JPH0421658B2 - - Google Patents
Info
- Publication number
- JPH0421658B2 JPH0421658B2 JP58199840A JP19984083A JPH0421658B2 JP H0421658 B2 JPH0421658 B2 JP H0421658B2 JP 58199840 A JP58199840 A JP 58199840A JP 19984083 A JP19984083 A JP 19984083A JP H0421658 B2 JPH0421658 B2 JP H0421658B2
- Authority
- JP
- Japan
- Prior art keywords
- xylene
- tds
- reaction
- water
- reaction solution
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- 229940078552 o-xylene Drugs 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000001816 cooling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 3
- -1 tetramethyl diphenyl sulfone Chemical compound 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 2
- ZSIACQWHDVUCHB-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)sulfonyl-1,2-dimethylbenzene Chemical compound C1=C(C)C(C)=CC=C1S(=O)(=O)C1=CC=C(C)C(C)=C1 ZSIACQWHDVUCHB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- 239000000843 powder Substances 0.000 description 10
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
Description
【発明の詳細な説明】
本発明は、テトラメチルジフエニルスルホンの
製造方法に関し、さらに詳しくは、ｏ−キシレン
と硫酸とから高純度の３，3′，４，4′−テトラメ
チルジフエニルスルホン（以下、３，3′，４，
4′−TDSと略称する）を効率よく製造する方法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing tetramethyldiphenylsulfone, and more particularly, to a method for producing tetramethyldiphenylsulfone from o-xylene and sulfuric acid. (Hereinafter, 3, 3′, 4,
4′-TDS).
一般にテトラメチルジフエニルスルホンは、例
えばポリイミドの原料であるテトラカルボン酸の
中間体として有用な化合物であり、特に３，3′，
４，4′−TDSはその対称性がよいこと、さらにテ
トラカルボン酸とした場合に２無水物を形成する
こと等から最も重要なものとされている。 In general, tetramethyl diphenyl sulfone is a compound useful as an intermediate for tetracarboxylic acid, which is a raw material for polyimide, and in particular, 3,3',
4,4'-TDS is considered to be the most important because of its good symmetry and its ability to form a dianhydride when used as a tetracarboxylic acid.
従来、３，3′，４，4′−TDSの製造方法として
は、キシレン−スルホニルクロライトとｏ−キシ
レンとを、FeCl3の存在下に反応させる方法
（Izr.Vyssh.Ucheb.Zaved.，Khim.Khim.
Tekhnol，1969 12(11)、1583−93）、ｏ−キシレン
と硫酸とからキシレンスルホン酸を合成し、次い
でこのキシレンスルホン酸とｏ−キシレンとか
ら、P2O5等の存在下または不存在下に３，3′，
４，4′−TDSを製造する方法（米国特許第
3729517号）等が知られている
しかしながら、前者の方法は反応中で腐食性の
塩化水素が発生する等の欠点があり、一方、後者
の方法は、安価なｏ−キシレンと硫酸のみから
TDSが得られ、工業的に有利な方法であると考
えられているが、本発明者らの詳細な研究によれ
ば、この方法により得られる生成物は目的とする
３，3′，４，4′−TDS以外に10〜15％の異性体を
含んでいることが分かつた。 Conventionally, a method for producing 3,3',4,4'-TDS is a method in which xylene-sulfonyl chlorite and o-xylene are reacted in the presence of FeCl 3 (Izr.Vyssh.Ucheb.Zaved., Khim.Khim.
Tekhnol, 1969 12(11), 1583-93), synthesize xylene sulfonic acid from o-xylene and sulfuric acid, and then synthesize xylene sulfonic acid from this xylene sulfonic acid and o-xylene in the presence or absence of P 2 O 5 etc. 3, 3′ below,
Method for producing 4,4′-TDS (U.S. Patent No.
However, the former method has drawbacks such as the generation of corrosive hydrogen chloride during the reaction, while the latter method uses only inexpensive o-xylene and sulfuric acid.
TDS is obtained, and it is considered to be an industrially advantageous method.According to detailed research by the present inventors, the product obtained by this method is the target 3,3',4, It was found that it contained 10-15% of isomers other than 4'-TDS.
本発明の目的は、ｏ−キシレンと硫酸とから、
異性体の含有量が５％以下であり、純度95％以上
の３，3′，４，4′−TDSを得る方法を提供するこ
とにある。 The object of the present invention is to obtain from o-xylene and sulfuric acid,
The object of the present invention is to provide a method for obtaining 3,3',4,4'-TDS having an isomer content of 5% or less and a purity of 95% or more.
本発明者らは、異性体の含有量の少ない、高純
度の３，3′，４，4′−TDSを得る方法について鋭
意研究を重ねた結果、硫酸に対して過剰のｏ−キ
シレンを用いて縮合反応を行い、得られる反応液
を50℃以下に冷却した後、水を添加して、反応液
の温度を20℃以下にすることにより、高純度の
３，3′，４，4′−TDSを析出させて回収すること
ができることを見い出し、本発明に到達した。 As a result of extensive research into a method for obtaining highly pure 3,3',4,4'-TDS with a low content of isomers, the present inventors discovered that using an excess of o-xylene relative to sulfuric acid After cooling the resulting reaction solution to below 50°C, water is added to lower the temperature of the reaction solution to below 20°C, resulting in highly pure 3,3',4,4' - It has been discovered that TDS can be precipitated and recovered, and the present invention has been achieved.
本発明はｏ−キシレンと硫酸とからテトラメチ
ルジフエニルスルホンを製造するに際し、硫酸に
対して２〜８倍モルのｏ−キシレンを用い、生成
する水を除去しながら、130〜180℃で反応を行
い、得られる反応液を50℃以下に冷却した後、水
を添加して20℃以下とし、高純度の３，3′，４，
4′−テトラメチルジフエニルスルホンを析出させ
て回収することを特徴とする。 In the present invention, when producing tetramethyl diphenyl sulfone from o-xylene and sulfuric acid, o-xylene is used in a molar amount 2 to 8 times that of sulfuric acid, and the reaction is carried out at 130 to 180°C while removing the water produced. After cooling the resulting reaction solution to below 50°C, water was added to bring the temperature below 20°C, and high purity 3,3',4,
It is characterized by precipitating and recovering 4'-tetramethyldiphenyl sulfone.
本発明の原料であるｏ−キシレンは通常98％以
上の高純度品が好ましく、硫酸は90％以上の高濃
度のものが好ましい。 O-xylene, which is a raw material of the present invention, is preferably of high purity of 98% or more, and sulfuric acid is preferably of high concentration of 90% or more.
本発明方法を実施するには、ｏ−キシレンの全
部または一部と硫酸を反応器に仕込み、130〜180
℃の温度で、生成する水を除去しながら反応を行
なう。反応当初ｏ−キシレンの一部を添加する場
合には、反応中にｏ−キシレンの残部を滴下して
いく方法も有効である。 To carry out the method of the present invention, all or part of o-xylene and sulfuric acid are charged into a reactor, and the
The reaction is carried out at a temperature of °C while removing the water produced. When a part of o-xylene is added at the beginning of the reaction, it is also effective to drop the remainder of the o-xylene during the reaction.
ｏ−キシレンの使用量は硫酸に対して過剰の量
が好ましく、通常、硫酸に対して２〜８倍モル量
が好適である。ｏ−キシレンが２倍モル未満の場
合には、TDSの収率が低く、８倍モルを越える
場合には、反応速度が遅く不経済である。反応温
度が、130℃に達しない場合には、反応速度が遅
く、180℃を越える場合には、重合物等の副生物
が生成して不都合である。なお反応温度がｏ−キ
シレンの沸点（144℃）を越える場合には通常加
圧系で反応を行う。反応時間は反応温度によつて
も異なるが、通常２〜50時間である。 The amount of o-xylene used is preferably in excess of sulfuric acid, and usually 2 to 8 times the molar amount relative to sulfuric acid. When o-xylene is less than 2 times the mole, the yield of TDS is low, and when it exceeds 8 times the mole, the reaction rate is slow and uneconomical. When the reaction temperature does not reach 130°C, the reaction rate is slow, and when it exceeds 180°C, by-products such as polymers are produced, which is disadvantageous. Note that when the reaction temperature exceeds the boiling point of o-xylene (144°C), the reaction is usually carried out in a pressurized system. The reaction time varies depending on the reaction temperature, but is usually 2 to 50 hours.
また反応で生成する水を除去するには、ｏ−キ
シレンとの共沸によつて水を留出させ、この留出
液を冷却した後、相分離を行つて水を除去し、一
方、ｏ−キシレン相は反応器に戻す方法が好まし
く用いられる。 In addition, in order to remove water produced in the reaction, water is distilled out by azeotropy with o-xylene, and after cooling this distillate, phase separation is performed to remove water. - A method is preferably used in which the xylene phase is returned to the reactor.
なお、本反応では特に触媒を必要としないが、
反応速度を少しでも早めるために五酸化リン等の
触媒を添加してもよい。 Note that this reaction does not particularly require a catalyst, but
A catalyst such as phosphorus pentoxide may be added to speed up the reaction rate.
このようにして得られた反応液は、未反応のｏ
−キシレン、微量の硫酸、反応の中間体であるキ
シレンスルホン酸および生成物であるTDSから
成り、そのTDSの中には目的とする３，3′，４，
4′−TDS以外に通常10〜15％の異性体が含まれて
いる。この異性体の大部分は２，3′3，4′−TDS
である。このような異性体を除去するには、前記
の反応液を50℃以下、好ましくは30℃以下まで冷
却した後、さらに水を添加して反応液の温度を20
℃以下、好ましくは20〜５℃にし、よく撹拌し、
析出する粉末を濾過する。なお、水を添加して反
応液の温度を25℃以下にする方法として、20℃以
下の水あるいは氷を添加して、反応液の温度を20
℃以下にする方法や、20℃をこえた水を添加し
て、外部から冷却することによつて反応液の温度
を25℃以下にする方法等がある。水を添加後の反
応液の温度が20℃を越えると、析出、回収させる
３，3′，４，4′−TDSの量が少なくなる。さらに
必要に応じて再度、この濾過粉末を水洗、濾過し
た後、乾燥することにより高純度の３，3′，４，
4′−TDSの粉末を回収することができる。水洗、
濾過した濾液は、有機相と水相とに分かれ、有機
相からｏ−キシレンを留去することにより、異性
体を多く含むTDSが回収される。一方、水相か
ら水を留去することにより、キシレンスルホン酸
が回収されるが、このキシレンスルホン酸は反応
に再使用してTDSに転化することができる。 The reaction solution thus obtained contains unreacted o
- consists of xylene, a trace amount of sulfuric acid, the reaction intermediate xylene sulfonic acid, and the product TDS, which contains the target 3,3',4,
It usually contains 10-15% of isomers other than 4'-TDS. Most of this isomer is 2,3′3,4′-TDS
It is. To remove such isomers, the reaction solution is cooled to below 50°C, preferably below 30°C, and then water is added to bring the temperature of the reaction solution up to 20°C.
℃ or less, preferably 20 to 5℃, stir well,
Filter the precipitated powder. In addition, as a method of adding water to lower the temperature of the reaction solution to 25°C or lower, add water or ice at 20°C or lower to lower the temperature of the reaction solution to 20°C or lower.
There are two methods: one method is to reduce the temperature of the reaction solution to below 25°C, and the other is to cool the reaction solution from the outside by adding water above 20°C. If the temperature of the reaction solution after adding water exceeds 20°C, the amount of 3,3',4,4'-TDS to be precipitated and recovered will decrease. Furthermore, if necessary, this filtered powder is washed with water, filtered, and dried to obtain highly pure 3,3',4,
4′-TDS powder can be recovered. washing with water,
The filtered filtrate is separated into an organic phase and an aqueous phase, and TDS containing many isomers is recovered by distilling off o-xylene from the organic phase. On the other hand, xylene sulfonic acid is recovered by distilling off water from the aqueous phase, and this xylene sulfonic acid can be reused in the reaction and converted into TDS.
以上、本発明方法によれば、ｏ−キシレンと硫
酸とから極めて高収率で高純度の３，3′，４，
4′−TDSを製造することができる。 As described above, according to the method of the present invention, highly purified 3,3',4,
4'-TDS can be produced.
以下、本発明を実施例により具体的に説明する
が、本発明は下記実施例に制約されるものではな
い。 EXAMPLES Hereinafter, the present invention will be specifically explained with reference to examples, but the present invention is not limited to the following examples.
実施例
反応器にｏ−キシレン130ｇ（1.2モル）および
98％硫酸100ｇ（1.0モル）を仕込み、攪拌しなが
ら反応温度を還流温度まで上昇させ、生成する水
を留去しながら水をｏ−キシレンと共に共沸さ
せ、冷却後相分離させ、ｏ−キシレンのみ反応器
に戻しながら、４時間反応を行つた。その間反応
温度は徐々に上昇し、133℃から154℃となつた。Example 130 g (1.2 mol) of o-xylene and
100 g (1.0 mol) of 98% sulfuric acid was charged, the reaction temperature was raised to reflux temperature while stirring, and water was azeotroped with o-xylene while distilling off the water produced, and after cooling, the phases were separated to form o-xylene. The reaction was carried out for 4 hours while only the mixture was returned to the reactor. During this time, the reaction temperature gradually increased from 133°C to 154°C.
さらにｏ−キシレン330ｇ（3.1モル）を反応器
に加えると共に、反応器に窒素を導入して反応系
を１Kg／cm2・Ｇに昇圧し、反応温度を165℃に上
昇させて、生成する水を留去しながら12時間反応
を行つた。 Furthermore, 330 g (3.1 mol) of o-xylene was added to the reactor, nitrogen was introduced into the reactor to increase the pressure of the reaction system to 1 Kg/cm 2 ·G, and the reaction temperature was raised to 165°C. The reaction was carried out for 12 hours while distilling off.
この反応液中の生成TDSの３，3′，４，4′−
TDSと他の異性体との割合はガスクロマトグラ
フ分析を行つた結果、89：11であつた。 3,3',4,4'- of TDS produced in this reaction solution
As a result of gas chromatography analysis, the ratio of TDS to other isomers was 89:11.
次いでこの反応液を25℃まで冷却し、10℃の水
500ｇを加えて反応液の温度を約16℃にし、反応
液を充分に攪拌したのち、析出物を濾過し、さら
に水洗を行つた後乾燥してTDSの粉末66ｇを得
た。この粉末をテトラヒドロフランに溶解してガ
スクロマトグラフ分析を行つた結果３，3′，４，
4′−TDSと他の異性体との割合は、96.5：3.5とな
り、高純度の３，3′，４，4′−TDSが得られた。 The reaction solution was then cooled to 25°C and added to 10°C water.
After adding 500 g of the reaction solution to bring the temperature of the reaction solution to about 16° C. and thoroughly stirring the reaction solution, the precipitate was filtered, further washed with water, and then dried to obtain 66 g of TDS powder. The results of dissolving this powder in tetrahydrofuran and performing gas chromatographic analysis were 3, 3', 4,
The ratio of 4'-TDS to other isomers was 96.5:3.5, and highly pure 3,3',4,4'-TDS was obtained.
一方反応液を水洗し、析出物を濾過した濾液の
有機相から、ｏ−キシレンを留去して回収された
粉末（16ｇ）について、ガスクロマトグラフ分析
を行つた結果、３，3′，４，4′−TDSと他の異性
体との割合は、60：40であつた。さらに濾液の水
相から水を留去すると、キシレンスルホン酸130
ｇが回収された。 On the other hand, the reaction solution was washed with water and the precipitate was filtered. From the organic phase of the filtrate, o-xylene was distilled off and the recovered powder (16 g) was analyzed by gas chromatography. The ratio of 4'-TDS to other isomers was 60:40. Furthermore, when water is distilled off from the aqueous phase of the filtrate, xylene sulfonic acid 130
g was recovered.
比較例
実施例において、反応液を50℃まで冷却し、10
℃の水500ｇを加えて反応液の温度を25℃とした
以外は実施例と同様にしてTDSの粉末を得た。
得られたTDS粉末は36ｇであり、この収率は実
施例の55％であつた。Comparative Example In the example, the reaction solution was cooled to 50°C and
TDS powder was obtained in the same manner as in Example, except that 500 g of water at 0.degree. C. was added to bring the temperature of the reaction solution to 25.degree.
The amount of TDS powder obtained was 36 g, and the yield was 55% of that of the example.
この粉末をテトラヒドロフランに溶解してガス
クロマトグラフ分析を行つた結果、３，3′，４，
4′−TDSと他の異性体との割合は94.5：5.5であつ
た。 As a result of dissolving this powder in tetrahydrofuran and performing gas chromatographic analysis, it was found that 3,3',4,
The ratio of 4'-TDS to other isomers was 94.5:5.5.
一方、反応液を水洗し、析出物を濾過した濾液
の有機相からｏ−キシレンを留去して回収された
粉末46ｇについて、ガスクロマトグラフ分析を行
つた結果、３，3′，４，4′−TDSと他の異性体と
の割合は、85：15であつた。 On the other hand, gas chromatographic analysis was performed on 46 g of powder recovered by distilling off o-xylene from the organic phase of the filtrate, which was obtained by washing the reaction solution with water and filtering the precipitate. The ratio of -TDS to other isomers was 85:15.
Claims (1)
エニルスルホンを製造するに際し、硫酸に対して
２〜８倍モルのｏ−キシレンを用い、生成する水
を除去しながら、130〜180℃で反応を行い、得ら
れる反応液を50℃以下に冷却した後、水を添加し
て20℃以下とし、高純度の３，3′，４，4′−テト
ラメチルジフエニルスルホンを析出させて回収す
ることを特徴とするテトラメチルジフエニルスル
ホンの製造方法。1. When producing tetramethyl diphenyl sulfone from o-xylene and sulfuric acid, the reaction is carried out at 130 to 180°C using 2 to 8 times the mole of o-xylene to sulfuric acid and removing the water produced. After cooling the resulting reaction solution to 50°C or lower, water was added to lower the temperature to 20°C or lower to precipitate and recover high-purity 3,3',4,4'-tetramethyldiphenylsulfone. Characteristic method for producing tetramethyldiphenyl sulfone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19984083A JPS6092256A (en) | 1983-10-25 | 1983-10-25 | Preparation of tetramethyldiphenylsulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19984083A JPS6092256A (en) | 1983-10-25 | 1983-10-25 | Preparation of tetramethyldiphenylsulfone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6092256A JPS6092256A (en) | 1985-05-23 |
| JPH0421658B2 true JPH0421658B2 (en) | 1992-04-13 |
Family
ID=16414516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19984083A Granted JPS6092256A (en) | 1983-10-25 | 1983-10-25 | Preparation of tetramethyldiphenylsulfone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6092256A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3729517A (en) * | 1970-11-09 | 1973-04-24 | Cosden Oil & Chem Co | Synthesis of dialkaryl sulfone |
| JPS5214744A (en) * | 1975-07-22 | 1977-02-03 | Teijin Ltd | Process for preparation of dinitrodichlo rodiphenylsulfone |
-
1983
- 1983-10-25 JP JP19984083A patent/JPS6092256A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3729517A (en) * | 1970-11-09 | 1973-04-24 | Cosden Oil & Chem Co | Synthesis of dialkaryl sulfone |
| JPS5214744A (en) * | 1975-07-22 | 1977-02-03 | Teijin Ltd | Process for preparation of dinitrodichlo rodiphenylsulfone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6092256A (en) | 1985-05-23 |
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