JP2002030003A - Method for removing bromine from organic bromine compound - Google Patents
Method for removing bromine from organic bromine compoundInfo
- Publication number
- JP2002030003A JP2002030003A JP2000211236A JP2000211236A JP2002030003A JP 2002030003 A JP2002030003 A JP 2002030003A JP 2000211236 A JP2000211236 A JP 2000211236A JP 2000211236 A JP2000211236 A JP 2000211236A JP 2002030003 A JP2002030003 A JP 2002030003A
- Authority
- JP
- Japan
- Prior art keywords
- bromine compound
- organic bromine
- organic
- bromine
- compound
- 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
Landscapes
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、固相系で有機臭素
化合物から臭素を除去する方法に関するものであり、有
機臭素化合物、あるいは有機臭素化合物を含む樹脂の廃
棄における環境問題を解決することを目的とする。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for removing bromine from an organic bromine compound in a solid phase system, and it is an object of the present invention to solve an environmental problem in disposing of an organic bromine compound or a resin containing an organic bromine compound. Aim.
【０００２】[0002]
【従来の技術】有機臭素化合物は熱分解時に難燃性を発
揮することから、樹脂等に配合して難燃性を付与する、
いわゆる難燃剤として広く使用されている。これらの有
機臭素化合物を含有する樹脂の廃棄処理は、従来燃焼処
理が一般的であるが、その際発生すると考えられる臭素
化合物、特にダイオキシン類は、有機塩素化合物と同
様、環境への影響が著しいと予想できる。従って、この
ような有機臭素化合物を含む樹脂処理は、一部のものが
特殊な燃焼処理をされているものの、主として土壌中へ
の埋め立てに頼っており、有機臭素化合物の無害化処理
という観点からみると未だ解決に至ってないのが実状で
ある。2. Description of the Related Art Since organic bromine compounds exhibit flame retardancy during thermal decomposition, they are added to resins and the like to impart flame retardancy.
Widely used as so-called flame retardants. Conventionally, the disposal treatment of resins containing these organic bromine compounds is generally performed by combustion treatment, but bromine compounds, especially dioxins, which are considered to be generated at that time, have a remarkable effect on the environment like organic chlorine compounds. Can be expected. Therefore, such a resin treatment containing an organic bromine compound, although a part of the resin is subjected to a special combustion treatment, mainly depends on landfill in soil, and from the viewpoint of detoxifying the organic bromine compound. The fact is that it has not been resolved yet.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、燃焼処理す
ることなく有機臭素化合物から臭素を除去し、有機臭素
化合物を臭素を含まない物質に変換することを目的とす
るものであり、更には、有機臭素化合物を含む樹脂を燃
焼処理することなく、脱臭素化する方法を提供するもの
である。脱臭素化された分解生成物及び生成した無機臭
素化合物はそれぞれ有効利用しうるものである。SUMMARY OF THE INVENTION It is an object of the present invention to remove bromine from an organic bromine compound without performing a burning treatment, and to convert the organic bromine compound into a bromine-free substance. Another object of the present invention is to provide a method for debrominating a resin containing an organic bromine compound without burning the resin. The debrominated decomposition product and the generated inorganic bromine compound can be effectively used.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、有機臭素
化合物の分解方法を鋭意検討した結果、有機臭素化合物
をアルカリ金属水酸化物の存在下、メカノケミカル処理
することにより、有機臭素化合物を脱臭素化する方法を
見出した。また、有機臭素化合物を含む樹脂又は樹脂硬
化物をアルカリ金属水酸化物の存在下、メカノケミカル
処理することにより、該樹脂又は樹脂硬化物から臭素を
除去する方法を見出した。Means for Solving the Problems The present inventors have conducted intensive studies on a method for decomposing an organic bromine compound. As a result, the organic bromine compound is subjected to mechanochemical treatment in the presence of an alkali metal hydroxide, thereby obtaining an organic bromine compound. A method for debrominating was found. Further, the present inventors have found a method of removing bromine from a resin or a cured resin obtained by subjecting a resin or a cured resin containing an organic bromine compound to mechanochemical treatment in the presence of an alkali metal hydroxide.
【０００５】[0005]
【発明の実施の形態】以下本発明を詳しく説明する。本
発明における有機臭素化合物は、特に限定されるもので
はなく、例えば、ヘキサブロモベンゼン（ＨＢＢ）、テ
トラブロモビスフェノールＡ（ＴＢＢＰＡ）、デカブロ
モジフェニルオキシド（ＤＢＤＰＯ）、ポリブロモジベ
ンゾダイオキシン（ＰＢＤＤ）、ポリブロモジベンゾフ
ラン（ＰＢＤＦ）、ポリブロモビフェニル（ＰＢＢ）、
ポリブロモシクロドデカン（ＰＢＣＤ）などが挙げられ
る。これらは、一般に臭素系難燃剤として樹脂等に配合
される。また、上記化合物を骨格に含む高分子化合物な
ども本発明における有機臭素化合物に含まれる。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The organic bromine compound in the present invention is not particularly limited. For example, hexabromobenzene (HBB), tetrabromobisphenol A (TBBPA), decabromodiphenyl oxide (DBDPO), polybromodibenzodioxin (PBDD), polybromine Bromodibenzofuran (PBDF), polybromobiphenyl (PBB),
And polybromocyclododecane (PBCD). These are generally blended with a resin or the like as a brominated flame retardant. Further, a high molecular compound containing the above compound in the skeleton is also included in the organic bromine compound in the present invention.
【０００６】本発明における有機臭素化合物を含む樹脂
又は樹脂硬化物は、特に限定されるものではなく、例え
ば、上記有機臭素化合物を難燃剤として配合したフェノ
ール樹脂、エポキシ樹脂、ポリエステル樹脂、アクリル
樹脂、あるいはこれらの樹脂を硬化反応させた樹脂硬化
物が挙げられる。The resin or cured resin containing an organic bromine compound in the present invention is not particularly limited. For example, a phenol resin, an epoxy resin, a polyester resin, an acrylic resin containing the above organic bromine compound as a flame retardant, Alternatively, a cured resin obtained by subjecting these resins to a curing reaction may be used.
【０００７】本発明におけるアルカリ金属水酸化物は、
ＬｉＯＨ、ＮａＯＨ、ＫＯＨに代表されるアルカリ金属
化合物である。これらの中でもＮａＯＨが、アルカリ性
が強く、安価に入手できるので好ましい。有機臭素化合
物とアルカリ金属水酸化物とは、前者の臭素に対する後
者の水酸基の当量比が１以上、更には１〜２程度が好ま
しい。この当量比が１未満ではメカノケミカル処理後に
おいても分解生成物中に臭素分が残ることとなる。In the present invention, the alkali metal hydroxide is
It is an alkali metal compound represented by LiOH, NaOH and KOH. Among them, NaOH is preferable because it is strongly alkaline and can be obtained at low cost. The organic bromine compound and the alkali metal hydroxide preferably have an equivalent ratio of the former hydroxyl group to the former bromine of 1 or more, and more preferably about 1 to 2. If the equivalent ratio is less than 1, bromine remains in the decomposition product even after the mechanochemical treatment.
【０００８】本発明で用いるメカノケミカル処理とは、
固体物質に摩砕、摩擦、延伸、圧縮などの機械的エネル
ギーを加えることにより、構造変化、相転位、反応性、
吸着性、触媒活性などを与える処理であり、表面積の増
加、格子欠陥の増加、結晶粒子の大きさの減少や無定形
化が期待できる［参考文献：理化学辞典，岩波書店（１
９８７）］。本発明においてメカノケミカル処理は、０
〜２００℃の範囲で行うことができ、通常は、加熱する
ことなく常温付近で行うことができる。２００℃を上回
ると有機臭素化物が熱により分解するおそれがあり、０
℃下回ると生成物にＨ2Ｏが含まれる場合など、処理が
著しく遅くなることがある。メカノケミカル処理を行う
ための装置は、ボールミル等、被処理物に機械的エネル
ギーを加えることができるものであればよく、特に限定
されない。本発明のメカノケミカル処理を行うには、有
機臭素化合物、あるいは有機臭素化合物を含む樹脂又は
樹脂硬化物は粉末状であることが好ましい。粒径は小さ
い方がよいが、特に限定されない。通常は適宜の大きさ
に粉砕した材料を使用し、メカノケミカル処理の際に処
理装置により粉砕も同時に行われる。また、アルカリ金
属水酸化物も粉末状であることが処理時間の短縮が図れ
より好ましい。The mechanochemical treatment used in the present invention is
By applying mechanical energy such as grinding, friction, stretching, and compression to a solid material, structural changes, phase transition, reactivity,
It is a treatment that gives adsorptivity, catalytic activity, etc., and can be expected to increase the surface area, increase lattice defects, reduce the size of crystal grains, and make it amorphous [References: RIKEN Dictionary, Iwanami Shoten (1)
987)]. In the present invention, the mechanochemical treatment is 0
The reaction can be carried out at a temperature in the range of 200 to 200 ° C., and usually at about room temperature without heating. If the temperature exceeds 200 ° C., the organic bromide may be decomposed by heat,
If the temperature is lower than ℃, the treatment may be remarkably slow, for example, when the product contains H 2 O. The apparatus for performing the mechanochemical treatment is not particularly limited as long as it can apply mechanical energy to the object to be processed, such as a ball mill. In order to carry out the mechanochemical treatment of the present invention, the organic bromine compound or the resin or the resin cured product containing the organic bromine compound is preferably in a powder form. The smaller the particle size, the better, but not particularly limited. Usually, a material pulverized to an appropriate size is used, and pulverization is simultaneously performed by a processing apparatus at the time of mechanochemical treatment. Further, it is more preferable that the alkali metal hydroxide is also in the form of a powder because the treatment time can be reduced.
【０００９】本発明においては、有機臭素化合物をアル
カリ金属水酸化物の存在下、メカノケミカル処理する
と、有機臭素化合物から臭素が除去される。これは、メ
カノケミカル処理により有機臭素化合物の臭素分がアル
カリ金属水酸化物と反応し、アルカリ金属の臭素化物が
生成することによる。例えば、有機臭素化合物としてテ
トラブロモビスフェノールＡ（ＴＢＢＰＡ）を、アルカ
リ土類金属水酸化物としてＮａＯＨを使用した場合、モ
デル的には以下のような反応により、テトラブロモビス
フェノールＡから臭素が除去された分解生成物とＮａＢ
ｒが主として生成するものと考えられる。ＴＢＢＰＡ
＋ ４ＮａＯＨ → 分解生成物 ＋ ４ＮａＢｒ実際の
反応機構は、中間生成物とＮａＯＨの反応、中間生成物
同士の反応等、種々の反応が平行して起こると考えら
れ、時間のファクターを考慮しつつ生成物を詳細に分析
することにより、解明されるものである。In the present invention, when an organic bromine compound is subjected to mechanochemical treatment in the presence of an alkali metal hydroxide, bromine is removed from the organic bromine compound. This is because the bromine component of the organic bromine compound reacts with the alkali metal hydroxide by the mechanochemical treatment to produce an alkali metal bromide. For example, when tetrabromobisphenol A (TBBPA) is used as an organic bromine compound and NaOH is used as an alkaline earth metal hydroxide, bromine was removed from tetrabromobisphenol A by the following reaction modelly. Decomposition products and NaB
It is considered that r mainly forms. TBBPA
+ 4NaOH → Decomposition product + 4NaBr The actual reaction mechanism is thought to be that various reactions such as the reaction between intermediate products and NaOH, the reaction between intermediate products, etc. occur in parallel, and is generated taking into account the time factor. It can be clarified by analyzing the object in detail.
【００１０】[0010]
【実施例】次に、本発明を実施例により更に詳しく説明
する。ただし、本発明はこれらの実施例によって限定さ
れるものではない。Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited by these examples.
【００１１】 実施例１ テトラブロモビスフェノールＡ（ＴＢＢＰＡ）エポキシ樹脂 １当量部（８００重量部） ＮａＯＨ ２当量部（３２０重量部） 上記組成物５０ｇを、遊星ボールミル（高木製作所製：
ポット容量４００ｍｌ、径１５ｍｍのジルコニアボール
４００ｇ充填、公転１５０ｒｐｍ、自転３００ｒｐｍ）
にて室温でメカノケミカル処理を行った。Example 1 Tetrabromobisphenol A (TBBPA) epoxy resin 1 equivalent part (800 parts by weight) NaOH 2 equivalent parts (320 parts by weight) 50 g of the above composition was placed in a planetary ball mill (manufactured by Takagi Sakusho:
(400 ml pot capacity, 400 g zirconia balls with a diameter of 15 mm, revolving at 150 rpm, rotating at 300 rpm)
Performed a mechanochemical treatment at room temperature.
【００１２】 実施例２ テトラブロモビスフェノールＡ（ＴＢＢＰＡ）エポキシ樹脂 １重量部 ビスフェノールＡ型エポキシ樹脂 １重量部 ジシアンジアミド ０.１重量部 上記各組成を配合し、ヘンシェルミキサーで混合、２軸
押出機にて溶融混合した後、１７０℃で１時間硬化させ
エポキシ樹脂硬化物を得た。この硬化物を粒子径５ｍｍ
程度に予備粉砕した。 エポキシ樹脂硬化物 １当量部（８００重量部） ＫＯＨ ２当量部（４５０重量部） 次いで、上記組成物５０ｇを、以下実施例１と同様にメ
カノケミカル処理を行った。Example 2 Tetrabromobisphenol A (TBBPA) epoxy resin 1 part by weight Bisphenol A type epoxy resin 1 part by weight Dicyandiamide 0.1 part by weight The above components were blended, mixed with a Henschel mixer, and with a twin screw extruder. After melt-mixing, the mixture was cured at 170 ° C. for 1 hour to obtain a cured epoxy resin. This cured product has a particle diameter of 5 mm.
Pre-crushed to a degree. 1 equivalent part (800 parts by weight) of epoxy resin cured product 2 equivalent parts (450 parts by weight) of KOH Next, 50 g of the above composition was subjected to a mechanochemical treatment in the same manner as in Example 1.
【００１３】[0013]
【表１】 [Table 1]
【００１４】（測定方法とその結果の考察） １．有機臭素化合物残存量 Ｘ線回折装置（理学電機製）を用い有機臭素化合物のピ
ーク高より残存量を算出した。 ２．生成物の分解挙動 熱重量測定装置（セイコー電子製）により生成物の分解
挙動を測定した。(Consideration of Measurement Method and Results) Residual amount of organic bromine compound The residual amount was calculated from the peak height of the organic bromine compound using an X-ray diffractometer (manufactured by Rigaku Corporation). 2. Decomposition behavior of product The decomposition behavior of the product was measured by a thermogravimeter (manufactured by Seiko Denshi).
【００１５】[0015]
【発明の効果】本発明によれば、有機臭素化合物をアル
カリ金属水酸化物の存在下、メカノケミカル処理を行う
ことにより、有機臭素化合物から臭素を除去することが
できる。メカノケミカル処理により得られた分解生成物
は燃料等に再利用が可能であり、臭素分は臭化アルカリ
等の無機臭素化合物に変換され、再利用されうるもので
ある。According to the present invention, bromine can be removed from an organic bromine compound by subjecting the organic bromine compound to mechanochemical treatment in the presence of an alkali metal hydroxide. Decomposition products obtained by the mechanochemical treatment can be reused for fuel and the like, and bromine is converted to an inorganic bromine compound such as alkali bromide and can be reused.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ０７Ｃ 43/29 Ｃ０７Ｃ 43/29 Ｃ Ｃ０８Ｊ 11/00 ＺＡＢ Ｃ０８Ｊ 11/00 ＺＡＢ Ｆターム(参考） 4F301 AA20 AA22 AA24 AA25 AB01 CA04 CA11 CA32 CA71 4H006 AA05 AC13 BA02 BA29 EA12 EA21 EA22 FC52 FE13 FE70 FE76 GP06 GP22 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C07C 43/29 C07C 43/29 C C08J 11/00 ZAB C08J 11/00 ZAB F-term (reference) 4F301 AA20 AA22 AA24 AA25 AB01 CA04 CA11 CA32 CA71 4H006 AA05 AC13 BA02 BA29 EA12 EA21 EA22 FC52 FE13 FE70 FE76 GP06 GP22
Claims (4)
の存在下、メカノケミカル処理することを特徴とする有
機臭素化合物の脱臭素化方法。1. A method for debrominating an organic bromine compound, comprising subjecting the organic bromine compound to mechanochemical treatment in the presence of an alkali metal hydroxide.
ン（ＨＢＢ）、テトラブロモビスフェノールＡ（ＴＢＢ
ＰＡ）、デカブロモジフェニルオキシド（ＤＢＤＰ
Ｏ）、ポリブロモジベンゾダイオキシン（ＰＢＤＤ）、
ポリブロモジベンゾフラン（ＰＢＤＦ）、ポリブロモビ
フェニル（ＰＢＢ）、及びポリブロモシクロドデカン
（ＰＢＣＤ）から選ばれる１種以上である請求項１記載
の有機臭素化合物の脱臭素化方法。2. An organic bromine compound comprising hexabromobenzene (HBB) and tetrabromobisphenol A (TBB).
PA), decabromodiphenyl oxide (DBDP)
O), polybromodibenzodioxin (PBDD),
The method for debrominating an organic bromine compound according to claim 1, wherein the method is at least one selected from polybromodibenzofuran (PBDF), polybromobiphenyl (PBB), and polybromocyclododecane (PBCD).
ン（ＨＢＢ）、テトラブロモビスフェノールＡ（ＴＢＢ
ＰＡ）、デカブロモジフェニルオキシド（ＤＢＤＰ
Ｏ）、ポリブロモジベンゾダイオキシン（ＰＢＤＤ）、
ポリブロモジベンゾフラン（ＰＢＤＦ）、ポリブロモビ
フェニル（ＰＢＢ）、及びポリブロモシクロドデカン
（ＰＢＣＤ）から選ばれる１種以上を骨格に含む高分子
化合物である請求項１記載の有機臭素化合物の脱臭素化
方法。3. An organic bromine compound comprising hexabromobenzene (HBB) and tetrabromobisphenol A (TBB).
PA), decabromodiphenyl oxide (DBDP)
O), polybromodibenzodioxin (PBDD),
2. The method for debrominating an organic bromine compound according to claim 1, wherein the skeleton is a polymer compound containing at least one member selected from the group consisting of polybromodibenzofuran (PBDF), polybromobiphenyl (PBB), and polybromocyclododecane (PBCD). .
硬化物をアルカリ金属水酸化物の存在下、メカノケミカ
ル処理することを特徴とする有機臭素化合物の脱臭素化
方法。4. A method for debrominating an organic bromine compound, comprising subjecting a resin or a cured resin containing the organic bromine compound to mechanochemical treatment in the presence of an alkali metal hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000211236A JP2002030003A (en) | 2000-07-12 | 2000-07-12 | Method for removing bromine from organic bromine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000211236A JP2002030003A (en) | 2000-07-12 | 2000-07-12 | Method for removing bromine from organic bromine compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002030003A true JP2002030003A (en) | 2002-01-29 |
Family
ID=18707378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000211236A Pending JP2002030003A (en) | 2000-07-12 | 2000-07-12 | Method for removing bromine from organic bromine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002030003A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019104005A (en) * | 2017-12-14 | 2019-06-27 | 株式会社栗本鐵工所 | Mechanical chemical modification method and modification device |
| WO2019141504A1 (en) | 2018-01-20 | 2019-07-25 | Bürkle Consulting Gmbh | Mechanochemical process for producing valuable products free from persistent organic pollutants and other organohalogen compounds from waste comprising plastics and plastic laminates |
| WO2022196796A1 (en) | 2021-03-19 | 2022-09-22 | 国立大学法人北海道大学 | Method for producing organic metal nucleophilic agent and reaction method using organic metal nucleophilic agent |
-
2000
- 2000-07-12 JP JP2000211236A patent/JP2002030003A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019104005A (en) * | 2017-12-14 | 2019-06-27 | 株式会社栗本鐵工所 | Mechanical chemical modification method and modification device |
| WO2019141504A1 (en) | 2018-01-20 | 2019-07-25 | Bürkle Consulting Gmbh | Mechanochemical process for producing valuable products free from persistent organic pollutants and other organohalogen compounds from waste comprising plastics and plastic laminates |
| US11807724B2 (en) | 2018-01-20 | 2023-11-07 | Gregor Luthe | Mechanochemical process for producing valuable products free from persistent organic pollutants and other organohalogen compounds from waste comprising plastics and plastic laminates |
| EP4293072A2 (en) | 2018-01-20 | 2023-12-20 | Smart Material Printing B.V. | Mechanochemical process for the production of persistent organic pollutants and other organohalogen compounds free valuables from waste of plastics and plastic laminates |
| WO2022196796A1 (en) | 2021-03-19 | 2022-09-22 | 国立大学法人北海道大学 | Method for producing organic metal nucleophilic agent and reaction method using organic metal nucleophilic agent |
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