JPH03258733A - Purification of alpha-methylstyrene - Google Patents
Purification of alpha-methylstyreneInfo
- Publication number
- JPH03258733A JPH03258733A JP5708890A JP5708890A JPH03258733A JP H03258733 A JPH03258733 A JP H03258733A JP 5708890 A JP5708890 A JP 5708890A JP 5708890 A JP5708890 A JP 5708890A JP H03258733 A JPH03258733 A JP H03258733A
- Authority
- JP
- Japan
- Prior art keywords
- methylstyrene
- column
- distillation
- alkali
- alpha
- 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
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 238000000746 purification Methods 0.000 title abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 29
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003513 alkali Substances 0.000 claims abstract description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims description 30
- 239000006227 byproduct Substances 0.000 claims description 10
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 10
- 239000007864 aqueous solution Substances 0.000 abstract description 8
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000000243 solution Substances 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 4
- 239000003957 anion exchange resin Substances 0.000 abstract description 3
- 239000000395 magnesium oxide Substances 0.000 abstract description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 abstract description 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical class CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 238000010543 cumene process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 241001550224 Apha Species 0.000 description 1
- MGSKVZWGBWPBTF-UHFFFAOYSA-N aebsf Chemical compound NCCC1=CC=C(S(F)(=O)=O)C=C1 MGSKVZWGBWPBTF-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- -1 caustic soda Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野〕
本発明はａ−メチルスチレンの精製方法に関し、特にク
メン法フェノールプラントにおいて副生分離された粗α
−メチルスチレンを色相の改善された高純度高品質のａ
−メチルスチレンに精製する、ａ−メチルスチレンの精
製方法に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a method for purifying α-methylstyrene, and in particular to a method for purifying α-methylstyrene, in particular crude α-methylstyrene separated as a by-product in a cumene process phenol plant.
- Methyl styrene with high purity and high quality a with improved hue
This invention relates to a method for purifying a-methylstyrene into methylstyrene.
α−メチルスチレンは、ＡＢＳ樹脂等の樹脂原料として
、或いは農薬、界面活性剤等の中間原料として極めて有
用な物質であり、一般に、クメン法によるフェノールの
製造の際に副生物として製造される。α-Methystyrene is an extremely useful substance as a raw material for resins such as ABS resins, or as an intermediate raw material for agricultural chemicals, surfactants, etc., and is generally produced as a by-product during the production of phenol by the cumene method.
〔従来の技術Ｊ
クメン法フェノール製造方法で副生じたα−メチルスチ
レンは、通常、蒸留によって分離精製されるが、蒸留塔
塔頂より留出するａ−メチルスチレンは黄緑色に着色し
ており、各種素材の原料として使用するには品質上問題
があった。この着色問題を解決する為に、従来は粗α−
メチルスチレンをアルカリ水で洗浄して着色成分を除去
した後、蒸留により精製を行なっていた。しかし該着色
成分は蒸留精製時にも重質物の熱分解により生成し、ま
た、その一部はα−メチルスチレンと極めて近い沸点を
有している為、α−メメチスメチン塔をでるまでα−メ
チルスチレンと同一行動をとり分離されない。特公昭４
８−１０１４２号公報には。[Prior art J] α-Methylstyrene produced as a by-product in the cumene process for producing phenol is usually separated and purified by distillation, but the α-methylstyrene distilled from the top of the distillation column is colored yellow-green. However, there were quality problems when using it as a raw material for various materials. In order to solve this coloring problem, conventionally coarse α-
Methylstyrene was washed with alkaline water to remove colored components, and then purified by distillation. However, this coloring component is generated by the thermal decomposition of heavy substances even during distillation purification, and some of it has a boiling point extremely close to that of α-methylstyrene, so it is difficult to use α-methylstyrene until it leaves the α-memethysmethine column. They act the same and are not separated. Tokuko Showa 4
In the publication No. 8-10142.
ａ−メチルスチレンの色相を改善する為、蒸留塔塔頂よ
り下の棚段部分からα−メチルスチレン留分を抜き出す
ことによって、色相の改善されたα−メチルスチレンを
得る方法が提案されている。In order to improve the hue of a-methylstyrene, a method has been proposed to obtain α-methylstyrene with improved hue by extracting the α-methylstyrene fraction from the tray section below the top of the distillation column. .
〔発明が解決しようとする課題１
しかしながら、このような精製方法では、ａ−メチルス
チレン留分を塔頂より抜き出す場合に比べて精製α−メ
チルスチレンの純度が低下し、更に精製されたα−メチ
ルスチレンの色相（ＡＰＨＡ表示、以下同様）も１５程
度であって、塔頂より抜きだす方法に比べて色相の点で
若干改善されるけれども、満足すべき品質のものが得ら
れるまでには至っていない。[Problem to be Solved by the Invention 1] However, in such a purification method, the purity of the purified α-methylstyrene is lower than in the case where the a-methylstyrene fraction is extracted from the top of the column, and the purity of the purified α-methylstyrene is lowered. The hue of methylstyrene (APHA indication, the same applies hereinafter) is about 15, and although it is slightly improved in hue compared to the method of extracting it from the top of the column, it is still not enough to obtain a product of satisfactory quality. not present.
本発明は、クメン法フェノール製造時において副生ずる
α−メチルスチレンの精製方法につき。The present invention relates to a method for purifying α-methylstyrene, which is produced as a by-product during the production of phenol using the cumene process.
色相のより改善され、かつ、高純度のα−メチルスチレ
ンを得ることのできるａ−メチルスチレンの製造方法を
提供しようとするものである。The object of the present invention is to provide a method for producing α-methylstyrene which has an improved hue and can yield highly purified α-methylstyrene.
［課題を解決するための手段］
本発明者らは、上記の目的を達成すべく鋭意研究を重ね
た結果、アルカリ処理に先立って、予め蒸留により重質
物を除去することにより、精製α−メチルスチレンの純
度及び色相を改善し得ることを見い出し、本発明を完成
した。[Means for Solving the Problems] As a result of intensive research to achieve the above object, the present inventors have found that purified α-methyl The present invention was completed based on the discovery that the purity and hue of styrene can be improved.
すなわち、本発明は、クメン法によるフェノール製造に
おいて副生分離された粗α−メチルスチレンを蒸留によ
って精製するａ−メチルスチレンの精製方法において、
蒸留を二段階で行い、一塔目の蒸留塔塔頂液をアルカリ
で処理した後、更に二塔目の蒸留塔で精留することを特
徴とするａ−メチルスチレンの精製方法である。That is, the present invention provides a method for purifying α-methylstyrene in which crude α-methylstyrene separated as a by-product in phenol production by the cumene method is purified by distillation.
This is a method for purifying a-methylstyrene, which is characterized in that distillation is carried out in two stages, and the top liquid of the first distillation column is treated with an alkali, and then further rectified in the second distillation column.
１１）原料
本発明における原料は、クメン法によるフェノールの製
造方法において副生ずる粗α−メチルスチレンである。11) Raw material The raw material in the present invention is crude α-methylstyrene which is produced as a by-product in the cumene method for producing phenol.
該クメン法によるフェノールの製造方法は、クメンを酸
化する事によって得られるクメンヒドロペルオキシドを
分解して、フェノール及びアセトンを併産するものであ
り、該方法における製造過程においてａ−メチルスチレ
ンが副生ずる。この副生ａ−メチルスチレンは、クメン
ヒドロペルオキシドの分解生成物からフェノール及びア
セトンを蒸留によって分離した後、炭化水素回収塔に供
給され、ここで軽沸点留分を除去してから、粗α−メチ
ルスチレンとして塔底より抜き比される。The cumene method for producing phenol decomposes cumene hydroperoxide obtained by oxidizing cumene to co-produce phenol and acetone, and a-methylstyrene is produced as a by-product during the production process in this method. . After separating phenol and acetone from the decomposition product of cumene hydroperoxide by distillation, this by-product α-methylstyrene is supplied to a hydrocarbon recovery column, where the light-boiling fraction is removed, and then the crude α- It is extracted from the bottom of the column as methylstyrene.
このようにして得られた粗ａ−メチルスチレンには、通
常７５〜９５重量％のα−メチルスチレンのほか、若干
量のクメン、ブチルベンゼン類及びａ−メチルスチレン
の二量化物以上の重質物などが含まれている。The crude α-methylstyrene obtained in this way usually contains 75 to 95% by weight of α-methylstyrene, as well as some amounts of cumene, butylbenzenes, and heavier substances such as dimers of α-methylstyrene. etc. are included.
（２）第一蒸留
本発明の精製方法においては、まず、この粗α−メチル
スチレンを蒸留することによって、高沸点物を分離して
、塔頂より高純度のα−メチルスチレンを得る。このと
きの蒸留条件は、高純度のα−メチルスチレンを得る事
ができれば任意の条件を選ぶ事ができる。(2) First Distillation In the purification method of the present invention, first, the crude α-methylstyrene is distilled to separate high-boiling substances, and highly purified α-methylstyrene is obtained from the top of the column. The distillation conditions at this time can be arbitrarily selected as long as highly pure α-methylstyrene can be obtained.
（３）アルカリ処理
上記の第一蒸留塔の塔頂より抜き出された高純度α−メ
チルスチレンをアルカリ処理する。使用するアルカリと
しては、苛性ソーダを始めとする一価又は二価のアルカ
リ金属及びアルカリ土類金属のヒドロキシド化合物、陰
イオン交換樹脂、マグネシアなどの固体塩基性物質が使
用される。(3) Alkali treatment The high purity α-methylstyrene extracted from the top of the first distillation column is subjected to alkali treatment. As the alkali to be used, solid basic substances such as monovalent or divalent alkali metal and alkaline earth metal hydroxide compounds such as caustic soda, anion exchange resins, and magnesia are used.
アルカリ処理方法としては、撹拌槽方式又は流通方式の
いずれでもよいが、苛性ソーダを始めとする一価又は二
価のアルカリ金属及びアルカリ土類金属のヒドロキシド
化合物は、水溶液にして撹拌槽を使用するアルカリ洗浄
方式が好ましい。また、陰イオン交換樹脂、マグネシア
などの固体塩基性物質の場合は流通方式による処理が好
ましい。The alkali treatment method may be either a stirred tank method or a distribution method, but monovalent or divalent alkali metal and alkaline earth metal hydroxide compounds, including caustic soda, are made into an aqueous solution and used in a stirred tank. An alkaline cleaning method is preferred. Furthermore, in the case of solid basic substances such as anion exchange resins and magnesia, treatment by a flow system is preferable.
アルカリ水溶液を使用する場合、該塔頂液とアルカリ水
溶液との割合は、容量比で１：１０〜１０：ｌ、好まし
くは、ｌ：５〜１．ｌである。処理温度としては、２０
〜ｌＯ口℃、好ましくは、６０〜９０℃である。When an alkaline aqueous solution is used, the ratio of the top liquid to the alkaline aqueous solution is 1:10 to 10:1 by volume, preferably 1:5 to 1. It is l. The processing temperature is 20
~10°C, preferably 60-90°C.
使用するアルカリ水濃度としては、０１規定以上が必要
で、好ましくは０５規定以上である。処理時間は３０秒
以上、好ましくは２分以上必要である。また、このアル
カリ処理を繰りかえし実施してもよい。The concentration of alkaline water used must be 0.01N or higher, preferably 0.05N or higher. The processing time is required to be 30 seconds or more, preferably 2 minutes or more. Further, this alkali treatment may be repeated.
アルカリ洗浄は、第二蒸留塔へのフィード液に対して実
施するのが効率的であるが、第一塔の還流液に対して実
施してもよい。Although it is efficient to carry out alkali washing on the feed liquid to the second distillation column, it may also be carried out on the reflux liquid from the first column.
洗浄方法としては、配管内にアルカリ水を注入して洗浄
してもよく、また、別に洗浄槽を設けて、そこで実施し
てもよい。As a cleaning method, alkaline water may be injected into the pipe for cleaning, or a separate cleaning tank may be provided and the cleaning may be carried out there.
固体塩基性物質を使用する場合の処理条件は、温度２０
〜１００℃、好ましくは６０〜９０℃、Ｌ）ＩＳＶは０
．５〜３０、好ましくは３〜１５である。When using a solid basic substance, the processing conditions are a temperature of 20
~100°C, preferably 60-90°C, L) ISV is 0
．． 5-30, preferably 3-15.
（４）第二蒸留 前記アルカリ処理後のα−メチルスチレンは。(4) Second distillation α-methylstyrene after the alkali treatment.
更に蒸留されることにより色相が改善される。この第二
蒸留の蒸留条件は任意に決められるが、アルカリ水によ
る洗浄を実施した場合は、水分を含むので、減圧条件下
で蒸留する事が好ましい。Further distillation improves the hue. Distillation conditions for this second distillation can be arbitrarily determined, but when washing with alkaline water contains water, it is preferable to distill under reduced pressure conditions.
蒸留操作は回分式でも連続式でもよいが、工業的には連
続方式が通常用いられる。The distillation operation may be carried out either batchwise or continuously, but the continuous method is usually used industrially.
（５）工程
第１図にアルカリ水溶液による洗浄を実施した場合の工
程を例示する。(5) Process FIG. 1 shows an example of the process when washing with an alkaline aqueous solution is carried out.
第１図において、炭化水素回収塔などの塔底から抜き出
された液ｌは粗ａ−メチルメチレン塔。In FIG. 1, the liquid l extracted from the bottom of a hydrocarbon recovery column is a crude a-methylmethylene column.
２に供給される。この粗ａ−メチルメチレン塔では、塔
頂２ａよりクメン留分３を抜き出し、塔底２ｂからα−
メチルスチレン４が抜き出される６
粗ａ−メチルスチレン４は、苛性ソーダ水溶液５と混合
されて、洗浄タンク６内で洗浄された後、精α−メチル
メチレン塔７の第一塔８に供給される。2. In this crude a-methylmethylene column, cumene fraction 3 is extracted from the top 2a, and α-
Methylstyrene 4 is extracted 6. The crude a-methylstyrene 4 is mixed with an aqueous caustic soda solution 5, washed in a washing tank 6, and then supplied to the first column 8 of the purified α-methylmethylene column 7. .
この塔８では、塔底８ｂからα−メメチスメチンニ量化
物などの重質物９を、また、塔頂８ｂから高純度のａ−
メチルスチレン留分１０を抜き出す。この塔頂液ｌＯは
熱分解等により生成した着色成分による着色が著しい。In this column 8, heavy substances 9 such as α-memethysmethine dimer are removed from the bottom 8b, and highly purified a-
Methystyrene fraction 10 is extracted. This tower overhead liquid 1O is significantly colored by colored components generated by thermal decomposition or the like.
塔頂液１０は、苛性ソーダ水溶液１１と混合されて、洗
浄タンク１２に送られ、タンク内でアルカリ洗浄され、
アルカリ廃液から分離された洗浄α−メチルスチレン１
３が、精α−メチルメチレン塔７の第２塔１４に供給さ
れる。第２塔では、塔頂１４ａより色相の改善された高
純度の精αメチルスチレン１５が得られる。The top liquid 10 is mixed with a caustic soda aqueous solution 11, sent to a washing tank 12, and washed with alkali in the tank.
Washed α-methylstyrene separated from alkaline waste liquid 1
3 is fed to the second column 14 of the purified α-methylmethylene column 7. In the second column, high purity purified α-methylstyrene 15 with improved hue is obtained from the column top 14a.
このとき、第１塔、第２塔のいずれか又は両方とも、精
α−メチルスチレンの抜き出しは塔頂より下の任意の段
で行なってもよい。At this time, in either or both of the first column and the second column, the purified α-methylstyrene may be extracted at any stage below the top of the column.
［実施例］ 以下、本発明を実施例によって詳細に説明する。[Example] Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１
第１図のα−メチルスチレンの精製工程図に従ってα−
メチルスチレンの精製を行った。Example 1 α-methylstyrene was purified according to the α-methylstyrene purification process diagram shown in
Methylstyrene was purified.
粗ａ−メチルメチレン塔２の塔底液４の組成は、ａ＝メ
チルスチレン９５．５重量％、クメン０．１重量％、ブ
チルベンゼン類１．０重量％、α−メチルスチレン二量
化物１．９重量％及びその他１．５重量％で、０．５規
定苛性ソーダ水溶液５で洗浄した後、洗浄タンク６で分
離した後、精α−メチルメチレン塔７の第１塔８の塔頂
８ａより３００段目ところに毎時５０ｇの速度で供給し
た。The composition of the bottom liquid 4 of the crude a-methylmethylene column 2 is as follows: a = 95.5% by weight of methylstyrene, 0.1% by weight of cumene, 1.0% by weight of butylbenzenes, and 1% by weight of α-methylstyrene dimer. .9% by weight and 1.5% by weight of others, after washing with 0.5N aqueous sodium hydroxide solution 5 and separating in a washing tank 6, from the top 8a of the first column 8 of the purified α-methylmethylene column 7. It was fed to the 300th stage at a rate of 50 g/hour.
第１塔８は、５ＵＳ３１６ステンレス製充填物を充填し
た理論段数５５段の充填塔で、大気圧、還流比１２の条
件で運転され、高純度のａ−メチルスチレン留分ｌＯが
毎時４１ｇの速度で塔頂より抜き出された。The first column 8 is a packed column with 55 theoretical plates filled with 5US316 stainless steel packing, and is operated at atmospheric pressure and a reflux ratio of 12, and the high-purity a-methylstyrene fraction 1O is produced at a rate of 41 g/hour. He was pulled out from the top of the tower.
この塔頂液のα−メチルスチレン留分１０の純度は９９
．５重量％であり、不純物としてクメン０．１重量％、
ブチルベンゼン類０．２重量％を含み、色相は２０であ
った。The purity of α-methylstyrene fraction 10, which is the top liquid, is 99.
．． 5% by weight, and 0.1% by weight of cumene as an impurity.
It contained 0.2% by weight of butylbenzenes and had a hue of 20.
この塔頂液ｌＯを、０．５規定の苛性ソーダ水滴液を等
容量使用して、温度７０〜８０℃で、１０分間洗浄した
処理液１３の色相はｌＯであった。This tower top liquid 1O was washed with an equal volume of 0.5N caustic soda aqueous solution at a temperature of 70 to 80°C for 10 minutes, and the hue of the treated liquid 13 was 1O.
更に、この処理液１３をステンレス製充填物を充填した
理論段数８段の第２塔１４の塔頂より４段目のところに
、毎時５０ｇの速度で供給し、５０ＩＩＩＩＩＨｇの減
圧下、還流比２で蒸留した。このようにして第２塔１４
の塔頂１４ａより毎時４９ｇの速度で得られた精製ミニ
メチルスチレンは、純度９９．６重量％で、不純物とし
てクメンを０．２重量％、ブチルベンゼン類を０．２重
量％を含み、色相は５以下であった。Furthermore, this treated liquid 13 was supplied at a rate of 50 g/hour to the fourth stage from the top of the second column 14 having eight theoretical plates packed with stainless steel packing, and the reflux ratio was 2 under a reduced pressure of 50IIIHg. It was distilled with. In this way, the second tower 14
The purified mini-methylstyrene obtained from the column top 14a at a rate of 49 g/hour has a purity of 99.6% by weight, contains 0.2% by weight of cumene and 0.2% by weight of butylbenzenes as impurities, and has a hue of was 5 or less.
実施例２
実施例１の精ａ−メチルメチレン塔７の第１塔から得ら
れた塔頂液１０を、０．５規定の苛性ソーダ水を等容量
使用して、温度２５℃で、１０分間洗浄したところ、処
理液１３の色相は１５であった。Example 2 The top liquid 10 obtained from the first column of the purified a-methylmethylene column 7 in Example 1 was washed for 10 minutes at a temperature of 25° C. using an equal volume of 0.5N caustic soda water. As a result, the hue of the treatment liquid 13 was 15.
この処理液を、実施例１の処理液１３と同様に理論段数
８段のステンレス製充填物を充填した第２塔１４で蒸留
したところ、塔頂１４ａより得られた精製α−メチルス
チレンの色相は５であった。When this treatment liquid was distilled in the second column 14 packed with stainless steel packing having 8 theoretical plates in the same manner as the treatment liquid 13 of Example 1, the color of purified α-methylstyrene obtained from the column top 14a was was 5.
実施例３
実施例１の塔頂液１０のアルカリ洗浄に代えて、ＫＷ−
２０００（協和化学■製、合成ハイドロタルサイト）８
３．５ｇを充填したガラス管の底部に、実施例１で得ら
れた塔頂液１０を、温度８０℃、毎時１２００ｍｊの速
度で供給してアルカリ処理し、頂部より処理液を抜き出
した。得られた処理液の色相は２５であった。Example 3 Instead of alkali washing of the top liquid 10 in Example 1, KW-
2000 (manufactured by Kyowa Kagaku ■, synthetic hydrotalcite) 8
The top liquid 10 obtained in Example 1 was supplied to the bottom of a glass tube filled with 3.5 g at a temperature of 80° C. at a rate of 1200 mj/hour for alkali treatment, and the treated liquid was extracted from the top. The hue of the obtained treatment liquid was 25.
この処理液を、実施例１の処理液１３と同様に精α−メ
チルメチレン塔７の理論段数８段のステンレス製充填物
を充填した第２塔１４で蒸留したところ、塔頂１４ａよ
り得られた精製ａ−メチルスチレンの色相は５以下であ
った。When this treated liquid was distilled in the second column 14 of the purified α-methylmethylene column 7 packed with stainless steel packing having 8 theoretical plates in the same manner as the treated liquid 13 of Example 1, the solution was obtained from the top 14a of the column. The hue of the purified a-methylstyrene was 5 or less.
比較例１
実施例１で得られた塔頂液ｌＯを、アルカリ洗浄の代わ
りに、蒸留水を等容量使用して、温度２５℃で、１０分
間洗浄した。得られた処理液の色相は２０であった。Comparative Example 1 Instead of alkaline washing, the tower overhead liquid 1O obtained in Example 1 was washed using an equal volume of distilled water at a temperature of 25° C. for 10 minutes. The hue of the obtained treatment liquid was 20.
この処理液を、実施例１の処理液１３と同様に精ａ−メ
チルメチレン塔７の理論段数８段のステンレス製充填物
を充填した第２塔１４で蒸留したところ、塔頂１４ａよ
り得られた精製ａ−メチルスチレンの色相は１５であっ
た。When this treated liquid was distilled in the second column 14 of the purified a-methylmethylene column 7 packed with stainless steel packing having 8 theoretical plates in the same manner as the treated liquid 13 of Example 1, the solution was obtained from the top 14a of the column. The hue of the purified a-methylstyrene was 15.
［発明の効果１
本発明のα−メチルスチレンの製造方法は、クメン法フ
ェノールプラントで副生じた粗ａ−メチルスチレンを、
二段階に分けて蒸留し、−段目の塔頂液をアルカリ処理
することによって、α−メチルスチレンの色相が大幅に
改善され、しかも、高純度に、かつ、安価に精製するこ
とができる。[Effect of the invention 1] The method for producing α-methylstyrene of the present invention is to process crude α-methylstyrene produced as a by-product in a cumene process phenol plant,
By carrying out the distillation in two stages and treating the top liquid of the second stage with an alkali, the hue of α-methylstyrene can be greatly improved, and it can be purified to high purity and at low cost.
本発明の方法により精製されたａ−メチルスチレンは、
ＡＢＳＦ＃４脂などの各種素材として用いても製品を着
色させることがないので、高品質な製品を得る事ができ
るThe a-methylstyrene purified by the method of the present invention is
Even when used as various materials such as ABSF#4 fat, it does not color the product, so high quality products can be obtained.
第一図は１本発明実施例のα−メチルスチレンの製造方
法に用いた精製工程図である。
１：炭化水素回収塔塔底液、
２：粗α−メチルメチレン塔、
３：クメン留分。
４：粗α−メチルスチレン
５．１１：苛性ソーダ水溶液、
６．１２：洗浄タンク、
７：精α−メチルメチレン塔。
８：第１塔、
９：重質物、
１０：高純度ａ−メチルスチレン留分、１２：洗浄タン
ク、
１３：洗浄ａ−メチルスチレン、
１４：第２塔、
１５：精製α−メチルスチレン。FIG. 1 is a diagram showing a purification process used in the method for producing α-methylstyrene according to an example of the present invention. 1: Hydrocarbon recovery column bottom liquid, 2: Crude α-methylmethylene column, 3: Cumene fraction. 4: Crude α-methylstyrene 5.11: Caustic soda aqueous solution, 6.12: Washing tank, 7: Purified α-methylmethylene tower. 8: First column, 9: Heavy material, 10: High purity a-methylstyrene fraction, 12: Washing tank, 13: Washed a-methylstyrene, 14: Second column, 15: Purified α-methylstyrene.
Claims (1)
された粗α−メチルスチレンを蒸留によって精製するα
−メチルスチレンの精製方法において、蒸留を二段階で
行い、一塔目の蒸留塔塔頂液をアルカリで処理した後、
更に二塔目の蒸留塔で精留することを特徴とするα−メ
チルスチレンの精製方法。(1) α Purifying crude α-methylstyrene, which is a by-product separated during phenol production by the cumene method, by distillation.
- In a method for purifying methylstyrene, distillation is carried out in two stages, and after treating the top liquid of the first distillation column with an alkali,
A method for purifying α-methylstyrene, which further comprises rectifying in a second distillation column.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5708890A JP2767755B2 (en) | 1990-03-08 | 1990-03-08 | Purification method of α-methylstyrene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5708890A JP2767755B2 (en) | 1990-03-08 | 1990-03-08 | Purification method of α-methylstyrene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03258733A true JPH03258733A (en) | 1991-11-19 |
| JP2767755B2 JP2767755B2 (en) | 1998-06-18 |
Family
ID=13045744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5708890A Expired - Lifetime JP2767755B2 (en) | 1990-03-08 | 1990-03-08 | Purification method of α-methylstyrene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2767755B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007119849A1 (en) | 2006-04-17 | 2007-10-25 | Asahi Kasei Chemicals Corporation | METHOD FOR PURIFYING α-METHYLSTYRENE, AND HEAT-RESISTANT STYRENE COPOLYMER USING THE α-METHYLSTYRENE |
| CN112047801A (en) * | 2020-09-17 | 2020-12-08 | 吉化集团油脂化工有限公司 | Equipment for improving quality of alpha-methyl styrene product and production method thereof |
-
1990
- 1990-03-08 JP JP5708890A patent/JP2767755B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007119849A1 (en) | 2006-04-17 | 2007-10-25 | Asahi Kasei Chemicals Corporation | METHOD FOR PURIFYING α-METHYLSTYRENE, AND HEAT-RESISTANT STYRENE COPOLYMER USING THE α-METHYLSTYRENE |
| EP2011807A1 (en) * | 2006-04-17 | 2009-01-07 | Asahi Kasei Chemicals Corporation | Method for purifying -methylstyrene, and heat-resistant styrene copolymer using the -methylstyrene |
| US7772336B2 (en) | 2006-04-17 | 2010-08-10 | Asahi Kasei Chemicals Corporation | Method for producing α-methylstyrene and heat-resistant styrene-based copolymer using the α-methylstyrene |
| EP2011807A4 (en) * | 2006-04-17 | 2013-10-02 | Asahi Kasei Chemicals Corp | Method for purifying -methylstyrene, and heat-resistant styrene copolymer using the -methylstyrene |
| EP2743246A1 (en) | 2006-04-17 | 2014-06-18 | Asahi Kasei Chemicals Corporation | Alpha-Metylstyrene-based copolymer |
| CN112047801A (en) * | 2020-09-17 | 2020-12-08 | 吉化集团油脂化工有限公司 | Equipment for improving quality of alpha-methyl styrene product and production method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2767755B2 (en) | 1998-06-18 |
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