JPH0145513B2 - - Google Patents
Info
- Publication number
- JPH0145513B2 JPH0145513B2 JP17813684A JP17813684A JPH0145513B2 JP H0145513 B2 JPH0145513 B2 JP H0145513B2 JP 17813684 A JP17813684 A JP 17813684A JP 17813684 A JP17813684 A JP 17813684A JP H0145513 B2 JPH0145513 B2 JP H0145513B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- tar
- tar acid
- aromatic
- 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.)
- Expired
Links
- 239000011289 tar acid Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000011269 tar Substances 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005486 naphthalic acid group Chemical group 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229910017464 nitrogen compound Inorganic materials 0.000 description 5
- 150000002830 nitrogen compounds Chemical class 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 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
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IBFJDBNISOJRCW-UHFFFAOYSA-N 3-methylphthalic acid Chemical class CC1=CC=CC(C(O)=O)=C1C(O)=O IBFJDBNISOJRCW-UHFFFAOYSA-N 0.000 description 1
- TWWAWPHAOPTQEU-UHFFFAOYSA-N 4-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)OC2=O TWWAWPHAOPTQEU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011847 coal-based material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
Landscapes
- Working-Up Tar And Pitch (AREA)
Description
産業上の利用分野
本発明は石炭乾留ないし石炭ガス化工程から副
生するタール酸の精製法に関する。
タール酸とは、元来フエノール、クレゾール
類、キシレノール類を総称していうが、前記ター
ル酸中には、通常タール塩基と総称せられるアニ
リン、ピリジン、ピコリン、ルチジン、キノリン
など塩基性窒素化合物その他の不純物が含有せら
れている。
タール酸は、それ自体で木材防腐剤、殺虫剤、
殺菌剤としての用途もあるが、合成樹脂や可塑剤
などの原料に供用する場合には、上記不純物は可
及的に除去されねばならない。しかも、近時資源
的な理由から、合成樹脂等の材料源として、石油
系から石炭系へ見かえられて来ているので、ター
ル酸精製法の開発は大きな課題となつている。
従来技術
従来、石炭乾留工程からタール酸を取得するに
は、原料たるタール軽油、カルボル油、ナフタリ
ン油ないし吸収油を、希薄苛性ソーダ水溶液で洗
滌し、それによつて原料中のタール酸をそのソー
ダ塩に転化し、ついで、これをスチーミング法や
軽油洗滌法によつて、中性油分、タール塩基を除
去したのち、硫酸もしくは炭酸ガスによつて中和
分解を行ない、さらに必要に応じて蒸留等の手段
を採つて来た。
ところが上記方法では、ピリジンのような比較
的低沸点塩基はスチーミング工程で除去され易い
が、アニリン、トルイジンのような高沸点塩基は
除去が困難であるのみならず、上記方法では、ス
チームないし軽油の大量が必要とされ経済採算上
も好ましくない。
発明が解決しようとする問題点
本発明は如上観点から、アニリンないしトルイ
ジンのような芳香族アミノ化合物を容易に減除す
るタール酸の精製法を提供するものである。
問題点を解決するための手段
本発明者らは、タール酸に特定の芳香族ジカル
ボン酸類を添加して蒸留に付することによつて、
上記問題点が解決できることを見出した。
本発明にいうタール酸とは、従来法で述べたタ
ール酸ソーダ塩の酸による中和分解後の粗タール
酸、粗タール酸を脱水および／または脱ピツチし
て得られる精製タール酸、精製タール酸を蒸留し
て得られるフエノール、ｏ−クレゾール、ｍ・ｐ
−クレゾール、キシレノール等をいう。換言すれ
ば塩基性窒素化合物、特に芳香族アミノ化合物を
含むタール酸をいう。
このようなタール酸に添加せられる芳香族α−
ジカルボン酸、芳香族α−ジカルボン酸類の無水
物としては、フタル酸、無水フタル酸、メチルフ
タル酸類、メチル無水フタル酸類、２・３−ナフ
タレンジカルボン酸、２・３−ナフタレンジカル
ボン酸無水物、ピロメリツト酸、無水ピロメリツ
ト酸、トリメリツト酸、無水トリメリツト酸など
である。
また、１・８−ナフタレンジカルボン酸類、
１・８−ナフタレンジカルボン酸類の無水物とし
ては、ナフタル酸、無水ナフタル酸などがあげら
れる。
タール酸に添加後はよくかきまぜ、直ちに蒸留
に着手しても差支えない。蒸留時間内に蒸留温度
で芳香族アミノ化合物は、添加された上記芳香族
ジカルボン酸等と下式により反応して高沸点（高
分解点）の芳香族イミドに転化し、留出すること
なく、ピツチ状の釜残として除去される。反応例
を次に示す。
添加物の添加量は、芳香族アミノ化合物と当量
以上が望ましい。また生成したイミド化合物の分
解を防ぐため、蒸留温度は低い方が望ましいが、
実用上は塔底温度200℃以下の常圧または減圧下
での蒸留が良い。
比較例
第１表記載の組成を有するタール酸200ｇを、
200mlのフラスコに装入し、常圧下ボトム温度180
℃で、理論段数15段の蒸留塔を用いて脱水を行な
つた。すなわち、まず塔頂より、水と油分33.5ｇ
を留去した。
INDUSTRIAL APPLICATION FIELD The present invention relates to a method for purifying tar acid produced as a by-product from coal carbonization or coal gasification processes. Tar acid is originally a general term for phenols, cresols, and xylenols, but tar acid also contains basic nitrogen compounds such as aniline, pyridine, picoline, lutidine, and quinoline, which are generally referred to as tar bases. Contains impurities. Tar acid is a wood preservative, insecticide, and
Although it is used as a disinfectant, when it is used as a raw material for synthetic resins and plasticizers, the above impurities must be removed as much as possible. Furthermore, due to resource considerations, the source of materials for synthetic resins and the like has recently been replaced by coal-based materials rather than petroleum-based ones, so the development of a tar acid purification method has become a major issue. Conventionally, in order to obtain tar acid from a coal carbonization process, the raw materials such as tar gas oil, carbol oil, naphthalene oil or absorption oil are washed with a dilute aqueous solution of caustic soda, thereby converting the tar acid in the raw material into its soda salt. Next, neutral oil and tar base are removed by steaming or light oil washing, followed by neutralization and decomposition with sulfuric acid or carbon dioxide gas, and if necessary, distillation, etc. I have taken the following measures. However, in the above method, relatively low boiling point bases such as pyridine are easily removed in the steaming process, but high boiling point bases such as aniline and toluidine are difficult to remove. This is not desirable from an economic point of view. Problems to be Solved by the Invention In view of the above, the present invention provides a method for purifying tar acid that easily reduces aromatic amino compounds such as aniline or toluidine. Means for Solving the Problems The present inventors have solved the problem by adding specific aromatic dicarboxylic acids to tar acid and subjecting it to distillation.
We have found that the above problems can be solved. The tar acid referred to in the present invention refers to crude tar acid after neutralization and decomposition of sodium tar acid salt with an acid as described in the conventional method, purified tar acid obtained by dehydrating and/or depitching crude tar acid, and purified tar. Phenol, o-cresol, m/p obtained by distilling acid
-Refers to cresol, xylenol, etc. In other words, it refers to tar acid containing basic nitrogen compounds, especially aromatic amino compounds. Aromatic α- added to such tar acid
Examples of anhydrides of dicarboxylic acids and aromatic α-dicarboxylic acids include phthalic acid, phthalic anhydride, methyl phthalic acids, methyl phthalic anhydride, 2,3-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic anhydride, pyromellitic acid , pyromellitic anhydride, trimellitic acid, trimellitic anhydride, etc. In addition, 1,8-naphthalene dicarboxylic acids,
Examples of anhydrides of 1,8-naphthalene dicarboxylic acids include naphthalic acid and naphthalic anhydride. After adding to the tar acid, stir well and start distilling immediately. During the distillation time and at the distillation temperature, the aromatic amino compound reacts with the added aromatic dicarboxylic acid, etc. according to the following formula, converting it into an aromatic imide with a high boiling point (high decomposition point), without distilling it off. It is removed as pit-like residue. A reaction example is shown below. The amount of the additive added is preferably equal to or greater than the amount of the aromatic amino compound. In addition, it is desirable that the distillation temperature be low to prevent the decomposition of the generated imide compound.
Practically speaking, distillation is preferably carried out under normal pressure or reduced pressure with a bottom temperature of 200°C or less. Comparative example: 200g of tar acid having the composition listed in Table 1,
Pour into a 200ml flask and keep the bottom temperature at 180°C under normal pressure.
Dehydration was carried out at ℃ using a distillation column with 15 theoretical plates. In other words, first, 33.5g of water and oil are poured from the top of the tower.
was removed.
【表】
油分とは水と共沸して留出するフエノールなど
である。
ついで、塔底温度を180℃に維持したまま減圧
蒸留に付し、最終圧力30mmHgに至らしめた。フ
ラスコ内にはピツチ状釜残14ｇが残存し、144ｇ
の脱水脱ピツチされたタール酸、換言すれば精製
タール酸が留出した。なお、ロスは8.5ｇであつ
た。
実施例
第１表記載の粗タール酸に、その含有する塩基
性窒素化合物の２倍当量の各種芳香族カルボン酸
を添加し、上記比較例と同様な操作を行ない、精
製タール酸を留取した。物質収支そのものは比較
例の場合と実質的に異ならない。
留取したタール酸中の塩基性窒素化合物の種類
およびその含量を、原料タール酸の場合を含め第
２表に一括表示する（単位はmg／Kg）。[Table] Oils include phenols and the like that are distilled out by azeotroping with water. Then, while maintaining the bottom temperature at 180°C, the mixture was subjected to vacuum distillation to reach a final pressure of 30 mmHg. 14g of pit-shaped pot residue remained in the flask, and 144g
Dehydrated and depitched tar acid, in other words purified tar acid, was distilled out. Incidentally, the loss was 8.5 g. Example: To the crude tar acid listed in Table 1, various aromatic carboxylic acids in an amount twice equivalent to the basic nitrogen compound contained therein were added, and the same operation as in the above comparative example was performed to distill purified tar acid. . The material balance itself is not substantially different from that of the comparative example. The types and contents of basic nitrogen compounds in the distilled tar acid, including the raw material tar acid, are listed in Table 2 (unit: mg/Kg).
【表】
第２表のとおり、既述の芳香族ジカルボン酸を
添加蒸留することにより、スチーミング等では除
去し難い高沸点塩基性物質であるアニリン、トル
イジンを完全に除去することができる。また、窒
素環化合物のうちでは、ルチジン、ピコリンを大
巾に低減できることも明白である。なお、ピリジ
ン、ピコリンは、通常のスチーミング工程でほと
んど除去されるので問題となることはない。
効 果
以上詳述したように、本発明方法によれば少量
の芳香族ジカルボン酸を添加して蒸留するという
簡単な操作だけで、タール酸中の塩基性窒素化合
物の大部分が除去できたのである。[Table] As shown in Table 2, aniline and toluidine, which are high-boiling basic substances that are difficult to remove by steaming, can be completely removed by additive distillation of the aromatic dicarboxylic acids described above. It is also clear that among nitrogen ring compounds, lutidine and picoline can be significantly reduced. It should be noted that pyridine and picoline do not pose a problem since most of them are removed in a normal steaming process. Effects As detailed above, according to the method of the present invention, most of the basic nitrogen compounds in tar acid could be removed by simply adding a small amount of aromatic dicarboxylic acid and distilling it. be.
Claims (1)
族α−ジカルボン酸類の無水物、ナフタル酸類、
無水ナフタル酸類の中から選ばれた１種または２
種以上の芳香族ジカルボン酸を添加し、塔底温度
200℃以下で蒸留することを特徴とするタール酸
の精製方法。 ２ 芳香族ジカルボン酸の添加量は、タール酸中
に含有されるタール塩基と当量ないしそれ以上で
あることを特徴とする特許請求の範囲第１項記載
のタール酸の精製方法。[Claims] 1 Tar acid, aromatic α-dicarboxylic acids, anhydrides of aromatic α-dicarboxylic acids, naphthalic acids,
One or two selected from naphthalic anhydride
By adding more than one aromatic dicarboxylic acid, the bottom temperature
A method for purifying tar acid, which is characterized by distillation at 200°C or lower. 2. The method for purifying tar acid according to claim 1, wherein the amount of the aromatic dicarboxylic acid added is equivalent to or more than the tar base contained in the tar acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17813684A JPS6155191A (en) | 1984-08-27 | 1984-08-27 | Refining of tar acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17813684A JPS6155191A (en) | 1984-08-27 | 1984-08-27 | Refining of tar acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6155191A JPS6155191A (en) | 1986-03-19 |
| JPH0145513B2 true JPH0145513B2 (en) | 1989-10-03 |
Family
ID=16043278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17813684A Granted JPS6155191A (en) | 1984-08-27 | 1984-08-27 | Refining of tar acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6155191A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6178052B2 (en) * | 2012-07-20 | 2017-08-09 | 東京応化工業株式会社 | Method for purifying cresol, method for producing novolak resin for photosensitive resin composition, and photosensitive resin composition |
-
1984
- 1984-08-27 JP JP17813684A patent/JPS6155191A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6155191A (en) | 1986-03-19 |
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