JPS6377855A - Production of chlorosulfonyl isocyanate - Google Patents
Production of chlorosulfonyl isocyanateInfo
- Publication number
- JPS6377855A JPS6377855A JP21941286A JP21941286A JPS6377855A JP S6377855 A JPS6377855 A JP S6377855A JP 21941286 A JP21941286 A JP 21941286A JP 21941286 A JP21941286 A JP 21941286A JP S6377855 A JPS6377855 A JP S6377855A
- Authority
- JP
- Japan
- Prior art keywords
- cyanogen chloride
- chlorosulfonyl isocyanate
- reaction
- liquid
- sulfuric anhydride
- 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.)
- Granted
Links
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- DQRLCTAGMVGVFH-UHFFFAOYSA-N cyanide;hydrochloride Chemical compound Cl.N#[C-] DQRLCTAGMVGVFH-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 14
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IPEUAGNKJVVHEH-UHFFFAOYSA-N 2,6-dichloro-1,4,3,5-oxathiadiazine 4,4-dioxide Chemical compound ClC1=NS(=O)(=O)N=C(Cl)O1 IPEUAGNKJVVHEH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 aromatic sulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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、クロロスルホニルイソシアネートの製造方法
に関するものでおる。詳しく述べると、高純度のクロロ
スルホニルイソシアネートを高収率で製造する方法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing chlorosulfonyl isocyanate. Specifically, the present invention relates to a method for producing highly purified chlorosulfonyl isocyanate in high yield.
クロロスルホニルイソシアネートは、Ｎ−カルボニルス
ルファモイルクロライドとも称され、化学式０＝Ｃ＝Ｎ
ＳＯ２ＣＱで示され、医薬、農薬、甘味剤等を製造する
だめの中間原料や、合成繊維、合成樹脂等の改質剤とし
て有用な化合物でおる。Chlorosulfonyl isocyanate is also called N-carbonylsulfamoyl chloride and has the chemical formula 0=C=N
It is represented by SO2CQ and is a useful compound as an intermediate raw material for producing medicines, agricultural chemicals, sweeteners, etc., and as a modifier for synthetic fibers, synthetic resins, etc.
（従来の技術）
クロロスルホニルイソシアネートは、無水（流酸と塩化
シアンとの反応により得られることは知られている［オ
ーガニック・シンセシス・コレクティブ（Ｏｒｇ、 ５
ｙｎｔｈ、 Ｃｏ１ｔ、 ）第５巻第２２６〜２３１頁
、アングヴアンテ・ヘミ−・インターナショナル・エデ
ィジョン（八ｎｇｃｗ、 Ｃｈｅ＋ｎ、 １ｎｔｅｒｎ
ａｔ、 Ｅｄｉ（、）第７巻第３号第１７２〜１７３頁
（１９６８年）、ヘミツシエ・ベリヒテ（Ｃｈｅｍ、
Ｂｅｒ、）第８９巻第１０７１〜１０７９頁（１９５６
年）、西独特許第９２８．８９６号（１９５５年）およ
び英国特許第７７４．２７６＠ （１９５７年）］。(Prior Art) Chlorosulfonyl isocyanate is known to be obtained by the reaction of anhydrous (fluid acid) with cyanogen chloride [Organic Synthesis Collective (Org, 5
ynth, Colt, ) Vol.
at, Edi (,) Vol. 7, No. 3, pp. 172-173 (1968), Chem.
Ber, ) Vol. 89, pp. 1071-1079 (1956
), West German Patent No. 928.896 (1955) and British Patent No. 774.276 @ (1957)].
しかしながら、これらの文献のうち前二名に記載されて
いる方法は、液体塩化シアン中へ一５°Ｃ以下の低温条
件下に無水硫酸を添加することによりスルホニルイソシ
アネートを”ｈＪＬする方法であり、無水硫酸に対して
１．５〜３倍モルの多量の液化塩化シアンを使用しなけ
ればならないので、経済的にかつ安全上も工業的生産に
適ざず、しかも単離収率も６０〜６２％程度と低く、ま
た得られる製品も品質が不充分である。However, the method described in the first two authors of these documents is a method of "hJL"ing sulfonylisocyanate by adding anhydrous sulfuric acid to liquid cyanogen chloride at a low temperature of 15°C or less. Since it is necessary to use a large amount of liquefied cyanogen chloride, which is 1.5 to 3 times the mole of sulfuric acid, it is not suitable for industrial production from an economic and safety standpoint, and the isolated yield is also 60 to 62%. The quality of the products obtained is also poor.
一方、後三者に記載されている方法は、無水硫酸と塩化
シアンとを１００°Ｃ以上、例えば１００〜２００℃の
温度条件下に混合することにより行なわれているが、こ
の方法では両者の流量の制御が困難でかつ反応条件によ
って副生物が多く、このため製品の品質が不充分であっ
た。On the other hand, the methods described in the latter three are carried out by mixing sulfuric anhydride and cyanogen chloride at a temperature of 100°C or higher, for example 100 to 200°C. It was difficult to control the flow rate, and depending on the reaction conditions, there were many by-products, which resulted in poor product quality.
高Ｎ！度のクロロスルホニルイソシアネートを得る方法
としては、無水Ｆｆｊｔ酸と塩化シアンとの反応により
得られる粗製クロロスルホニルイソシアネートをベンゾ
ニトリルまたはその誘導体で処理することにより精製す
る方法が知られている（米国特許第３．３７５．０８８
＠ ）。しかしながら、このような方法では、無水硫酸
と塩化シアンとの反応による反応工程と、粗製クロロス
ルホニルイソシアネートを精製する工程とを別々に設け
る必要があり、ざらにベンゾニトリル等の処理剤の回収
精製工程も必要であるので、工程が複雑であり、設備費
が高価となり、さらに操作工程に時間がかかり、かつ煩
雑であり、工業的な製法としては満足できるものではな
かった。High N! A known method for obtaining chlorosulfonyl isocyanate is to purify crude chlorosulfonyl isocyanate obtained by the reaction of Ffjt acid anhydride and cyanogen chloride by treating it with benzonitrile or its derivatives (U.S. Patent No. 3.375.088
@). However, in such a method, it is necessary to separately provide a reaction step for reacting anhydrous sulfuric acid with cyanogen chloride and a step for purifying crude chlorosulfonyl isocyanate. The process is complicated, equipment costs are high, and the operation process is time-consuming and complicated, making it unsatisfactory as an industrial manufacturing method.
（発明が解決しようとする問題点）
したがって、本発明の目的はクロロスルホニルイソシア
ネートの新規な製造方法を提供することにある。本発明
の他の目的は、無水Ｆａｎと塩化シアンとの反応により
高純度のクロロスルホニルイソシアネートを高収率で経
済的に製造する方法を提供するものである。(Problems to be Solved by the Invention) Therefore, an object of the present invention is to provide a novel method for producing chlorosulfonyl isocyanate. Another object of the present invention is to provide a method for economically producing high-purity chlorosulfonyl isocyanate in high yield by reacting anhydrous Fan with cyanogen chloride.
（問題点を解決するための手段）
これらの諸口的は、無水５Ａ酸と塩化シアンとを反応さ
せｔクロロスルホニルイソシアネートを製造する方法に
おいて、液体無水硫酸中へ塩化シアンを添加して反応を
行ない、該塩化シアン添加時の反応系の温度を２０〜５
０℃に保つことを特徴とするクロロスルホニルイソシア
ネートの製造方法により達成される。(Means for Solving the Problems) In a method for producing t-chlorosulfonyl isocyanate by reacting 5A acid anhydride with cyanogen chloride, the reaction is carried out by adding cyanogen chloride to liquid sulfuric anhydride. , the temperature of the reaction system when adding the cyanogen chloride was set at 20-5.
This is achieved by a method for producing chlorosulfonyl isocyanate characterized by maintaining the temperature at 0°C.
（作用） 以下、本発明方法をざらに詳細に説明する。(effect) The method of the present invention will be explained in detail below.
本発明において使用される無水Ｗｔ酸は、液状のもので
あればいずれも使用できるが、特にγ型が望ましい。ま
た無水硫酸の重合防止のために、少量、例えば０．００
０１〜５重量％、好ましくは０．００１〜１重最％の安
定剤を添加しであるものであってもさしつかえない。安
定剤としては、有機ケイ素、四塩化炭素、ジメチル硫酸
、ホウ素化合物、リン化合物、芳香族炭化水素、芳香族
スルホン酸等がある。Any liquid Wt acid can be used as the anhydrous Wt acid used in the present invention, but the γ type is particularly preferable. In addition, to prevent polymerization of sulfuric anhydride, a small amount, for example 0.00
A stabilizer may be added in an amount of 0.01 to 5% by weight, preferably 0.001 to 1% by weight. Stabilizers include organosilicon, carbon tetrachloride, dimethyl sulfate, boron compounds, phosphorus compounds, aromatic hydrocarbons, aromatic sulfonic acids, and the like.
本発明方法において使用される塩化シアンは、気体およ
び液体のいずれでもよいが、気体状態で使用することが
より望ましい。塩化シアンは、青酸と塩素とから工業的
に製造され得るもので、通常９６〜９９徂吊％のＩＴｉ
度を有しているが、９５重屯％以上の純度のものであっ
てもさしつかえない。塩化シアンの使用量は、無水硫酸
に対して０゜８〜１．３モル倍、好ましくは０．９〜１
．１モル倍でおる。すなわち、０．８モル倍未満および
１．３モル倍を越えるとクロロピロスルホニルイソシア
ネート、２．６−ジクロロ−１，４，３，５−オキザチ
アジアジン−４，４−ジオキシド等の副生成物の形成が
多くなり、収率および純度ともに低下する。The cyanogen chloride used in the method of the present invention may be either gaseous or liquid, but it is more desirable to use it in a gaseous state. Cyanogen chloride can be produced industrially from hydrocyanic acid and chlorine, and is usually 96-99% ITi.
It has a purity of 95% by weight or more. The amount of cyanogen chloride used is 0.8 to 1.3 times the mole of anhydrous sulfuric acid, preferably 0.9 to 1.
．． Dilute by 1 mole. In other words, if the amount is less than 0.8 mole times or more than 1.3 times by mole, secondary substances such as chloropyrosulfonylisocyanate, 2,6-dichloro-1,4,3,5-oxathiadiazine-4,4-dioxide, etc. More product is formed, reducing both yield and purity.
塩化シアンの液体無水硫１への添加方法は、例えば塩化
シアンが気体状態でおる場合には、ガス導入管をその反
応器底部付近に達するように液体無水硫酸中へ浸漬し、
該ガス導入管により液体無水硫酸中へ泡出させ、撹拌し
ながら気液接触を充分行なわせる。一方、塩化シアンが
液体状態である場合にも、前記のごとき導入管より液状
塩化シアンを導出させるかめるいは上部より滴下して撹
拌しながら液液接触を充分行なわせる。The method for adding cyanogen chloride to liquid anhydrous sulfur 1 is, for example, when cyanogen chloride is in a gaseous state, immersing the gas introduction pipe into liquid sulfuric anhydride so that it reaches near the bottom of the reactor.
The gas is bubbled into the liquid sulfuric anhydride through the gas introduction tube, and the gas is brought into sufficient contact with the liquid while stirring. On the other hand, even when the cyanogen chloride is in a liquid state, the liquid cyanide chloride is introduced dropwise from the upper part of the tank or the above-mentioned inlet tube, and the liquid is sufficiently brought into contact with the liquid while being stirred.
液体無水硫酸中への塩化シアンの添加時の反応系の温度
は２０〜５０℃１好ましくは２５〜４０°Ｃでおり、こ
の温度に保って反応を行なう。すなわち、２０℃未満お
よび５０℃を越えると、複生成物の形成が多くなり、収
率および純度ともに低下する。塩化シアンの添加時間は
、反応系内の温度により多少変動するが、０．５〜５時
間、特に１〜３時間が望ましい。すなわち、０．５時間
未満では転化が不充分で必り、一方、５時間を越えると
副生成物の形成が起こり好ましくないからである。The temperature of the reaction system when cyanogen chloride is added to liquid anhydrous sulfuric acid is 20 to 50°C, preferably 25 to 40°C, and the reaction is carried out while maintaining this temperature. That is, if the temperature is lower than 20°C or higher than 50°C, the formation of multiple products increases, resulting in a decrease in both yield and purity. The addition time of cyanogen chloride varies somewhat depending on the temperature within the reaction system, but is preferably 0.5 to 5 hours, particularly 1 to 3 hours. That is, if the reaction time is less than 0.5 hours, the conversion will necessarily be insufficient, while if it exceeds 5 hours, by-products will be formed, which is undesirable.
前記のごとき方法でｊｑられだクロロスルホニルイソシ
アネートは、必要によりさらに精製される。The chlorosulfonyl isocyanate obtained by the above method is further purified if necessary.
精製は、通常反応後の反応溶液を常圧下または減圧下に
通常の蒸留塔を用いて蒸留することにより行なうことが
できる。Purification can be carried out by distilling the reaction solution after the reaction using a conventional distillation column under normal pressure or reduced pressure.
（実施例） 以下、実施例を挙げて本発明をざらに詳細に説明する。(Example) EXAMPLES Hereinafter, the present invention will be roughly described in detail with reference to Examples.
実施例１
容ｆｉｌｔ２００ｄの四つロフラスコに、攪拌器、温度
計、還流管およびフラスコの底部にほぼとどく長さのガ
ラス管（内径６ｍｍ＞のガス導入管をとりつけた。この
四つロフラスコ内に、γ型の液体無水硫酸り商品名 自
費サルファン＞７９．５ｇを入れ、撹拌下に塩化シアン
ガス（６２，９ｑ相当）を２時間かけて導入した。その
間、反応系内の温度が２５〜３５°Ｃになるように、外
部浴を用いて調整した。その後２５〜３０℃で０．５時
間撹拌した。反応終了後、四つロフラスコの還流管およ
びガス導入管部をはずし、充てん物（Ｇｌａｓｓ ｈｅ
ｌｉｃｅｓ ）のはいった内径１．５ｃｍ、高さ１０ｃ
ｍの蒸留塔をとりつけ、常圧で蒸留し、沸点１０６〜１
０７°Ｃ／ ７６０ｍｍｔｌ＋の留分として１１９．１
Ｃｌ（８４，６％収率）のクロロスルホニルイソシアネ
ートを得た。Example 1 A four-loop flask with a filt size of 200 d was equipped with a stirrer, a thermometer, a reflux tube, and a glass tube (inner diameter 6 mm) long enough to reach the bottom of the flask.Inside the four-loop flask, 79.5g of γ-type liquid anhydrous sulfuric acid (trade name) was added, and cyanogen chloride gas (equivalent to 62.9q) was introduced over 2 hours with stirring.During this time, the temperature in the reaction system was 25-35°. C using an external bath.Then, it was stirred at 25 to 30°C for 0.5 hours.After the reaction was completed, the reflux tube and gas introduction tube of the four-bottle flask were removed, and the filling material (Glass he
inner diameter 1.5 cm, height 10 cm
Equipped with a distillation column of
07°C/ 119.1 as a fraction of 760mm tl+
Chlorosulfonyl isocyanate of Cl (84.6% yield) was obtained.
実施例２
実施例１と同じ装置を用い、フラスコ中にγ型液体無水
硫酸７９．５Ｑを入れ、撹拌下に塩化シアンガス６８．
ＯＣＩを１時間かけて導入した。その間、反応系内の温
度が２０〜４８°Ｃの範囲になるように外部浴を用いて
調整した。その後３０℃で１時間撹拌した後、実施例１
と同じ蒸留塔を用いて、圧力１００ｍｍＨｇで減圧蒸留
し、沸点５５〜５６℃／ １００ｍｍＨｇの留分として
１０４．２ｇ（７４％収率）のクロロスルホニルイソシ
アネートを得た。Example 2 Using the same equipment as in Example 1, 79.5Q of γ-type liquid sulfuric anhydride was placed in a flask, and 68.5Q of cyanogen chloride gas was added under stirring.
OCI was introduced over 1 hour. During this time, the temperature in the reaction system was adjusted to be in the range of 20 to 48°C using an external bath. After stirring at 30°C for 1 hour, Example 1
Using the same distillation column as above, vacuum distillation was performed at a pressure of 100 mmHg to obtain 104.2 g (74% yield) of chlorosulfonyl isocyanate as a fraction with a boiling point of 55-56°C/100 mmHg.
比較例１
容ｆｆ１２００ｍ１の四つロフラスコに、撹拌器、温度
計、還流管および滴下ロートをとりつけた。この四つロ
フラスコ内に液体塩化シアン６１．５ｇを入れ、Ｏ′Ｃ
に冷却し撹拌下に、滴下ロートから無水１ａ酸８０．１
ｇを、約１．５時間かけて添加した。その間、反応系内
の温度がＯ′Ｃ以下になるように、外部浴を用いて調整
した。添加終了後、反応系内の温度を２５〜３０℃で２
時間撹拌した。Comparative Example 1 A four-bottle flask with a volume of 1200 ml was equipped with a stirrer, a thermometer, a reflux tube, and a dropping funnel. Put 61.5 g of liquid cyanogen chloride into this four-bottle flask, and
80.1 of 1a acid anhydride from the dropping funnel while stirring.
g was added over about 1.5 hours. During this time, the temperature in the reaction system was adjusted to below O'C using an external bath. After the addition is complete, the temperature in the reaction system is kept at 25-30°C.
Stir for hours.
反応後、実施例１と同じ蒸留塔を用いて常圧蒸留し、沸
点１０４〜１０８°Ｃ／７６０ｍｍＨｇの留分として２
８．３ｇ（２０％収率）のクロロスルホニルイソシアネ
ートを得た。After the reaction, distillation was carried out at normal pressure using the same distillation column as in Example 1, and 2
8.3 g (20% yield) of chlorosulfonyl isocyanate was obtained.
比較例２
比較例１と同様に、液体塩化シアン６１．５ＣＩ中へ、
無水硫酸８０．１Ｃ］を添加し、添加後、反応系内の温
度を２５へ一３０℃で２時間撹拌した後、滴下ロートお
よび還流管をフラスコからはずし、フラスコの底部にほ
ぼとどく長さのガラス管（内径６ｍｍ＞のガス導入管を
、実施例１と同じ蒸留塔にとりつけた。Comparative Example 2 In the same manner as Comparative Example 1, into liquid cyanogen chloride 61.5CI,
80.1 C of anhydrous sulfuric acid] was added, and after the addition, the temperature in the reaction system was reduced to 25°C. After stirring at 30°C for 2 hours, the dropping funnel and reflux tube were removed from the flask, and a pipe of a length almost reaching the bottom of the flask was added. A glass tube (inner diameter 6 mm> gas introduction tube) was attached to the same distillation column as in Example 1.
反応混合物を１００〜１３０℃に加温し、撹拌下に塩化
シアンガス（約６０ｇ＞を１分間に約０１０１モルの速
度で吹きこみながら、蒸留塔の上部から流出する粗クロ
ロスルホニルイソシアネートを得た。フラスコ内の残留
物が５ｍｌ程度になったとき、塩化シアンガスの導入を
やめ、蒸留を中止した。粗生成物を実施例２と同じ蒸留
塔を用いて減圧蒸留し、沸点５２〜５６°Ｃ／ １００
ｍｍＨｇの留分として７７．９ｇ（５５％収率）のクロ
ロスルホニルイソシアネートを得た。The reaction mixture was heated to 100-130° C., and while stirring, cyanogen chloride gas (about 60 g) was blown into the reaction mixture at a rate of about 0.101 mol per minute to obtain crude chlorosulfonyl isocyanate flowing out from the top of the distillation column. When the residue in the flask reached about 5 ml, the introduction of cyanogen chloride gas was stopped and the distillation was stopped.The crude product was distilled under reduced pressure using the same distillation column as in Example 2, and the boiling point was 52-56°C/ 100
77.9 g (55% yield) of chlorosulfonyl isocyanate was obtained as a mmHg fraction.
（発明の効果）
以上述べたように、本発明は、無水硫酸と塩化シアンと
を反応させてクロロスルホニルイソシアネートを製造す
る方法において、液体無水′５Ａ酸中へ塩化シアンを添
加し、反応系の温度を２０〜５０°Ｃに保って反応を行
なうことを特徴とするクロロスルホニルイソシアネート
の製造方法であるから、従来法の問題点であったクロロ
スルホニルイソシアネートの低収率および副生成物に基
づく低純度という欠点を解消し、高純度のクロロスルホ
ニルイソシアネートを高収率で、しかも工業的に極めて
簡単な方法で得ることができるという利点がある。(Effects of the Invention) As described above, the present invention provides a method for producing chlorosulfonyl isocyanate by reacting sulfuric anhydride and cyanogen chloride, in which cyanogen chloride is added to liquid anhydrous '5A acid, and the reaction system is Since this method of producing chlorosulfonyl isocyanate is characterized by carrying out the reaction while maintaining the temperature at 20 to 50°C, the problem of the conventional method is low yield of chlorosulfonyl isocyanate and low yield due to by-products. It has the advantage of overcoming the drawback of purity and being able to obtain highly pure chlorosulfonyl isocyanate in high yield and in an industrially extremely simple manner.
特許出願人 協和ガス化学工業株式会社（ほか
１名）Patent applicant: Kyowa Gas Chemical Industry Co., Ltd. (and 1 other person)
Claims (1)
イソシアネートを製造する方法において、液体無水硫酸
中へ塩化シアンを添加し、反応系の温度を２０〜５０℃
に保って反応を行なうことを特徴とするクロロスルホニ
ルイソシアネートの製造方法。In a method for producing chlorosulfonyl isocyanate by reacting anhydrous sulfuric acid with cyanide chloride, cyanogen chloride is added to liquid anhydrous sulfuric acid, and the temperature of the reaction system is adjusted to 20 to 50°C.
1. A method for producing chlorosulfonyl isocyanate, characterized in that the reaction is carried out while maintaining the chlorosulfonyl isocyanate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21941286A JPH072709B2 (en) | 1986-09-19 | 1986-09-19 | Method for producing chlorosulfonyl isocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21941286A JPH072709B2 (en) | 1986-09-19 | 1986-09-19 | Method for producing chlorosulfonyl isocyanate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6377855A true JPS6377855A (en) | 1988-04-08 |
| JPH072709B2 JPH072709B2 (en) | 1995-01-18 |
Family
ID=16734996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21941286A Expired - Lifetime JPH072709B2 (en) | 1986-09-19 | 1986-09-19 | Method for producing chlorosulfonyl isocyanate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH072709B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118487A (en) * | 1990-09-11 | 1992-06-02 | Kuraray Co., Ltd. | Process for producing chlorosulfonyl isocyanate |
| JP2008031116A (en) * | 2006-07-31 | 2008-02-14 | Nippon Soda Co Ltd | Method for subjecting chlorosulfonyl isocyanate to decomposition treatment |
| US7468174B2 (en) | 2003-12-16 | 2008-12-23 | Nippon Soda Co., Ltd. | Method for producing chlorosulfonyl isocyanate |
-
1986
- 1986-09-19 JP JP21941286A patent/JPH072709B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118487A (en) * | 1990-09-11 | 1992-06-02 | Kuraray Co., Ltd. | Process for producing chlorosulfonyl isocyanate |
| US7468174B2 (en) | 2003-12-16 | 2008-12-23 | Nippon Soda Co., Ltd. | Method for producing chlorosulfonyl isocyanate |
| JP2008031116A (en) * | 2006-07-31 | 2008-02-14 | Nippon Soda Co Ltd | Method for subjecting chlorosulfonyl isocyanate to decomposition treatment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH072709B2 (en) | 1995-01-18 |
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