JPS6360962A - Production of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid - Google Patents
Production of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acidInfo
- Publication number
- JPS6360962A JPS6360962A JP20282986A JP20282986A JPS6360962A JP S6360962 A JPS6360962 A JP S6360962A JP 20282986 A JP20282986 A JP 20282986A JP 20282986 A JP20282986 A JP 20282986A JP S6360962 A JPS6360962 A JP S6360962A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- naphthalenedisulfonic acid
- naphthalenedisulfonic
- sulfuric acid
- naphthalenesulfonic
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 title claims description 14
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 title claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 10
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 18
- 239000002994 raw material Substances 0.000 abstract description 12
- 239000006227 byproduct Substances 0.000 abstract description 8
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000010306 acid treatment Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 7
- KVEFEYBJNJQGHD-UHFFFAOYSA-N naphthalene-2-sulfonic acid trihydrate Chemical compound O.O.O.C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O KVEFEYBJNJQGHD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WZZLWPIYWZEJOX-UHFFFAOYSA-L disodium;naphthalene-2,6-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(S(=O)(=O)[O-])=CC=C21 WZZLWPIYWZEJOX-UHFFFAOYSA-L 0.000 description 1
- HYFMZOAPNQAXHU-UHFFFAOYSA-N naphthalene-1,7-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 HYFMZOAPNQAXHU-UHFFFAOYSA-N 0.000 description 1
- XXOPHNFSAIFMHP-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid;sodium Chemical compound [Na].C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 XXOPHNFSAIFMHP-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は２−ナフタレンスルホン酸をスルホン化剤によ
りスルホン化し、染料中間体、ポリマー原料としてＴ業
的に価値の高い化合物である２、６−ナフタレンジスル
ホン酸および２．７−ナフタレンジスルホン酸を製造す
る方法に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention is a compound in which 2-naphthalenesulfonic acid is sulfonated with a sulfonating agent, and is a compound of high value in the T industry as a dye intermediate and a polymer raw material. - A method for producing naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid.
く従来技術〉
従来、２．６−ナフタレンジスルホン酸および２．７−
ナフタレンジスルホン酸はナフタレンにＣ硫酸、発煙硫
酸等のスルホン化剤を作用させ、高温でスルホン化する
ことによって製造されていた。特開昭５４−１６３５６
３吟に開示されているように、従来の方法を詳述すると
、ナフタレン１モルに対してスルホン化剤として９８％
濃硫酸を４〜６モル用いて、２．６−ナフタレンジスル
ホン酸および２，７−ナフタレンジスルホン酸を製造せ
しめることである。Conventional technology> Conventionally, 2,6-naphthalenedisulfonic acid and 2,7-
Naphthalene disulfonic acid has been produced by reacting naphthalene with a sulfonating agent such as C sulfuric acid or fuming sulfuric acid and sulfonating it at high temperature. Japanese Patent Publication No. 54-16356
To elaborate on the conventional method, as disclosed in Sangin, 98% of the sulfonating agent is used per mole of naphthalene.
2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid are produced using 4 to 6 moles of concentrated sulfuric acid.
この従来法によりｆＦられな反応生成混合物中には、２
．６−ナフタレンジスルホン酸が１５〜２０１■ｉ＋Ｌ
％、２．７−ナフタレンジスルホン酸か２５〜３０屯：
１：ニ％含まれている。In the reaction product mixture that was not fF determined by this conventional method, 2
．． 6-naphthalenedisulfonic acid is 15 to 201■i+L
%, 25-30 tons of 2.7-naphthalenedisulfonic acid:
Contains 1:2%.
しかし、この際目的とする２、６−ナフタレンジスルホ
ン酸および２．７−ナフタレンジスルホン酸以外のナフ
タレンジスルホン酸穴性体、あるいはナフタレンモノス
ルホン酸およびジナフチルスルホン類の副生が避けられ
ず、′それがため２．６−ナフタレンジスルホン酸およ
び２．７−ナフタレンジスルホン酸の収率が低丁してい
るなどの問題点があった。However, in this case, the by-product of naphthalenedisulfonic acid holes other than the target 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid, or naphthalene monosulfonic acid and dinaphthylsulfones is unavoidable. Therefore, there were problems such as low yields of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid.
それとともに反応生成混合物中よりの２．６−ナフタレ
ンジスルホン酸および２．７−ナフタレンジスルホン酸
の分離精製工程において、例えばこの２つのナフタレン
ジスルホン酸のナトリウム塩の溶解度差を利用して、両
者を分離する方法などにおいても、多ｈ１の副生物の影
響のため純度の高い２，６−ナフタレンジスルホン酸ソ
ーダおよび２．７−ナフタレンジスルホン酸ソーダをそ
れぞれｒｒＬＩ！！することが困難であるなどの問題点
もあった。At the same time, in the separation and purification process of 2.6-naphthalenedisulfonic acid and 2.7-naphthalenedisulfonic acid from the reaction product mixture, for example, the difference in solubility of the sodium salts of these two naphthalenedisulfonic acids is used to separate them. Due to the influence of multi-H1 by-products, highly pure sodium 2,6-naphthalenedisulfonate and sodium 2,7-naphthalenedisulfonic acid are used as rrLI! ! There were also problems such as the difficulty of doing so.
〈発明の目的〉
本発明の目的は上記した従来技術の問題点を解消し、目
的とする２、６−ナフタレンジスルホン酸および２，７
−ナフタレンジスルホン酸以外の副生物の生成を抑制し
、２．６−ナフタレンジスルホン酸および２．７−ナフ
タレンジスルホン酸を高収率で選択的に得ることのでき
る２、６−ナフタレンジスルホン酸および２，７−ナフ
タレンジスルホン酸の製造方法を提供することにある。<Objective of the invention> The object of the present invention is to solve the problems of the prior art described above, and to obtain the target 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid.
- 2,6-naphthalenedisulfonic acid and 2,6-naphthalenedisulfonic acid that can suppress the production of by-products other than naphthalenedisulfonic acid and selectively obtain 2.6-naphthalenedisulfonic acid and 2.7-naphthalenedisulfonic acid in high yields. , 7-naphthalenedisulfonic acid.
〈発明の構成〉
本発明によれば、２−ナフタレンスルホン酸をスルホン
化剤でスルホン化し、２．トナフタレンジスルホン酸お
よび２，７−ナフタレンジスルホン酸を製造するにあた
り、２−ナフタレンスルホン酸に対して、スルホン化剤
を１．５モル倍以上、４モル倍未満使用し、１６０〜２
１０℃の温度でスルホン化を行なうことを特徴とする２
、６−ナフタレンジスルホン酸及び２，７−ナフタレン
ジスルホン酸の製造方法が提供される。<Configuration of the Invention> According to the present invention, 2-naphthalenesulfonic acid is sulfonated with a sulfonating agent, and 2. In producing tonaphthalene disulfonic acid and 2,7-naphthalene disulfonic acid, the sulfonating agent is used at least 1.5 times and less than 4 times by mole relative to 2-naphthalenesulfonic acid, and
2, characterized in that the sulfonation is carried out at a temperature of 10°C.
, 6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid are provided.
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.
本発明において、原料となる２−ナフタレンスルホン酸
は一般的には三水和物の結晶体が安定であるが、原料と
して用いる場合は無水物、水和物のいずれでもよい。In the present invention, 2-naphthalenesulfonic acid, which is a raw material, is generally stable as a trihydrate crystal, but when used as a raw material, it may be either an anhydride or a hydrate.
本発明に用いられるスルホン化剤は２−ナフタレンスル
ホン酸をスルホン化できるものなら何でもよいが、例え
ば硫酸、発煙硫酸等があげられる。The sulfonating agent used in the present invention may be any agent as long as it can sulfonate 2-naphthalenesulfonic acid, and examples thereof include sulfuric acid, fuming sulfuric acid, and the like.
本発明において、スルホン化反応は、前記２−ナフタレ
ンスルホン酸に対して １．５モル倍以上、４モル倍未
満の前記スルホン化剤を作用させ、１６０〜２１０℃の
温度で行なうのが好ましい。In the present invention, the sulfonation reaction is preferably carried out at a temperature of 160 to 210° C. by allowing the sulfonating agent to act on the 2-naphthalenesulfonic acid in an amount of 1.5 times or more and less than 4 times by mole.
この理由は前記２−ナフタレンスルホン酸に対する前記
スルホン化剤の使用晴を１．５モル倍未満にすると未反
応の２−ナフタレンスルホン酸が増加し、逆に４モル倍
以上にするとナフタレントリスルホン酸及びジナフチル
スルホンのスルホン酸等の高度にスルホン化されたスル
ホン酸類の副生か多くなるためである。The reason for this is that if the amount of the sulfonating agent used is less than 1.5 times the amount of 2-naphthalenesulfonic acid by mole, the amount of unreacted 2-naphthalenesulfonic acid increases; This is because the amount of by-products of highly sulfonated sulfonic acids such as the sulfonic acid of dinaphthylsulfone increases.
また、本発明において航述のようにスルホン化反応の好
適な反応温度を１６０〜２１０℃とする理由は＋ｉ？ｒ
記反応温度を１６０℃未満に設定した場合は、１．６−
ナフタレンジスルホン酸およびｌ、７−ナフタレンジス
ルホン酸の生成が増加し、また２１０℃超に設定した場
゛合は、高度にスルホン化されたスルホン酸類の副生が
増大する。Also, what is the reason why the preferred reaction temperature for the sulfonation reaction is 160 to 210°C as described above in the present invention? r
When the reaction temperature is set below 160℃, 1.6-
The production of naphthalenedisulfonic acid and 1,7-naphthalenedisulfonic acid increases, and if the temperature is set above 210°C, the by-product of highly sulfonated sulfonic acids increases.
本発明においてスルホン化反応の反応時間はスルホン化
条件により種々の時間を選択できるが、例えば一般には
０．１〜１００時間を選択することができる。In the present invention, various reaction times can be selected for the sulfonation reaction depending on the sulfonation conditions, and for example, 0.1 to 100 hours can generally be selected.
〈実施例〉 本発明を実施例について、具体的に説明する。<Example> The present invention will be specifically described with reference to Examples.
原料として２−ナフタレンスルホン酸三水和物またはナ
フタレンとスルホン化剤として９７％硫酸または６０％
発煙硫酸とを用いて、２−ナフタレンスルホン酸とスル
ホン化剤中のｌｌ２ＳＯ，のモル比、反応温度、反応時
間を袖々変化させて、スルホン化反応を行った。2-naphthalenesulfonic acid trihydrate or naphthalene as raw material and 97% sulfuric acid or 60% as sulfonating agent
A sulfonation reaction was carried out using fuming sulfuric acid while varying the molar ratio of 2-naphthalenesulfonic acid and ll2SO in the sulfonating agent, reaction temperature, and reaction time.
（実施例１〜実施例５）
原料として２−ナフタレンスルホン酸三水和物およびス
ルホン化剤として９７％硫酸を用いた。(Examples 1 to 5) 2-naphthalenesulfonic acid trihydrate was used as a raw material and 97% sulfuric acid was used as a sulfonating agent.
（実施例６）
原料として２−ナフタレンスルホン酸三水和物およびス
ルホン化剤として６０％発煙硫酸を用いた。(Example 6) 2-naphthalenesulfonic acid trihydrate was used as a raw material and 60% fuming sulfuric acid was used as a sulfonating agent.
（比較例１．比較例２）
原料として２−ナフタレンスルホン酸三水和物およびス
ルホン化剤として９７％硫酸を用いているが、それぞわ
、小モル比かつ高温の場合および大モル比かつ低温の場
合である。(Comparative Example 1. Comparative Example 2) 2-naphthalenesulfonic acid trihydrate is used as a raw material and 97% sulfuric acid is used as a sulfonating agent. This is the case at low temperatures.
（比較例３）
原料としてナフタレンおよびスルホン化剤として９７％
硫酸を用いた場合である。(Comparative Example 3) Naphthalene as raw material and 97% as sulfonating agent
This is the case using sulfuric acid.
１ｉｔられた反応生成物を分析し、各生成物の用量百分
率および原料の２−ナフタレンスルホン酸に対する収率
およびナフタレン換算収率を求め、その結果を第１表に
示す。ここでナフタレン換算収率とは、ナフタレンに濃
硫酸を作用させて２−ナフタレンスルホン酸を製造する
際に得られる収率９３％の値を用いて、本発明の２．６
−ナフタレンジスルホン酸および２．７−ナフタレンジ
スルホン酸の収率を補正した値である。The reaction products obtained were analyzed to determine the dosage percentage of each product, the yield relative to the raw material 2-naphthalenesulfonic acid, and the yield in terms of naphthalene. The results are shown in Table 1. Here, the yield in terms of naphthalene refers to the yield of 93% obtained when 2-naphthalene sulfonic acid is produced by reacting concentrated sulfuric acid with naphthalene.
- This is a value corrected for the yield of naphthalenedisulfonic acid and 2.7-naphthalenedisulfonic acid.
第１表から明らかなように、得られた反応生成物中には
実施例１ないし実施例６のいずれの場合も、２．６−ナ
フタレンジスルホン酸が約１０〜２０ｗＬ％（収率２１
〜３２％）かつ２，７−ナフタレンジスルホン酸が１８
〜４４ｗＬ％（収率４１〜５８％）含まれていた。As is clear from Table 1, in each of Examples 1 to 6, 2,6-naphthalenedisulfonic acid was present in the reaction products of about 10 to 20 wL% (yield: 21%).
~32%) and 2,7-naphthalenedisulfonic acid is 18
It contained ~44 wL% (yield 41-58%).
これに対し、比較例１および比較例２では、得られた反
応生成物中に２．６−ナフタレンジスルホン酸が７〜１
５ｗＬ％（収率１６〜１８％）および２．７−ナフタレ
ンジスルホン酸が１４〜２７胃Ｌ％（収率２９〜３２％
）しか含まれていなかった。On the other hand, in Comparative Example 1 and Comparative Example 2, 2,6-naphthalenedisulfonic acid was present in the obtained reaction product at 7 to 1
5 wL% (16-18% yield) and 14-27 wL% (29-32% yield) of 2,7-naphthalenedisulfonic acid.
) were included.
また比較例３では、得られた反応生成物中に２．６−ナ
フタレンジスルホン酸８．４ｗＬ％（収率１５．１％）
、２．７−ナフタレンジスルホン酸１９．９ｗＬ％（収
率３５．６％）しか含まれていなかった。Furthermore, in Comparative Example 3, 8.4 wL% (yield 15.1%) of 2.6-naphthalenedisulfonic acid was present in the obtained reaction product.
, 2.7-naphthalenedisulfonic acid contained only 19.9 wL% (yield 35.6%).
以上より、本発明の実施例はいずれも、比較例に比べて
２．６−ナフタレンジスルホン酸および２，７−ナフタ
レンジスルホン酸の収率の著しい向上が認められる。ま
た、得られた反応生成物中に副生物の生成の減少が認め
られる。さらに、未反応ｌＩ２ＳＯ４の！１ｔも０．５
〜３モルにまで相対的に低減させることができ、廃酸処
理に要する負担を軽減させる効果が１！ｌられる。From the above, it can be seen that in all of the Examples of the present invention, the yields of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid were significantly improved compared to the comparative examples. Furthermore, a reduction in the formation of by-products in the obtained reaction product was observed. Furthermore, unreacted lI2SO4! 1 ton is also 0.5
It can be relatively reduced to ~3 moles, and the effect of reducing the burden required for waste acid treatment is 1! I will be beaten.
〈発明の効果〉
本発明によれば、２．６−ナフタレンジスルホン酸およ
び２．７−ナフタレンジスルホン酸を高収率で得て、副
生物の生成を抑制することができた。それゆえ、反応生
成物中より、２，６−ナフタレンジスルホン酸と２．７
−ナフタレンジスルホン酸を分離精製することか容易に
なり、高純度の２．６−ナフタレンジスルホン酸および
２．７−ナフタレンジスルホン酸を得ることができる。<Effects of the Invention> According to the present invention, 2.6-naphthalenedisulfonic acid and 2.7-naphthalenedisulfonic acid could be obtained in high yield, and the generation of by-products could be suppressed. Therefore, from the reaction product, 2,6-naphthalenedisulfonic acid and 2.7
- It becomes easy to separate and purify naphthalenedisulfonic acid, and highly pure 2.6-naphthalenedisulfonic acid and 2.7-naphthalenedisulfonic acid can be obtained.
それとともに、従来原料１モルに対して２〜４モル残存
していた未反応硫酸を０．５〜３モルにまで相対的に低
減させることかてさ、廃酸処理に要するｆ＋担を軽減さ
せる効果も得られる。At the same time, by relatively reducing unreacted sulfuric acid, which conventionally remained 2 to 4 moles per mole of raw materials, to 0.5 to 3 moles, the F+ carrier required for waste acid treatment is reduced. Effects can also be obtained.
Claims (1)
ホン化し、２，６−ナフタレンジスルホン酸および２，
７−ナフタレンジスルホン酸を製造するにあたり、２−
ナフタレンスルホン酸に対して、スルホン化剤を１．５
モル倍以上、４モル倍未満使用し、１６０〜２１０℃の
温度でスルホン化を行なうことを特徴とする２，６−ナ
フタレンジスルホン酸および２，７−ナフタレンジスル
ホン酸の製造方法。(1) 2-naphthalenesulfonic acid is sulfonated with a sulfonating agent, and 2,6-naphthalenedisulfonic acid and 2,
In producing 7-naphthalenedisulfonic acid, 2-
1.5 sulfonating agent for naphthalene sulfonic acid
A method for producing 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid, characterized in that 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid are used in a molar amount or more and less than 4 times mole, and the sulfonation is carried out at a temperature of 160 to 210°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20282986A JPS6360962A (en) | 1986-08-29 | 1986-08-29 | Production of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20282986A JPS6360962A (en) | 1986-08-29 | 1986-08-29 | Production of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6360962A true JPS6360962A (en) | 1988-03-17 |
Family
ID=16463879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20282986A Pending JPS6360962A (en) | 1986-08-29 | 1986-08-29 | Production of 2,6-naphthalenedisulfonic acid and 2,7-naphthalenedisulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6360962A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993060A (en) * | 2012-07-30 | 2013-03-27 | 枣庄市泰瑞精细化工有限公司 | Preparation method of 1,6-naphthalenedisulfonic acid disodium salt |
-
1986
- 1986-08-29 JP JP20282986A patent/JPS6360962A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993060A (en) * | 2012-07-30 | 2013-03-27 | 枣庄市泰瑞精细化工有限公司 | Preparation method of 1,6-naphthalenedisulfonic acid disodium salt |
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