JPH0555492B2 - - Google Patents
Info
- Publication number
- JPH0555492B2 JPH0555492B2 JP14819686A JP14819686A JPH0555492B2 JP H0555492 B2 JPH0555492 B2 JP H0555492B2 JP 14819686 A JP14819686 A JP 14819686A JP 14819686 A JP14819686 A JP 14819686A JP H0555492 B2 JPH0555492 B2 JP H0555492B2
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- water
- yield
- aromatic carboxylic
- acid
- 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 - Lifetime
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 aromatic iodine compound Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000005711 Benzoic acid Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 235000013675 iodine Nutrition 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000013078 crystal Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- VHEGXFQQYZIMMF-UHFFFAOYSA-N 1-iodo-4-(4-iodophenoxy)benzene Chemical compound C1=CC(I)=CC=C1OC1=CC=C(I)C=C1 VHEGXFQQYZIMMF-UHFFFAOYSA-N 0.000 description 1
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical group [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
〔産業上の利用分野〕
本発明は芳香族カルボン酸の製造法に関する。
〔従来の技術〕
芳香族ヨウ素化合物のカルボニル化法による芳
香族カルボン酸の製法については既に知られてい
る。例えば、ニツケル触媒を用いて、ヨードベン
ゼンから安息香酸を合成する方法〔ブレテイン・
オブ・ザ・ケミカル・ソサイアテイ・オブ・ジヤ
パン（Bull.Chem.Soc.Japan）、第27巻、第389頁
（1954年）〕や、塩化パラジウム一塩化鉄系触媒を
用いて酢酸−無水酢酸混合物中でヨードベンゼン
を一酸化炭素と反応させた後、加水分解すること
によつて安息香酸とする方法（USP2634274号公
報）などが知られている。
しかしながら、これらのいずれの方法において
も金属元素を含む触媒が必要であつた。
〔発明が解決しようとする問題点〕
前記のように、従来の方法においては触媒を必
須成分として用いなければならず、触媒を用いる
場合には反応後に触媒成分を分離・回収する面倒
な工程も必要であつた。
〔問題点を解決するための手段〕
そこで本発明者らは、より安価に、また、より
容易に芳香族カルボン酸を製造する方法について
鋭意研究を重ねた結果、高収率、高選択率で目的
とする芳香族カルボン酸を製造できる新しい方法
を見出し、本発明を完成するに至つた。
すなわち本発明は、塩基及び水の存在下に、触
媒を使用せずに芳香族ヨウ素化合物を一酸化炭素
と反応させることを特徴とする芳香族カルボン酸
の製造法である。
本発明で用いられる芳香族ヨウ素化合物とは、
芳香族基の芳香環に結合している水素が１個以上
のヨウ素によつて置換された化合物であればどの
ようなものであつてもよい。このような芳香族ヨ
ウ素化合物としては例えば。ベンゼン、トルエ
ン、キシレン、エチルベンゼン、ジエチルベンゼ
ン、プロピルベンゼン、キユメン、トリメチルベ
ンゼン、テトラメチルベンゼン、ナフタリン、ア
ンスラセンなどの芳香族炭化水素の芳香環の水素
が１個以上のヨウ素によつて置換された化合物
類；ピリジン、キノリン、ビピリジンなどのヘテ
ロ芳香族化合物の芳香環の水素が１個以上のヨウ
素によつて置換された化合物類；式
[Industrial Application Field] The present invention relates to a method for producing aromatic carboxylic acids. [Prior Art] A method for producing aromatic carboxylic acid by carbonylation of an aromatic iodine compound is already known. For example, a method for synthesizing benzoic acid from iodobenzene using a nickel catalyst [Bretain
of the Chemical Society of Japan (Bull.Chem.Soc.Japan), Vol. 27, p. 389 (1954)] or acetic acid-acetic anhydride mixture using a palladium chloride monochloride-based catalyst. A method is known in which iodobenzene is reacted with carbon monoxide and then hydrolyzed to produce benzoic acid (USP No. 2,634,274). However, all of these methods require a catalyst containing a metal element. [Problems to be solved by the invention] As mentioned above, in the conventional method, a catalyst must be used as an essential component, and when a catalyst is used, a troublesome step of separating and recovering the catalyst component is also required after the reaction. It was necessary. [Means for Solving the Problems] Therefore, the present inventors have conducted extensive research on a method for producing aromatic carboxylic acids more cheaply and more easily, and as a result, have developed a method for producing aromatic carboxylic acids with high yield and high selectivity. We have discovered a new method for producing the desired aromatic carboxylic acid, and have completed the present invention. That is, the present invention is a method for producing an aromatic carboxylic acid, which is characterized by reacting an aromatic iodine compound with carbon monoxide in the presence of a base and water without using a catalyst. The aromatic iodine compound used in the present invention is
Any compound may be used as long as the hydrogen bonded to the aromatic ring of the aromatic group is replaced by one or more iodine. Examples of such aromatic iodine compounds include: Compounds in which hydrogen in the aromatic ring of aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, diethylbenzene, propylbenzene, kyumene, trimethylbenzene, tetramethylbenzene, naphthalene, and anthracene is substituted with one or more iodines ; Compounds in which hydrogen in the aromatic ring of heteroaromatic compounds such as pyridine, quinoline, and bipyridine is substituted with one or more iodine;
以下、実施例により本発明をさらに説明する
が、本発明は、これらの実施例に限定されるもの
ではない。なおオートクレーブはハステロイーＣ
製のものを用いた。
実施例 １
ヨードベンゼン20.4ｇ、安息香酸ナトリウム
14.4ｇ、水40ｇをオートクレーブに入れ、オート
クレーブの内部を一酸化炭素で置換した後、一酸
化炭素100Kg／cm2を圧入した。撹拌下に250〜260
℃で２時間反応させた後、冷却したところ、白色
の固形物が多量生成していた。この固形物を粉砕
し、水で洗浄した後、この白色結晶を減圧下70〜
80℃で乾燥した。この白色結晶は融点が121〜122
℃であることと、赤外線吸収スペクトルが安息香
酸のそれと全く同一であることから、安息香酸で
あると固定された。収量は23.7ｇであつた。この
ことはヨードベンゼン及び安息香酸ナトリウムを
合わせた芳香族原料基準で97％の収率を示してい
る。
実施例 ２
ヨードベンゼン20.4ｇ、水酸化ナトリウム８
ｇ、水50ｇを用いて実施例１と同様な方法で反応
させた後、冷却し、希塩酸で酸性にすることによ
つて白色固体である安息香酸を得た。収率96％、
選択率97％であつた。
実施例 ３
パラフルオロヨードベンゼン22.2ｇ、パラフル
オロ安息香酸カリウム17.8ｇ、水50ｇを用いて、
実施例１と同様な方法で反応及び後処理を行つた
結果、パラフルオロ安息香酸を芳香族原料基準で
収率98％で得た。
実施例 ４
パラフエノキシヨードベンゼン23.7ｇ、ピリジ
ン15ｇ、水40ｇを用いて実施例１と同様な方法で
反応させた後、冷却し、希塩酸で酸性にすること
によつて白色固体であるパラフエノキシ安息香酸
を収率97％、選択率98％で得た。
実施例 ５
４，4′−ジヨードビフエニル20.3ｇ、酢酸ナト
リウム8.5ｇ、水50ｇを用いて実施例１と同様な
方法で反応させた結果、１，1′−ビフエニル−
４，4′−ジカルボン酸が収率93％、選択率95％で
得られた。
実施例 ６
４，4′−ジヨードジフエニルエーテル21.1ｇ、
トリ−ｎ−ブチルアミン20ｇ、水50ｇを用いて実
施例１と同様な方法で反応を行つた結果、１，
1′−ジフエニルエテール−４，4′−ジカルボン酸
が収率92％、選択率93％で得られた。
実施例
メタヨードトルエン21.8ｇ、メタトルイル酸ナ
トリウム16ｇ、水50ｇをオートクレーブに入れ一
酸化炭素100Kg／cm2を圧入し、180℃で２時間反応
させた結果メタヨードトルエンの反応率は66％、
メタトルイル酸が収率65％、選択率98％で得られ
た。
実施例 ８
反応温度を150℃にする以外は実施例１と同様
な方法で反応を行つた結果、ヨードベンゼンの反
応率は2.5％で、安息香酸が収率2.4％、選択率96
％で得られた。
〔発明の効果〕
本発明の方法によつて、芳香族ヨウ素化合物と
一酸化炭素と水から芳香族カルボン酸を、触媒を
使用せずに、高収率、高選択率で得ることができ
る。
また生成物の分離も容易に行える。
EXAMPLES Hereinafter, the present invention will be further explained with reference to Examples, but the present invention is not limited to these Examples. The autoclave is Hastelloy C.
I used one made by Example 1 20.4 g of iodobenzene, sodium benzoate
14.4 g and 40 g of water were placed in an autoclave, and after replacing the inside of the autoclave with carbon monoxide, 100 kg/cm 2 of carbon monoxide was injected under pressure. 250-260 under stirring
After reacting at ℃ for 2 hours, when the mixture was cooled, a large amount of white solid was produced. After crushing this solid and washing with water, the white crystals were collected under reduced pressure for 70~
Dry at 80°C. This white crystal has a melting point of 121-122
℃, and the infrared absorption spectrum was exactly the same as that of benzoic acid, so it was determined to be benzoic acid. The yield was 23.7g. This shows a yield of 97% based on the aromatic raw materials including iodobenzene and sodium benzoate. Example 2 20.4g of iodobenzene, 8g of sodium hydroxide
After reacting in the same manner as in Example 1 using 50 g of water and 50 g of water, the mixture was cooled and acidified with dilute hydrochloric acid to obtain benzoic acid as a white solid. Yield 96%,
The selection rate was 97%. Example 3 Using 22.2 g of parafluoroiodobenzene, 17.8 g of potassium parafluorobenzoate, and 50 g of water,
As a result of performing the reaction and post-treatment in the same manner as in Example 1, parafluorobenzoic acid was obtained in a yield of 98% based on the aromatic raw material. Example 4 After reacting in the same manner as in Example 1 using 23.7 g of paraphenoxyiodobenzene, 15 g of pyridine, and 40 g of water, the mixture was cooled and acidified with dilute hydrochloric acid to produce paraphenoxybenzoin, which is a white solid. The acid was obtained in 97% yield and 98% selectivity. Example 5 As a result of reaction in the same manner as in Example 1 using 20.3 g of 4,4'-diiodobiphenyl, 8.5 g of sodium acetate, and 50 g of water, 1,1'-biphenyl-
4,4'-dicarboxylic acid was obtained with a yield of 93% and a selectivity of 95%. Example 6 21.1 g of 4,4'-diiodo diphenyl ether,
A reaction was carried out in the same manner as in Example 1 using 20 g of tri-n-butylamine and 50 g of water. As a result, 1.
1'-diphenylether-4,4'-dicarboxylic acid was obtained in a yield of 92% and a selectivity of 93%. Example 21.8g of metaiodotoluene, 16g of sodium metatoluate, and 50g of water were placed in an autoclave, 100Kg/cm 2 of carbon monoxide was introduced under pressure, and the reaction was carried out at 180°C for 2 hours. As a result, the reaction rate of metaiodotoluene was 66%.
Metatoluic acid was obtained with a yield of 65% and a selectivity of 98%. Example 8 A reaction was carried out in the same manner as in Example 1 except that the reaction temperature was 150°C. As a result, the reaction rate of iodobenzene was 2.5%, the yield of benzoic acid was 2.4%, and the selectivity was 96.
Obtained in %. [Effects of the Invention] According to the method of the present invention, aromatic carboxylic acid can be obtained from an aromatic iodine compound, carbon monoxide, and water in high yield and high selectivity without using a catalyst. Furthermore, product separation can be easily performed.
Claims (1)
香族ヨウ素化合物を一酸化炭素と反応させること
を特徴とする芳香族カルボン酸の製造法。 ２ 150℃以上の温度で実施する特許請求の範囲
第１項記載の方法。 ３ 塩基が生成する芳香族カルボン酸と同じ骨格
を有する芳香族カルボン酸のアルカリ金属塩であ
る特許請求の範囲第１項または第２項に記載の方
法。[Claims] 1. A method for producing an aromatic carboxylic acid, which comprises reacting an aromatic iodine compound with carbon monoxide in the presence of a base and water without using a catalyst. 2. The method according to claim 1, which is carried out at a temperature of 150°C or higher. 3. The method according to claim 1 or 2, wherein the base is an alkali metal salt of an aromatic carboxylic acid having the same skeleton as the aromatic carboxylic acid to be produced.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14819686A JPS635052A (en) | 1986-06-26 | 1986-06-26 | Production of aromatic carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14819686A JPS635052A (en) | 1986-06-26 | 1986-06-26 | Production of aromatic carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS635052A JPS635052A (en) | 1988-01-11 |
| JPH0555492B2 true JPH0555492B2 (en) | 1993-08-17 |
Family
ID=15447405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14819686A Granted JPS635052A (en) | 1986-06-26 | 1986-06-26 | Production of aromatic carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS635052A (en) |
-
1986
- 1986-06-26 JP JP14819686A patent/JPS635052A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS635052A (en) | 1988-01-11 |
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