JPH04187671A - Method for purifying lactam oil - Google Patents
Method for purifying lactam oilInfo
- Publication number
- JPH04187671A JPH04187671A JP31420590A JP31420590A JPH04187671A JP H04187671 A JPH04187671 A JP H04187671A JP 31420590 A JP31420590 A JP 31420590A JP 31420590 A JP31420590 A JP 31420590A JP H04187671 A JPH04187671 A JP H04187671A
- Authority
- JP
- Japan
- Prior art keywords
- water
- caprolactam
- extraction
- laurolactam
- lactam
- 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
- 150000003951 lactams Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims abstract description 6
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006462 rearrangement reaction Methods 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 abstract description 21
- 239000000839 emulsion Substances 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000010410 layer Substances 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 alicyclic hydrocarbons Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000003809 water extraction Methods 0.000 description 2
- RQXXCWHCUOJQGR-UHFFFAOYSA-N 1,1-dichlorohexane Chemical compound CCCCCC(Cl)Cl RQXXCWHCUOJQGR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、ラクタム油の精製方法に関する。詳しくは、
シクロヘキサノンオキシムとシクロドデカノンオキシム
との混合物を、ベックマン転位によりカプロラクタムと
ラウロラクタムを製造する方法において、生成したラク
タム油の効果的な精製方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for refining lactam oil. For more information,
The present invention relates to an effective method for purifying lactam oil produced in a method for producing caprolactam and laurolactam by Beckmann rearrangement of a mixture of cyclohexanone oxime and cyclododecanone oxime.
（従来の技術）
カプロラクタムとラウロラクタムとを製造する方法は、
シクロヘキサノンとシクロドデカノンとの混合物をオキ
シム化し、生成したシクロヘキサノンオキシム又はその
塩とシクロドデカノンオキシム又はその塩との混合物を
硫酸又は発煙硫酸の存在下にベックマン転位し、続いて
、アンモニアガス又はアンモニア水で中和してラクタム
混合物を取得し、そのラクタム混合物を、水と混和しな
い有機溶剤で抽出するか又はそのラクタム混合物の屡分
離によって、硫安水から分離されたラクタム油層（以下
、ラクタム油という）を水と混和しない有機溶剤で抽出
して、ラクタム成分を含む抽出液を得、更に、この抽出
液を水で逆抽出して、カプロラクタムを水層に移行させ
、ラウロラクタムを有機溶剤層に残存させる方法（以下
、コラクタム化法という）が知られている（例えば、特
公昭４６−７２５４号及び同４６−１０１６８号各公報
）。(Prior art) A method for producing caprolactam and laurolactam is as follows:
A mixture of cyclohexanone and cyclododecanone is converted into an oxime, and the resulting mixture of cyclohexanone oxime or its salt and cyclododecanone oxime or its salt is subjected to Beckmann rearrangement in the presence of sulfuric acid or fuming sulfuric acid, followed by ammonia gas or ammonia gas. The lactam oil layer (hereinafter referred to as lactam oil) is separated from the ammonium sulfate water by neutralizing with water to obtain a lactam mixture, and extracting the lactam mixture with an organic solvent that is immiscible with water, or frequently separating the lactam mixture. ) is extracted with an organic solvent that is immiscible with water to obtain an extract containing lactam components, and this extract is further back-extracted with water to transfer caprolactam to the aqueous layer and laurolactam to the organic solvent layer. A method of making it remain (hereinafter referred to as a colactamization method) is known (for example, Japanese Patent Publications No. 46-7254 and No. 46-10168).
このコラククム化法によるカプロラクタムとうクロラク
タムとの同時製造方法においては、従来前記ラクタム成
分を含む抽出液をそのまま水抽出していたが、この抽出
液中には、原料のシクロドデカノン中に含まれる直鎖状
又は分岐状のアルキルアルコールなどに起因するアルキ
ル硫酸塩などの陰イオン界面活性物質が存在しているた
めに、前記水抽出に際して、エマルジョンを形成し、有
機溶剤層と水層との分離不良等が起こり易く、塔径の大
きな抽出塔が必要となるとともに、水層中に有機物が同
伴して白濁し、カプロラクタムの品質に悪影響を及ぼし
たり、また、有機溶剤層へ水溶性の不純物が同伴してラ
ウロラクタムの品質にも悪影響を及ぼしていた。In this method of simultaneously producing caprolactam and chlorlactam using the corakucum conversion method, conventionally the extract containing the lactam component was directly extracted with water, but this extract contains the direct components contained in the raw material cyclododecanone. Due to the presence of anionic surfactants such as alkyl sulfates caused by chain or branched alkyl alcohols, an emulsion is formed during the water extraction, resulting in poor separation between the organic solvent layer and the aqueous layer. etc. are likely to occur, requiring a large diameter extraction column, and the aqueous layer may be entrained with organic matter, causing cloudiness, which may adversely affect the quality of caprolactam, and water-soluble impurities may be entrained into the organic solvent layer. This also had a negative effect on the quality of laurolactam.
（発明が解決しようとする課題）
本発明は、上記の問題を解決し、水抽出の際、エマルジ
ョンの形成がなく、短時間で容易に静置分離できるラク
タム油の精製方法を提供することを目的とする。(Problems to be Solved by the Invention) The present invention solves the above problems and provides a method for refining lactam oil that does not form an emulsion during water extraction and can be easily separated by standing in a short time. purpose.
Ｃ課題を解決するための手段）
本発明者らは、このため鋭意検討を重ねた結果、ラクタ
ム油のｐＨを特定の値に保って、ラクタムを有機溶剤で
抽出することによって、上記目的が達成できることを見
出し、本発明を完成するに至った。C) As a result of intensive studies, the present inventors have achieved the above object by keeping the pH of lactam oil at a specific value and extracting the lactam with an organic solvent. We have discovered that this can be done, and have completed the present invention.
すなわち、本発明は、シクロヘキサノンオキシムとシク
ロドデカノンオキシムとの混合物を硫酸及び発煙硫酸の
存在下に、ベックマン転位させて、カプロラクタムとラ
ウロラクタムを製造する方法において、転位反応で生成
したラクタム油の水層のｐＨを６〜１２に保って、水と
混和しない有機溶剤でカプロラクタムとラウロラクタム
を抽出することを特徴とするラクタム油の精製方法であ
る。That is, the present invention provides a method for producing caprolactam and laurolactam by subjecting a mixture of cyclohexanone oxime and cyclododecanone oxime to Beckmann rearrangement in the presence of sulfuric acid and fuming sulfuric acid. This method of purifying lactam oil is characterized by maintaining the pH of the layer at 6 to 12 and extracting caprolactam and laurolactam with an organic solvent that is immiscible with water.
以下に、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明で、ｐ）ｌ調整用に使用するアルカリ性物質とし
ては、アンモニア若しくはアンモニア水。In the present invention, the alkaline substance used for adjusting p)l is ammonia or aqueous ammonia.
水酸化ナトリウム、水酸化カリウム等のアルカリ金属水
酸化物、炭酸ナトリウム、炭酸カリウム等のアルカリ金
属炭酸化物、又はそれらの混合物が例示される。これら
の中で、アンモニア若しくはアンモニア水、水酸化ナト
リウム又は水酸化カリウム等が好適である６アンモニア
若しくはアンモニア水を使用する場合は、その一部が抽
出に用いる有機溶剤に混入するが、この場合稀硫酸等で
水洗して中和し、ｐＨを４〜８、好ましくは５〜７に再
調整することが望ましい、 ｐＨの再調整に使用する酸
性物質としては硫酸、塩酸等が挙げられる。Examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and mixtures thereof. Among these, ammonia or aqueous ammonia, sodium hydroxide, potassium hydroxide, etc. are preferred. 6 When ammonia or aqueous ammonia is used, a part of it will be mixed into the organic solvent used for extraction, but in this case it is rare. It is desirable to wash with water and neutralize with sulfuric acid or the like and readjust the pH to 4 to 8, preferably 5 to 7. Examples of acidic substances used for readjusting the pH include sulfuric acid and hydrochloric acid.
ラクタム油の中和は、水層すなわち重液側のｐＨを６〜
１２とすることが必要で、好ましくは７〜ＩＯの範囲に
調整する。Neutralization of lactam oil is done by adjusting the pH of the aqueous layer, i.e. the heavy liquid side, to 6-6.
12, preferably adjusted to a range of 7 to IO.
本発明で使用する有機溶剤としては、ベンゼン、トルエ
ン、キシレン、イソプロピルベンゼンなどの芳香族炭化
水素二ジクロヘキサン、シクロオクタンなどの脂環式炭
化水素：ｎ−ヘキサン、ｎ−へブタン、ｎ−オクタンな
どの炭素数６〜８の脂肪族炭化水素二トリクロルエチレ
ン、四塩化炭素、クロロホルムなどのハロゲン原子で置
換した炭化水素などの抽出温度で液体であり、水と混和
しない溶剤が挙げられるが、中でもベンゼン及びトルエ
ンを最も好適に挙げることができる。もちろん、上記の
溶剤の２種以上の混合物の使用が可能であることは言う
までもない。The organic solvents used in the present invention include aromatic hydrocarbons such as benzene, toluene, xylene, and isopropylbenzene; alicyclic hydrocarbons such as dichlorohexane and cyclooctane; n-hexane, n-hebutane, and n-octane; Examples include solvents that are liquid at the extraction temperature and are immiscible with water, such as hydrocarbons substituted with halogen atoms such as ditrichloroethylene, carbon tetrachloride, and chloroform, which have 6 to 8 carbon atoms. Benzene and toluene can be mentioned most preferably. Of course, it is possible to use mixtures of two or more of the above-mentioned solvents.
前記ラクタム油の有機溶剤による抽出の抽出温度、抽出
剤比率及び抽出時間などの抽出操作条件や抽出装置の型
式などの抽出方法は、通常の液−液抽出において適用さ
れる範囲のものであれば、特に限定されるものではなく
、抽出及びそれに続く冷却の結果得られる前記有機溶液
中のカプロラクタム及びラウロラクタムの含有量が、共
に、前記の１０〜２０重量％の範囲内になるように、前
記抽出操作条件や抽出方法を決定すればよい。The extraction operation conditions such as the extraction temperature, extractant ratio and extraction time for extraction of the lactam oil with an organic solvent, and the extraction method such as the type of extraction device may be within the range applicable to ordinary liquid-liquid extraction. , without particular limitation, so that the contents of caprolactam and laurolactam in the organic solution obtained as a result of extraction and subsequent cooling are both within the range of 10 to 20% by weight. What is necessary is to determine the extraction operation conditions and extraction method.
例えば、抽出温度について言えば、抽出装置内において
、前記ラクタム油や有機溶剤が液体として存在する温度
であり、従って、前記ラクタム油の融点以上、かつ抽出
の結果得られる抽出液や重液の沸点以下の温度範囲、好
ましくは４０〜８０℃であることが望ましい。また、抽
出装置も、工業的には、例えば、充填塔や目皿板式の１
苔など、自流式の液−液抽出装置を使用することが好ま
しい。For example, the extraction temperature is the temperature at which the lactam oil and organic solvent exist as a liquid in the extraction device, and is therefore higher than the melting point of the lactam oil and the boiling point of the extract liquid or heavy liquid obtained as a result of extraction. It is desirable that the temperature be in the following temperature range, preferably 40 to 80°C. In addition, extraction equipment is also used industrially, for example, packed towers or perforated plates.
It is preferable to use a self-flowing liquid-liquid extractor, such as moss.
以上述べたｐＨの調整によって抽出時のエマルジョンの
発生が大巾に減少するか又は消失し、層分離が短時間に
効果的に実施できるようになる。By adjusting the pH as described above, the generation of emulsions during extraction is greatly reduced or eliminated, and layer separation can be carried out effectively in a short period of time.
これはラクタム油に不純物として含有されていたアルキ
ル硫酸塩等の界面活性物質が、水層側すなわち重液側に
移行し易くなるためである。This is because surface active substances such as alkyl sulfates contained in lactam oil as impurities tend to migrate to the water layer side, that is, the heavy liquid side.
更に、本発明の大きな利点として、ラクタム油中の着色
性不純物も、ｐＨの調整によって重液側に移行するため
ラクタムの品質が、−段と向上するものである。Furthermore, a great advantage of the present invention is that the coloring impurities in the lactam oil are also transferred to the heavy liquid side by adjusting the pH, so that the quality of the lactam is significantly improved.
（実施例）
以下、実施例を挙げ、本発明を更に詳しく説明するが、
本発明は、これによりその範囲が限定されるものではな
い。(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples.
The scope of the present invention is not limited thereby.
実施例１
カプロラクタム４０重量％、ラウロラクタム４４重量％
及び水分１２重量％を含むラクタム油４００ｇを撹拌機
を備えたガラス容器（容量５ｆ２）に仕込み、次いて、
１５８０ｇのトルエンを加え、温度６８℃で撹拌しなが
ら、ｐＨが８となるようにアンモニアガスを吹き込み、
そのまま１０分間撹拌した後静置分離すると、１９，３
重 ′量％のカプロラクタムと１６重量％のラ
ウロラクタムを含む分離重液３８ｇと、８０重量％のカ
プロラクタムと９．２重量％のラウロラクタムを含むト
ルエン溶液（以下、「トルエン溶液−１」という）１９
２６ｇが得られた。Example 1 40% by weight of caprolactam, 44% by weight of laurolactam
and 400 g of lactam oil containing 12% water by weight were charged into a glass container (capacity 5 f2) equipped with a stirrer, and then,
Add 1,580 g of toluene, and while stirring at a temperature of 68°C, blow in ammonia gas so that the pH becomes 8.
After stirring for 10 minutes and separating by standing, 19,3
38 g of separated heavy liquid containing 16% by weight of caprolactam and 16% by weight of laurolactam, and a toluene solution containing 80% by weight of caprolactam and 9.2% by weight of laurolactam (hereinafter referred to as "toluene solution-1") 19
26g was obtained.
この重液を分離した「トルエン溶液−１」の−部８００
ｇに、更に水５１０ｇを加えて５８〜６２℃で撹拌混合
し、カプロラクタムを水層側へ逆抽出したところ、エマ
ルジョンの生成もなく短時間の静置分離で容易に分離し
、９９重量％のラウロラクタムを含む有機層（トルエン
層）７３３ｇと、９８重量％のカプロラクタムを含む水
層５６６ｇとが得られた。-800 parts of "toluene solution-1" from which this heavy liquid was separated
When 510 g of water was further added and mixed at 58 to 62°C with stirring, and caprolactam was back-extracted to the aqueous layer, it was easily separated by standing for a short time without forming an emulsion, and 99% by weight of caprolactam was obtained. 733 g of an organic layer (toluene layer) containing laurolactam and 566 g of an aqueous layer containing 98% by weight of caprolactam were obtained.
実施例２
実施例１で得た「トルエン溶液−ＩＪ １０００ｇに、
更に１９ｇの水を加え、撹拌しなから７５％硫酸を添加
してｐＨ６に調整した。そのまま６６〜６８°Ｃで１０
分間攪拌した後、静置分離すると、１７７重量％のカプ
ロラクタムと０９重量％のラウロラクタムとを含む分離
重液２９ｇと、７．６重量％のカプロラクタムと９３重
量％のラウロラクタムとを含むトルエン抽出液９８８ｇ
が得られた。Example 2 To 1000 g of toluene solution-IJ obtained in Example 1,
Further, 19 g of water was added, and while stirring, 75% sulfuric acid was added to adjust the pH to 6. 10 at 66-68°C
After stirring for a minute and separating by standing, 29 g of separated heavy liquid containing 177% by weight of caprolactam and 0.9% by weight of laurolactam and toluene extraction containing 7.6% by weight of caprolactam and 93% by weight of laurolactam are obtained. 988g of liquid
was gotten.
得られたトルエン抽出液に、さらに６００ｇの水を加え
て５８〜６２℃で撹拌混合し、カプロラクタムを水層側
へ逆抽出したところエマルジョンの生成もなく、短時間
の静置で容易に分離した。An additional 600 g of water was added to the obtained toluene extract and mixed with stirring at 58 to 62°C, and caprolactam was back-extracted to the aqueous layer. No emulsion was formed, and it was easily separated by standing for a short time. .
比較例１
ラクタム油をトルエンで抽出する時に、アンモニアガス
でのｐＨ調整をしなかった他は、実施例１と同様に行い
、「トルエン溶液−１」を得た。この際、ラクタム油を
トルエンで抽出したときのｐＨ値は４８であった。得ら
れた「トルエン溶液−１」に水１２３０ｇを加え逆抽出
したところ、エマルジョンが生成し、撹拌停止後３０分
間静置しても、有機層と水層の分離ができなかった。Comparative Example 1 "Toluene Solution-1" was obtained in the same manner as in Example 1, except that when extracting lactam oil with toluene, the pH was not adjusted with ammonia gas. At this time, the pH value when the lactam oil was extracted with toluene was 48. When 1,230 g of water was added to the obtained "Toluene Solution-1" and back extracted, an emulsion was formed, and the organic layer and the aqueous layer could not be separated even if the emulsion was allowed to stand for 30 minutes after stopping stirring.
（発明の効果）
以上のように、本発明によれば、コラクタム油の精製の
際、エマルジョンを形成することなく、極めて効率的に
抽出液を分離することができる。(Effects of the Invention) As described above, according to the present invention, during the purification of colactam oil, an extract can be separated very efficiently without forming an emulsion.
Claims (1)
との混合物を、硫酸及び発煙硫酸の存在下に、ベックマ
ン転位させて、カプロラクタムとラウロラクタムを製造
する方法において、転位反応で生成したラクタム油の水
層のｐＨを６〜１２に保って、水と混和しない有機溶剤
でカプロラクタムとラウロラクタムを抽出することを特
徴とするラクタム油の精製方法In a method for producing caprolactam and laurolactam by subjecting a mixture of cyclohexanone oxime and cyclododecanone oxime to Beckmann rearrangement in the presence of sulfuric acid and oleum, the pH of the aqueous layer of lactam oil produced by the rearrangement reaction is set to 6. 12 and extracting caprolactam and laurolactam with an organic solvent that is immiscible with water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314205A JP2601945B2 (en) | 1990-11-21 | 1990-11-21 | Lactam oil refining method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314205A JP2601945B2 (en) | 1990-11-21 | 1990-11-21 | Lactam oil refining method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04187671A true JPH04187671A (en) | 1992-07-06 |
| JP2601945B2 JP2601945B2 (en) | 1997-04-23 |
Family
ID=18050541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2314205A Expired - Lifetime JP2601945B2 (en) | 1990-11-21 | 1990-11-21 | Lactam oil refining method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2601945B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3498758A1 (en) * | 2017-12-13 | 2019-06-19 | Evonik Degussa GmbH | Method for the preparation of polymers from monomers comprising laurolactam |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4852785A (en) * | 1971-10-29 | 1973-07-24 | ||
| JPS5262289A (en) * | 1975-11-13 | 1977-05-23 | Bayer Ag | Purification of caprolactam |
| JPS53147085A (en) * | 1977-05-28 | 1978-12-21 | Bayer Ag | Method of purifying caprolactum |
| JPS60199873A (en) * | 1984-03-23 | 1985-10-09 | Ube Ind Ltd | Recovery of epsilon-caprolactam |
-
1990
- 1990-11-21 JP JP2314205A patent/JP2601945B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4852785A (en) * | 1971-10-29 | 1973-07-24 | ||
| JPS5262289A (en) * | 1975-11-13 | 1977-05-23 | Bayer Ag | Purification of caprolactam |
| JPS53147085A (en) * | 1977-05-28 | 1978-12-21 | Bayer Ag | Method of purifying caprolactum |
| JPS60199873A (en) * | 1984-03-23 | 1985-10-09 | Ube Ind Ltd | Recovery of epsilon-caprolactam |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3498758A1 (en) * | 2017-12-13 | 2019-06-19 | Evonik Degussa GmbH | Method for the preparation of polymers from monomers comprising laurolactam |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2601945B2 (en) | 1997-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2782919B2 (en) | Method for purifying lactam-containing organic solution | |
| US5245029A (en) | Ion exchange purification method of aqueous caprolactam solution | |
| US4036830A (en) | Process for the recovery of pure ε-caprolactam from an aqueous solution thereof | |
| NL1005927C2 (en) | Method for recovering caprolactam from a neutralized rearrangement mixture. | |
| JP2003534321A (en) | Lactam purification method | |
| JPH04187671A (en) | Method for purifying lactam oil | |
| JP2020514350A (en) | Method for purification of caprolactam from solution of crude caprolactam without organic solvent extraction | |
| US4239682A (en) | Purification of caprolactam | |
| US3794647A (en) | Process for purifying lactams | |
| DE2163259A1 (en) | Process for purifying lactams | |
| JP2601946B2 (en) | Method for purifying lactam-containing solution | |
| US2993889A (en) | Separation of a lactam from an acid | |
| US3544562A (en) | Process for the manufacture of omega-decalactam using epsilon-caprolactam as a solvent therefor | |
| JP2649736B2 (en) | Purification of lactam-containing organic solutions | |
| US2797216A (en) | Production of caprolagtam | |
| JPH03275663A (en) | Preparation of paraffin sulfonic acid | |
| US4015946A (en) | Process for recovering ammonium sulphate from aqueous solutions of ammonium sulphate which contain organic compounds | |
| US3248388A (en) | 6alpha-fluoro-delta1, 4-pregnadien-16alpha, 17alpha, 21-triol-3, 20-diones and intermediates in the production thereof | |
| EP0787039A1 (en) | Process for reprocessing and utilizing boron trifluoride catalyst residues | |
| CA1132546A (en) | Method for the prufication of raw caprolactam which contains amides and other by-products | |
| JP2559068B2 (en) | Method for producing aqueous 4-hydroxyacetophenone stable at room temperature | |
| DE2532308C3 (en) | Process for separating serotonin from coffee wax | |
| SU145585A1 (en) | The method of extraction of E-caprolactam | |
| JPS6293251A (en) | Production of 2-alkylanthraquinone | |
| RU2030385C1 (en) | Method of benzoic acid isolation from industrial waste at its production |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080129 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090129 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090129 Year of fee payment: 12 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100129 Year of fee payment: 13 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110129 Year of fee payment: 14 |
|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110129 Year of fee payment: 14 |