JPH03118365A - Production of quinophthalone compound from tar base oil - Google Patents
Production of quinophthalone compound from tar base oilInfo
- Publication number
- JPH03118365A JPH03118365A JP25504989A JP25504989A JPH03118365A JP H03118365 A JPH03118365 A JP H03118365A JP 25504989 A JP25504989 A JP 25504989A JP 25504989 A JP25504989 A JP 25504989A JP H03118365 A JPH03118365 A JP H03118365A
- Authority
- JP
- Japan
- Prior art keywords
- base oil
- tar
- tar base
- quinaldine
- distillation
- 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
- 239000002199 base oil Substances 0.000 title claims abstract description 31
- -1 quinophthalone compound Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000011269 tar Substances 0.000 claims abstract description 33
- 238000009835 boiling Methods 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 9
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011280 coal tar Substances 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 7
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 13
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract description 36
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004821 distillation Methods 0.000 abstract description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 abstract description 3
- 239000001052 yellow pigment Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FBOFHVFMPNNIKN-UHFFFAOYSA-N dimethylquinoline Natural products C1=CC=C2N=C(C)C(C)=CC2=C1 FBOFHVFMPNNIKN-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- AAUXBJGBQRZEPY-UHFFFAOYSA-N 2-methylquinoline Chemical compound C1=CC=CC2=NC(C)=CC=C21.C1=CC=CC2=NC(C)=CC=C21 AAUXBJGBQRZEPY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B25/00—Quinophthalones
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、顔料として使用されるキノフタロン化合物を
工業的に、かつ安価にタール塩基油から製造する方法に
関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for industrially and inexpensively producing a quinophthalone compound used as a pigment from tar base oil.
〈従来の技術〉
キナルジン（２−メチルキノリン）と無水フタル酸との
縮合反応により、キノフタロンを製造する下記（１）式
に示す方法は公知である。<Prior Art> A method shown in the following formula (1) for producing quinophthalone by a condensation reaction of quinaldine (2-methylquinoline) and phthalic anhydride is known.
反応条件としては、反応温度が１９０〜２２０℃、反応
時間が２〜１０時間、さらには収率向上のために反応系
への塩化亜鉛の添加および反応に不活性な溶媒を利用す
る等の工夫がなされている。The reaction conditions include a reaction temperature of 190 to 220°C, a reaction time of 2 to 10 hours, and measures such as adding zinc chloride to the reaction system and using an inert solvent for the reaction to improve the yield. is being done.
〈発明が解決しようとする問題〉
しかしながら、現在までの研究報告の中には原料のキナ
ルジン純度を明記している報告例がなく、恐らく９９％
以上の純度を有するキナルジンが使用されているものと
予想される。 このようなキナルジンはアニリンからの
合成法で得ることができるが、高価である。<Problem to be solved by the invention> However, none of the research reports to date specify the purity of quinaldine as a raw material, and it is probably 99%.
It is expected that quinaldine having a purity higher than that is used. Such quinaldine can be obtained synthetically from aniline, but it is expensive.
また、キナルジンは石炭系のコールタールに含まれてい
るが、キナルジンの異性体も含まれることから、キナル
ジンのみを安価に分動精製することは技術的に困難であ
るために、得られる高純度キナルジンは高価になると予
想される。In addition, although quinaldine is contained in coal-based coal tar, it also contains isomers of quinaldine, so it is technically difficult to perform partial refining of quinaldine alone at low cost. Quinaldine is expected to be expensive.
本発明は、上記問題点を解消して部品な１ｆｆｉ （’
１で工業的に有利にタール塩基油からキノフタロン化合
物を製造する方法を提供することを目的としている。The present invention solves the above-mentioned problems and provides a component 1ffi ('
The object of the present invention is to provide an industrially advantageous method for producing quinophthalone compounds from tar base oil.
く課題を解決するための手段〉
本発明は、上記観点に鑑みコールタールに含まれるキナ
ルジンを高度に精製することなく、タール塩基油を原料
とするキノフタロン化合物の安価な製造方法を提供する
ものである。Means for Solving the Problems> In view of the above points, the present invention provides an inexpensive method for producing a quinophthalone compound using tar base oil as a raw material without highly refining quinaldine contained in coal tar. be.
前記タール塩基油は、タール塩基成分を含有するコール
タールの分留油から酸抽出法によって製造される。
このようにして得られるタール塩基油には、キノリン、
イソキノリン、キナルジン、８−メチルキノリン、およ
びジメチルキノリン等のキノリン系化合物が含まれてい
る。The tar base oil is produced from fractionated coal tar oil containing tar base components by an acid extraction method.
The tar base oil obtained in this way contains quinoline,
It includes quinoline compounds such as isoquinoline, quinaldine, 8-methylquinoline, and dimethylquinoline.
即ち、本発明は、このタール塩基油を原料としてキノフ
タロン化合物を製造する方法である。That is, the present invention is a method for producing a quinophthalone compound using this tar base oil as a raw material.
しかしながら、このタール塩ａｔ由をｆ吏ｍして、前記
（■）式に従い、キノフタロンの合成を試みたところ、
得られた合成物がポリマー状にタール化してその後の処
理を著しく困難にするばかりか、キノフタロン化合物の
回収がてぎなかった。However, when we attempted to synthesize quinophthalone using this tar salt according to the formula (■), we found that
Not only did the resulting compound turn into a polymer tar, making subsequent processing extremely difficult, but it was also difficult to recover the quinophthalone compound.
前述したことからコールタール分留油から酸抽出法によ
り製造されるタール塩基油には、キノフタロン合成反応
温度（１９０〜２２０℃）においてポリマー状になる成
分が含まれていると予想される。From the above, it is expected that the tar base oil produced from coal tar fractionated oil by the acid extraction method contains components that become polymeric at the quinophthalone synthesis reaction temperature (190 to 220°C).
従フて、タール塩基油を使用する場合、合成反応に供す
る前工程で、ポリマー状になる成分を除いておく必要が
あるとの知見を得た。 ポリマー状になる成分の構造は
明らかではないが、タール塩基油の成分の構成から、高
沸点物質と予想されるため前工程において、蒸留処理に
よりキナルジンを多く含む留分と高沸点物質とを分離す
る必要がある。Therefore, it has been found that when using tar base oil, it is necessary to remove components that become polymeric in a step before being subjected to the synthesis reaction. Although the structure of the component that becomes a polymer is not clear, it is expected to be a high-boiling point substance based on the composition of the components of tar base oil, so in the previous step, the fraction containing a large amount of quinaldine and the high-boiling point substance are separated by distillation treatment. There is a need to.
即ち、上記目的を達成するために本発明によれば、ター
ル塩基油と無水フタル酸とを反応させてキノフタロン化
合物を製造するに際し、２５０℃以上の高沸点物質を分
離除去したタール塩基油と無水フタル酸とを反応させる
ことを特徴とするタール塩基油からのキノフタロン化合
物の製造法が提供される。That is, in order to achieve the above object, according to the present invention, when producing a quinophthalone compound by reacting tar base oil and phthalic anhydride, tar base oil and anhydrous tar base oil from which substances with a high boiling point of 250° C. or higher have been separated and removed are used. Provided is a method for producing a quinophthalone compound from tar base oil, which comprises reacting the compound with phthalic acid.
前記タール塩基油が、コールタールから酸抽出法により
製造されたものであるのが好ましい。Preferably, the tar base oil is produced from coal tar by an acid extraction method.
以下に本発明をさらに詳細に説明する。The present invention will be explained in more detail below.
本発明は、キノフタロン合成反応に供する前にタール塩
基油に含まれる高沸点物質を蒸留により分離除去するこ
とが重要な要件である。An important requirement of the present invention is to separate and remove high-boiling substances contained in the tar base oil by distillation before subjecting it to the quinophthalone synthesis reaction.
この蒸留では、塔頂部からキノリン、イソキノリン、キ
ナルジン等の成分を留出させ、塔底部から高沸点物質を
得る。 この時の蒸留条件としては、常圧下に塔頂部の
温度が２５０℃となる条件を満足すればよい。 蒸留方
式（例えば、連続式か回分式のいずれか。 また、常圧
式か減圧式のいずれか。 あるいは、段数および還流比
の条件等）は、特に限定されないが、段数、還流比を大
きくして塔頂留出留分中のキナルジン含有率を高めるこ
とは本発明の目的とするところではない。In this distillation, components such as quinoline, isoquinoline, and quinaldine are distilled out from the top of the column, and high-boiling substances are obtained from the bottom of the column. The distillation conditions at this time may be such that the temperature at the top of the column is 250° C. under normal pressure. The distillation method (e.g. continuous or batch method, normal pressure method or reduced pressure method, or conditions such as number of stages and reflux ratio) is not particularly limited, but it is possible to increase the number of stages and reflux ratio. It is not an objective of the present invention to increase the quinaldine content in the overhead fraction.
塔頂留出留分は、キノフタロン合成原料に供され無水フ
タル酸と混合された後、公知の方法でキノフタロン化合
物を合成す′ることができる。The overhead fraction is provided as a raw material for quinophthalone synthesis and mixed with phthalic anhydride, after which a quinophthalone compound can be synthesized by a known method.
〈実施例〉 以下に本発明を実施例に基づぎ具体的に説明する。<Example> The present invention will be specifically explained below based on Examples.
（実施例１）
コールタールから酸抽出法により製造されたタール塩基
油１００重量部を、常圧にて塔頂温度が２５０℃となる
まで単蒸留し、キノリン、イソキノリン、キナルジン（
キナルジン含有量＝１１重量部）等を含む留分８５重皿
部を塔頂部から得、高沸点物質１５重量部を塔底部から
得た。(Example 1) 100 parts by weight of tar base oil produced from coal tar by the acid extraction method was subjected to simple distillation at normal pressure until the top temperature reached 250°C.
85 parts by weight of a fraction containing quinaldine (content = 11 parts by weight) etc. were obtained from the top of the column, and 15 parts by weight of high-boiling substances were obtained from the bottom of the column.
この塔頂留出物８５重量部に無水フタル酸１２重量部を
加えて加熱し、２１０℃で２時間保持した後、室温まで
冷却した。12 parts by weight of phthalic anhydride was added to 85 parts by weight of the overhead distillate, heated, held at 210°C for 2 hours, and then cooled to room temperature.
この反応物にエタノール１５０重量部を加えた。 キノ
リン、イソキノリンおよび未反応キナルジン等がエタノ
ールに溶解され、次の濾過操作で濾液として回収された
。 一方、エタノールに不溶のキノフタロンは濾過操作
で結晶として得られた。150 parts by weight of ethanol was added to this reaction mixture. Quinoline, isoquinoline, unreacted quinaldine, etc. were dissolved in ethanol and recovered as a filtrate in the next filtration operation. On the other hand, quinophthalone, which is insoluble in ethanol, was obtained as crystals by filtration.
得られたキノフタロン結晶をさらにエタノール１５０重
量部を用いて再結晶し濾過した。The obtained quinophthalone crystals were further recrystallized using 150 parts by weight of ethanol and filtered.
得られた結晶を乾燥し、キノフタロンの黄色系の針状結
晶が８重量部得られた。 この時の収率は４０％（対理
論量）である。The obtained crystals were dried to obtain 8 parts by weight of yellowish needle-like crystals of quinophthalone. The yield at this time was 40% (based on theoretical amount).
（比較例）
実施例１で使用した酸抽出法により製造されたタール塩
基油を用い、単蒸留操作を行なわず、そのままキノフタ
ロン合成に供した。(Comparative Example) Using the tar base oil produced by the acid extraction method used in Example 1, it was directly subjected to quinophthalone synthesis without performing a simple distillation operation.
このタール塩基油には、キナルジン１２重量部が含有さ
れており、これに無水フタル酸１３重量部を加え、実施
例１と同様にして２１０℃で２時間の反応経過後、室温
まで冷却した。This tar base oil contained 12 parts by weight of quinaldine, to which 13 parts by weight of phthalic anhydride was added, and after reaction at 210° C. for 2 hours in the same manner as in Example 1, it was cooled to room temperature.
この反応物はポリマー状となり、粘性が高く、実施例と
同様にエタノール１５０重量部を加えて濾過を試みたが
分離できずキノフタロン結晶の回収ができなかった。This reaction product became a polymer and had high viscosity, and although 150 parts by weight of ethanol was added and filtration was attempted in the same manner as in the example, separation was not possible and quinophthalone crystals could not be recovered.
〈発明の効果〉
本発明は以上説明したように構成されているので、黄色
系顔料として利用されるキノフタロン化合物の合成には
、これまで、高価な高純度キナルジンが使用されていた
が、本発明の製造法によればコールタールから簡易な操
作で工業的に有利にキノフタロン化合物を製造すること
ができる。<Effects of the Invention> Since the present invention is configured as described above, expensive and highly purified quinaldine has been used to synthesize quinophthalone compounds used as yellow pigments, but the present invention According to the production method, a quinophthalone compound can be industrially advantageously produced from coal tar with a simple operation.
Claims (2)
フタロン化合物を製造するに際し、２５０℃以上の高沸
点物質を分離除去したタール塩基油と無水フタル酸とを
反応させることを特徴とするタール塩基油からのキノフ
タロン化合物の製造法。(1) A tar characterized by reacting tar base oil and phthalic anhydride with a tar base oil from which substances with a high boiling point of 250°C or higher have been separated and removed when producing a quinophthalone compound by reacting tar base oil and phthalic anhydride. A method for producing quinophthalone compounds from base oils.
により製造されたものである請求項１記載のタール塩基
油からのキノフタロン化合物の製造法。(2) The method for producing a quinophthalone compound from tar base oil according to claim 1, wherein the tar base oil is produced from coal tar by an acid extraction method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25504989A JPH03118365A (en) | 1989-09-29 | 1989-09-29 | Production of quinophthalone compound from tar base oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25504989A JPH03118365A (en) | 1989-09-29 | 1989-09-29 | Production of quinophthalone compound from tar base oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03118365A true JPH03118365A (en) | 1991-05-20 |
Family
ID=17273449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25504989A Pending JPH03118365A (en) | 1989-09-29 | 1989-09-29 | Production of quinophthalone compound from tar base oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03118365A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106220561A (en) * | 2016-07-25 | 2016-12-14 | 东南大学 | High temperature resistant blue-light absorbers of specific absorption wavelength and preparation method thereof |
| CN115850995A (en) * | 2022-12-09 | 2023-03-28 | 河北中化鑫宝化工科技有限公司 | Preparation method of solvent yellow 33 |
-
1989
- 1989-09-29 JP JP25504989A patent/JPH03118365A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106220561A (en) * | 2016-07-25 | 2016-12-14 | 东南大学 | High temperature resistant blue-light absorbers of specific absorption wavelength and preparation method thereof |
| CN115850995A (en) * | 2022-12-09 | 2023-03-28 | 河北中化鑫宝化工科技有限公司 | Preparation method of solvent yellow 33 |
| CN115850995B (en) * | 2022-12-09 | 2023-12-12 | 河北中化鑫宝化工科技有限公司 | Preparation method of solvent yellow 33 |
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