JPH0319225B2 - - Google Patents
Info
- Publication number
- JPH0319225B2 JPH0319225B2 JP61078169A JP7816986A JPH0319225B2 JP H0319225 B2 JPH0319225 B2 JP H0319225B2 JP 61078169 A JP61078169 A JP 61078169A JP 7816986 A JP7816986 A JP 7816986A JP H0319225 B2 JPH0319225 B2 JP H0319225B2
- Authority
- JP
- Japan
- Prior art keywords
- maleimide
- weight
- carbon dioxide
- pressure
- temperature
- 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 - Lifetime
Links
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 82
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 66
- 239000001569 carbon dioxide Substances 0.000 claims description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 26
- 239000012043 crude product Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 21
- -1 amine compound Chemical class 0.000 description 16
- MFBWWGXSZLGPRU-UHFFFAOYSA-N 1-octadec-1-enylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CN1C(=O)C=CC1=O MFBWWGXSZLGPRU-UHFFFAOYSA-N 0.000 description 15
- 239000000539 dimer Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- KIKBJYQCJJXCBZ-UHFFFAOYSA-N 1-octylpyrrole-2,5-dione Chemical compound CCCCCCCCN1C(=O)C=CC1=O KIKBJYQCJJXCBZ-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- PZQWVKKXPIZFHC-UHFFFAOYSA-N 1-decylpyrrole-2,5-dione Chemical compound CCCCCCCCCCN1C(=O)C=CC1=O PZQWVKKXPIZFHC-UHFFFAOYSA-N 0.000 description 1
- GHPSXHPCIXRTFW-UHFFFAOYSA-N 1-dodec-1-enylpyrrole-2,5-dione Chemical compound CCCCCCCCCCC=CN1C(=O)C=CC1=O GHPSXHPCIXRTFW-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- KZCSJWFLPQFDNW-UHFFFAOYSA-N 1-ethenylpyrrole-2,5-dione Chemical compound C=CN1C(=O)C=CC1=O KZCSJWFLPQFDNW-UHFFFAOYSA-N 0.000 description 1
- UMUNOXKIUHCIIR-UHFFFAOYSA-N 1-heptadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O UMUNOXKIUHCIIR-UHFFFAOYSA-N 0.000 description 1
- COEKMFUFXAWJGI-UHFFFAOYSA-N 1-heptylpyrrole-2,5-dione Chemical compound CCCCCCCN1C(=O)C=CC1=O COEKMFUFXAWJGI-UHFFFAOYSA-N 0.000 description 1
- QKMBVFKXQWIKOZ-UHFFFAOYSA-N 1-hexadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCN1C(=O)C=CC1=O QKMBVFKXQWIKOZ-UHFFFAOYSA-N 0.000 description 1
- FBPVUBVZRPURIU-UHFFFAOYSA-N 1-hexylpyrrole-2,5-dione Chemical compound CCCCCCN1C(=O)C=CC1=O FBPVUBVZRPURIU-UHFFFAOYSA-N 0.000 description 1
- NXPHNRSAYBXVMF-UHFFFAOYSA-N 1-icosylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O NXPHNRSAYBXVMF-UHFFFAOYSA-N 0.000 description 1
- ROEZFSDXTWGAQU-UHFFFAOYSA-N 1-nonadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O ROEZFSDXTWGAQU-UHFFFAOYSA-N 0.000 description 1
- UNJAMUMWPRRGHF-UHFFFAOYSA-N 1-nonylpyrrole-2,5-dione Chemical compound CCCCCCCCCN1C(=O)C=CC1=O UNJAMUMWPRRGHF-UHFFFAOYSA-N 0.000 description 1
- HOLZCMFSCBLOLX-UHFFFAOYSA-N 1-octadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCN1C(=O)C=CC1=O HOLZCMFSCBLOLX-UHFFFAOYSA-N 0.000 description 1
- JHKVBRBZDVWQOE-UHFFFAOYSA-N 1-pentadecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCCN1C(=O)C=CC1=O JHKVBRBZDVWQOE-UHFFFAOYSA-N 0.000 description 1
- CZUQOPAKOZMIPQ-UHFFFAOYSA-N 1-pentylpyrrole-2,5-dione Chemical compound CCCCCN1C(=O)C=CC1=O CZUQOPAKOZMIPQ-UHFFFAOYSA-N 0.000 description 1
- XJVXUUFIBPLYFK-UHFFFAOYSA-N 1-prop-1-enylpyrrole-2,5-dione Chemical compound CC=CN1C(=O)C=CC1=O XJVXUUFIBPLYFK-UHFFFAOYSA-N 0.000 description 1
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 1
- FDQMDCGTDRRHJO-UHFFFAOYSA-N 1-tetradecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCCN1C(=O)C=CC1=O FDQMDCGTDRRHJO-UHFFFAOYSA-N 0.000 description 1
- AACVWGWQMWGCFL-UHFFFAOYSA-N 1-tridecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCCN1C(=O)C=CC1=O AACVWGWQMWGCFL-UHFFFAOYSA-N 0.000 description 1
- SGWFSFTYSPSADW-UHFFFAOYSA-N 1-undecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCN1C(=O)C=CC1=O SGWFSFTYSPSADW-UHFFFAOYSA-N 0.000 description 1
- VOYQCFMGTRPFKT-UHFFFAOYSA-N 3-octylpyrrole-2,5-dione Chemical compound CCCCCCCCC1=CC(=O)NC1=O VOYQCFMGTRPFKT-UHFFFAOYSA-N 0.000 description 1
- OCKONLRSFDLRRU-UHFFFAOYSA-N C(=CCCC)N1C(C=CC1=O)=O Chemical compound C(=CCCC)N1C(C=CC1=O)=O OCKONLRSFDLRRU-UHFFFAOYSA-N 0.000 description 1
- RSBQNXCLOVEWFN-UHFFFAOYSA-N CCC=CN1C(=O)C=CC1=O Chemical compound CCC=CN1C(=O)C=CC1=O RSBQNXCLOVEWFN-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は新規なマレイミドの精製方法に関す
る。詳しくは、超臨界状態の二酸化炭素を用いて
マレイミドの粗製物からマレイミドを抽出分離す
るマレイミドの精製方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a novel method for purifying maleimide. Specifically, the present invention relates to a method for purifying maleimide in which maleimide is extracted and separated from a crude product of maleimide using carbon dioxide in a supercritical state.
マレイミドは樹脂原料、医薬品、農薬等の原料
として広く使用されている。 Maleimide is widely used as a raw material for resins, pharmaceuticals, agricultural chemicals, etc.
（従来技術）
マレイミドを製造する方法としては各種のもの
が知られている。一般的なものとしては、
(1) 無水マレイン酸とアミン化合物とを有機溶媒
中で反応させ生成するマレインアミド酸類を単
離し、単離したマレインアミド酸類を無水酢酸
のような脱水剤を用いてイミド化させる方法が
米国特許第2444536号明細書に開示されている。(Prior Art) Various methods are known for producing maleimide. Generally speaking, (1) Maleamic acids produced by reacting maleic anhydride with an amine compound in an organic solvent are isolated, and the isolated maleamic acids are treated with a dehydrating agent such as acetic anhydride. A method of imidization is disclosed in US Pat. No. 2,444,536.
(2) 単離したマレインアミド酸類をトルエン、キ
シレン、クロロベンゼンなどの有機溶剤を稀釈
剤として用い、酸触媒の存在下に加熱してイミ
ド化させる方法が特公昭57−42043号公報明細
書に開示されている。(2) Japanese Patent Publication No. 57-42043 discloses a method of imidizing isolated maleamidic acids by heating them in the presence of an acid catalyst using an organic solvent such as toluene, xylene, or chlorobenzene as a diluent. has been done.
(3) 稀釈剤を用いずにマレインアミド酸類を酸触
媒の存在下に直接加熱してイミド化させる方法
が特開昭47−27974号公報明細書に開示されて
いる。(3) JP-A-47-27974 discloses a method of imidizing maleamidic acids by directly heating them in the presence of an acid catalyst without using a diluent.
(4) 生成したマレインアミド酸類を有機溶媒から
単離することなしにこの反応混合物に酸触媒を
添加してイミド化する方法が特公昭51−40078
号、特開昭53−68770号および特公昭59−42043
号各公報明細書等に数多く開示されている。(4) A method of imidizing the generated maleamic acids by adding an acid catalyst to the reaction mixture without isolating them from the organic solvent was disclosed in Japanese Patent Publication No. 51-40078.
No., JP-A-53-68770 and JP-A-59-42043
There are many disclosures in the specifications of each publication.
しかしながらこれらの何れのマレイミドの製造
方法においても問題があり、イミド化反応の過程
において無視しえない量の副生成物が生成し、高
純度のマレイミドを得ようとすれば精製する必要
がある。 However, there are problems with any of these methods for producing maleimide; a non-negligible amount of by-products are produced during the imidization reaction, and purification is required in order to obtain highly pure maleimide.
従来、マレイミドの精製方法としては、
従来、マレイミドの精製方法としては、
(1) 反応液を大量の冷水中へ注入して、析出する
結晶を別し、この結晶を更に多量の水で洗浄
したり、或いは稀薄な炭酸ナトリウム水溶液や
苛性ソーダ水溶液で洗浄したのち乾燥させる方
法が特開昭55−149253号公報明細書に開示され
ている。 Conventionally, maleimide purification methods have been as follows: (1) The reaction solution is injected into a large amount of cold water, the precipitated crystals are separated, and the crystals are washed with an even larger amount of water. JP-A-55-149253 discloses a method in which the material is washed with a dilute aqueous sodium carbonate solution or a dilute aqueous caustic soda solution and then dried.
(2) マレイミド含有の有機溶媒の反応液を稀薄な
弱アルカリ水溶液で中和後、水洗し、有機溶媒
を分離する方法が特開昭53−68770号公報明細
書に開示されている。(2) JP-A-53-68770 discloses a method in which a reaction solution of an organic solvent containing maleimide is neutralized with a dilute aqueous weak alkaline solution and then washed with water to separate the organic solvent.
しかし、上記のような方法では、イミド化工程
で生成する副生成物が樹脂状の物質やマレイミド
と同様に水に不溶性の物質であるため高純度のマ
レイミドを得ることは困難である。 However, with the above method, it is difficult to obtain highly pure maleimide because by-products produced in the imidization step are resinous substances and substances insoluble in water like maleimide.
（発明が解決しようとする問題点）
マレイミドには蒸留による精製方法もあるが、
マレイミドは沸点が高く、しかもその分子内に反
応性に富むエチレン型不飽和結合を有しているた
めに蒸留塔内で加熱されることにより重合、分
解、着色が促進される。(Problem to be solved by the invention) Maleimide can be purified by distillation, but
Since maleimide has a high boiling point and has a highly reactive ethylenically unsaturated bond in its molecule, polymerization, decomposition, and coloration are promoted by heating in a distillation column.
その結果、蒸留精製収率が低く、しかも分解に
よつて生成する不純物が製品に混入し、製品の品
質を低下させている。 As a result, the distillation purification yield is low, and impurities generated by decomposition are mixed into the product, degrading the quality of the product.
一方、再結晶法または分別結晶法ではマレイミ
ドの粗製物に含まれているダイマー等の分離が十
分に行なえず、しかも溶媒の除去に多大のエネル
ギーを要し、しかも溶媒の完全な除去が不可能で
あるなど、従来の技術では精製収率、品質、純度
の点で満足のできる製品を得ることが困難であつ
た。 On the other hand, the recrystallization method or the fractional crystallization method cannot sufficiently separate the dimer etc. contained in the crude maleimide, and furthermore, it requires a large amount of energy to remove the solvent, and it is impossible to completely remove the solvent. With conventional techniques, it has been difficult to obtain products that are satisfactory in terms of purification yield, quality, and purity.
本発明者等は上記問題点を解決するため鋭意検
討した結果、マレイミドがそのダイマー、重合高
分子、着色物質など、粗マレイミドに含まれる不
純物に比較し、格段に超臨界二酸化炭素への溶解
度が大きく、そのためマレイミドの粗製物に超臨
界状態の二酸化炭素を接触させることにより、マ
レイミドの粗製物から主としてマレイミドを超臨
界二酸化炭素に抽出溶解させ、マレイミドの溶解
度が温度または／および圧力を低下させることに
よつて著しく低下することを利用して高純度のマ
レイミドを分離回収できることを見い出し、本発
明を完成した。 As a result of intensive studies to solve the above problems, the present inventors found that maleimide has a much lower solubility in supercritical carbon dioxide than impurities contained in crude maleimide, such as dimers, polymerized polymers, and colored substances. Therefore, by bringing the crude product of maleimide into contact with carbon dioxide in a supercritical state, mainly maleimide from the crude product of maleimide is extracted and dissolved in the supercritical carbon dioxide, and the solubility of maleimide is reduced by lowering the temperature and/or pressure. The present invention was completed based on the discovery that highly pure maleimide can be separated and recovered by taking advantage of the fact that maleimide is significantly reduced by .
（問題を解決するための手段）
本発明は
一般式、
〔式中、Ｒは炭素数１〜20のアルキル基、炭素
数２〜20のアルケニル基またはシクロアルキル基
を示す。〕
で示されるマレイミドの粗製物に超臨界状態の二
酸化炭素を接触させて得られる、マレイミドを含
有する二酸化炭素からマレイミドを分離回収する
ことを特徴とするマレイミドの精製方法に関する
ものである。(Means for solving the problem) The present invention has the general formula: [In the formula, R represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or a cycloalkyl group. ] This invention relates to a method for purifying maleimide, which is characterized by separating and recovering maleimide from carbon dioxide containing maleimide, which is obtained by contacting the crude product of maleimide shown in the following with carbon dioxide in a supercritical state.
本発明の超臨界状態の二酸化炭素は、温度31.1
℃〜200℃、圧力が74.2〜500Kg／cm2Ｇ、好ましく
は温度40〜140℃、圧力75〜300Kg／cm2Ｇの範囲が
抽出条件として採用できる。 The supercritical carbon dioxide of the present invention has a temperature of 31.1
C. to 200.degree. C. and pressure of 74.2 to 500 kg/ cm.sup.2G , preferably temperature of 40 to 140.degree. C. and pressure of 75 to 300 kg/ cm.sup.2G .
本発明の抽出条件は、温度および圧力が共に高
い方がマレイミドの溶解度が大きく、抽出効率を
向上させることができる。 Regarding the extraction conditions of the present invention, the higher the temperature and pressure are, the higher the solubility of maleimide is, and the extraction efficiency can be improved.
しかし抽出圧力を高めることは一方で高圧設備
の費用の増大を招き、経済性の問題を生じる。ま
た抽出温度を上げることは抽出目的物であるマレ
イミドの重合、分解、着色等の変質を促進させる
ものである。 However, increasing the extraction pressure on the other hand increases the cost of high-pressure equipment, creating an economical problem. In addition, raising the extraction temperature promotes alterations such as polymerization, decomposition, and coloring of maleimide, which is the object of extraction.
一方、マレイミドを含む二酸化炭素から、マレ
イミドを分離するには温度を下げ、または／およ
び圧力を下げ、その結果溶解度を下げることによ
つてマレイミドのみを析出させる方法がある。 On the other hand, in order to separate maleimide from carbon dioxide containing maleimide, there is a method of precipitating only maleimide by lowering the temperature and/or pressure, thereby lowering the solubility.
本発明が対象とするマレイミドの粗製物は従来
公知の製造方法によつて得られるものである。す
なわち、原料マレインアミド酸類は通常無水マレ
イン酸とアミン類との反応により容易に得られる
ものであり、このもののイミド化閉環反応として
は、本明細書の従来技術の項で既に記述したよう
に、トルエン、キシレン、クロロベンゼンなどの
有機溶剤を稀釈剤として用いて酸触媒の存在下加
熱してイミド化させる方法、稀釈剤を用いない
で、マレインアミド酸類を酸触媒の存在下に直接
加熱してイミド化させる方法、あるいは無水酢酸
のような脱水剤を用いてイミド化させる方法、酸
触媒および安定剤、金属含有化合物の存在下、有
機溶媒を稀釈剤として用い、加熱してイミド化さ
せる方法などがあり、いずれの方法によつて製造
されるマレイミドの粗製物も本発明の精製方法は
優れた効果を与える。 The crude product of maleimide to which the present invention is directed is obtained by a conventionally known production method. That is, the raw material maleamic acids are usually easily obtained by the reaction of maleic anhydride and amines, and the imidization ring-closing reaction of these acids is performed by, as already described in the prior art section of this specification, A method of imidization by heating in the presence of an acid catalyst using an organic solvent such as toluene, xylene, or chlorobenzene as a diluent, or a method of imidizing maleamic acids by heating directly in the presence of an acid catalyst without using a diluent. or imidization using a dehydrating agent such as acetic anhydride, or heating to imidize using an organic solvent as a diluent in the presence of an acid catalyst, stabilizer, or metal-containing compound. The purification method of the present invention provides excellent effects on the crude maleimide produced by either method.
上述の方法によつて得られるマレイミドは例え
ば一般式、
〔式中、Ｒは炭素数１〜20のアルキル基、好ま
しくは炭素数８〜20のアルキル基、炭素数２〜20
のアルケニル基好ましくは炭素数８〜20のアルケ
ニル基またはシクロアルキル基を示す。〕
で表わされるものであり、さらに具体的に例示す
るならば、Ｎ−メチルマレイミド、Ｎ−エチルマ
レイミド、Ｎ−プロピルマレイミド、Ｎ−ブチル
マレイミド、Ｎ−ペンチルマレイミド、Ｎ−ヘキ
シルマレイミド、Ｎ−ヘプチルマレイミド、Ｎ−
オクチルマレイミド、Ｎ−ノニルマレイミド、Ｎ
−デシルマレイミド、Ｎ−ウンデシルマレイミ
ド、Ｎ−ドデシルマレイミド、Ｎ−トリデシルマ
レイミド、Ｎ−テトラデシルマレイミド、Ｎ−ペ
ンタデシルマレイミド、Ｎ−ヘキサデシルマレイ
ミド、Ｎ−ヘプタデシルマレイミド、Ｎ−オクタ
デシルマレイミド、Ｎ−ノナデシルマレイミド、
Ｎ−エイコシルマレイミド等のＮ−アルキルマレ
イミドが挙げられる。また、Ｎ−エテニルマレイ
ミド、Ｎ−プロペニルマレイミド、Ｎ−ブテニル
マレイミド、Ｎ−ペンテニルマレイミド、Ｎ−ヘ
キセニルマレイミド、Ｎ−ヘプテニルマレイミ
ド、Ｎ−オクテニルマレイミド、Ｎ−ノネニルマ
レイミド、Ｎ−デセニルマレイミド、Ｎ−ウンデ
セニルマレイミド、Ｎ−ドデセニルマレイミド、
Ｎ−トリデセニルマレイミド、Ｎ−テトラデセニ
ルマレイミド、Ｎ−ペンタデセニルマレイミド、
Ｎ−ヘキサデセニルマレイミド、Ｎ−ヘプタデセ
ニルマレイミド、Ｎ−オクタデセニルマレイミド
（Ｎ−オレイルマレイミド）、Ｎ−ノナデセニルマ
レイミド、Ｎ−エイコセニルマレイミド等のＮ−
アルケニルマレイミドまたはＮ−シクロヘキシル
マレイミド等のＮ−シクロアルキルマレイミドが
挙げられる。 The maleimide obtained by the above method has, for example, the general formula: [In the formula, R is an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 8 to 20 carbon atoms, and 2 to 20 carbon atoms.
The alkenyl group preferably represents an alkenyl group or a cycloalkyl group having 8 to 20 carbon atoms. ], and more specific examples include N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-pentylmaleimide, N-hexylmaleimide, N-heptyl Maleimide, N-
Octylmaleimide, N-nonylmaleimide, N
-decylmaleimide, N-undecylmaleimide, N-dodecylmaleimide, N-tridecylmaleimide, N-tetradecylmaleimide, N-pentadecylmaleimide, N-hexadecylmaleimide, N-heptadecylmaleimide, N-octadecylmaleimide, N-nonadecylmaleimide,
Examples include N-alkylmaleimides such as N-eicosylmaleimide. Also, N-ethenylmaleimide, N-propenylmaleimide, N-butenylmaleimide, N-pentenylmaleimide, N-hexenylmaleimide, N-heptenylmaleimide, N-octenylmaleimide, N-nonenylmaleimide, N-de Cenylmaleimide, N-undecenylmaleimide, N-dodecenylmaleimide,
N-tridecenylmaleimide, N-tetradecenylmaleimide, N-pentadecenylmaleimide,
N- such as N-hexadecenylmaleimide, N-heptadecenylmaleimide, N-octadecenylmaleimide (N-oleylmaleimide), N-nonadecenylmaleimide, N-eicosenylmaleimide, etc.
N-cycloalkylmaleimides such as alkenylmaleimide or N-cyclohexylmaleimide are mentioned.
（作用）
本発明によれば、超臨界二酸化炭素はマレイミ
ドに対して高い溶解能を有する。そのため、高い
沸点を有するマレイミドを、マレイミドの粗製物
から比較的低い温度で溶解し抽出することができ
る。そうすることによつて、マレイミドはその分
子内に反応性に富む二重結合を有するにもかかわ
らず、抽出操作中に重合、分解、着色物質生成等
によるマレイミドの損失および品質劣化が起るこ
とを防ぐことができる。(Function) According to the present invention, supercritical carbon dioxide has a high ability to dissolve maleimide. Therefore, maleimide having a high boiling point can be dissolved and extracted from crude maleimide at a relatively low temperature. By doing so, even though maleimide has a highly reactive double bond in its molecule, loss of maleimide and quality deterioration due to polymerization, decomposition, formation of colored substances, etc. will occur during the extraction operation. can be prevented.
また、超臨界二酸化炭素はマレイミドに対して
マレイミドの粗製物中に含有される重合物、分解
物、着色物質等の不純物に比較して、格段に大き
な溶解能を有する。 In addition, supercritical carbon dioxide has a much greater ability to dissolve maleimide than impurities such as polymers, decomposition products, and colored substances contained in the crude product of maleimide.
したがつて、超臨界二酸化炭素を使用すること
によつて、マレイミドの粗製物からほとんどマレ
イミドのみを選択的に抽出することができる。さ
らには、マレイミドの粗製物を超臨界二酸化炭素
抽出処理して得られるマレイミドを含有する二酸
化炭素からマレイミドを分離するには、単に温度
または／および圧力を下げるだけで良く、重合、
分解等の起こる危険性のある加熱操作を必要とし
ない。 Therefore, by using supercritical carbon dioxide, almost only maleimide can be selectively extracted from the maleimide crude product. Furthermore, in order to separate maleimide from carbon dioxide containing maleimide obtained by subjecting crude maleimide to supercritical carbon dioxide extraction, it is sufficient to simply lower the temperature and/or pressure;
Does not require heating operations that may cause decomposition.
したがつて、本発明によればマレイミドの粗製
物に超臨界二酸化炭素を作用させることによつ
て、マレイミドの純度・品質の良好なものをしか
も収率よく得ることができる作用を有する。 Therefore, according to the present invention, maleimide having good purity and quality can be obtained in good yield by allowing supercritical carbon dioxide to act on a crude product of maleimide.
（実施例）
以下、本発明の実施例を示すが、本発明はこれ
らに限定されるものでない。(Examples) Examples of the present invention will be shown below, but the present invention is not limited thereto.
実施例 １
Ｎ−オクチルマレイミド75重量％、ダイマー15
重量％およびポリマー、その他10重量％の組成の
マレイミドの粗組物40.0gを0.3lのステンレス製耐
圧容器に仕込み、ガス吹き込み口より、温度50
℃、圧力200Kg／cm2Ｇの超臨界二酸化炭素を供給
し、容器内を温度50℃、圧力200Kg／cm2Ｇに保ち
ながら、一方のガス抜き出し口から連続的にＮ−
オクチルマレイミドを含有する超臨界二酸化炭素
を抜き出し、セパレーターで常温、大気圧とし二
酸化炭素と抽出物26.4gとに分離した。得られた
抽出物は白色結晶であり、その組成はＮ−オクチ
ルマレイミド98重量％、その他２重量％であつ
た。Example 1 N-octylmaleimide 75% by weight, dimer 15
40.0g of maleimide coarse assembly with a composition of 10% by weight, polymer, and other materials was placed in a 0.3L stainless steel pressure-resistant container, and heated to a temperature of 50% from the gas inlet.
℃ and a pressure of 200 Kg/cm 2 G, and while keeping the inside of the container at a temperature of 50 ℃ and a pressure of 200 Kg/cm 2 G, N- was continuously supplied from one gas outlet.
Supercritical carbon dioxide containing octylmaleimide was extracted and separated into carbon dioxide and 26.4 g of extract at room temperature and atmospheric pressure using a separator. The obtained extract was white crystals, and its composition was 98% by weight of N-octylmaleimide and 2% by weight of other substances.
実施例 ２
Ｎ−オクタデセニル（Ｎ−オレイル）マレイミ
ド65重量％、ダイマー15重量％およびポリマー、
その他20重量％の組成のマレイミドの粗製物
40.0gを0.3lのステンレス製耐圧容器に仕込み、ガ
ス吹き口より、温度50℃、圧力200Kg／cm2Ｇの超
臨界二酸化炭素を供給し、容器内を温度50℃、圧
力200Kg／cm2Ｇに保ちながら、一方のガス抜き出
し口から連続的にＮ−オクタデセニルマレイミド
を含有する超臨界二酸化炭素を抜き出し、セパレ
ーターで常温、大気圧とし二酸化炭素と抽出物
21.8gとに分離した。Example 2 65% by weight N-octadecenyl (N-oleyl)maleimide, 15% by weight dimer and polymer,
Other crude maleimide with a composition of 20% by weight
40.0g was placed in a 0.3L stainless steel pressure-resistant container, and supercritical carbon dioxide was supplied from the gas outlet at a temperature of 50℃ and a pressure of 200Kg/cm 2 G, and the inside of the container was heated to a temperature of 50℃ and a pressure of 200Kg/cm 2 G Supercritical carbon dioxide containing N-octadecenylmaleimide is continuously extracted from one gas outlet while maintaining the temperature at room temperature and atmospheric pressure with a separator, and the carbon dioxide and extract are separated.
It was separated into 21.8g.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド97重量％、その
他３重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 97% by weight of N-octadecenylmaleimide and 3% by weight of other substances.
実施例 ３
Ｎ−オクタデセニルマレイミド65重量％、ダイ
マー15重量％およびポリマー、その他20重量％の
組成のマレイミドの粗組物40.0gを0.3lのステンレ
ス製耐圧容器に仕込み、ガス吹き込み口より、温
度50℃、圧力150Kg／cm2Ｇの超臨界二酸化炭素を
供給し、容器内を温度50℃、圧力150Kg／cm2Ｇに
保ちながら、一方のガス抜き出し口から連続的に
Ｎ−オクタデセニルマレイミドを含有する超臨界
二酸化炭素を抜き出し、セパレーターで常温、大
気圧とし二酸化炭素と抽出物20.8gとに分離した。Example 3 40.0 g of a rough assembly of maleimide with a composition of 65% by weight of N-octadecenylmaleimide, 15% by weight of dimer, polymer, and 20% by weight of other materials was charged into a 0.3 L stainless steel pressure-resistant container, and the mixture was injected from the gas inlet. , supercritical carbon dioxide at a temperature of 50°C and a pressure of 150 kg/cm 2 G was supplied, and while maintaining the inside of the container at a temperature of 50°C and a pressure of 150 kg/cm 2 G, N-octade was continuously supplied from one gas outlet. Supercritical carbon dioxide containing cenylmaleimide was extracted and separated into carbon dioxide and 20.8 g of extract at room temperature and atmospheric pressure using a separator.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド98重量％、その
他２重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 98% by weight of N-octadecenylmaleimide and 2% by weight of other substances.
実施例 ４
Ｎ−オクタデセニル（Ｎ−オレイル）マレイミ
ド65重量％、ダイマー15重量％およびポリマー、
その他20重量％の組成のマレイミドの粗製物を
40.0g0.3lのステンレス製耐圧容器に仕込み、ガス
吹き込み口より、温度50℃、圧力175Kg／cm2Ｇの
超臨界二酸化炭素を供給し、容器内を温度50℃、
圧力175Kg／cm2Ｇに保ちながら、一方のガス抜き
出し口から連続的にＮ−オクタデセニルマレイミ
ドを含有する超臨界二酸化炭素を抜き出し、セパ
レーターで常温、大気圧とし二酸化炭素と抽出物
21.2gとに分離した。Example 4 65% by weight N-octadecenyl (N-oleyl)maleimide, 15% by weight dimer and polymer,
Other crude maleimide with a composition of 20% by weight
Pour into a 40.0g 0.3l stainless steel pressure-resistant container, supply supercritical carbon dioxide at a temperature of 50℃ and a pressure of 175Kg/cm 2 G from the gas inlet, and bring the inside of the container to a temperature of 50℃ and a pressure of 175Kg/cm2G.
While maintaining the pressure at 175 Kg/cm 2 G, supercritical carbon dioxide containing N-octadecenylmaleimide was continuously extracted from one gas outlet, and the mixture was heated to room temperature and atmospheric pressure using a separator, and the carbon dioxide and extract were extracted.
It was separated into 21.2g.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド98重量％、その
他２重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 98% by weight of N-octadecenylmaleimide and 2% by weight of other substances.
実施例 ５
Ｎ−オクタデセニル（Ｎ−オレイル）マレイミ
ド65重量％、ダイマー15重量％およびポリマー、
その他20重量％の組成のマレイミドの粗製物
40.8gを0.3lのステンレス製耐圧容器に仕込み、ガ
ス吹き込み口より、温度50℃、圧力220Kg／cm2Ｇ
の超臨界二酸化炭素を供給し、容器内を温度50
℃、圧力220Kg／cm2Ｇに保ちながら、一方のガス
抜き出し口から連続的にＮ−オクタデセニルマレ
イミドを含有する超臨界二酸化炭素を抜き出し、
セパレーターで常温、大気圧とし二酸化炭素と抽
出物23.1gとに分離した。Example 5 65% by weight N-octadecenyl (N-oleyl)maleimide, 15% by weight dimer and polymer,
Other crude maleimide with a composition of 20% by weight
Pour 40.8g into a 0.3L stainless steel pressure-resistant container, and inject it from the gas inlet at a temperature of 50℃ and a pressure of 220Kg/cm 2 G.
Supercritical carbon dioxide is supplied, and the temperature inside the container is kept at 50℃.
While maintaining the temperature at ℃ and the pressure at 220 kg/cm 2 G, supercritical carbon dioxide containing N-octadecenylmaleimide was continuously extracted from one gas outlet.
Using a separator at room temperature and atmospheric pressure, carbon dioxide and 23.1 g of extract were separated.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド97重量％、その
他３重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 97% by weight of N-octadecenylmaleimide and 3% by weight of other substances.
実施例 ６
Ｎ−オクタデセニル（Ｎ−オレイル）マレイミ
ド65重量％、ダイマー15重量％およびポリマー、
その他20重量％の組成のマレイミドの粗製物
40.0gを0.3lのステンレス製耐圧容器に仕込み、ガ
ス吹き込み口より、温度50℃、圧力200Kg／cm2Ｇ
の超臨界二酸化炭素を供給し、容器内を温度50
℃、圧力200Kg／cm2Ｇに保ちながら、一方のガス
抜き出し口から連続的にＮ−オクタデセニルマレ
イミドを含有する超臨界二酸化炭素を抜き出し、
セパレーターで常温、大気圧とし二酸化炭素と抽
出物21.1gとに分離した。Example 6 65% by weight N-octadecenyl (N-oleyl)maleimide, 15% by weight dimer and polymer,
Other crude maleimide with a composition of 20% by weight
Pour 40.0g into a 0.3L stainless steel pressure-resistant container, and inject it from the gas inlet at a temperature of 50℃ and a pressure of 200Kg/cm 2 G.
Supercritical carbon dioxide is supplied, and the temperature inside the container is kept at 50℃.
While maintaining the temperature at ℃ and the pressure at 200 kg/cm 2 G, supercritical carbon dioxide containing N-octadecenylmaleimide was continuously extracted from one gas outlet.
Using a separator at room temperature and atmospheric pressure, carbon dioxide and 21.1 g of extract were separated.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド98重量％、その
他２重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 98% by weight of N-octadecenylmaleimide and 2% by weight of other substances.
実施例 ７
Ｎ−オクタデセニル（Ｎ−オレイル）マレイミ
ド65重量％、ダイマー15重量％およびポリマー、
その他20重量％の組成のマレイミドの粗製物
40.0gを0.3lのステンレス製耐圧容器に仕込み、ガ
ス吹き込み口より、温度60℃、圧力200Kg／cm2Ｇ
の超臨界二酸化炭素を供給し、容器内を温度60
℃、圧力200Kg／cm2Ｇに保ちながら、一方のガス
抜き出し口から連続的にＮ−オクタデセニルマレ
イミドを含有する超臨界二酸化炭素を抜き出し、
セパレーターで常温、大気圧とし二酸化炭素と抽
出物22.5gとに分離した。Example 7 65% by weight N-octadecenyl (N-oleyl)maleimide, 15% by weight dimer and polymer,
Other crude maleimide with a composition of 20% by weight
Pour 40.0g into a 0.3L stainless steel pressure-resistant container, and inject it from the gas inlet at a temperature of 60℃ and a pressure of 200Kg/cm 2 G.
Supercritical carbon dioxide is supplied, and the temperature inside the container is 60℃.
While maintaining the temperature at ℃ and the pressure at 200 kg/cm 2 G, supercritical carbon dioxide containing N-octadecenylmaleimide was continuously extracted from one gas outlet.
Using a separator at room temperature and atmospheric pressure, carbon dioxide and 22.5 g of extract were separated.
得られた抽出物は淡黄色結晶であり、その組成
はＮ−オクタデセニルマレイミド97重量％、その
他３重量％であつた。 The obtained extract was pale yellow crystals, and its composition was 97% by weight of N-octadecenylmaleimide and 3% by weight of other substances.
実施例 ８
Ｎ−シクロヘキシルマレイミド80重量％、ダイ
マーその他20重量％の組成のマレイミドの粗製物
40.0gを0.3lのステンレス製耐圧容器に仕込み、ガ
ス吹き込み口より、温度50℃、圧力200Kg／cm2Ｇ
の超臨界二酸化炭素を供給し、容器内を温度50
℃、圧力200Kg／cm2Ｇに保ちながら、一方のガス
抜き出し口から連続的にＮ−シクロヘキシルマレ
イミドを含有する超臨界二酸化炭素を抜き出し、
セパレーターで常温、大気圧とし二酸化炭素と抽
出物29.1gとに分離した。Example 8 Crude maleimide with a composition of 80% by weight of N-cyclohexylmaleimide and 20% by weight of dimer and others
Pour 40.0g into a 0.3L stainless steel pressure-resistant container, and inject it from the gas inlet at a temperature of 50℃ and a pressure of 200Kg/cm 2 G.
Supercritical carbon dioxide is supplied, and the temperature inside the container is kept at 50℃.
While maintaining the temperature at ℃ and the pressure at 200 kg/cm 2 G, supercritical carbon dioxide containing N-cyclohexylmaleimide was continuously extracted from one gas outlet.
Using a separator at room temperature and atmospheric pressure, carbon dioxide and 29.1 g of extract were separated.
得られた抽出物は白色結晶であり、その組成は
Ｎ−シクロヘキシルマレイミド98重量％、その他
２重量％であつた。 The obtained extract was white crystals, and its composition was 98% by weight of N-cyclohexylmaleimide and 2% by weight of other substances.
比較例 １
Ｎ−オクチルマレイミド75重量％、ダイマー15
重量％およびポリマー、その他10重量％のマレイ
ミドの粗製物110gを温度計、撹拌機、加熱装置
を備えた0.3lのガラス製蒸留装置に仕込み、温度
142℃、圧力４mmHgで３時間蒸留し、留出物
60.2gを分離した。Comparative example 1 N-octylmaleimide 75% by weight, dimer 15
% by weight, polymer, and other 10% by weight of maleimide were charged into a 0.3 l glass distillation apparatus equipped with a thermometer, stirrer, and heating device,
Distilled at 142℃ and pressure 4mmHg for 3 hours, distillate
60.2g was isolated.
得られた留出物は白色結晶であり、その組成は
Ｎ−オクチルマレイミド95重量％、その他５重量
％であつた。 The obtained distillate was a white crystal, and its composition was 95% by weight of N-octylmaleimide and 5% by weight of other substances.
比較例 ２
Ｎ−オクタデセニルマレイミド65重量％、ダイ
マー15重量％およびポリマー、その他20重量％の
組成のマレイミドの粗製物180gをオルソキシレ
ン550gに溶解し、冷却後不溶解物を別し、減
圧下でオルソキシレンを留去して油状物を得た。
さらにこの油状物に330gのアセトンを加え、十
分に撹拌して混合した後、アセトン不溶解物を
別し、減圧下でアセトンを留去して132gの油状
物を得た。この油状物の組成はＮ−オクタデセニ
ルマレイミド72重量％、ダイマー12重量％および
ポリマーその他16重量％であつた。Comparative Example 2 180 g of a crude maleimide having a composition of 65% by weight N-octadecenylmaleimide, 15% by weight of dimer, 20% by weight of polymer, and other materials was dissolved in 550g of ortho-xylene, and after cooling, the undissolved matter was separated, Ortho-xylene was distilled off under reduced pressure to obtain an oil.
Further, 330 g of acetone was added to this oil, and after thorough stirring and mixing, acetone-insoluble matter was separated, and the acetone was distilled off under reduced pressure to obtain 132 g of an oil. The composition of this oil was 72% by weight N-octadecenylmaleimide, 12% by weight dimer and 16% by weight other polymers.
（発明の効果）
本発明によれば、マレイミド粗製物に超臨界二
酸化炭素を作用させることによつて、マレイミド
の純度、品質の良好なものをしかも収率よく得る
ことができる。比較例でも明らかなように従来の
蒸留法、再結晶法等では純度および収率が低く、
Ｎ−オクタデセニルマレイミドにあつては、事実
上、工業的に精製品が得られなかつたが、これに
対して本発明では、十分に工業的規模で、純度95
重量％以上のマレイミドが得られる。(Effects of the Invention) According to the present invention, maleimide having good purity and quality can be obtained in good yield by allowing supercritical carbon dioxide to act on a maleimide crude product. As is clear from the comparative examples, conventional distillation methods, recrystallization methods, etc. have low purity and yield;
In the case of N-octadecenylmaleimide, it was virtually impossible to obtain a purified product on an industrial scale, but in the present invention, a purified product with a purity of 95% can be obtained on a sufficiently industrial scale.
% by weight or more of maleimide is obtained.
Claims (1)
数２〜20のアルケニル基またはシクロアルキル基
を示す。〕 で示されるマレイミドの粗製物に超臨界状態の二
酸化炭素を接触させて得られる、マレイミドを含
有する二酸化炭素からマレイミドを分離回収する
ことを特徴とするマレイミドの精製方法。 ２ 超臨界状態の二酸化炭素が温度31.1℃〜200
℃、圧力が74.2〜500Kg／cm2Ｇの範囲であること
を特徴とする特許請求の範囲第１項の精製方法。 ３ 超臨界状態の二酸化炭素が温度40〜140℃、
圧力75〜300Kg／cm2Ｇの範囲であることを特徴と
する特許請求の範囲第１項の精製方法。[Claims] 1 General formula, [In the formula, R represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or a cycloalkyl group. ] A method for purifying maleimide, which comprises separating and recovering maleimide from carbon dioxide containing maleimide, which is obtained by contacting a crude product of maleimide with carbon dioxide in a supercritical state. 2 Carbon dioxide in supercritical state has a temperature of 31.1℃~200℃
The purification method according to claim 1, characterized in that the temperature and pressure are in the range of 74.2 to 500 kg/cm 2 G. 3 Carbon dioxide in a supercritical state has a temperature of 40 to 140℃,
The purification method according to claim 1, characterized in that the pressure is in the range of 75 to 300 kg/cm 2 G.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61078169A JPS62238262A (en) | 1986-04-07 | 1986-04-07 | Purification of maleimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61078169A JPS62238262A (en) | 1986-04-07 | 1986-04-07 | Purification of maleimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62238262A JPS62238262A (en) | 1987-10-19 |
| JPH0319225B2 true JPH0319225B2 (en) | 1991-03-14 |
Family
ID=13654434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61078169A Granted JPS62238262A (en) | 1986-04-07 | 1986-04-07 | Purification of maleimide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62238262A (en) |
-
1986
- 1986-04-07 JP JP61078169A patent/JPS62238262A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62238262A (en) | 1987-10-19 |
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