JPH01272564A - Production of inner olefin sulfonate - Google Patents
Production of inner olefin sulfonateInfo
- Publication number
- JPH01272564A JPH01272564A JP9901988A JP9901988A JPH01272564A JP H01272564 A JPH01272564 A JP H01272564A JP 9901988 A JP9901988 A JP 9901988A JP 9901988 A JP9901988 A JP 9901988A JP H01272564 A JPH01272564 A JP H01272564A
- Authority
- JP
- Japan
- Prior art keywords
- hydrolysis
- olefin
- reaction product
- inner olefin
- sulfur trioxide
- 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 olefin sulfonate Chemical class 0.000 title claims description 6
- 150000001336 alkenes Chemical class 0.000 claims abstract description 34
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 19
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000007062 hydrolysis Effects 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 150000008053 sultones Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 3
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241001302210 Sida <water flea> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VSANMHWDSONVEE-UHFFFAOYSA-N carbyl sulfate Chemical compound O=S1(=O)CCOS(=O)(=O)O1 VSANMHWDSONVEE-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940095068 tetradecene Drugs 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、オレフィン系二重結合が長鎖分子の末端には
存在せず、内部にのみ存在しているいわゆるインナーオ
レフィンのスルホン化物の製法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention is a method for producing a sulfonated product of a so-called inner olefin in which an olefinic double bond does not exist at the end of a long chain molecule, but only in the inside. Regarding.
Ｄ、Ｗ、ロバーツ（Ｒｏｂｅｒｔｓ）等の報告（Ｔｅｎ
ｓｉｄａＤｅｔｅｒｇｅｎｔｓ ２２，１９８５．４
ｐ１９３）によれば、インナーオレフィンはスルホン化
されにくいものと認識されていた。そして、インナーオ
レフィンがスルホン化されにくいのは、スルホン化中間
体としてオレフィン１モルに対し、三酸化いおう２モル
が付加しカルビルサルフェートが生ずるためではないか
と考えられていた。Report by D. W. Roberts et al.
sida Detergents 22, 1985.4
According to p. 193), inner olefins were recognized as being difficult to be sulfonated. It was thought that the reason why inner olefins are difficult to be sulfonated is that 2 moles of sulfur trioxide is added to 1 mole of olefin as a sulfonation intermediate to form carbyl sulfate.
インナーオレフィンのスルホン化を効率よく進行させる
手段としては、オレフィンに対する三酸化いおうの比率
を高くすることが提案されているが、このような苛酷な
条件で反応を行うと、製品の色調が悪くなって市場性が
そこなわれる。Increasing the ratio of sulfur trioxide to olefin has been proposed as a means to efficiently progress the sulfonation of inner olefins, but if the reaction is carried out under such harsh conditions, the color tone of the product will deteriorate. Therefore, marketability is damaged.
そこで、色調をそこなわずにインナーオレフィンスルホ
ネートを製造するためには、オレフィンに対する三酸化
いおうのモル比を低く押える方法があるが、そうすると
反応生成物中に未反応オレフィンが多量に含まれる結果
となり、残存する未反応オレフィンの分離工程が必要で
あった（本出願人の特開昭５４−１４９１８号参照）。Therefore, in order to produce inner olefin sulfonate without damaging the color tone, there is a method of keeping the molar ratio of sulfur trioxide to olefin low, but this results in a large amount of unreacted olefin being included in the reaction product. , a step for separating the remaining unreacted olefin was required (see Japanese Patent Application Laid-open No. 14918/1983 by the present applicant).
そこで、本発明の目的は、色調が良好で、かつスルホネ
ートへの転換率が９０％以上になるようなインナーオレ
フィンスルホネートの製法を提供する点にある。Therefore, an object of the present invention is to provide a method for producing an inner olefin sulfonate that has a good color tone and a conversion rate of 90% or more to the sulfonate.
本発明は、インナーオレフィンスルホネートの製法であ
って、Ｃ８〜Ｃ１８の長鎖インナーオレフィン１モルに
対して三酸化いおうを反応させることにより得られたサ
ルトンを主成物とする反応生成物を、４０℃以下の温度
のアルカリ水溶液で第１次加水分解を行い、ついで９０
〜１８０℃の温度で第２次加水分解を行うことを特徴と
する２段階加水分解法によるインナーオレフィンスルホ
ネートの製法である。The present invention is a method for producing an inner olefin sulfonate, in which a reaction product containing sultone as a main component obtained by reacting sulfur trioxide with 1 mole of a C8 to C18 long-chain inner olefin is Primary hydrolysis is carried out in an alkaline aqueous solution at a temperature below 90°C.
This is a method for producing inner olefin sulfonate by a two-step hydrolysis method characterized by performing secondary hydrolysis at a temperature of ~180°C.
Ｃ８〜Ｃ１８の長鎖インナーオレフィンは出発原料中に
少くとも５０％以上含有されていることが好ましい。Ｃ
，〜Ｃ１８の長鎖インナーオレフィンの例としては、二
重結合が２〜７の位置にあるテトラデセン、二重結合が
２〜８の位置にあるヘキサデセン、二重結合が２〜９の
位置にあるオクタデセンなどをあげることができるが、
出発原料としては、これら長鎖インナーオレフィンの二
重結合の位置がいろいろの位置にあるインナーオレフィ
ンの混合物、さらには０８〜Ｃ１８の範囲の各種炭素数
をもつインナーオレフィンの混合物であっても差障りな
い。It is preferable that the C8 to C18 long-chain inner olefin is contained in the starting material in an amount of at least 50% or more. C
, ~C18 long chain inner olefins include tetradecene with double bonds in positions 2-7, hexadecene with double bonds in positions 2-8, and hexadecene with double bonds in positions 2-9. Octadecene etc. can be given, but
As starting materials, mixtures of inner olefins in which the double bonds of these long-chain inner olefins are located at various positions, and even mixtures of inner olefins having various carbon numbers in the range of 08 to C18 are acceptable. do not have.
サルトンの生成反応は通常２５〜４０℃においてインナ
ーオレフィンを膜状に流しつつ、ＳＯ３ガスを１〜２０
％Ｖ／Ｖで供給することによって実施することができる
。インナーオレフィンに対するＳＯｌのモル比としては
等モル程度が好ましい。The saltone production reaction is usually carried out at 25-40°C while flowing the inner olefin in a film form, and at 1-20°C of SO3 gas.
This can be done by supplying %V/V. The molar ratio of SOI to the inner olefin is preferably approximately equimolar.
このようにして得られた反応生成物は、β−サルトンが
５０〜９０％、アルケンスルホン酸７〜３０％、γ−サ
ルトン３〜２０％を含有する混合物である。The reaction product thus obtained is a mixture containing 50-90% β-sultone, 7-30% alkenesulfonic acid, and 3-20% γ-sultone.
本発明者等はこの混合物を加水分解するにあたり、加水
分解条件を適切に設定しないと、β−サルトンがオレフ
ィンとＮ ａ ２ Ｓ Ｏ４に分解してしまい、スルホ
ネートへの転換率が低下してしまうこと、およびγ−サ
ルトン等は熱的に安定で９０℃以上の温度でないとスル
ホネートに転換できないことを発見し、本発明を完成す
るに至ったものである。When hydrolyzing this mixture, the present inventors discovered that if the hydrolysis conditions were not set appropriately, the β-sultone would decompose into olefin and Na 2 SO 4 and the conversion rate to sulfonate would decrease. Furthermore, they discovered that γ-sultone and the like are thermally stable and cannot be converted to sulfonate unless the temperature is 90° C. or higher, leading to the completion of the present invention.
ちなみに、下記の表−１で示すとおりの二重結合位置分
布をもつＣ１４オレフィンに対し、３８℃において、モ
ル比１：１でＳｏ、を反応させて得られた表−２に示す
β−サルトン含有組成物である反応生成物を種々の加水
分解温度で第１次加水分解し、ついで１３０〜１４０℃
の温度で第２次加水分解したところ、そのスルホネート
への転換率は表−３のにようになった。Incidentally, the β-sultones shown in Table 2 were obtained by reacting C14 olefins with the double bond position distribution shown in Table 1 below with So at a molar ratio of 1:1 at 38°C. The reaction product containing the composition is firstly hydrolyzed at various hydrolysis temperatures, and then at 130-140°C.
When the secondary hydrolysis was carried out at a temperature of , the conversion rate to sulfonate was as shown in Table 3.
（以下余白）
表−１
表−２
反応生成物の組成
表−３
加水分解温度と転換率
この表から明らかなように、 ４０℃前後を境にしてオ
レフィンのスルホネートへの転換率は急激に低下し、副
生ずるオレフィンとＮａ２５Ｏ１が増加することがわか
る。(Leaving space below) Table 1 Table 2 Composition of reaction products 3 Hydrolysis temperature and conversion rate As is clear from this table, the conversion rate of olefin to sulfonate decreases rapidly at around 40℃. However, it can be seen that by-produced olefins and Na25O1 increase.
第１次加水分解は温度４０℃以下で行う必要がある。好
ましくは３０〜３５℃の範囲が良好である。The primary hydrolysis must be carried out at a temperature of 40°C or lower. Preferably, the range of 30 to 35°C is good.
゛十分な攪拌下で１〜３時間行うのが良い。``It is best to carry out the reaction for 1 to 3 hours with sufficient stirring.
第２次加水分解は温度９０〜１８０℃で、第１次加水分
解よりは短かい時間でよい。The second hydrolysis may be performed at a temperature of 90 to 180°C and for a shorter time than the first hydrolysis.
本発明は、前述のような二段階加水分解によりインナー
オレフィンのスルホネートへの転換率を大巾に向上する
ことができ、かつ、従来の加水分解条件よりマイルドな
条件であるため、副反応等が抑えられ良好な品質のもの
が得られる。The present invention can greatly improve the conversion rate of inner olefin to sulfonate by the two-step hydrolysis described above, and because the conditions are milder than conventional hydrolysis conditions, side reactions etc. A product of good quality can be obtained.
実施例１
表−２で示した組成物１００ｇ（０，３６３モル）を、
それと当量のＮａＯＨを含む水１３０ｇ中に分散させ、
３０〜３５℃に温度を保ち、２時間攪拌した。Example 1 100 g (0,363 mol) of the composition shown in Table 2 was
Dispersed in 130 g of water containing an equivalent amount of NaOH,
The temperature was maintained at 30-35°C and stirred for 2 hours.
反応分散液中はフェノールフタレイン指示薬によりアル
カリ性であることを確認しながら反応を行った。その後
、当量より１０％過剰になるようＮａＯＨを追加し、オ
ートクレーブ中で１３０〜１４０℃で３０分間反応させ
た。かくして加水分解物中のオレフィン量より算出した
スルホネートへの転換率は９５．７％であった。The reaction was carried out while confirming that the reaction dispersion was alkaline using a phenolphthalein indicator. Thereafter, NaOH was added in an amount of 10% excess over the equivalent amount, and the mixture was reacted in an autoclave at 130 to 140°C for 30 minutes. Thus, the conversion rate to sulfonate calculated from the amount of olefin in the hydrolyzate was 95.7%.
比較例１
一方、同じ表−２の組成物を同量のアルカリ水溶液に分
散後、すぐに９０〜９５℃の湯浴中で攪拌反応させると
、すぐにフェノールフタレインによるアルカリ呈色が消
失したので、適宜アルカリ条件が確保できるよう１０％
ＮａＯＨ水溶液を添加した。９０〜９５℃で２時間反応
後、当量より１０％過剰になるようにＮａＯＨ−３加え
、さらに１３０〜１４０℃で３０分反応を行った。加水
分解物中のオレフィン量より算出したスルホネートの転
換率は８１．９％であった。Comparative Example 1 On the other hand, when the same composition shown in Table 2 was dispersed in the same amount of alkaline aqueous solution and immediately stirred and reacted in a water bath at 90 to 95°C, the alkaline coloring caused by phenolphthalein disappeared immediately. Therefore, to ensure appropriate alkaline conditions, 10%
Aqueous NaOH solution was added. After reacting at 90 to 95°C for 2 hours, NaOH-3 was added in an amount of 10% excess over the equivalent amount, and the reaction was further carried out at 130 to 140°C for 30 minutes. The sulfonate conversion rate calculated from the amount of olefin in the hydrolyzate was 81.9%.
実施例２
表−４
Ｃ１４−１８インナーオレフィンの性状表−４のような
炭素分布、２重結合位置分布を持つオレフィンを、オレ
フィンに対する三酸化イオウのモル比１．０５で反応さ
せて表−５のような反応生成物を得た。Example 2 Table-4 Properties of C14-18 inner olefin An olefin having carbon distribution and double bond position distribution as shown in Table-4 was reacted at a molar ratio of sulfur trioxide to olefin of 1.05 to obtain Table-5. The reaction product was obtained.
表−５
この反応生成物１００ｇ（０，３２９モル）を実施例１
と同様な処理を行い、加水分解物中のオレフィン量から
算出したスルホネートへの転換率は９５．８％であった
。Table-5 100g (0,329 mol) of this reaction product was added to Example 1.
The same treatment as above was carried out, and the conversion rate to sulfonate calculated from the amount of olefin in the hydrolyzate was 95.8%.
実施例３
トランス２−Ｏｃｔｅｎａを四塩化炭素溶媒中でＤｉｏ
ｘａｎｅ−三酸化イオウ錯体により、オレフィンに対す
るＳ○、のモル比０．５で反応後、精製して表−６のよ
うな反応生成物を得た。Example 3 Trans 2-Octena in carbon tetrachloride solvent
After reaction with a xane-sulfur trioxide complex at a molar ratio of SO to olefin of 0.5, the reaction product was purified to obtain the reaction products shown in Table 6.
表−６
２−○ｃｔｅｎｅのスルホン化物
この反応生成物約５Ｏｎ＋ｇを１００ｍｇのＮａＯＨを
含む水溶液２ｍ１２中に分散させガラス封管内で室温（
約２５℃）で３時間、９０〜９５℃で１時間ときどき封
管を振りながら加水分解させた。この加水分解反応によ
り新たに生成したオレフィンはほとんどなく、ＮＭＲ，
ＨＰＬＣの分析より９０％以上がスルホネートに転換さ
れた。Table 6 Sulfonated product of 2-○ctene Approximately 5 On+g of this reaction product was dispersed in 2 ml of an aqueous solution containing 100 mg of NaOH and placed in a glass sealed tube at room temperature (
Hydrolysis was carried out for 3 hours at 90-95°C for 1 hour while occasionally shaking the sealed tube. There are almost no new olefins produced by this hydrolysis reaction, and NMR,
According to HPLC analysis, more than 90% was converted to sulfonate.
比較例２
一方、同様の試料を室温で反応させることなく、９０〜
９５℃で１時間反応させると新たに生成したオレフィン
は５２％にもなり、スルホネートへの転換率は半分以下
となった。Comparative Example 2 On the other hand, a similar sample was prepared at room temperature without reacting.
When reacted at 95° C. for 1 hour, the amount of newly generated olefin was 52%, and the conversion rate to sulfonate was less than half.
Claims (1)
酸化いおうとの反応生成物を、４０℃以下の温度のアル
カリ水溶液で第１次加水分解を行い、ついで９０〜１８
０℃の温度で第２次加水分解を行うことを特徴とするイ
ンナーオレフィンスルホネートの製法。1. The reaction product of the long chain inner olefin of C_8 to C_1_8 and sulfur trioxide is subjected to primary hydrolysis in an alkaline aqueous solution at a temperature of 40°C or less, and then 90 to 18
A method for producing an inner olefin sulfonate, which comprises performing secondary hydrolysis at a temperature of 0°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63099019A JP2625150B2 (en) | 1988-04-21 | 1988-04-21 | Manufacturing method of inner olefin sulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63099019A JP2625150B2 (en) | 1988-04-21 | 1988-04-21 | Manufacturing method of inner olefin sulfonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01272564A true JPH01272564A (en) | 1989-10-31 |
| JP2625150B2 JP2625150B2 (en) | 1997-07-02 |
Family
ID=14235477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63099019A Expired - Fee Related JP2625150B2 (en) | 1988-04-21 | 1988-04-21 | Manufacturing method of inner olefin sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2625150B2 (en) |
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| JP7491853B2 (en) | 2019-02-13 | 2024-05-28 | 花王株式会社 | Surfactant Composition |
| EP3977977B1 (en) | 2020-09-30 | 2024-06-12 | Kao Corporation | Cleansing composition comprising internal olefin sulfonate surfactant |
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|---|---|---|---|---|
| JPS5414918A (en) * | 1977-07-01 | 1979-02-03 | Lion Corp | Preparation of olefinsulfonic acid salt |
| JPS5436216A (en) * | 1977-08-25 | 1979-03-16 | Lion Corp | Preparation of internal olefin sulfonate |
| JPS6032759A (en) * | 1983-07-29 | 1985-02-19 | Lion Corp | Production of inner olefinsulfonic acid salt |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5414918A (en) * | 1977-07-01 | 1979-02-03 | Lion Corp | Preparation of olefinsulfonic acid salt |
| JPS5436216A (en) * | 1977-08-25 | 1979-03-16 | Lion Corp | Preparation of internal olefin sulfonate |
| JPS6032759A (en) * | 1983-07-29 | 1985-02-19 | Lion Corp | Production of inner olefinsulfonic acid salt |
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| JP2015028123A (en) * | 2012-09-20 | 2015-02-12 | 花王株式会社 | Internal olefin sulfonate composition and detergent composition containing the same |
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| Publication number | Publication date |
|---|---|
| JP2625150B2 (en) | 1997-07-02 |
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