JPH0272155A - Purification of thioglycolic acid - Google Patents
Purification of thioglycolic acidInfo
- Publication number
- JPH0272155A JPH0272155A JP22389288A JP22389288A JPH0272155A JP H0272155 A JPH0272155 A JP H0272155A JP 22389288 A JP22389288 A JP 22389288A JP 22389288 A JP22389288 A JP 22389288A JP H0272155 A JPH0272155 A JP H0272155A
- Authority
- JP
- Japan
- Prior art keywords
- thioglycolic acid
- acid
- organic solvent
- distillation
- thioglycol acid
- 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
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 title claims description 126
- 238000000746 purification Methods 0.000 title claims description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 abstract description 10
- 238000009833 condensation Methods 0.000 abstract description 5
- 230000005494 condensation Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract description 3
- QUGNZNCOLVCQKW-UHFFFAOYSA-M S[Sn] Chemical compound S[Sn] QUGNZNCOLVCQKW-UHFFFAOYSA-M 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000003317 industrial substance Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 abstract 6
- 239000006210 lotion Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- -1 isopropyl ether Chemical class 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 description 1
- 229940046307 sodium thioglycolate Drugs 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000008096 xylene Substances 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、チオグリコール酸の精製法に関するものであ
る。チオグリコール酸は、コールドパーマネントウェー
ブ用薬剤やメルカプト錫系樹脂安定剤等、工業薬品およ
び医薬品の中間原料として汎用され、工業的に重要であ
る。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for purifying thioglycolic acid. Thioglycolic acid is widely used as an intermediate raw material for industrial chemicals and pharmaceuticals, such as cold permanent wave agents and mercaptotin resin stabilizers, and is industrially important.
（従来技術および発明が解決しようとする課題）チオグ
リコール酸は、工業的には水硫化ソーダ法または多硫化
ソーダ法により製造される０例えば特開昭５１−２９４
４０号公報では、モノクロル酢酸ナトリウム水溶液と水
硫化ナトリウム水溶液を反応させてチオグリコール酸ナ
トリウム水溶液とし、次いで硫酸または塩酸のような鉱
酸を加え、チオグリコール酸水溶液としてチオグリコー
ル酸を得る事が示されている。この様にして得られたチ
オグリコール酸水溶液は副生物として硫酸ナトリウムま
たは塩酸ナトリウムのような塩を含有している。これら
のような塩とチオグリコール酸を分難する方法としては
、有機溶媒によりチオグリコール酸を抽出する方法が採
用されている。(Prior Art and Problems to be Solved by the Invention) Thioglycolic acid is industrially produced by the sodium hydrogen sulfide method or the soda polysulfide method.
No. 40 discloses that thioglycolic acid can be obtained as a thioglycolic acid aqueous solution by reacting an aqueous sodium monochloroacetate solution and an aqueous sodium hydrogen sulfide solution to form a sodium thioglycolate aqueous solution, and then adding a mineral acid such as sulfuric acid or hydrochloric acid. has been done. The aqueous thioglycolic acid solution thus obtained contains salts such as sodium sulfate or sodium hydrochloride as by-products. As a method for separating these salts and thioglycolic acid, a method of extracting thioglycolic acid with an organic solvent has been adopted.
例えば、特開昭５６−１５２４５３号公報ではテトラ−
ｎ−ブチル尿素を使用してチオグリコール酸を抽出する
方法が示されている。チオグリコール酸水溶液からチオ
グリコール酸を抽出した抽出液からチオグリコール酸を
分難する方法としては減圧蒸留法が採用されている。減
圧蒸留法が用いられているのは、（イ）チオグリコール
酸は熱負荷を受けると自己縮合を起こし縮合物に変化す
ること、（ロ）チオグリコール酸の沸点が非常に高いた
め、常圧蒸留ではりボイラーでの液溝点が高く、チオグ
リコール酸の縮合物への変化による損失が大きいこと、
による、しかしながら、この減圧蒸留法は工業的な使用
の際に種々の欠点を有する０例えば、チオグリコール酸
の抽出溶剤として分配係数が大きく公知であるものにエ
ーテル、例えばイソプロピルエーテル、エステル、例え
ば酢酸ブチル、アルコール、例えば２−エチルヘキサノ
ール等の有機溶媒があるが、これらはいずれも低沸点で
あるなめ、これらを用いて得た抽出液がらチオグリコー
ル酸を分難する際減圧蒸留法を使用すると、冷却凝縮等
による有機溶媒の回収操作が効率よく行われず、チオグ
リコール酸の製造コストが上がる欠点がある。また特開
昭５６＝１５２４５３号公報では、逆にチオグリコール
酸より高い沸点を持つ有機溶媒を用いてチオグリコール
酸を抽出し、抽出液から減圧蒸留法によってチオグリコ
ール酸を分難しているが、この際にはチオグリコール酸
より高い沸点を持つ製造副生成物、例えばチオジグリコ
ール酸またはジチオグリコール酸が有機溶媒中に残留す
るため、有機溶媒を再使用する際これらを除去する操作
が必要となる欠点がある。For example, in Japanese Patent Application Laid-Open No. 56-152453, tetra-
A method for extracting thioglycolic acid using n-butyl urea is shown. A vacuum distillation method is employed as a method for separating thioglycolic acid from an extract obtained by extracting thioglycolic acid from an aqueous thioglycolic acid solution. The vacuum distillation method is used because (a) thioglycolic acid undergoes self-condensation and turns into a condensate when subjected to heat load, and (b) thioglycolic acid has a very high boiling point, so it can be distilled under normal pressure. In distillation, the liquid groove point in the girder boiler is high, and the loss due to conversion of thioglycolic acid to a condensate is large;
However, this vacuum distillation method has various drawbacks in industrial use. For example, ethers, such as isopropyl ether, and esters, such as acetic acid, are known to have large partition coefficients as extraction solvents for thioglycolic acid. There are organic solvents such as butyl and alcohol, such as 2-ethylhexanol, but all of these have low boiling points, so when separating thioglycolic acid from the extract obtained using these solvents, it is recommended to use vacuum distillation. However, the recovery operation of the organic solvent by cooling condensation or the like is not performed efficiently, which has the drawback of increasing the production cost of thioglycolic acid. On the other hand, in JP-A-152453, thioglycolic acid is extracted using an organic solvent with a boiling point higher than that of thioglycolic acid, and thioglycolic acid is separated from the extract by vacuum distillation. In this case, production by-products with a boiling point higher than that of thioglycolic acid, such as thiodiglycolic acid or dithioglycolic acid, remain in the organic solvent, so it is necessary to remove these when reusing the organic solvent. There is a drawback.
本発明はこれらの欠点を解決することを目標とするもの
であり、チオグリコール酸および有機溶媒を主成分とす
る混合溶液からチオグリコール酸を分難するのに工業的
に有利なチオグリコール酸の精製法を提供するものであ
る。The present invention aims to solve these drawbacks, and aims to develop thioglycolic acid, which is industrially advantageous for separating thioglycolic acid from a mixed solution containing thioglycolic acid and an organic solvent as main components. A purification method is provided.
（課題を解決するための手段）
本発明は前述の課題を解決するため鋭意研究を重ねた結
果、蒸留塔リボイラーのチオグリコール酸中に水を存在
させると、熱負荷を受けてもチオグリコール酸の縮合物
変化による損失を低く抑え得ることを見いだし、この知
見に基すいて本発明をなすに至った。(Means for Solving the Problems) As a result of extensive research in order to solve the above-mentioned problems, the present invention has found that when water is present in thioglycolic acid in a distillation column reboiler, thioglycolic acid remains stable even under heat load. It has been discovered that the loss due to condensate change can be suppressed to a low level, and the present invention has been completed based on this knowledge.
即ち、本発明は、チオグリコール酸およびチオグリコー
ル酸よりも低沸点の有機溶媒を主成分とする混合液を蒸
留分難するに際し、蒸留塔リボイラー中に１重量パーセ
ント以上の水分を共存させることを特徴とするチオグリ
コール酸の精製方法である。That is, the present invention allows for the coexistence of water of 1% by weight or more in the distillation column reboiler when distilling a mixture mainly consisting of thioglycolic acid and an organic solvent with a lower boiling point than the thioglycolic acid. This is a distinctive method for purifying thioglycolic acid.
本発明方法において精製原料とするチオグリコール酸お
よびチオグリコール酸よりも低沸点の有機溶媒（以下単
に有機溶媒という）を主成分とする混合液とは、例えば
粗チオグリコール酸水溶液から有機溶媒を用いてチオグ
リコール酸を抽出して得た抽出液であり、その質量比率
は通常チオグリコール酸１に対し有機溶媒１〜２ｏのも
のである。In the method of the present invention, the mixed liquid mainly consisting of thioglycolic acid and an organic solvent with a lower boiling point than the thioglycolic acid (hereinafter simply referred to as an organic solvent) as a raw material for purification refers to, for example, a mixture containing an organic solvent from a crude aqueous thioglycolic acid solution. It is an extract obtained by extracting thioglycolic acid, and its mass ratio is usually 1 to 2 parts of the organic solvent to 1 part of thioglycolic acid.
この際粗チオグリコール酸水溶液は、水硫化ソーダ法ま
たは多硫化ソーダ法のいずれの方法で製造されたもので
あってもよく特に制限を受けるものではない。At this time, the crude thioglycolic acid aqueous solution may be produced by either the sodium hydrogen sulfide method or the sodium polysulfide method and is not particularly limited.
また、本発明において有機溶媒とは、エチルエーテル、
イソプロピルエーテル、ｎ−ブチルエーテルのごときエ
ーテル類、＃酸エチル、＃酸プロピル、酢酸ブチルのご
ときエステル類、ｎ−ヘキシルアルコール、イソオクチ
ルアルコール、２−エチルヘキシルアルコールのごとき
アルコール類およびベンゼン、トルエン、キシレン、シ
クロヘキサン、クロロホルムのごとき炭化水素またはそ
のハロゲン化物からｉ５Ｊばれる溶剤まなはこｈら溶剤
の混合物である。In addition, in the present invention, organic solvents include ethyl ether,
Ethers such as isopropyl ether and n-butyl ether, esters such as ethyl acid, propyl acid, and butyl acetate, alcohols such as n-hexyl alcohol, isooctyl alcohol, and 2-ethylhexyl alcohol, and benzene, toluene, xylene, It is a mixture of solvents derived from hydrocarbons such as cyclohexane, chloroform, or their halides.
蒸留塔リボイラー中で、チオグリコール酸と共存させる
水の温度は、チオグリコール酸が熱負荷を受ける時間お
よびその温度等の蒸留操作条件によって適宜決定される
が、通常１歌量パ一セント以上、好ましくは１０〜２０
重量パーセン１〜である。The temperature of the water coexisting with thioglycolic acid in the distillation column reboiler is appropriately determined depending on the distillation operation conditions such as the time when thioglycolic acid is subjected to heat load and its temperature, but it is usually 1% by volume or more, Preferably 10-20
Weight percent is 1~.
蒸留塔リボイラー中に１重量％以上の水分を共存させる
方法としては、水を単独で、あるいは原料液に添加する
こと等により、連続的あるいは回分的に蒸留系内に導入
すればよい。As a method for coexisting 1% by weight or more of water in the distillation column reboiler, water may be introduced into the distillation system continuously or batchwise, either alone or by adding it to the raw material liquid.
なお、この水には有機溶媒、チオグリコール酸、および
製造副生成物、例えばチオグリコール酸、ジチオジグリ
コール酸を含んでいてもさしつがえないが、製造副生成
物の白基類および反応において中和に用いる鉱酸等の含
有は、有機溶媒とチオグリコール酸の分難の際、塩類の
析出あるいはチオグリコール酸の縮合物の生成を増長す
るためあまり好ましくない。Note that this water may contain organic solvents, thioglycolic acid, and production by-products such as thioglycolic acid and dithiodiglycolic acid, but white groups of production by-products and reaction The inclusion of a mineral acid or the like used for neutralization is not very preferable because it increases the precipitation of salts or the formation of a condensate of thioglycolic acid when the organic solvent and thioglycolic acid are separated.
本発明法の蒸留分難は次の様に実施される。即ち、チオ
グリコール酸および有１１溶媒を主成分とする混合液を
それ自体公知の方法により蒸留し、この際前述したよう
に水を連続的あるいは回分的に系内に供給すれはよい。Distillation separation according to the method of the present invention is carried out as follows. That is, a mixture containing thioglycolic acid and the 11 solvents as main components may be distilled by a method known per se, and water may be supplied into the system continuously or batchwise as described above.
又、蒸留塔のりボイラー温度はチオグリコール酸か熱負
荷を受ける時間によるか、好ましくは１５０℃以下、更
には１３０℃以下が望ましい。The boiler temperature of the distillation column is preferably 150°C or lower, more preferably 130°C or lower, depending on the time during which the thioglycolic acid is subjected to heat load.
これは、温度か１５０°Ｃより高い条件下では、例えば
チオグリコール酸か熱負荷を受ける時間が約１５０分で
は、チオグリコール酸の縮合物変化による損失か１０％
以上と大きくなり好ましくないためである。同様にリボ
イラー中でのチオグリコール酸の滞留時１ｍは、熱負荷
温度にもよるが通常５時間以内、好ましくは１時間以内
がよい。Under conditions where the temperature is higher than 150°C, for example, when thioglycolic acid is subjected to heat load for about 150 minutes, the loss due to condensation of thioglycolic acid is 10%.
This is because it is undesirably large. Similarly, the residence time of 1 m of thioglycolic acid in the reboiler is usually within 5 hours, preferably within 1 hour, although it depends on the heat load temperature.
なお、蒸留操作それ自体は回分法または連続法のいずれ
も採用でき、また蒸留操作に使用する装置に特に制限を
受けるものではない、また上記蒸留操作は通常常圧下で
行われるが、減圧下で行うこともできる。The distillation operation itself can be carried out either batchwise or continuously, and there are no particular restrictions on the equipment used for the distillation operation.Although the above distillation operation is usually carried out under normal pressure, it can be carried out under reduced pressure. You can also do this.
以下実施例を示して本発明法をさらに詳しく説明する。The method of the present invention will be explained in more detail below with reference to Examples.
（実施例）
実施例１
オールダシヨウ式蒸留糖を用いて常圧下で操作を行った
。液容積２４０ ｄｌｌのりボイラーを備えた直径５■
、段数１０段のオールダシヨウ式蒸留塔において、塔頂
より４段目に設けられたチオグリコール酸抽出液供給管
からチオグリコール酸７重量％、水１重量％を含むイン
１０ビルエーテル溶液を１ｋｇ／Ｈｒの速度で供給しさ
らに塔頂に設けられた水供給管から純水を０．０６に＋
ｒ／Ｈｒの速度で供給しチオグリコール酸とイン１０ビ
ルエーテルの蒸留分難を行った０缶出液缶出管より０．
０８ｈｇ／ｈｒで缶出するチオグリコール酸溶液を分析
したところイン１０ピルエーテルは含まれておらず、カ
ールフィッシャー法分析によると水濃度が１３１１量％
、ヨウ度分析によるとチオグリコール酸濃度８２重量％
、縮合物濃度２．６重量％であり、チオグリコール酸の
縮合物に変化したことによる損失は３重量％であった。(Example) Example 1 The operation was carried out under normal pressure using old distilled sugar. Diameter 5■ with liquid volume 240 dll glue boiler
In an all-dash distillation column with 10 plates, 1 kg/in-10V ether solution containing 7% by weight of thioglycolic acid and 1% by weight of water was added from the thioglycolic acid extract supply pipe provided in the fourth stage from the top of the column. Pure water is supplied at a rate of 0.06 Hr from the water supply pipe installed at the top of the tower.
The 0-bottom solution was supplied at a rate of r/Hr and distilled to separate thioglycolic acid and in-10-byl ether.
An analysis of the thioglycolic acid solution canned at 0.8hg/hr revealed that it did not contain 10-pyl ether, and according to Karl Fischer analysis, the water concentration was 1311% by weight.
According to iodine analysis, thioglycolic acid concentration was 82% by weight.
The condensate concentration was 2.6% by weight, and the loss due to conversion to a thioglycolic acid condensate was 3% by weight.
また、この際リボイラー内温度は１１８°Ｃであった。Further, at this time, the temperature inside the reboiler was 118°C.
比較ｍｌ １
水の供給を行わなかった以外実施例１と同様にしてチオ
グリコール酸の蒸留分難を行ったところチオグリコール
酸の縮合物変化による損失は４３重量％であった。Comparative ml 1 Distillation of thioglycolic acid was carried out in the same manner as in Example 1 except that no water was supplied, and the loss due to change in thioglycolic acid condensate was 43% by weight.
又、缶出液中の水分、ｄ度は不検出であった。In addition, moisture and degree d in the bottoms were undetectable.
（発明の効果）
チオグリコール酸および有機溶媒を主成分とする混合液
よりチオグリコール酸を分難８？製するに際し、本発明
の方法によれば、チオグリコール酸の熱負荷による縮合
を著しく抑制することができる。このため常圧でも蒸留
分難することが可能になり、従って、留出する有機溶媒
の回収操作も効率的に行うことができ、又、この有機溶
媒は未処理で粗チオグリコール酸水溶液の抽出溶媒とし
て再使用できる。(Effect of the invention) It is difficult to separate thioglycolic acid from a mixture containing thioglycolic acid and an organic solvent as main components. According to the method of the present invention, condensation of thioglycolic acid due to heat load can be significantly suppressed during production. For this reason, it is possible to perform distillation even under normal pressure, and therefore the operation for recovering the distilled organic solvent can be carried out efficiently.In addition, this organic solvent can be used for extraction of crude thioglycolic acid aqueous solution without treatment. Can be reused as a solvent.
手続補正書く自発） 昭和６３年１０月２１日Voluntary writing of procedural amendments) October 21, 1986
Claims (1)
の有機溶媒を主成分とする混合液を蒸留分難するに際し
、蒸留塔リボイラー中に１重量パーセント以上の水分を
共存させることを特徴とするチオグリコール酸の精製方
法。Thioglycolic acid characterized by allowing 1% by weight or more of water to coexist in a distillation column reboiler when distilling thioglycolic acid and a mixed liquid mainly consisting of an organic solvent with a lower boiling point than thioglycolic acid. Purification method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22389288A JPH0272155A (en) | 1988-09-06 | 1988-09-06 | Purification of thioglycolic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22389288A JPH0272155A (en) | 1988-09-06 | 1988-09-06 | Purification of thioglycolic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0272155A true JPH0272155A (en) | 1990-03-12 |
Family
ID=16805343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22389288A Pending JPH0272155A (en) | 1988-09-06 | 1988-09-06 | Purification of thioglycolic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0272155A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590625A (en) * | 2019-09-30 | 2019-12-20 | 黄河三角洲京博化工研究院有限公司 | Method for improving rectification yield of thioglycollic acid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5481220A (en) * | 1977-12-09 | 1979-06-28 | Denki Kagaku Kogyo Kk | Purification of thioglycolic acid |
| JPS56152453A (en) * | 1980-04-01 | 1981-11-26 | Cassella Farbwerke Mainkur Ag | Method of extracting and obtaining thioglycolic acid from aqueous medium |
-
1988
- 1988-09-06 JP JP22389288A patent/JPH0272155A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5481220A (en) * | 1977-12-09 | 1979-06-28 | Denki Kagaku Kogyo Kk | Purification of thioglycolic acid |
| JPS56152453A (en) * | 1980-04-01 | 1981-11-26 | Cassella Farbwerke Mainkur Ag | Method of extracting and obtaining thioglycolic acid from aqueous medium |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590625A (en) * | 2019-09-30 | 2019-12-20 | 黄河三角洲京博化工研究院有限公司 | Method for improving rectification yield of thioglycollic acid |
| CN110590625B (en) * | 2019-09-30 | 2021-12-14 | 山东益丰生化环保股份有限公司 | Method for improving rectification yield of thioglycollic acid |
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