JPH0482849A - Decoloring of nucleus-brominated styrene - Google Patents
Decoloring of nucleus-brominated styreneInfo
- Publication number
- JPH0482849A JPH0482849A JP19504390A JP19504390A JPH0482849A JP H0482849 A JPH0482849 A JP H0482849A JP 19504390 A JP19504390 A JP 19504390A JP 19504390 A JP19504390 A JP 19504390A JP H0482849 A JPH0482849 A JP H0482849A
- Authority
- JP
- Japan
- Prior art keywords
- brominated styrene
- alumina
- aliphatic hydrocarbon
- ring
- silica
- 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.)
- Pending
Links
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003463 adsorbent Substances 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 9
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 5
- 239000010452 phosphate Substances 0.000 claims abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- -1 cyclic brominated styrene Chemical class 0.000 claims description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 5
- 235000012239 silicon dioxide Nutrition 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 4
- 239000001095 magnesium carbonate Substances 0.000 claims description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000306 component Substances 0.000 claims description 3
- 235000001465 calcium Nutrition 0.000 claims description 2
- 235000014380 magnesium carbonate Nutrition 0.000 claims description 2
- 229960002261 magnesium phosphate Drugs 0.000 claims description 2
- 235000010994 magnesium phosphates Nutrition 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 abstract description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 6
- JVPKLOPETWVKQD-UHFFFAOYSA-N 1,2,2-tribromoethenylbenzene Chemical compound BrC(Br)=C(Br)C1=CC=CC=C1 JVPKLOPETWVKQD-UHFFFAOYSA-N 0.000 abstract description 4
- 229910003481 amorphous carbon Inorganic materials 0.000 abstract description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052791 calcium Inorganic materials 0.000 abstract description 3
- 239000011575 calcium Substances 0.000 abstract description 3
- 229910052749 magnesium Inorganic materials 0.000 abstract description 3
- 239000011777 magnesium Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 239000003063 flame retardant Substances 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 1
- 238000002845 discoloration Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 16
- 238000002835 absorbance Methods 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- YMOONIIMQBGTDU-UHFFFAOYSA-N 2-bromoethenylbenzene Chemical compound BrC=CC1=CC=CC=C1 YMOONIIMQBGTDU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006103 coloring component Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 239000000391 magnesium silicate Substances 0.000 description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 description 2
- 235000019792 magnesium silicate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BMSUWQXMTMGEOM-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-ethenylbenzene Chemical compound BrC1=C(Br)C(Br)=C(C=C)C(Br)=C1Br BMSUWQXMTMGEOM-UHFFFAOYSA-N 0.000 description 1
- XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は、着色環臭素化スチレンの脱色方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for decolorizing colored ring-brominated styrene.
環臭素化スチレン、特にモノ、ジ、トリブロモスチレン
及びそれらの混合物は、高分子材料の反応型難燃剤若し
くは光学材料のモノマーとして有用な化合物である。Cyclobrominated styrenes, especially mono-, di-, and tribromostyrenes and mixtures thereof, are useful compounds as reactive flame retardants for polymeric materials or as monomers for optical materials.
［従来の技術］ 環臭素化スチレンは、公知の方法で製造される。[Conventional technology] Ring brominated styrene is produced by a known method.
例えばポリマー（１９６９年）１０巻、４７９〜４８７
頁には、β−ブロモエチルベンゼンの環臭素化により環
臭素化β−ブロモエチルベンゼンを得て、さらにそれを
脱臭化水素して環臭素化スチレンを製造する方法が示さ
れている。しかし、このようにして製造された環臭素化
スチレンは、米国特許第４６３３０２６号に示されるよ
うに黄色等に着色しているのが現状である。このように
着色した環臭素化スチレンを単独重合、あるいは種々の
共重合体やグラフト重合体にして各種樹脂に配合した場
合、当然のことながら配合樹脂も着色することとなり外
観等大きな問題点となる。しかしながら、このように着
色した環臭素化スチレンを有効に脱色する方法は示され
ていない。For example, Polymer (1969) Vol. 10, 479-487.
The page describes a method for producing ring-brominated styrene by ring-brominating β-bromoethylbenzene to obtain ring-brominated β-bromoethylbenzene, which is then dehydrobrominated. However, the ring brominated styrene produced in this manner is currently colored yellow or the like as shown in US Pat. No. 4,633,026. When such colored ring-brominated styrene is homopolymerized or made into various copolymers or graft polymers and blended into various resins, the blended resin will of course be colored, causing major problems such as appearance. . However, no method has been shown to effectively decolorize such colored ring brominated styrene.
［発明が解決しようとする課題］
本発明の目的は、着色した環臭素化スチレンを経済的か
つ工業的に脱色する方法を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide a method for economically and industrially decolorizing colored ring-brominated styrene.
［課題を解決するための手段］
本発明者らは、上記脱色方法について鋭意検討した結果
、着色した環臭素化スチレンを、シリカ若しくはアルミ
ナを主成分とする酸化物、カルシウム若しくはマグネシ
ウムの炭酸塩、リン酸塩若しくはケイ酸または無定形炭
素から選ばれる１種以上を吸着剤として接触させ処理す
ることにより極めて効果的に脱色できるという特異な事
実を見出だし本発明を完成させるに至った。[Means for Solving the Problems] As a result of intensive studies on the above-mentioned decolorization method, the present inventors have found that colored ring-brominated styrene can be treated with an oxide containing silica or alumina as a main component, a calcium or magnesium carbonate, or a carbonate of calcium or magnesium. We have completed the present invention by discovering the unique fact that decolorization can be achieved extremely effectively by contacting and treating with one or more selected from phosphate, silicic acid, or amorphous carbon as an adsorbent.
すなわち、本発明は、着色した環臭素化スチレンを脱色
するにあたり、該着色した環臭素化スチレンを、シリカ
若しくはアルミナを主成分とする酸化物、カルシウム若
しくはマグネシウムの炭酸塩、リン酸塩若しくはケイ酸
または無定形炭素から選ばれる１種以上を吸着剤として
接触させ処理することを特徴とする環臭素化スチレンの
脱色方法である。That is, in decolorizing colored ring-brominated styrene, the present invention provides an oxide containing silica or alumina as a main component, calcium or magnesium carbonate, phosphate, or silicic acid. This is a method for decolorizing ring-brominated styrene, which is characterized in that the treatment is carried out by bringing it into contact with one or more types selected from amorphous carbon as an adsorbent.
以下、本発明を更に詳細に説明する。The present invention will be explained in more detail below.
［作用］
本発明の脱色方法の対象となる環臭素化スチレンに含有
される着色成分は、先に述べた環臭素化スチレンの製造
方法の環臭素化及び脱臭化水素反応の双方で生成するも
のであり、本発明の方法によって脱色可能である。[Function] The coloring component contained in the ring brominated styrene that is the subject of the decolorization method of the present invention is one that is produced in both the ring bromination and dehydrobromation reactions of the ring brominated styrene manufacturing method described above. and can be decolorized by the method of the present invention.
本発明でいう環臭素化スチレンとは、スチレンの芳香環
水素を臭素で少なくとも１個以上置換した化合物である
。具体的には、モノブロモスチレン、ジプロモスチレン
、トリブロモスチレン テトラブロモスチレン、ペンタ
ブロモスチレン及びそれらの混合物を指す。The ring-brominated styrene referred to in the present invention is a compound in which at least one hydrogen atom in the aromatic ring of styrene is replaced with bromine. Specifically, it refers to monobromostyrene, dipromostyrene, tribromostyrene, tetrabromostyrene, pentabromostyrene, and mixtures thereof.
特にモノ、ジ、 ｌ−ジプロモスチレン及びそれらの
混合物が、本発明に好適に使用されつる化合物である。In particular, mono-, di-, l-dipromostyrene and mixtures thereof are preferred compounds for use in the present invention.
本発明で使用される脂肪族炭化水素とは、環臭素化スチ
レンを溶解出来る炭素数５〜８程度の環状、鎖状の飽和
脂肪族炭化水素を指す。具体的には、石油エーテル、ペ
ンタン、シクロベンクン、２−メチルブタン、２，２−
ジメチルプロパン、メチルシクロペンクン、シクロヘキ
サン、ヘキサン、２−メチルペンタン、３−メチルペン
タン、２．２−ジメチルブタン、２，３−ジメチルブタ
ン、メチルシクロヘキサン、ヘプタン、２−メチルヘキ
サン、３−メチルヘキサン、２．３−ジメチルペンタン
、２，４−ジメチルペンタン、エチルシクロヘキサン、
オクタン、２，２．３−トリメチルペンタン、２，２．
４−トリメチルペンタン等が挙げられる。これらの中で
もヘキサン、ヘプタン、オクタンが特に取扱い及び、回
収の容易さから好ましい。The aliphatic hydrocarbon used in the present invention refers to a cyclic or chain saturated aliphatic hydrocarbon having about 5 to 8 carbon atoms that can dissolve cyclic brominated styrene. Specifically, petroleum ether, pentane, cyclobencune, 2-methylbutane, 2,2-
Dimethylpropane, methylcyclopenkune, cyclohexane, hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane, methylcyclohexane, heptane, 2-methylhexane, 3-methylhexane , 2,3-dimethylpentane, 2,4-dimethylpentane, ethylcyclohexane,
Octane, 2,2.3-trimethylpentane, 2,2.
Examples include 4-trimethylpentane. Among these, hexane, heptane, and octane are particularly preferred from the viewpoint of ease of handling and recovery.
一方、本発明に使用される吸着剤は、シリカ若しくはア
ルミナを主成分とする酸化物、カルシウム若しくはマグ
ネシウムの炭酸塩、リン酸塩若しくはケイ酸または無定
形炭素であり、具体的には、活性炭、シリカゲル、アル
ミナ、ケイ酸マグネシウム、マグネシア、ケイソウ土、
シリカアルミナ。On the other hand, the adsorbent used in the present invention is an oxide mainly composed of silica or alumina, carbonate, phosphate or silicic acid of calcium or magnesium, or amorphous carbon, and specifically, activated carbon, Silica gel, alumina, magnesium silicate, magnesia, diatomaceous earth,
silica alumina.
゛ｆオライド、炭酸カルシウム、リン酸カルシウム。゛Folide, calcium carbonate, calcium phosphate.
炭酸マグネシウム、ケイ酸マグネシウム活性炭。Magnesium carbonate, magnesium silicate activated carbon.
木炭、コークス、カーボンブラック等があげられる。こ
れらの中でもアルミナ、シリカゲル、活性炭が脱色効果
が高く特に好ましい。その形状は粒状、粉状を問わない
。Examples include charcoal, coke, carbon black, etc. Among these, alumina, silica gel, and activated carbon are particularly preferred because they have a high decolorizing effect. Its shape does not matter whether it is granular or powdery.
吸着剤に、脂肪族炭化水素に溶解させた環臭素化スチレ
ン溶液（以下、被処理液と記す）を接触させる方法は、
回分式、連続式のいずれも有効である。The method of contacting the adsorbent with a cyclic brominated styrene solution (hereinafter referred to as the liquid to be treated) dissolved in an aliphatic hydrocarbon is as follows:
Both batch and continuous methods are effective.
被処理液を吸着剤と接触させる場合、被処理液中の脂肪
族炭化水素（以下、ＨＣと記す）と着色環臭素化スチレ
ン（以下、ＢＳと記す）の使用割合は、Ｂ５１００容量
部に対してＨＣ５０容量部から２０００容量部の範囲で
任意に選択できるが、実用上５０容量部から５００容量
部の使用割合が好ましい。When the liquid to be treated is brought into contact with an adsorbent, the proportion of aliphatic hydrocarbons (hereinafter referred to as HC) and colored ring brominated styrene (hereinafter referred to as BS) in the liquid to be treated is 100 parts by volume of B5. The amount of HC can be arbitrarily selected within the range of 50 parts by volume to 2000 parts by volume, but in practice, a usage ratio of 50 parts by volume to 500 parts by volume is preferred.
一方、吸着剤の使用量は、Ｂ５１００容量部に対して５
０容量部から１０００容量部の範囲で任意に選択できる
が、実用上５０容量部から５００容量部の使用が好まし
い。On the other hand, the amount of adsorbent used is 5 parts by volume of B5100.
Although it can be arbitrarily selected from 0 parts by volume to 1000 parts by volume, it is practically preferable to use 50 parts by volume to 500 parts by volume.
被処理液と吸着剤との接触は、回分式では容器内で両者
を撹はんまたは振とうさせて接触させればよく、連続式
では吸着剤を充填したカラムに被処理液を通液させて接
触させればよい。接触の際の温度は当該着色成分の吸着
に殆ど影響はないか、高い温度ではＢＳの安定性及びＨ
Ｃの蒸散に問題があるため、通常Ｏ〜４０℃が選択され
る。In the batch method, the liquid to be treated and the adsorbent may come into contact by stirring or shaking the two in a container; in the continuous method, the liquid to be treated is passed through a column filled with the adsorbent. Just touch it. The temperature during contact has little effect on the adsorption of the coloring component, and high temperatures may affect the stability of BS and H
Since there is a problem with transpiration of C, a temperature of 0 to 40°C is usually selected.
また、着色成分を吸着した吸着剤は脂肪族炭化水素以外
の溶剤、例えばアセトン、ベンゼン、テトラヒドロフラ
ン、メタノール、塩化メチレン。Further, the adsorbent adsorbing the coloring component is a solvent other than aliphatic hydrocarbons, such as acetone, benzene, tetrahydrofuran, methanol, and methylene chloride.
イソプロピルエーテル等で脱着再生され、再使用するこ
とができる。It can be desorbed and regenerated with isopropyl ether and can be reused.
［発明の効果］
以上述べたことから明らかように、従来の製造工程で得
られた環臭素化スチレンに、本発明の脱色方法を適用す
ることにより、効果的に脱色できる。その結果、得られ
る環臭素化スチレンは、重合後に樹脂成型体に着色を及
ぼさない特徴がある。[Effects of the Invention] As is clear from the above description, by applying the decolorizing method of the present invention to ring brominated styrene obtained through conventional manufacturing processes, it is possible to effectively decolorize the ring brominated styrene obtained by the conventional manufacturing process. As a result, the ring brominated styrene obtained has the characteristic that it does not color the resin molded product after polymerization.
また本発明の操作法は、極めて簡便で、工業的な利用価
値が大きく実用性に富んだ脱色方法である。Furthermore, the operating method of the present invention is a decolorizing method that is extremely simple, has great industrial value, and is highly practical.
［実施例］
以下に、本発明の方法を実施例により具体的に説明する
が、本発明はこれら実施例のみに限定されるものではな
い。[Examples] The method of the present invention will be specifically explained below using Examples, but the present invention is not limited only to these Examples.
尚、脱色効果は、被処理液、処理液ともに以下の条件で
７１１１＋定した吸光度（ＡＢＳ）を比較することで見
た。The decolorizing effect was determined by comparing the absorbance (ABS) determined by 7111+ for both the liquid to be treated and the liquid to be treated under the following conditions.
・測定セル・・・１ｃｍ角石英セル
・測定波長・・・４６０ｎｍ
実施例１
温度計、撹はん機及び還流冷却管を有する容量５００ｄ
の四つロセパラブルフラスコに、ＡＢＳ＝０．２０８の
黄色に着色した環ブロモ化スチレン混合物（モノブロモ
スチレン４重量％、ジプロモスチレン８１重量９ｇ、）
’リブロモスチレン１５重量％含有）１０Ｃ１ｄとロー
ヘキサン２００ｒｎｌ！を加えた。次に、活性アルミナ
（塩基性）１００ｍｊ２を加え、２０℃で２０分間撹は
ん処理した。その後、処理液をろ過し、ろ液を濃縮して
ｎ−ヘキサンを除去した。得られた濃縮液のＡＢＳは、
０．０１５でほとんど無色透明液であり、効果的に脱色
されていた。・Measurement cell: 1 cm square quartz cell ・Measurement wavelength: 460 nm Example 1 Capacity: 500 d with thermometer, stirrer, and reflux cooling pipe
A ring-brominated styrene mixture colored yellow with ABS = 0.208 (monobromostyrene 4% by weight, dipromostyrene 81% by weight, 9 g) was placed in four separable flasks.
'Contains 15% by weight of Libromostyrene) 10C1d and 200rnl of rhohexane! added. Next, 100 mj2 of activated alumina (basic) was added and stirred at 20°C for 20 minutes. Thereafter, the treated solution was filtered, and the filtrate was concentrated to remove n-hexane. The ABS of the obtained concentrate is
0.015, the liquid was almost colorless and transparent, indicating that it had been effectively decolored.
実施例２
ｎ−へキサンをオクタンにした以外は実施例１と同一の
処理量、条件で処理をした。得られた濃縮液のＡＢＳは
、０．０１８でほとんど無色透明液であった。Example 2 The treatment was carried out using the same amount and conditions as in Example 1, except that octane was used instead of n-hexane. The ABS of the obtained concentrate was 0.018, and it was an almost colorless transparent liquid.
実施例３
濃黄色に着色した環ブロモ化スチレン混合物モノブロモ
スチレン２重量％、ジプロモスチレン７８重２％、トリ
ブロモスチレン２０重量％含有）１００ｄ （ＡＢＳｏ
、４１．２）とｎ−ヘキサン２００ｍ１を加えた。次に
、活性アルミナ（塩基性）１５０ｍｌを加えた以外は実
施例１と同一の条件で処理をした。得られた濃縮液のＡ
ＢＳは、０．０２０でほとんど無色透明液であった。Example 3 Ring-brominated styrene mixture colored deep yellow (containing 2% by weight of monobromostyrene, 2% by weight of dipromostyrene 78, and 20% by weight of tribromostyrene) 100d (ABSo
, 41.2) and 200 ml of n-hexane were added. Next, treatment was carried out under the same conditions as in Example 1 except that 150 ml of activated alumina (basic) was added. A of the obtained concentrate
BS was 0.020 and was an almost colorless transparent liquid.
実施例４
処理温度を４０℃にした以外は実施例１と同一の処理量
、条件で処理をした。得られた濃縮液のＡＢＳは、０．
０１８でほとんど無色透明液であった。Example 4 The treatment was carried out under the same treatment amount and conditions as in Example 1, except that the treatment temperature was 40°C. The ABS of the obtained concentrate was 0.
018 and was an almost colorless transparent liquid.
実施例５
内径７６ｍｍの円塔型ガラスカラムに、活性アルミナ（
塩基性）１０００ｄを充填した。このカラムに実施例１
で使用した、黄色に着色した環ブロモ化スチレン混合物
１１００ｍｊとｎ−ヘキサン４０００ｍ１の混合液を、
２０°Ｃで５Ｖ＝２で通液した。全流出液を実施例１と
同様の処理をした。Example 5 Activated alumina (
Basic) 1000d was filled. Example 1 for this column
A mixture of 1,100 mj of the yellow-colored ring-brominated styrene mixture and 4,000 ml of n-hexane used in
The solution was passed at 20°C and 5V=2. The entire effluent was treated as in Example 1.
得られた濃縮液のＡＢＳは、０．０２０でほとんど無色
透明液であった。The obtained concentrated liquid had an ABS of 0.020 and was an almost colorless transparent liquid.
実施例６
活性アルミナ（塩基性）をシリカゲル（カラムクロマト
グラフ用）にした以外は実施例４と同一の処理量、条件
で処理をした。得られた濃縮液のＡＢＳは、０．０２２
でほとんど無色透明液であった。Example 6 The treatment was carried out using the same amount and conditions as in Example 4, except that silica gel (for column chromatography) was used instead of activated alumina (basic). The ABS of the obtained concentrate is 0.022
It was an almost colorless transparent liquid.
実施例７
活性アルミナ（塩基性）を活性炭（カラムクロマトグラ
フ用）にした以外は実施例４と同一の処理量、条件で処
理をした。得られた濃縮液のＡＢＳは、０．０２４でほ
とんど無色透明液であった。Example 7 The treatment was carried out using the same amount and conditions as in Example 4, except that activated carbon (for column chromatography) was used instead of activated alumina (basic). The obtained concentrated liquid had an ABS of 0.024 and was an almost colorless transparent liquid.
比較例］
ｎ−ヘキサンをベンゼンにした以外は、実施例１と同一
の処理量、条件で処理をした。黄色の濃縮液が得られＡ
ＢＳは、０．１．９０で、はとんど脱色されていなかっ
た。Comparative Example] The treatment was carried out under the same treatment amount and conditions as in Example 1, except that benzene was used instead of n-hexane. A yellow concentrate was obtained.
BS was 0.1.90 and was hardly bleached.
比較例２
ｎ−へキサンをアセトンにした以外は、実施例１と同一
の処理量、条件で処理をした。黄色の濃縮液が得られＡ
ＢＳは、０．２０５で、はとんど脱色されていなかった
。Comparative Example 2 The treatment was carried out in the same amount and under the same conditions as in Example 1, except that acetone was used instead of n-hexane. A yellow concentrate was obtained.
BS was 0.205 and was hardly bleached.
比較例３
ｎ−ヘキサンを四塩化炭素にした以外は、実施例１と同
一の処理量、条件で処理をした。黄色の濃縮液が得られ
ＡＢＳは、０．２００で、はとんど脱色されていなかっ
た。Comparative Example 3 The treatment was carried out in the same amount and under the same conditions as in Example 1, except that carbon tetrachloride was used instead of n-hexane. A yellow concentrate was obtained with an ABS of 0.200 and was hardly decolorized.
特許出願人 東ソー株式会社Patent applicant: Tosoh Corporation
Claims (1)
に溶解させた該環臭素化スチレンを、シリカ若しくはア
ルミナを主成分とする酸化物、カルシウム若しくはマグ
ネシウムの炭酸塩、リン酸塩若しくはケイ酸または無定
形炭素から選ばれる１種以上を吸着剤として接触させ処
理することを特徴とする環臭素化スチレンの脱色方法In decolorizing cyclobrominated styrene, the cyclic brominated styrene dissolved in an aliphatic hydrocarbon is treated with an oxide containing silica or alumina as a main component, calcium or magnesium carbonate, phosphate or silicic acid, or an aliphatic hydrocarbon. A method for decolorizing cyclic brominated styrene, characterized by contacting and treating with one or more types selected from regular carbon as an adsorbent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19504390A JPH0482849A (en) | 1990-07-25 | 1990-07-25 | Decoloring of nucleus-brominated styrene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19504390A JPH0482849A (en) | 1990-07-25 | 1990-07-25 | Decoloring of nucleus-brominated styrene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0482849A true JPH0482849A (en) | 1992-03-16 |
Family
ID=16334595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19504390A Pending JPH0482849A (en) | 1990-07-25 | 1990-07-25 | Decoloring of nucleus-brominated styrene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0482849A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447192A (en) * | 2013-09-13 | 2015-03-25 | 山东天一化学股份有限公司 | Purification method for tribromostyrene |
-
1990
- 1990-07-25 JP JP19504390A patent/JPH0482849A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447192A (en) * | 2013-09-13 | 2015-03-25 | 山东天一化学股份有限公司 | Purification method for tribromostyrene |
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