JP2786602B2 - Purification method of dibromobenzanthrone - Google Patents
Purification method of dibromobenzanthroneInfo
- Publication number
- JP2786602B2 JP2786602B2 JP22289094A JP22289094A JP2786602B2 JP 2786602 B2 JP2786602 B2 JP 2786602B2 JP 22289094 A JP22289094 A JP 22289094A JP 22289094 A JP22289094 A JP 22289094A JP 2786602 B2 JP2786602 B2 JP 2786602B2
- Authority
- JP
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- Prior art keywords
- formula
- parts
- compound
- sulfur
- solvent
- 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.)
- Expired - Fee Related
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、染料および顔料の中間
体として、また有機光電材料等の中間体としても極めて
有用なジブロモベンザンスロンの精製法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying dibromobenzanthrone which is extremely useful as an intermediate for dyes and pigments and also as an intermediate for organic photoelectric materials and the like.
【０００２】[0002]
【従来技術】下記式（１）（化２）2. Description of the Related Art The following formula (1)
【化２】 で示される化合物はＩｎｄａｎｔｈｒｅｎｅ Ｏｌｉｖ
ｅ Ｔ，Ｉｎｄａｎｔｈｒｅｎｅ Ｇｒｅｙ Ｍ，Ｉｎ
ｄａｎｔｈｒｅｎｅ Ｏｌｉｖｅ ＭＷの中間体として
極めて有用である。式（１）の化合物の製造法として
は、「理論製造染料化学」（著者；細田豊、技報堂）記
載の方法、ロシア特許第３５５１５０号公報、ロシア特
許第５９２２８３号公報記載の方法等、ベンザンスロン
をブロム化する方法が知られている。Embedded image Is a compound represented by Indianthrene Olive
e T, Indianthrene Gray M, In
It is extremely useful as an intermediate of dantrene Olive MW. Examples of the method for producing the compound of the formula (1) include a method described in "Theoretical Production Dye Chemistry" (author: Yutaka Hosoda, Gihodo), a method described in Russian Patent No. 355150, a method described in Russian Patent No. 592283, and the like. Methods for brominating are known.
【０００３】[0003]
【発明が解決しようとする課題】この式（１）の化合物
を上記の従来技術で製造すると、不純物としてモノブロ
モ化物、トリブロモ化物等のブロモ化物に加えタール状
物を含有するために、最終製品である染料の品質が悪
く、染色物の色調が不鮮明となるため精製する必要があ
った。When the compound of the formula (1) is produced by the above-mentioned prior art, the final product contains tar-like substances in addition to bromides such as monobromide and tribromide as impurities. The quality of a certain dye was poor, and the color tone of the dyed product was unclear.
【０００４】しかしながら、この式（１）は一般の溶媒
に不溶または難溶であるため、高溶解度を必要とする再
結晶精製やカラム精製は、工業的かつ安価に得るために
は不適切な精製方法であった。However, since this formula (1) is insoluble or hardly soluble in general solvents, recrystallization purification or column purification requiring high solubility is not suitable for industrial and inexpensive purification. Was the way.
【０００５】本発明は、このような粗ジブロモベンザン
スロンを工業的に精製することを目的とするものであ
る。The object of the present invention is to purify such crude dibromobenzanthrone industrially.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記課題
を解決するため鋭意検討した結果、式（１）で示される
粗ジブロモベンザンスロン中の不純物は、アミド系溶媒
および／または含イオウ系溶媒を用いて加熱処理するこ
とで、溶解できることを見出し、本発明を完成した。即
ち、本発明は式（１）（化３）Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, the impurities in the crude dibromobenzanthrone represented by the formula (1) were found to contain amide solvents and / or impurities. The present inventors have found out that they can be dissolved by heat treatment using a sulfur-based solvent, and have completed the present invention. That is, the present invention relates to a compound of the formula (1)
【０００７】[0007]
【化３】 で示される粗ジブロモベンザンスロンをアミド系溶媒お
よび／または含イオウ系溶媒を用いて、加熱処理し、不
純物を溶解させ、その懸濁液を冷却、濾過することを特
徴とするジブロモベンザンスロンの精製法である。Embedded image A heat treatment of the crude dibromobenzanthrone represented by the formula (1) using an amide solvent and / or a sulfur-containing solvent to dissolve the impurities, and cooling and filtering the suspension; Is a purification method.
【０００８】以下、本発明を詳細に説明する。本発明方
法は、式（１）の化合物をアミド系溶媒および／または
含イオウ系溶媒と共に加熱処理して不純物を溶解させ、
その後懸濁液を冷却して濾過を行うことにより、高純度
の式（１）の化合物を得るものである。Hereinafter, the present invention will be described in detail. In the method of the present invention, the compound of the formula (1) is heat-treated with an amide solvent and / or a sulfur-containing solvent to dissolve impurities,
Thereafter, the suspension is cooled and filtered to obtain a highly pure compound of the formula (1).
【０００９】本発明方法に使用するアミド系溶媒は、ア
ミド系溶媒ならば特に制限はないが、好ましい例として
は、１，３−ジメチル−２−イミダゾリジノン、Ｎ−メ
チル−２−ピロリドン、Ｎ，Ｎ−ジメチルホルムアミ
ド、Ｎ，Ｎ−ジメチルアセトアミド、１，３，６−トリ
メチルヘキサヒドロ−１，３，６−トリアゾシン−２−
オン等が挙げられる。好ましくはＮ，Ｎ−ジメチルホル
ムアミドを使用する。The amide solvent used in the method of the present invention is not particularly limited as long as it is an amide solvent. Preferred examples thereof include 1,3-dimethyl-2-imidazolidinone, N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3,6-trimethylhexahydro-1,3,6-triazocine-2-
ON and the like. Preferably, N, N-dimethylformamide is used.
【００１０】含イオウ系溶媒は、使用するものに特に制
限はないが、スルホラン、ジメチルスルホキシド等を使
用するのが好ましい。これらアミド系溶媒や含イオウ系
溶媒は、単独で使用しても構わないし、２種以上混合し
て使用することもできる。The sulfur-containing solvent used is not particularly limited, but it is preferable to use sulfolane, dimethyl sulfoxide or the like. These amide solvents and sulfur-containing solvents may be used alone or in combination of two or more.
【００１１】本発明方法において、式（１）の化合物を
アミド系溶媒および／または含イオウ系溶媒を用いて加
熱処理する際の温度は、好ましくは５０〜２００℃、特
に好ましくは８０〜１５０℃の範囲である。In the method of the present invention, the temperature at which the compound of formula (1) is heat-treated with an amide solvent and / or a sulfur-containing solvent is preferably from 50 to 200 ° C, particularly preferably from 80 to 150 ° C. Range.
【００１２】使用するアミド系溶媒および／または含イ
オウ系溶媒の量は、式（１）の化合物に対して好ましく
は１〜１００重量部、更に好ましくは３〜３０重量部で
ある。The amount of the amide solvent and / or the sulfur-containing solvent used is preferably 1 to 100 parts by weight, more preferably 3 to 30 parts by weight, based on the compound of the formula (1).
【００１３】式（１）の化合物をアミド系溶媒および／
または含イオウ系溶媒を用いて加熱処理する時間は、通
常０．５〜１０時間程度である。この熱処理によって、
不純物がアミド系溶媒および／または含イオウ系溶媒に
溶解する。The compound of the formula (1) is converted to an amide solvent and / or
Alternatively, the time of the heat treatment using the sulfur-containing solvent is usually about 0.5 to 10 hours. By this heat treatment,
The impurities dissolve in the amide solvent and / or the sulfur-containing solvent.
【００１４】加熱処理後の冷却は、通常１０〜１００℃
の範囲で行い、好ましくは１０〜８０℃で行う。Cooling after the heat treatment is usually 10 to 100 ° C.
And preferably at 10 to 80 ° C.
【００１５】濾過後得られた式（１）の化合物の結晶
は、アミド系溶媒および／または含イオウ系溶媒で洗浄
し、水洗、乾燥させることにより、更に高純度のものを
得ることができる。The crystals of the compound of the formula (1) obtained after the filtration can be washed with an amide solvent and / or a sulfur-containing solvent, washed with water and dried to obtain a higher purity crystal.
【００１６】濾過により得られた式（１）の化合物の結
晶をアミド系溶媒および／または含イオウ系溶媒で洗浄
する際のアミド系溶媒および／または含イオウ系溶媒の
量は、式（１）の化合物に対して２０重量部程度で良
く、通常０．１〜１０重量部である。When the crystals of the compound of the formula (1) obtained by filtration are washed with an amide solvent and / or a sulfur-containing solvent, the amount of the amide solvent and / or the sulfur-containing solvent is determined by the formula (1) About 20 parts by weight, usually 0.1 to 10 parts by weight, based on the weight of the compound.
【００１７】[0017]
【実施例】以下、実施例により本発明を説明するが、こ
れらより本発明は限定されるものではない。実施例中の
「部」は重量部を示す。尚、純度測定はガスクロマトグ
ラフィにより行い、算出した。 実施例１EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited thereto. “Parts” in the examples indicates parts by weight. The purity was measured by gas chromatography and calculated. Example 1
【００１８】[0018]
【化４】 で表される化合物の粗製物（純度８２％）１００部を
１，３−ジメチル−２−イミダゾリジノン２０００部
中、１２０℃で１時間攪拌して不純物を溶解させた。こ
の懸濁液を５０℃に冷却後、結晶を濾過、１，３−ジメ
チル−２−イミダゾリジノン、水で洗浄後、乾燥させ、
式（１）の化合物７１部を得た。純度は９８％であっ
た。Embedded image 100 parts of a crude product (purity: 82%) of the compound represented by the formula (1) was stirred in 2,000 parts of 1,3-dimethyl-2-imidazolidinone at 120 ° C. for 1 hour to dissolve impurities. After cooling this suspension to 50 ° C., the crystals were filtered, washed with 1,3-dimethyl-2-imidazolidinone, water, and dried,
71 parts of the compound of formula (1) are obtained. Purity was 98%.
【００１９】実施例２ 式（１）で表される化合物の粗製物（純度８２％）１０
０部をＮ−メチル−２−ピロリドン１５００部およびジ
メチルスルホキシド３００部の混合溶媒中、１５０℃で
１時間攪拌して不純物を溶解させた。この懸濁液を６０
℃に冷却後、結晶を濾過、Ｎ−メチル−２−ピロリド
ン、水で洗浄後、乾燥させ、式（１）の化合物６８部を
得た。純度は９７％であった。Example 2 Crude product of the compound represented by the formula (1) (purity: 82%) 10
0 parts was stirred at 150 ° C. for 1 hour in a mixed solvent of 1500 parts of N-methyl-2-pyrrolidone and 300 parts of dimethyl sulfoxide to dissolve impurities. This suspension is
After cooling to ℃, the crystals were filtered, washed with N-methyl-2-pyrrolidone and water, and dried to obtain 68 parts of the compound of the formula (1). Purity was 97%.
【００２０】実施例３ 式（１）で表される化合物の粗製物（純度８２％）１０
０部とＮ，Ｎ−ジメチルホルムアミド１０００部中、１
３０℃で１時間攪拌して不純物を溶解させた。この懸濁
液を６０℃に冷却後、結晶を濾過、Ｎ，Ｎ−ジメチルホ
ルムアミド、水で洗浄後、乾燥させ、式（１）の化合物
７２部を得た。純度は９８％であった。Example 3 A crude product of the compound represented by the formula (1) (purity: 82%) 10
0 parts and 1000 parts of N, N-dimethylformamide, 1
The mixture was stirred at 30 ° C. for 1 hour to dissolve the impurities. After cooling this suspension to 60 ° C., the crystals were filtered, washed with N, N-dimethylformamide and water, and dried to obtain 72 parts of a compound of the formula (1). Purity was 98%.
【００２１】実施例４ 式（１）で表される化合物の粗製物（純度８２％）１０
０部とＮ，Ｎ−ジメチルアセトアミド１０００部中、１
２０℃で１時間攪拌して不純物を溶解した。この懸濁液
を５０℃に冷却後、結晶を濾過、Ｎ，Ｎ−ジメチルアセ
トアミド、水で洗浄後、乾燥させ、式（１）の化合物７
５部を得た。純度は９６％であった。Example 4 A crude product of the compound represented by the formula (1) (purity: 82%) 10
0 parts and 1,000 parts of N, N-dimethylacetamide
Stirring at 20 ° C. for 1 hour dissolved the impurities. After cooling the suspension to 50 ° C., the crystals were filtered, washed with N, N-dimethylacetamide and water, and dried, to give compound 7 of the formula (1).
5 parts were obtained. Purity was 96%.
【００２２】実施例５ 式（１）で表される化合物の粗製物（純度８２％）１０
０部とスルホラン１０００部中、１３０℃で１時間攪拌
して不純物を溶解させた。この懸濁液を６０℃に冷却
後、結晶を濾過、スルホラン、水で洗浄後、乾燥させ、
式（１）の化合物７１部を得た。純度は９７％であっ
た。Example 5 Crude product of the compound represented by the formula (1) (purity: 82%)
In 0 parts and 1000 parts of sulfolane, the mixture was stirred at 130 ° C. for 1 hour to dissolve impurities. After cooling the suspension to 60 ° C., the crystals were filtered, washed with sulfolane and water, and dried,
71 parts of the compound of formula (1) are obtained. Purity was 97%.
【００２３】比較例 実施例４で用いたＮ，Ｎ−ジメチルアセトアミド１００
０部の代わりにキシレン１０００部を用いた以外は実施
例４と同様の操作を行い、式（１）の化合物を９６部得
た。純度は８５％であった。Comparative Example N, N-dimethylacetamide 100 used in Example 4
The same operation as in Example 4 was carried out except that 1000 parts of xylene was used instead of 0 parts, to obtain 96 parts of the compound of the formula (1). Purity was 85%.
【００２４】[0024]
【発明の効果】本発明方法により、高品質の式（１）の
化合物を得ることができ、それにより、最終製品である
染料、顔料及び有機光電材料等を安定供給することがで
きる。According to the method of the present invention, a high-quality compound of the formula (1) can be obtained, whereby the final products such as dyes, pigments and organic photoelectric materials can be stably supplied.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C09B 67/54 C09B 3/02 ＢＥＩＬＳＴＥＩＮ（ＳＴＮ) ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Fields surveyed (Int. Cl. 6 , DB name) C09B 67/54 C09B 3/02 BEILSTEIN (STN) CA (STN) REGISTRY (STN)
Claims (2)
よび／または含イオウ系溶媒を用いて、加熱処理し、不
純物を溶解させ、その懸濁液を冷却、濾過することを特
徴とするジブロモベンザンスロンの精製法。(1) Formula (1) (Formula 1) A heat treatment of the crude dibromobenzanthrone represented by the formula (1) using an amide solvent and / or a sulfur-containing solvent to dissolve the impurities, and cooling and filtering the suspension; Purification method.
イミダゾリジノン、Ｎ−メチル−２−ピロリドン、Ｎ，
Ｎ−ジメチルアセトアミド、１，３，６−トリメチルヘ
キサヒドロ−１，３，６−トリアゾシン−２−オンであ
り、含イオウ系溶媒がスルホラン、ジメチルスルホキシ
ドである請求項１記載の方法。2. The method according to claim 1, wherein the amide solvent is 1,3-dimethyl-2-.
Imidazolidinone, N-methyl-2-pyrrolidone, N,
2. The method according to claim 1, wherein N-dimethylacetamide and 1,3,6-trimethylhexahydro-1,3,6-triazocin-2-one are used, and the sulfur-containing solvent is sulfolane or dimethylsulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22289094A JP2786602B2 (en) | 1994-09-19 | 1994-09-19 | Purification method of dibromobenzanthrone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22289094A JP2786602B2 (en) | 1994-09-19 | 1994-09-19 | Purification method of dibromobenzanthrone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0885764A JPH0885764A (en) | 1996-04-02 |
| JP2786602B2 true JP2786602B2 (en) | 1998-08-13 |
Family
ID=16789478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22289094A Expired - Fee Related JP2786602B2 (en) | 1994-09-19 | 1994-09-19 | Purification method of dibromobenzanthrone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2786602B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5575825B2 (en) * | 2011-03-17 | 2014-08-20 | 富士フイルム株式会社 | Colored radiation-sensitive composition, colored cured film, color filter, method for producing color filter, solid-state imaging device, liquid crystal display device, and method for producing dye |
-
1994
- 1994-09-19 JP JP22289094A patent/JP2786602B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0885764A (en) | 1996-04-02 |
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