JPH03236333A - Production of chlorinated saturated hydrocarbon - Google Patents
Production of chlorinated saturated hydrocarbonInfo
- Publication number
- JPH03236333A JPH03236333A JP2029638A JP2963890A JPH03236333A JP H03236333 A JPH03236333 A JP H03236333A JP 2029638 A JP2029638 A JP 2029638A JP 2963890 A JP2963890 A JP 2963890A JP H03236333 A JPH03236333 A JP H03236333A
- Authority
- JP
- Japan
- Prior art keywords
- chlorine
- reaction
- chlorine dioxide
- saturated hydrocarbon
- saturated hydrocarbons
- 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
- 229930195734 saturated hydrocarbon Natural products 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000004155 Chlorine dioxide Substances 0.000 claims abstract description 14
- 235000019398 chlorine dioxide Nutrition 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 20
- 239000000460 chlorine Substances 0.000 abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 15
- 238000005660 chlorination reaction Methods 0.000 abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 abstract description 15
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004880 explosion Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- -1 Specifically Natural products 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910001902 chlorine oxide Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XGIAHMUOCFHQTI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.CC Chemical compound Cl.Cl.Cl.Cl.CC XGIAHMUOCFHQTI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MAYPHUUCLRDEAZ-UHFFFAOYSA-N chlorine peroxide Chemical compound ClOOCl MAYPHUUCLRDEAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
イ）発明の目的
［産業上の利用分野］
本発明は、塩素化飽和炭化水素の製造方法に関するもの
であり、更に詳しくは新規な置換塩素化触媒を用いた塩
素化飽和炭化水素の製造方法を提供するところにある。Detailed Description of the Invention A) Purpose of the Invention [Field of Industrial Application] The present invention relates to a method for producing chlorinated saturated hydrocarbons, and more specifically to a method for producing chlorinated saturated hydrocarbons using a novel substituted chlorination catalyst. The present invention provides a method for producing saturated hydrocarbons.
従来、置換塩素化による塩素化飽和炭化水素の製造方法
において、置換塩素化触媒としては、光、アゾビスニト
リル類、有機過酸化物、ヨード等の７１Ｊ−ラジカル形
成性触媒等のラジカル開始剤、エチレン、塩化ビニルモ
ノマーまたはプロピレン等のごとき不飽和炭化水素また
はその一塩化物等が知られている。Conventionally, in the method for producing chlorinated saturated hydrocarbons by substitutional chlorination, substitutional chlorination catalysts include light, azobisnitriles, organic peroxides, radical initiators such as 71J-radical-forming catalysts such as iodine, Unsaturated hydrocarbons such as ethylene, vinyl chloride monomer, propylene, and their monochlorides are known.
しかしながら、従来の置換塩素化触媒では、置換塩素化
の反応速度が遅く、原料塩素の塩素転化率が低い等の点
に問題点があった。However, conventional substitutional chlorination catalysts have problems in that the reaction rate of substitutional chlorination is slow and the chlorine conversion rate of raw chlorine is low.
〔発明が解決しようとする課題］
本発明者らは置換塩素化飽和炭化水素を高い置換塩素化
率で、簡単でかつ有利に製造する方法につき鋭意研究し
た結果、本発明を完成した。[Problems to be Solved by the Invention] The present inventors have completed the present invention as a result of intensive research into a simple and advantageous method for producing substituted chlorinated saturated hydrocarbons at a high substitutional chlorination rate.
口）発明の構成
〔課題を解決するための手段］
本発明は塩素で置換された又は非置換の飽和炭化水素（
以下単に飽和炭化水素類と総称する）を置換塩素化する
に際し、触媒として二酸化塩素を用いる事を特徴とする
塩素化飽和炭化水素の製造方法である。[Explanation] Structure of the invention [Means for solving the problem] The present invention relates to a chlorine-substituted or unsubstituted saturated hydrocarbon (
This method for producing chlorinated saturated hydrocarbons is characterized in that chlorine dioxide is used as a catalyst in substituting chlorination of saturated hydrocarbons (hereinafter simply referred to as saturated hydrocarbons).
本発明の飽和炭化水素類としては、好ましくは炭素数１
〜４の飽和炭化水素または塩素化飽和炭化水素であり、
具体的にはエタン、メタン、プロパン、ブタン等の飽和
炭化水素、１．２−ジクロロエタン、１．１．１−トリ
クロロエタン、テトラクロロエタンまたはペンタクロロ
エタン等の塩素化飽和炭化水素が挙げられ、特に好まし
い飽和炭化水素類としては、炭素数２の塩素化飽和炭化
水素、例えば１．１．２−トリクロロエタン等が挙げら
れる。The saturated hydrocarbons of the present invention preferably have a carbon number of 1
~4 saturated hydrocarbon or chlorinated saturated hydrocarbon,
Specifically, saturated hydrocarbons such as ethane, methane, propane, and butane, and chlorinated saturated hydrocarbons such as 1.2-dichloroethane, 1.1.1-trichloroethane, tetrachloroethane, and pentachloroethane are mentioned, and saturated hydrocarbons are particularly preferred. Examples of hydrocarbons include chlorinated saturated hydrocarbons having 2 carbon atoms, such as 1.1.2-trichloroethane.
反応系への飽和炭化水素類と塩素の供給割合は、目的と
する塩素化飽和炭化水素を得るために通常採用される割
合でよいが、塩素転化率を更に高めるため、また高次塩
化物の抑制のために、飽和炭化水素類を過剰に供給して
も差し支えない。The ratio of saturated hydrocarbons and chlorine to the reaction system may be the ratio normally adopted to obtain the desired chlorinated saturated hydrocarbon, but in order to further increase the chlorine conversion rate, For suppression, it is acceptable to supply an excess of saturated hydrocarbons.
塩素化剤としては塩素ガスが最適である。Chlorine gas is most suitable as the chlorinating agent.
本発明における置換塩素化触媒である二酸化塩素は、用
いる形態を特定されるものではないが、取扱い易さの点
から気体で用いるのが好ましい。Although the form used for chlorine dioxide, which is the substitutional chlorination catalyst in the present invention, is not specified, it is preferably used in gaseous form from the viewpoint of ease of handling.
二酸化塩素の反応系への供給割合は、塩素を基準として
、二酸化塩素のモル比が０．００１〜０゜０５が好まし
い。二酸化塩素のモル比が０．００１未満では置換塩素
化触媒としての効果が乏しく、また０、０５を超えると
塩素転化率が低下する恐れがあり好ましくない。Regarding the supply ratio of chlorine dioxide to the reaction system, the molar ratio of chlorine dioxide to chlorine is preferably 0.001 to 0.05. If the molar ratio of chlorine dioxide is less than 0.001, the effect as a substitutional chlorination catalyst is poor, and if it exceeds 0.05, the chlorine conversion rate may decrease, which is not preferable.
反応系に供給する二酸化塩素は、濃硫酸で充分に脱水し
たものを用いるのがよく、防爆の為に反応系に窒素等の
不活性ガスを存在させても差し支えない。また反応系へ
の供給は、単独で供給してもよいが、原料塩素に随伴さ
せて供給するのが好ましい。The chlorine dioxide supplied to the reaction system is preferably one that has been sufficiently dehydrated with concentrated sulfuric acid, and an inert gas such as nitrogen may be present in the reaction system for explosion protection. Further, although it may be supplied alone to the reaction system, it is preferable to supply it together with the raw material chlorine.
本発明において塩素化反応は、前記の如く飽和炭化水素
類に塩素および二酸化塩素を接触させて行えばよい。反
応温度は３０°Ｃ〜１００ ’Ｃが好ましく、温度制御
が行い易いという観点から、液相反応が好ましい。反応
圧力は常圧〜６．７ ／ｃｍ”・Ｇが好ましい。In the present invention, the chlorination reaction may be carried out by bringing chlorine and chlorine dioxide into contact with saturated hydrocarbons as described above. The reaction temperature is preferably 30°C to 100'C, and a liquid phase reaction is preferred from the viewpoint of ease of temperature control. The reaction pressure is preferably normal pressure to 6.7/cm".G.
本発明方法は塩素化飽和炭化水素、特に炭素数１〜４の
飽和炭化水素類の高次塩化物の製法として、具体例とし
ては四塩化エタン、五塩化エタンの製法として好適であ
る。The method of the present invention is suitable as a method for producing higher chlorides of chlorinated saturated hydrocarbons, particularly saturated hydrocarbons having 1 to 4 carbon atoms, and specific examples are suitable for producing ethane tetrachloride and ethane pentachloride.
本発明におてるその他の塩素化反応条件については、通
常の塩素化反応における諸条件に従えばよい。Regarding other chlorination reaction conditions in the present invention, conditions for ordinary chlorination reactions may be followed.
〔実施例および比較例］
以下本発明を、実施例および比較例によって更に詳細に
説明する。[Examples and Comparative Examples] The present invention will be explained in more detail below using Examples and Comparative Examples.
実施例１〜２及び比較例
直径２８ｍｍ、高さ５００ｍｍのグラス製チューフに直
径５１のグラス球を３５０ｍｍ充填した反応器を用い、
塔頂から純度９９．８％の１．１．２トリクロロエタン
約３． ４１／ｈｒ （３６，５モル／ｈｒ）を供給し
、また濃硫酸により充分脱水後の酸化塩素ガス（実施例
１〜２）またはエチレン（比較例）を各第１表記載の割
合で含有させた塩素を、窒素で希釈して塔底から第１表
記載の割合で供給し、窒素雰囲気下で、鉄および酸素が
存在せず、かつ遮光した状態で５時間にわたり連続向流
接触状態で反応させた。反応圧力は０．０２ｋｇ／ｃ１
・Ｇ、反応温度は第１表に記載の通りであり、反応生成
物は反応器塔底より冷却管に導き取得し、また未反応塩
素は塔底の塩素吸収液に吸収させた。Examples 1 to 2 and Comparative Examples Using a reactor in which a glass tube with a diameter of 28 mm and a height of 500 mm was filled with 350 mm of glass spheres with a diameter of 51 mm,
Approximately 3.1.2 trichloroethane with a purity of 99.8% was collected from the top of the column. 41/hr (36.5 mol/hr), and also contained chlorine oxide gas (Examples 1 to 2) or ethylene (Comparative Example) after sufficient dehydration with concentrated sulfuric acid in the proportions listed in Table 1. The chlorine diluted with nitrogen was supplied from the bottom of the tower at the rate shown in Table 1, and the reaction was carried out in a continuous countercurrent contact state for 5 hours under a nitrogen atmosphere in the absence of iron and oxygen and in the absence of light. I let it happen. Reaction pressure is 0.02kg/c1
-G, the reaction temperature was as shown in Table 1, the reaction product was introduced from the bottom of the reactor into a cooling pipe and was obtained, and unreacted chlorine was absorbed into the chlorine absorption liquid at the bottom of the tower.
取得した反応液は、反応生成物である１、１゜１２−テ
トラクロロエタン、１．１．２．２テトラクロロエタン
および１．１．１．２．２ペンタクロロエタンと未反応
１，１．．２−）ジクロロエタンの混合物であり、二酸
化塩素が有効な置換塩素化触媒であることが確認された
。また、下式により塩素転化率を求めた結果を第１表に
示す。The obtained reaction solution contains the reaction products 1,1.12-tetrachloroethane, 1.1.2.2 tetrachloroethane and 1.1.1.2.2 pentachloroethane and unreacted 1,1. ．． 2-) dichloroethane, and chlorine dioxide was confirmed to be an effective displacement chlorination catalyst. Further, Table 1 shows the results of determining the chlorine conversion rate using the following formula.
第１表
ハ）発明の効果
本発明は、塩素で置換された又は非置換の飽和炭化水素
を、新規な触媒である二酸化塩素を用いる事により、高
い塩素化率で置換塩素化することを可能とし、塩素化飽
和炭化水素を工業的に効率よく製造する事ができる。Table 1 c) Effect of the invention The present invention makes it possible to substitutively chlorinate saturated hydrocarbons substituted or unsubstituted with chlorine at a high chlorination rate by using a new catalyst, chlorine dioxide. As a result, chlorinated saturated hydrocarbons can be produced industrially and efficiently.
Claims (1)
塩素化するに際し、触媒として二酸化塩素を用いる事を
特徴とする塩素化飽和炭化水素の製造方法。1. A method for producing chlorinated saturated hydrocarbons, which comprises using chlorine dioxide as a catalyst in substituting chlorine-substituted or unsubstituted saturated hydrocarbons.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2029638A JPH03236333A (en) | 1990-02-13 | 1990-02-13 | Production of chlorinated saturated hydrocarbon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2029638A JPH03236333A (en) | 1990-02-13 | 1990-02-13 | Production of chlorinated saturated hydrocarbon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03236333A true JPH03236333A (en) | 1991-10-22 |
Family
ID=12281626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2029638A Pending JPH03236333A (en) | 1990-02-13 | 1990-02-13 | Production of chlorinated saturated hydrocarbon |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03236333A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022186162A1 (en) * | 2021-03-03 | 2022-09-09 | 国立大学法人大阪大学 | Method for producing nucleophilic reaction product and reagent for production of nucleophilic reaction product |
-
1990
- 1990-02-13 JP JP2029638A patent/JPH03236333A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022186162A1 (en) * | 2021-03-03 | 2022-09-09 | 国立大学法人大阪大学 | Method for producing nucleophilic reaction product and reagent for production of nucleophilic reaction product |
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