JPH0377181B2 - - Google Patents
Info
- Publication number
- JPH0377181B2 JPH0377181B2 JP24968983A JP24968983A JPH0377181B2 JP H0377181 B2 JPH0377181 B2 JP H0377181B2 JP 24968983 A JP24968983 A JP 24968983A JP 24968983 A JP24968983 A JP 24968983A JP H0377181 B2 JPH0377181 B2 JP H0377181B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- lower alkyl
- acid ester
- saturated fatty
- acid lower
- 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
Links
- -1 Alkylene glycol Chemical compound 0.000 claims description 33
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 24
- 238000000926 separation method Methods 0.000 claims description 19
- 125000005907 alkyl ester group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- 230000003068 static effect Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は飽和脂肪酸エステルの共存下に不飽和
脂肪酸エステルをスルホン化した後、これを中
和・加水分解して得られる不飽和脂肪酸エステル
スルホン酸塩の分離回収技術に関する。
本発明者らは先に、(A)不飽和脂肪酸エステルと
(B)飽和脂肪酸エステルとを(A)／(B)＝90／10〜５／
95の重量比で含む脂肪酸エステル混合物を、該混
合物中の未反応分に於ける前記(A)成分の含有量が
0.3重量％以上になるようスルホン化し、次いで
中和・加水分解することを特徴とする不飽和脂肪
酸エステルスルホン酸塩の製造方法を提案した
（特願昭58−119776号参照）。この方法によれば、
スルホン化剤に対する反応性の大小に由来して、
(A)成分を優先的にスルホン化することができるの
で、(A)成分のポリスルホン化物乃至(B)成分のスル
ホン化物が実質的に生成されない範囲に、換言す
れば(A)成分の所定量が未反応のまま反応系に残留
するようなスルホン化条件を選ぶことで、色調劣
化を伴うことなく高反応率で(A)成分をスルホン化
することができ、従つて淡色な不飽和脂肪酸エス
テルスルホン酸塩を高収率で得ることができる。
ところで、上記の方法で製造された不飽和脂肪
酸エステルのスルホン酸塩を、例えば合成洗剤の
活性成分として利用する場合、そのスルホン酸塩
の未反応油分から分離するのが一般的である。未
反応油分の分離方法としては、ｎ−ヘキサンなど
の有機溶媒あるいは臭化エチレンなどのハロゲン
化炭化水素にて抽出する方法（特開昭54−14918
号）、水蒸気蒸留法、高温高圧下での静置分離法、
活性炭による吸着除去法（特公昭56−8026号）な
どが従来知られており、飽和脂肪酸エステルの共
存下で製造された不飽和脂肪酸エステルスルホン
酸塩を、飽和脂肪酸エステルから分離する場合に
も、上に紹介した従来法の適用は不可能ではな
い。
しかしながら、従来知られている未反応油分の
分離法は、飽和脂肪酸エステルの分離効率乃至は
作業性の点で一長一短があり、必ずしも満足でき
ない。
本発明は簡易な手段で未反応油分を効率よく分
離して、不飽和脂肪酸エステルのスルホン酸塩を
取得する方法を提供するものであつて、その方法
は不飽和脂肪酸低級アルキルエステル及び飽和脂
肪酸低級アルキルエステルの混合物をSO3により
スルホン化した後、中和・加水分解して得た不飽
和脂肪酸低級アルキルエステルのスルホン酸塩と
飽和脂肪酸低級アルキルエステルとの混合物に、
下記の(イ)〜(ハ)から選ばれる少なくとも１種の分離
助剤を加え、静置分離により飽和脂肪酸低級アル
キルエステルを除去することを特徴とする。
(イ) 炭素数２〜８の多価アルコール
(ロ) 常温で液状のアルキレングリコール
(ハ) 炭素数６〜30のオレフイン
本発明に於て、不飽和脂肪酸低級アルキルエス
テルと飽和脂肪酸低級アルキルエステルとの混合
物とを、スルホン化し、中和・加水分解するまで
の工程は、先に紹介した特願昭58−119776号のそ
れと実質的に異ならない。従つて、不飽和脂肪酸
低級アルキルエステル及び飽和脂肪酸低級アルキ
ルエステルとしては、それぞれ脂肪酸残基の炭素
数が８〜22、好ましくは12〜18であり、アルキル
基の炭素数が１〜６、好ましくは１〜３のものが
使用される。また、スルホン化に際しての不飽和
脂肪酸エステル対飽和脂肪酸エステルの混合比
は、90／10〜５／95、好ましくは80／20〜10／90
の範囲に保持される。
スルホン化は液状SO3、ガス状SO3、発煙硫
酸、クロルスルホン酸などをスルホン化剤に用い
て、薄膜型反応器又は槽型反応器で行なわれ、ス
ルホン化条件としては、不飽和脂肪酸エステルに
対するSO3のモル比0.5〜2.0、好ましくは1.0〜
1.5、温度30〜120℃、好ましくは40〜90℃が採用
される。そして未反応不飽和脂肪酸エステル量が
全未反応油分（主として飽和脂肪酸エステルから
なる）の0.3重量％より低下する以前に、スルホ
ン化反応は停止される。スルホン化反応終了後
は、反応混合物を中和・加水分解することによ
り、これに含まれる不飽和脂肪酸エステルのスル
ホン化物を対応するスルホン酸塩に転化させる。
本発明の方法によれば、中和・加水分解された
上記の反応混合物に、前記(イ)〜(ハ)から選ばれる少
なくとも１種の分離助剤が添加混合されて静置さ
れる。本発明で使用可能な分離助剤の具体例とし
ては、エチレングリコール、プロピレングリコー
ル、ジエチレングリコール、トリエチレングリコ
ール、ジプロピレングリコール、グリセリン、ポ
リエチレングリコール#400、同じく#600、ポリ
プロピレングリコール、C3〜C20の内部オレフイ
ンなどを挙げることができ、なかでもエチレング
リコール、プロピレングリコール、ジエチレング
リコール、グリセリン、C10内部オレフイン、C12
内部オレフイン、C14内部オレフインの使用が好
ましい。
分離助剤の添加量は、不飽和脂肪酸エステルの
スルホン酸塩量の30〜500重量％、好ましくは50
〜200重量％の範囲で選択され、分離助剤が添加
された混合物は80〜200℃、好ましくは100〜150
℃の温度で１〜120分間静置される。この静置に
よつて、分離助剤が水溶性である場合には、混合
物は不飽和脂肪酸エステルスルホン酸塩と分離助
剤を含有する水性層と、飽和脂肪酸エステルを主
成分とする油性層とに分離する。また分離助剤が
非水溶性乃至は難水溶性である場合には、混合物
が不飽和脂肪酸エステルスルホン酸塩を含有する
水性層と、飽和脂肪酸エステル及び分離助剤を含
有する油性層とに分離する。そして前者の場合、
水性層はそのままでもよいが、必要に応じて薄膜
蒸発等により分離助剤を除去してもよい。後者の
場合にはデカンテーシヨンもしくは分液ロートな
どの適宜の手段で水性層を回収すれば、不飽和脂
肪酸エステルのスルホン酸塩が容易に取得される
のである。
以上の通り、本発明の方法によれば、分離助剤
を加えて静置するという極めて簡易な手段で、飽
和脂肪酸エステルや分離助剤をほとんど含まない
不飽和脂肪酸エステルのスルホン酸塩を得ること
ができる。
実施例
オレイン酸メチル対極度硬化パーム油脂肪酸メ
チルの重量比が40／60の混合物を、ガラス製薄膜
型反応器にてSO3モル比1.2、温度70〜80℃でス
ルホン化し、次いで中和・加水分解した。しかる
後、この混合物に分離助剤を加えて静置し、未反
応油分を分離する一連の実験を行ない、混合物中
の不飽和脂肪酸エステルスルホン酸塩に対する未
反応油分の量を、分離操作前と分離操作後とで対
比した。結果を表−１に示す。
尚、実験No.８のみ極度硬化パール油メチルに代
えてパームカーネルメチルを使用した。
The present invention relates to a technique for separating and recovering an unsaturated fatty acid ester sulfonate obtained by sulfonating an unsaturated fatty acid ester in the presence of a saturated fatty acid ester, and then neutralizing and hydrolyzing the same. The present inventors previously discovered that (A) unsaturated fatty acid ester and
(B) Saturated fatty acid ester and (A)/(B)=90/10~5/
A fatty acid ester mixture containing a fatty acid ester mixture in a weight ratio of
We proposed a method for producing unsaturated fatty acid ester sulfonate, which is characterized by sulfonation to a concentration of 0.3% by weight or more, followed by neutralization and hydrolysis (see Japanese Patent Application No. 119776/1983). According to this method,
Derived from the degree of reactivity to sulfonating agents,
Since component (A) can be sulfonated preferentially, the polysulfonated product of component (A) or the sulfonated product of component (B) can be suppressed within a range in which substantially no polysulfonated product of component (B) is produced, in other words, a predetermined amount of component (A). By selecting sulfonation conditions such that Component (A) remains unreacted in the reaction system, component (A) can be sulfonated at a high reaction rate without deterioration of color tone, thus producing a pale unsaturated fatty acid ester. Sulfonate salts can be obtained in high yields. By the way, when the sulfonate of an unsaturated fatty acid ester produced by the above method is used, for example, as an active ingredient in a synthetic detergent, it is common to separate the sulfonate from the unreacted oil component. A method for separating unreacted oil is a method of extraction with an organic solvent such as n-hexane or a halogenated hydrocarbon such as ethylene bromide (Japanese Unexamined Patent Publication No. 14918-1989).
No.), steam distillation method, static separation method under high temperature and high pressure,
Adsorption removal methods using activated carbon (Japanese Patent Publication No. 56-8026) are known, and can also be used to separate unsaturated fatty acid ester sulfonates produced in the coexistence of saturated fatty acid esters from saturated fatty acid esters. It is not impossible to apply the conventional method introduced above. However, conventionally known methods for separating unreacted oil components have advantages and disadvantages in terms of efficiency in separating saturated fatty acid esters and workability, and are not necessarily satisfactory. The present invention provides a method for efficiently separating unreacted oil components by simple means to obtain sulfonate salts of unsaturated fatty acid esters. After sulfonating the mixture of alkyl esters with SO 3 , the mixture of sulfonate of unsaturated fatty acid lower alkyl ester and saturated fatty acid lower alkyl ester obtained by neutralization and hydrolysis,
It is characterized in that at least one separation aid selected from the following (a) to (c) is added, and the saturated fatty acid lower alkyl ester is removed by static separation. (a) Polyhydric alcohol having 2 to 8 carbon atoms (b) Alkylene glycol that is liquid at room temperature (c) Olefin having 6 to 30 carbon atoms In the present invention, unsaturated fatty acid lower alkyl ester and saturated fatty acid lower alkyl ester The steps from sulfonation to neutralization and hydrolysis of the mixture are substantially the same as those of Japanese Patent Application No. 119776/1983 introduced above. Therefore, in the unsaturated fatty acid lower alkyl ester and the saturated fatty acid lower alkyl ester, the fatty acid residue has 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, and the alkyl group has 1 to 6 carbon atoms, preferably 1 to 6 carbon atoms. 1 to 3 are used. In addition, the mixing ratio of unsaturated fatty acid ester to saturated fatty acid ester during sulfonation is 90/10 to 5/95, preferably 80/20 to 10/90.
is maintained within the range of Sulfonation is carried out in a thin film reactor or tank reactor using liquid SO 3 , gaseous SO 3 , fuming sulfuric acid, chlorosulfonic acid, etc. as a sulfonating agent, and the sulfonation conditions include unsaturated fatty acid ester. molar ratio of SO 3 to 0.5 to 2.0, preferably 1.0 to
1.5, a temperature of 30-120°C, preferably 40-90°C is adopted. The sulfonation reaction is stopped before the amount of unreacted unsaturated fatty acid ester falls below 0.3% by weight of the total unreacted oil (consisting mainly of saturated fatty acid ester). After the sulfonation reaction is completed, the reaction mixture is neutralized and hydrolyzed to convert the sulfonated product of the unsaturated fatty acid ester contained therein into the corresponding sulfonate. According to the method of the present invention, at least one separation aid selected from (a) to (c) above is added to and mixed with the neutralized and hydrolyzed reaction mixture, and the mixture is allowed to stand. Specific examples of separation aids that can be used in the present invention include ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, glycerin, polyethylene glycol #400 and #600, polypropylene glycol, and C3 to C20. internal olefins, among others ethylene glycol, propylene glycol, diethylene glycol, glycerin, C10 internal olefins, C12
The use of internal olefins, C14 internal olefins, is preferred. The amount of separation aid added is 30 to 500% by weight, preferably 50% by weight of the amount of sulfonate of unsaturated fatty acid ester.
~200% by weight, the mixture with added separation aids is heated at 80-200°C, preferably at 100-150°C.
It is left to stand for 1-120 minutes at a temperature of °C. By this standing, when the separation aid is water-soluble, the mixture is divided into an aqueous layer containing the unsaturated fatty acid ester sulfonate and the separation aid, and an oily layer containing the saturated fatty acid ester as the main component. Separate into In addition, when the separation aid is water-insoluble or poorly water-soluble, the mixture is separated into an aqueous layer containing the unsaturated fatty acid ester sulfonate and an oily layer containing the saturated fatty acid ester and the separation aid. do. And in the former case,
The aqueous layer may be left as is, but if necessary, the separation aid may be removed by thin film evaporation or the like. In the latter case, the sulfonate of the unsaturated fatty acid ester can be easily obtained by recovering the aqueous layer using an appropriate means such as decantation or a separating funnel. As described above, according to the method of the present invention, a sulfonate of an unsaturated fatty acid ester containing almost no saturated fatty acid ester or separation aid can be obtained by an extremely simple method of adding a separation aid and allowing it to stand. I can do it. Example A mixture of methyl oleate and extremely hardened palm oil fatty acid methyl in a weight ratio of 40/60 was sulfonated in a glass thin film reactor at an SO 3 molar ratio of 1.2 and a temperature of 70 to 80°C, and then neutralized. Hydrolyzed. After that, a series of experiments were carried out to separate the unsaturated fatty acid ester sulfonate by adding a separation aid to the mixture and allowing it to stand still. A comparison was made with after the separation operation. The results are shown in Table-1. In addition, only in Experiment No. 8, palm kernel methyl was used instead of extremely hardened pearl oil methyl.
【表】
＊ 不飽和脂肪酸エステルのスルホン酸塩に対す
る重量％で表示。
＊＊ 比較例
[Table] * Expressed as weight percent of unsaturated fatty acid ester based on sulfonate.
** Comparative example
Claims (1)
脂肪酸低級アルキルエステルの混合物をSO3によ
りスルホン化した後、中和・加水分解して得た不
飽和脂肪酸低級アルキルエステルのスルホン酸塩
と飽和脂肪酸低級アルキルエステルとの混合物
に、下記の(イ)〜(ハ)から選ばれる少なくとも１種の
分離助剤を加え、静置分離により飽和脂肪酸低級
アルキルエステルを除去することを特徴とする不
飽和脂肪酸低級アルキルエステルスルホン酸塩の
製造法。 (イ) 炭素数２〜８の多価アルコール (ロ) 常温で液状のアルキレングリコール (ハ) 炭素数６〜30のオレフイン ２ 前記分離助剤の添加量が不飽和脂肪酸低級ア
ルキルエステルスルホン酸塩の30〜500重量％で
あり、静置分離を80〜120℃で１〜120分間行なう
特許請求の範囲第１項記載の方法。[Claims] 1. A sulfonate of an unsaturated fatty acid lower alkyl ester obtained by sulfonating a mixture of an unsaturated fatty acid lower alkyl ester and a saturated fatty acid lower alkyl ester with SO 3 , and then neutralizing and hydrolyzing the mixture. A method for removing saturated fatty acid lower alkyl esters by adding at least one separation aid selected from (a) to (c) below to a mixture with saturated fatty acid lower alkyl esters, and removing the saturated fatty acid lower alkyl esters by static separation. A method for producing saturated fatty acid lower alkyl ester sulfonate. (b) Polyhydric alcohol having 2 to 8 carbon atoms (b) Alkylene glycol that is liquid at room temperature (c) Olefin having 6 to 30 carbon atoms 2 30 to 500% by weight, and the method according to claim 1, wherein the static separation is carried out at 80 to 120°C for 1 to 120 minutes.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24968983A JPS60139662A (en) | 1983-12-27 | 1983-12-27 | Method for producing unsaturated fatty acid lower alkyl ester sulfonate |
| DE8484304246T DE3468020D1 (en) | 1983-07-01 | 1984-06-22 | Process for producing sulfonate of unsaturated fatty acid ester |
| EP84304246A EP0130753B1 (en) | 1983-07-01 | 1984-06-22 | Process for producing sulfonate of unsaturated fatty acid ester |
| US06/626,081 US4545939A (en) | 1983-07-01 | 1984-06-29 | Process for producing sulfonate of unsaturated fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24968983A JPS60139662A (en) | 1983-12-27 | 1983-12-27 | Method for producing unsaturated fatty acid lower alkyl ester sulfonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60139662A JPS60139662A (en) | 1985-07-24 |
| JPH0377181B2 true JPH0377181B2 (en) | 1991-12-09 |
Family
ID=17196735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24968983A Granted JPS60139662A (en) | 1983-07-01 | 1983-12-27 | Method for producing unsaturated fatty acid lower alkyl ester sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60139662A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6379865A (en) * | 1986-09-25 | 1988-04-09 | Nippon Mining Co Ltd | Removing method of sulfate from photosulfonation reaction mixture liquid of paraffin |
-
1983
- 1983-12-27 JP JP24968983A patent/JPS60139662A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60139662A (en) | 1985-07-24 |
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