable to exist in trace amount. However, in the conventional method for recovering the solvent during the polymerization of the styrene-butadiene solution, the water content is 10 ppm or more even after passing through the adsorption column, and the catalyst is unnecessarily reacted with water, resulting in low activity. In order to maintain this, additional catalyst should be added which must be used as a scavenger.

As described above, the method for recovering the solvent in the polymerization of the styrene-butadiene solution known to date has various problems. Therefore, to solve the above problems, there is a need for the development of a method capable of efficiently reducing impurities in the solvent recovered during styrene-butadiene solution polymerization.

When preparing styrene-butadiene (rubber) using the solution polymerization method, impurities such as moisture in the solvent used for the polymerization not only shorten the regeneration cycle of the adsorption column, but also cause the catalyst to react unnecessarily with water. The cost increases, for example, the amount of catalyst used increases.

Therefore, an object of the present invention for solving this problem, in the process of producing a styrene-butadiene copolymer by solution polymerization, impurities in the solvent during styrene-butadiene solution polymerization, which can reduce the impurities in the solvent by recovering the solvent It is to provide a reduction method.

Another object of the present invention is to provide a method for reducing impurities in a solvent during styrene-butadiene solution polymerization, which can reduce the amount of catalyst used by reducing impurities in the solvent recovered during polymerization of the styrene-butadiene solution.

In order to achieve the above object, the present invention, after the solution polymerization reaction of the raw material containing styrene and butadiene in the polymerization reactor, the polymer is discharged from the stripper, the remaining unreacted monomer and solvent is supplied to the decanter to remove the water component Becoming; By transferring and supplying the unreacted monomer and the solvent to the first distillation column, the C4 fraction or the light impurities and the residual water component containing the unreacted butadiene having a lower boiling point than the solvent are discharged through the upper portion and flushed in the solvent. Recovering the solvent used in the low purity through a stage located below the feed stage of the first distillation column is supplied with the unreacted monomer and the solvent; And a solvent used for the polymerization reaction in the solvent is supplied to a second distillation column, and then, the unreacted monomer and heavy impurities including unreacted styrene having a higher boiling point than the solvent are removed and recovered in high purity. Provided is a method for reducing impurities in a solvent during styrene-butadiene solution polymerization.

According to the method for reducing impurities in a solvent during polymerization of a styrene-butadiene solution according to the present invention, in the process of preparing a styrene-butadiene copolymer by solution polymerization, not only the solvent can be recovered to reduce impurities, but also the recovery. The amount of catalyst used can be reduced by reducing impurities in the solvent.

1 is a process chart illustrating a method for recovering a solvent in the polymerization of a conventional styrene-butadiene solution.
FIG. 2 is a flowchart illustrating a detailed process of a distillation column in a method for recovering a solvent in a conventional styrene-butadiene solution polymerization.
3 is a flowchart illustrating a method for reducing impurities in a solvent when styrene-butadiene solution polymerization according to an embodiment of the present invention.
FIG. 4 is a flowchart illustrating a detailed process of a distillation column in the method of reducing impurities in a solvent during polymerization of a styrene-butadiene solution according to an embodiment of the present invention.

Hereinafter, with reference to the accompanying drawings, the present invention will be described in detail.

3 is a flowchart illustrating a method for reducing impurities in a solvent during polymerization of a styrene-butadiene solution according to an embodiment of the present invention, and FIG. 4 is a view for reducing impurities in a solvent during polymerization of a styrene-butadiene solution according to an embodiment of the present invention. In the method, it is a flowchart showing the detailed process of the distillation column. Referring to Figures 3 and 4, when describing the method for reducing impurities in the solvent during the polymerization of the styrene-butadiene solution according to the present invention, the method for reducing impurities in the solvent during the polymerization of the styrene-butadiene solution, styrene and butadiene After solution polymerization of the raw material including butadiene in the polymerization reactor 100, the polymer is discharged from the stripper 200, and the remaining unreacted monomer and solvent are supplied to the decanter 300. The water component is removed, and the unreacted monomer and the solvent are transferred and supplied to the first distillation column 400, so that the C4 fraction or lights impurities and the residual water component including the unreacted butadiene having a lower boiling point than the solvent. Silver is discharged through the upper part, and the solvent used for flushing 700 of the solvent is lower than the supply stage of the first distillation column 400 to which the unreacted monomer and the solvent are supplied. Recovered with low purity through a stage located in the solvent and the solvent used for the polymerization reaction 800 in the solvent is supplied to the second distillation column 500, the unreacted monomer containing unreacted styrene having a higher boiling point than the solvent And recovering with high purity after the heavy impurities are removed.

Referring to the process of the present invention in more detail, first, a raw material containing styrene and butadiene (components required for the polymerization reaction, such as a solvent and a catalyst, can be added without limitation) to the polymerization reactor 100 and then reacted. The remaining polymers after supplying and mixing the discharged polymer (polymer), unreacted monomer and solvent together with the reaction additives such as stabilizer and oil to the mixer (120) and removing impurities (dirt) by using a filter The stripping process is carried to the stripper 200 is performed. Meanwhile, since the raw material (monomer) supplied to the polymerization reactor 100 may include impurities, an impurity adsorption tower 420 for removing impurities may be installed in front of the polymerization reactor 100, in which case The raw material (monomer) is first passed through the impurity adsorption tower 420 and then introduced into the polymerization reactor 100.

Subsequently, in the stripping process, ie, stripper 200, unreacted monomers and solvents are transferred to the upper side with steam using steam, and polymers and water are sent to the lower side, and only polymer except water is produced. It is sent to process to do. The unreacted monomer and the solvent discharged to the upper portion of the stripper 200 are subjected to a decanting process in the decanter 300, separated from most water, and then to the first distillation column 400 where the distillation process is performed. In the first distillation column 400, unreacted monomers having a lower boiling point than the solvent (that is, C4 fractions and light impurities containing unreacted butadiene) and residual components form azeotropes (azeotropic distillation). The solvent discharged through the upper part and used for the flushing 700 among the solvents is located below the supply end of the first distillation column 400 to which the unreacted monomer and the solvent are supplied, that is, The unreacted monomer and the solvent are recovered with low purity through a stage positioned between the feed stage of the first distillation column 400 and the bottom of the column. At this time, the low purity solvent recovered is used for the flushing and lubricating action in the transfer pump, mixer and filter for transferring the materials after the reaction (700).

Here, the feed (Feed) is supplied to the first distillation column 400, 95 to 99% by weight of the solvent (C6), 1 to 4% by weight of C4 fraction and 0 to 1% by weight of styrene monomer (Styrene monomer) ; SM).

Finally, the solvent used in the polymerization reaction 800 of the solvent is supplied to the second distillation column 500, the unreacted monomer and heavy impurities containing unreacted styrene having a higher boiling point than the solvent through the bottom After separation and removal, the second distillation column 500 is recovered with high purity. At this time, the high-purity solvent to be recovered is impurity remaining in the solvent, that is, a small amount of catalyst poison (moisture, etc.) is removed by adsorption in the adsorption tower 520 and then supplied to the reactor 100 again (800). . On the other hand, by using the two distillation tower (400, 500), it is possible to prevent the accumulation of C4 fraction in the process.

That is, one of the characteristics of the present invention, the low-purity solvent recovered through the stage located below the supply stage of the first distillation column 400 to which the unreacted monomer and the solvent is supplied, conveys the material after the reaction It is used for flushing and lubrication in feed pumps, mixers and filters, which can reduce water in the solvent without additional distillation column. That is, the water in the solvent circulated to the reactor 100 is reduced by discharging the low-purity solvent from the first distillation column 400 including water, and in addition, the water in the process is the decanter 300 and the first distillation column 400. ) Is removed by the top.

Another feature of the present invention is to recover the high-purity solvent from which the water is reduced by passing through the decanter 300 and the first distillation column 400 from the second distillation column 500, and then supplied to the reactor 100 again As it is used for the polymerization reaction, the moisture in the solvent is reduced, so that the regeneration cycle of the adsorption tower 520 becomes long, and in particular, the moisture content in the solvent after passing through the adsorption tower 520 is further lowered to 10 ppm or less, so that the moisture It is possible to reduce the amount of catalyst added for use as a scavenger.

The solvents recovered from the first distillation column 400 and the second distillation column 500 are both normal-hexane (n-Hexane), mainly as a liquid phase (may be recovered in a gas phase), and the first distillation column 400. Low-purity solvent for flushing means a solvent having a purity of about 80-98%, preferably 85-95%, and the high-purity solvent for polymerization recovered from the second distillation column 500 has a purity. A solvent that is about 98 to 100%, preferably 99 to 100%, more preferably 99 to 99.99%. On the other hand, the operating temperature and pressure of the first distillation column 400 and the second distillation column 500 may follow the operating temperature and pressure of a conventional distillation column. In addition, the ratio of the low-purity solvent and the high-purity solvent to be recovered is 1: 5 to 1:75, preferably about 1:25 by weight.

Hereinafter, preferred examples are provided to aid the understanding of the present invention, but the following examples are merely illustrative of the present invention, and various changes and modifications within the scope and spirit of the present invention are apparent to those skilled in the art. Naturally, such changes and modifications fall within the scope of the appended claims.

Example 1 Recovery of Solvents with Reduced Impurities in Styrene-Butadiene Solution Polymerization

The tower operation temperature of the first distillation column was about 48 ° C., the operating pressure was about 4.3 barg, the tower operation temperature was about 132.8 ° C., and the operating pressure was about 4.4 barg, and the inflow of raw materials through the polymerization reactor, stripper, and decanter was 34.5. After distillation proceeded to T / hr, the unreacted monomer was recovered at an average flow rate of 0.16 T / hr from the column top, and 2 T / hr to be used for flushing at the stage located below two stages than the stage into which the raw material was added. N-Hexane solvent (purity 92.9 wt%) was recovered. Subsequently, the second distillation column was subjected to secondary distillation at a top operating temperature of about 73 ° C., an operating pressure of about 0.2 barg, a tower bottom operating temperature of about 145 ° C., and an operating pressure of about 0.4 barg. After recovering 32.3 T / hr of normal-hexane solvent from the column top, the mixture was passed through an adsorption column and introduced into a reactor for polymerization. Meanwhile, the amount of steam used in the first distillation column was 2.9 T / hr, and the amount of steam used in the second distillation column was 3.5 T / hr.

Example 2 Recovery of Solvents with Reduced Impurities in Styrene-Butadiene Solution Polymerization

The amount of steam used in the first distillation column was increased to 3.1 T / hr, and the same operation as in Example 1 was performed except that the tower operating temperature was increased to 0.3 ° C. to 133.1 ° C.

Comparative Example 1 Recovery of Solvent During Styrene-Butadiene Solution Polymerization

Instead of recovering 2 T / hr of normal-hexane solvent from the first distillation column, 34.3 T / hr of normal-hexane solvent was recovered from the column top of the second distillation column together with the solvent used for the polymerization reaction. After passing through the adsorption column, the solvent was introduced into the reactor for the polymerization reaction, and the remaining 2 T / hr solvent was used as the flushing solvent, and the amount of steam used to adjust the column bottom operating temperature of the first distillation column to 131.5 ° C. was 2.9 T / hr, and the amount of steam used was increased to 3.7 T / hr as the input amount to be treated in the second distillation column was performed in the same manner as in Example 1.

[Example 1-2, Comparative Example 1] Evaluation of Impurity Content in Recovered Solvent

After performing as described in Examples 1, 2 and Comparative Example 1, respectively, the recovered normal-hexane solvent was fed and passed through the adsorption column, and then stored in a tank and the composition of each solvent was measured, and the results are shown in Table 1 below. Shown in

Example 1 Example 2 Comparative Example 1 1,3-Butadiene (unreacted monomer) 0.08 wt% 0.06 wt% 0.10 wt% Trans-2-Butene 0.04 wt% 0.04 wt% 0.05 wt% Cis-2-butene 0.55 wt% 0.55 wt% 0.56 wt% C4's 0.01 wt% - 0.01 wt% n-Hexane 99.31 wt% 99.34 wt% 99.28 wt% H 2 O 3 ppm 1 ppm 21 ppm Dimers 9 ppm 9 ppm 10 ppm Heavies 74 ppm 74 ppm 79 ppm The amount of steam used in the first distillation column 2.9 T / hr 3.1 T / hr 2.9 T / hr Steam amount used in the second distillation column 3.5 T / hr 3.5 T / hr 3.7 T / hr Total amount of steam used in the distillation column 6.4 T / hr 6.6 T / hr 6.6 T / hr

As described above, as a result of measuring the composition of each solvent, as shown in Table 1, it can be seen that the content of moisture (H 2 O) is lowered in the order of Comparative Example 1, Example 1 and 2 (21 ppm → 3 ppm → 1 ppm). Thus, using the method of reducing impurities in a solvent in the polymerization of the styrene-butadiene solution according to the present invention, it is possible to lower the water content in the solvent by using the same energy without an additional distillation column.

Claims (8)

Solution polymerization of a raw material comprising styrene and butadiene in a polymerization reactor, followed by discharge of a polymer from a stripper, and the remaining unreacted monomer and solvent are fed to a decanter to remove water components;
By transferring and supplying the unreacted monomer and the solvent to the first distillation column, the C4 fraction or the light impurities and the residual water component containing the unreacted butadiene having a lower boiling point than the solvent are discharged through the upper portion and flushed in the solvent. Recovering the solvent used in the low purity through a stage located below the feed stage of the first distillation column is supplied with the unreacted monomer and the solvent; And
The solvent used for the polymerization reaction in the solvent is supplied to the second distillation column, the styrene comprising a step of recovering in high purity after removing the unreacted monomer and heavy impurities including the unreacted styrene having a higher boiling point than the solvent A method for reducing impurities in a solvent during butadiene solution polymerization. The method of claim 1, wherein the solvent recovered in the second distillation column with high purity is supplied to the reactor after the remaining impurities are removed from the adsorption column. The method of claim 2, wherein the water content in the solvent after passing through the adsorption column is 10 ppm or less, characterized in that the impurity reduction in the solvent during styrene-butadiene solution polymerization. The method of claim 1, wherein the solvent recovered with low purity in the first distillation column, the transfer pump for transferring the materials after the reaction, the polymer and the impurities discharged after the reaction, a mixer and impurities for mixing the reaction additives with the reaction additives A method for reducing impurities in a solvent during styrene-butadiene solution polymerization, which is used for flushing and lubricating action in a filter to be removed. The method of claim 1, wherein the low purity solvent recovered from the first distillation column has a purity of 80 to 98 wt%. The method of claim 1, wherein the high purity solvent recovered from the second distillation column has a purity of 98 to 100% by weight. The method of claim 1, wherein the solvent recovered from the first distillation column and the second distillation column is a normal-hexane, the method of reducing impurities in the solvent during styrene-butadiene solution polymerization. The method according to claim 1, wherein the ratio of the recovered low-purity solvent and high-purity solvent is 1: 5 to 1: 75 by weight ratio, styrene-butadiene solution polymerization method for reducing impurities in the solvent.
KR1020150150994A 2015-10-29 2015-10-29 Method for reduction of impurity in solvent using during a solution polymerization of styrene-butadiene KR101988508B1 (en)

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KR102106806B1 (en) * 2018-02-09 2020-05-06 주식회사 엘지화학 Method for preparing conjugated diene based polymer and apparatus for preparing conjugated diene based polymer
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KR102520447B1 (en) * 2018-11-22 2023-04-10 주식회사 엘지화학 Solvent recovery method and solvent recovery apparatus
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JP2004189904A (en) 2002-12-12 2004-07-08 Denki Kagaku Kogyo Kk Apparatus for removing foreign material, and method for recovering block copolymer using the apparatus
US20090234172A1 (en) 2008-03-12 2009-09-17 Minghua Wang Process of butadiene-1, 3 extraction

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JP2004189904A (en) 2002-12-12 2004-07-08 Denki Kagaku Kogyo Kk Apparatus for removing foreign material, and method for recovering block copolymer using the apparatus
US20090234172A1 (en) 2008-03-12 2009-09-17 Minghua Wang Process of butadiene-1, 3 extraction

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