JPH0725801A - Highly concentrated aqueous solution of tribromophenolate and its preparation - Google Patents
Highly concentrated aqueous solution of tribromophenolate and its preparationInfo
- Publication number
- JPH0725801A JPH0725801A JP17028593A JP17028593A JPH0725801A JP H0725801 A JPH0725801 A JP H0725801A JP 17028593 A JP17028593 A JP 17028593A JP 17028593 A JP17028593 A JP 17028593A JP H0725801 A JPH0725801 A JP H0725801A
- Authority
- JP
- Japan
- Prior art keywords
- tribromophenolate
- aqueous solution
- tribromophenol
- added
- hours
- 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
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 8
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract description 4
- 150000008282 halocarbons Chemical class 0.000 abstract description 3
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000001816 cooling Methods 0.000 description 15
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 7
- 235000010265 sodium sulphite Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- -1 trichloroethylene, perchloroethylene Chemical group 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- FNAKEOXYWBWIRT-UHFFFAOYSA-N 2,3-dibromophenol Chemical compound OC1=CC=CC(Br)=C1Br FNAKEOXYWBWIRT-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、高濃度トリブロモフェ
ノラート水溶液およびその調製方法に関する。FIELD OF THE INVENTION The present invention relates to a high-concentration tribromophenolate aqueous solution and a method for preparing the same.
【０００２】[0002]
【従来の技術と発明が解決しようとする課題】従来、ト
リブロモフェノラート水溶液を調製するには、トリブロ
モフェノールを等モルもしくはそれ以上のアルカリ、例
えば苛性ソーダ等、で処理して水溶液としていた。2. Description of the Related Art Conventionally, in order to prepare an aqueous solution of tribromophenolate, tribromophenol was treated with an equimolar or more alkali such as caustic soda to prepare an aqueous solution.
【０００３】しかしながら、公知の方法で調製したトリ
ブロモフェノラート水溶液は、調製中にトリブロモフェ
ノールが酸化重合を起こして赤褐色のポリマーが生成す
ることや、トリブロモフェノラートの水に対する溶解度
から、その濃度は４８重量％以下であった。このような
トリブロモフェノラート水溶液を用いて他の化合物と反
応させると、目的とする反応生成物にポリマーが混入し
たり、反応器の単位容量当たりの製品の生産量が低いと
いう問題があった。However, the aqueous solution of tribromophenolate prepared by a known method is liable to undergo oxidation polymerization of tribromophenol during the preparation to produce a reddish brown polymer and the solubility of tribromophenolate in water. The concentration was 48% by weight or less. When such an aqueous solution of tribromophenolate is used to react with other compounds, there are problems that a polymer is mixed in a target reaction product and that the amount of product produced per unit volume of the reactor is low. .
【０００４】本発明の課題は、赤褐色のポリマーが容易
に生成しない安定な高濃度トリブロモフェノラート水溶
液およびその調製方法を提供する処にある。An object of the present invention is to provide a stable high-concentration tribromophenolate aqueous solution in which a reddish brown polymer is not easily formed and a method for preparing the same.
【０００５】[0005]
【課題を解決するための手段】本発明の高濃度トリブロ
モフェノラート水溶液は、非親水性溶剤と還元剤を混合
したことを特徴とする。The high-concentration tribromophenolate aqueous solution of the present invention is characterized by mixing a non-hydrophilic solvent and a reducing agent.
【０００６】また、本発明の高濃度トリブロモフェノラ
ート水溶液の調製方法は、トリブロモフェノールとアル
カリとからトリブロモフェノラート水溶液を調製する際
に非親水性溶剤と還元剤を添加することを特徴とする。The method for preparing a high-concentration aqueous solution of tribromophenolate of the present invention is characterized by adding a non-hydrophilic solvent and a reducing agent when preparing an aqueous solution of tribromophenolate from tribromophenol and an alkali. And
【０００７】本発明において、高濃度トリブロモフェノ
ラート水溶液とは、５０％（重量％、以下同様）以上の
濃度のトリブロモフェノラート水溶液のことをいう。In the present invention, the high-concentration tribromophenolate aqueous solution means a tribromophenolate aqueous solution having a concentration of 50% (wt%, the same applies hereinafter) or more.
【０００８】（１）トリブロモフェノラートの調製 トリブロモフェノラートの調製は、あらかじめ水に水酸
化ナトリウムや水酸化カリウム等のアルカリと還元剤を
溶解し、冷却した水溶液に非親水性溶剤を添加し、そこ
へトリブロモフェノールを添加し、加熱するかまたは室
温で完全に溶解させて行なう。非親水性溶剤を添加する
ことにより、５０％以上の高濃度のトリブロモフェノラ
ート水溶液を調製することができる。また、非親水性溶
剤を添加することにより、トリブロモフェノールの酸化
重合が抑制される。(1) Preparation of tribromophenolate To prepare tribromophenolate, an alkali such as sodium hydroxide or potassium hydroxide and a reducing agent are previously dissolved in water, and a non-hydrophilic solvent is added to the cooled aqueous solution. Then, tribromophenol is added thereto, and the mixture is heated or completely dissolved at room temperature. By adding a non-hydrophilic solvent, a tribromophenolate aqueous solution having a high concentration of 50% or more can be prepared. Further, the addition of the non-hydrophilic solvent suppresses the oxidative polymerization of tribromophenol.
【０００９】本発明において、トリブロモフェノラート
水溶液の濃度とは、水溶液中のトリブロモフェノラート
をトリブロモフェノールに換算して求めた値である。具
体的には、下式のように、水に対するトリブロモフェノ
ールの濃度として求められる。In the present invention, the concentration of the aqueous tribromophenolate solution is a value obtained by converting the tribromophenolate in the aqueous solution into tribromophenol. Specifically, it is calculated as the concentration of tribromophenol with respect to water as in the following formula.
【数１】 [Equation 1]
【００１０】操作性においては、あらかじめ非親水性溶
剤を添加しておくと、容易にトリブロモフェノラートを
調製できる。さらに、トリブロモフェノラート調製後の
トリブロモフェノラート水溶液は比重が重く、水層と非
親水性溶剤層に容易に分離し、トリブロモフェノラート
は非親水性溶剤に溶解しないため、分離した非親水性溶
剤を抜き取り、新たにトリブロモフェノールを添加して
溶解すると、反応器の容量に対して一度に多量のトリブ
ロモフェノラートを調製できる。抜き取った非親水性溶
剤は再度使用できる。生産性においても、反応器の容量
に対して一度に多量のトリブロモフェノラートを調製で
きるため、一回の製造による生産量を高めることができ
る。In terms of operability, tribromophenolate can be easily prepared by adding a non-hydrophilic solvent in advance. Furthermore, the tribromophenolate aqueous solution after the preparation of tribromophenolate has a high specific gravity and easily separates into an aqueous layer and a non-hydrophilic solvent layer, and tribromophenolate does not dissolve in the non-hydrophilic solvent. If a hydrophilic solvent is taken out and tribromophenol is newly added and dissolved, a large amount of tribromophenolate can be prepared at once with respect to the capacity of the reactor. The extracted non-hydrophilic solvent can be reused. Also in terms of productivity, a large amount of tribromophenolate can be prepared at once with respect to the capacity of the reactor, so that the production amount in one production can be increased.
【００１１】本発明のトリブロモフェノラート水溶液の
濃度には特に上限はないが、他の化合物との反応に使用
することを考慮すると、上限を８０％とするのが好まし
い。より好ましい濃度範囲は６０〜８０％である。There is no particular upper limit to the concentration of the aqueous tribromophenolate solution of the present invention, but in view of its use in the reaction with other compounds, the upper limit is preferably 80%. A more preferable concentration range is 60 to 80%.
【００１２】（２）非親水性溶剤 本発明に使用される非親水性溶剤としては、例えば塩化
メチレン、クロロホルム、四塩化炭素、トリクロロエチ
レン、パークロロエチレン、テトラクロロエチレン等の
ハロゲン化炭化水素類、ベンゼン、トルエン、キシレン
等の芳香族炭化水素類、ヘキサン等の飽和炭化水素類、
クロロベンゼン等のハロゲン置換芳香族炭化水素類が挙
げられる。好ましくは、クロロホルム、塩化メチレン等
のハロゲン化炭化水素類である。非親水性溶剤は２種以
上併用しても差し支えない。(2) Non-hydrophilic solvent Examples of the non-hydrophilic solvent used in the present invention include halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene and tetrachloroethylene, benzene, Aromatic hydrocarbons such as toluene and xylene, saturated hydrocarbons such as hexane,
Examples thereof include halogen-substituted aromatic hydrocarbons such as chlorobenzene. Preferred are halogenated hydrocarbons such as chloroform and methylene chloride. Two or more non-hydrophilic solvents may be used in combination without any problem.
【００１３】非親水性溶剤はトリブロモフェノラート調
製後に反応器上部より抜き取ることができるため、その
添加量は特に限定されないが、トリブロモフェノールに
対して０．１〜１．０倍重量であるのが好ましい。０．
１倍重量未満であると、トリブロモフェノラートの調製
が困難である。Since the non-hydrophilic solvent can be withdrawn from the upper part of the reactor after the preparation of tribromophenolate, its addition amount is not particularly limited, but it is 0.1 to 1.0 times the weight of tribromophenol. Is preferred. 0.
If the amount is less than 1 time, it is difficult to prepare tribromophenolate.
【００１４】トリブロモフェノラート水溶液調製後にお
ける、非親水性溶剤層とトリブロモフェノラート水溶液
層との重量比は、１：５〜１：２であるのが好ましい。The weight ratio of the non-hydrophilic solvent layer and the tribromophenolate aqueous solution layer after the preparation of the tribromophenolate aqueous solution is preferably 1: 5 to 1: 2.
【００１５】（３）還元剤 本発明において、還元剤は、トリブロモフェノールの酸
化重合を抑制する働きをする。非親水性溶剤と併用する
ことにより、トリブロモフェノールの酸化重合を抑制す
る効果は著しく高まる。(3) Reducing agent In the present invention, the reducing agent functions to suppress the oxidative polymerization of tribromophenol. When used in combination with a non-hydrophilic solvent, the effect of suppressing the oxidative polymerization of tribromophenol is significantly enhanced.
【００１６】使用される還元剤としては、例えば、フェ
ノール、ブロモフェノール、ジブロモフェノール、２，
６−ジ−ｔ−ブチル−４−メチルフェノール（ＢＨＴ）
等のフェノール類、亜硫酸アンモニウム、亜硫酸カリウ
ム、亜硫酸ナトリウム、亜硫酸水素ナトリウム等の亜硫
酸塩、硫化ナトリウム、硫化アンモニウム、硫化カリウ
ム等の硫化物が挙げられる。還元剤の添加量は、トリブ
ロモフェノール１００重量部に対して０．０１〜１．０
重量部である。添加量が０．０１重量部未満だと、トリ
ブロモフェノラート水溶液の安定時間が短く、赤褐色の
ポリマーが生成する。また、１．０重量部を超えると、
還元剤の水に対する溶解性が劣り、効果の差は見られな
い。Examples of the reducing agent used include phenol, bromophenol, dibromophenol, 2,
6-di-t-butyl-4-methylphenol (BHT)
Examples thereof include phenols, ammonium sulfite, potassium sulfite, sodium sulfite, sodium hydrogen sulfite, and other sulfites; and sodium sulfide, ammonium sulfide, potassium sulfide, and other sulfides. The amount of the reducing agent added is 0.01 to 1.0 with respect to 100 parts by weight of tribromophenol.
Parts by weight. If the amount added is less than 0.01 part by weight, the stabilization time of the aqueous tribromophenolate solution is short and a reddish brown polymer is produced. Further, when it exceeds 1.0 part by weight,
Solubility of the reducing agent in water is inferior, and there is no difference in effect.
【００１７】[0017]
【実施例】次に、本発明を実施例に基づいて説明する
が、本発明はかかる実施例のみに限定されるものではな
い。EXAMPLES Next, the present invention will be explained based on examples, but the present invention is not limited to such examples.
【００１８】実施例１ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、表１に示す量の水、水酸化ナトリウム
６．１ｇ（０．１５モル）、亜硫酸ナトリウム０．０５
ｇを加えて溶解し、冷却した。そこへ表１に示す非親水
性溶剤２５ｇを加えた後、２，４，６−トリブロモフェ
ノール５０ｇ（０．１５モル）を加えて溶解させた。溶
解後に、１０℃以下に冷却した。 Example 1 300 ml with stirrer, cooling condenser, thermometer
In a reactor having a capacity, the amount of water shown in Table 1, 6.1 g (0.15 mol) of sodium hydroxide, and 0.05 of sodium sulfite were added.
g was added and dissolved, followed by cooling. After 25 g of the non-hydrophilic solvent shown in Table 1 was added thereto, 50 g (0.15 mol) of 2,4,6-tribromophenol was added and dissolved. After dissolution, it was cooled to 10 ° C or lower.
【００１９】溶解状態を目視した結果を表１に示す。The results of visual observation of the dissolved state are shown in Table 1.
【００２０】ＴＢＰ（２，４，６−トリブロモフェノー
ル）の濃度は、下式により求めた。The concentration of TBP (2,4,6-tribromophenol) was determined by the following formula.
【数２】 [Equation 2]
【００２１】比較例１ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、表１に示す量の水、水酸化ナトリウム
６．１ｇ（０．１５モル）、亜硫酸ナトリウム０．０５
ｇを加えて溶解し、冷却した。そこへ２，４，６−トリ
ブロモフェノール５０ｇ（０．１５モル）を加えて溶解
させた。溶解後に、１０℃以下に冷却した。 Comparative Example 1 300 ml equipped with a stirrer, cooling condenser and thermometer
In a reactor having a capacity, the amount of water shown in Table 1, 6.1 g (0.15 mol) of sodium hydroxide and 0.05 of sodium sulfite were added.
g was added and dissolved, followed by cooling. 50 g (0.15 mol) of 2,4,6-tribromophenol was added and dissolved therein. After dissolution, it was cooled to 10 ° C or lower.
【００２２】溶解状態を目視した結果を表１に示す。Table 1 shows the results of visual observation of the dissolved state.
【００２３】[0023]
【表１】 [Table 1]
【００２４】実施例２ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、表２に示す量の水、水酸化ナトリウム
６．１ｇ（０．１５モル）、亜硫酸ナトリウム０．０５
ｇを加えて溶解し、冷却した。そこへ塩化メチレン２５
ｇを加えた後、２，４，６−トリブロモフェノール５０
ｇ（０．１５モル）を加えて溶解させた。溶解後に、１
０℃以下に冷却し、水層部分の容量を測定した。その結
果を表２に示す。 Example 2 300 ml with stirrer, cooling condenser, thermometer
In a reactor having a capacity, the amount of water shown in Table 2, 6.1 g (0.15 mol) of sodium hydroxide, and 0.05 of sodium sulfite were added.
g was added and dissolved, followed by cooling. 25 methylene chloride there
g, and then 2,4,6-tribromophenol 50
g (0.15 mol) was added and dissolved. After dissolution 1
After cooling to 0 ° C. or less, the volume of the water layer portion was measured. The results are shown in Table 2.
【００２５】[0025]
【表２】 [Table 2]
【００２６】実施例３ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、水２７ｇ、水酸化ナトリウム６．１ｇ
（０．１５モル）、亜硫酸ナトリウム０．０５ｇを加え
て溶解し、冷却した。そこへ塩化メチレン２５ｇを加え
た後、２，４，６−トリブロモフェノール５０ｇ（０．
１５モル）を加えて溶解させた（ＴＢＰ濃度６５％）。
溶解後、撹拌を停止し、５時間後、１０時間後、４８時
間後、７２時間後および１２０時間後に、赤褐色の不溶
解物が生成しているかどうかを目視にて判定した。 Example 3 300 ml with stirrer, cooling condenser, thermometer
27 g of water and 6.1 g of sodium hydroxide in a reactor of capacity.
(0.15 mol) and 0.05 g of sodium sulfite were added and dissolved, followed by cooling. After adding 25 g of methylene chloride thereto, 50 g of 2,4,6-tribromophenol (0.
15 mol) was added and dissolved (TBP concentration 65%).
After dissolution, stirring was stopped, and after 5 hours, 10 hours, 48 hours, 72 hours, and 120 hours, it was visually determined whether or not a reddish brown insoluble matter had been formed.
【００２７】結果を表３に示す。The results are shown in Table 3.
【００２８】比較例２ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、水２７ｇ、水酸化ナトリウム６．１ｇ
（０．１５モル）を加えて溶解し、冷却した。そこへ塩
化メチレン２５ｇを加えた後、２，４，６−トリブロモ
フェノール５０ｇ（０．１５モル）を加えて溶解させた
（ＴＢＰ濃度６５％）。溶解後、撹拌を停止し、５時間
後、１０時間後、４８時間後、７２時間後および１２０
時間後に、赤褐色の不溶解物が生成しているかどうかを
目視にて判定した。 Comparative Example 2 300 ml equipped with a stirrer, cooling condenser and thermometer
27 g of water and 6.1 g of sodium hydroxide in a reactor of capacity.
(0.15 mol) was added and dissolved, followed by cooling. After 25 g of methylene chloride was added thereto, 50 g (0.15 mol) of 2,4,6-tribromophenol was added and dissolved (TBP concentration 65%). After dissolution, stirring was stopped and after 5 hours, 10 hours, 48 hours, 72 hours and 120 hours.
After a lapse of time, it was visually judged whether or not a reddish brown insoluble matter had been formed.
【００２９】結果を表３に示す。The results are shown in Table 3.
【００３０】比較例３ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、水６５ｇ、水酸化ナトリウム６．１ｇ
（０．１５モル）を加えて溶解し、冷却した。そこへ
２，４，６−トリブロモフェノール５０ｇ（０．１５モ
ル）を加えて溶解させた（ＴＢＰ濃度４３％）。溶解
後、撹拌を停止し、５時間後、１０時間後、４８時間
後、７２時間後および１２０時間後に、赤褐色の不溶解
物が生成しているかどうかを目視にて判定した。 Comparative Example 3 300 ml equipped with a stirrer, cooling condenser and thermometer
In a reactor of capacity, 65 g of water, 6.1 g of sodium hydroxide
(0.15 mol) was added and dissolved, followed by cooling. 50 g (0.15 mol) of 2,4,6-tribromophenol was added thereto and dissolved (TBP concentration 43%). After dissolution, stirring was stopped, and after 5 hours, 10 hours, 48 hours, 72 hours, and 120 hours, it was visually determined whether or not a reddish brown insoluble matter had been formed.
【００３１】結果を表３に示す。The results are shown in Table 3.
【００３２】比較例４ 撹拌機、冷却コンデンサー、温度計を有する３００ｍｌ
容量の反応器に、水６５ｇ、水酸化ナトリウム６．１ｇ
（０．１５モル）、亜硫酸ナトリウム０．０５ｇを加え
て溶解し、冷却した。そこへ２，４，６−トリブロモフ
ェノール５０ｇ（０．１５モル）を加えて溶解させた
（ＴＢＰ濃度４３％）。溶解後、撹拌を停止し、５時間
後、１０時間後、４８時間後、７２時間後および１２０
時間後に、赤褐色の不溶解物が生成しているかどうかを
目視にて判定した。 Comparative Example 4 300 ml equipped with stirrer, cooling condenser and thermometer
In a reactor of capacity, 65 g of water, 6.1 g of sodium hydroxide
(0.15 mol) and 0.05 g of sodium sulfite were added and dissolved, followed by cooling. 50 g (0.15 mol) of 2,4,6-tribromophenol was added thereto and dissolved (TBP concentration 43%). After dissolution, stirring was stopped and after 5 hours, 10 hours, 48 hours, 72 hours and 120 hours.
After a lapse of time, it was visually judged whether or not a reddish brown insoluble matter had been formed.
【００３３】結果を表３に示す。The results are shown in Table 3.
【００３４】[0034]
【表３】 [Table 3]
【００３５】[0035]
【発明の効果】本発明の高濃度トリブロモフェノラート
水溶液は、安定性が高く、種々の反応に応用できる。The highly concentrated tribromophenolate aqueous solution of the present invention has high stability and can be applied to various reactions.
【００３６】また、本発明の調製方法によれば、安定な
高濃度トリブロモフェノラート水溶液を容易に得ること
ができる。Further, according to the preparation method of the present invention, a stable high-concentration tribromophenolate aqueous solution can be easily obtained.
Claims (2)
特徴とする高濃度トリブロモフェノラート水溶液。1. A high-concentration tribromophenolate aqueous solution comprising a non-hydrophilic solvent and a reducing agent mixed therein.
トリブロモフェノラート水溶液を調製する際に非親水性
溶剤と還元剤を添加することを特徴とする高濃度トリブ
ロモフェノラート水溶液の調製方法。2. A method for preparing a high-concentration tribromophenolate aqueous solution, which comprises adding a non-hydrophilic solvent and a reducing agent when preparing a tribromophenolate aqueous solution from tribromophenol and an alkali.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170285A JP2678339B2 (en) | 1993-07-09 | 1993-07-09 | Highly concentrated tribromophenolate aqueous solution and method for preparing the same |
| US08/264,385 US5498714A (en) | 1993-07-08 | 1994-06-23 | Process for production of tris(tribromophenoxy)-s-triazine |
| DE69428557T DE69428557T2 (en) | 1993-07-08 | 1994-06-28 | Process for the preparation of tris (tribromphenoxy) -s-triazine |
| IL11015494A IL110154A (en) | 1993-07-08 | 1994-06-28 | Process for the production of tris(tribromophenoxy)-s-triazine and a tribromophenolate solution for use therein |
| EP94110024A EP0634407B1 (en) | 1993-07-08 | 1994-06-28 | Process for production of tris(tribromophenoxy)-s-triazine |
| US08/579,496 US5696302A (en) | 1993-07-08 | 1995-12-27 | Highly concentrated aqueous tribromophenolate solution and a method for preparing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170285A JP2678339B2 (en) | 1993-07-09 | 1993-07-09 | Highly concentrated tribromophenolate aqueous solution and method for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0725801A true JPH0725801A (en) | 1995-01-27 |
| JP2678339B2 JP2678339B2 (en) | 1997-11-17 |
Family
ID=15902118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5170285A Expired - Lifetime JP2678339B2 (en) | 1993-07-08 | 1993-07-09 | Highly concentrated tribromophenolate aqueous solution and method for preparing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2678339B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5444625A (en) * | 1977-09-16 | 1979-04-09 | Asahi Glass Co Ltd | Production of tribromophenol |
| JPS62238226A (en) * | 1986-04-09 | 1987-10-19 | Nippon Kayaku Co Ltd | Production of thermally stable fluorophenol or such |
-
1993
- 1993-07-09 JP JP5170285A patent/JP2678339B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5444625A (en) * | 1977-09-16 | 1979-04-09 | Asahi Glass Co Ltd | Production of tribromophenol |
| JPS62238226A (en) * | 1986-04-09 | 1987-10-19 | Nippon Kayaku Co Ltd | Production of thermally stable fluorophenol or such |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2678339B2 (en) | 1997-11-17 |
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