JPH085867B2 - Method for producing 1,3-dimethyl-2-imidazolidinone - Google Patents
Method for producing 1,3-dimethyl-2-imidazolidinoneInfo
- Publication number
- JPH085867B2 JPH085867B2 JP60069044A JP6904485A JPH085867B2 JP H085867 B2 JPH085867 B2 JP H085867B2 JP 60069044 A JP60069044 A JP 60069044A JP 6904485 A JP6904485 A JP 6904485A JP H085867 B2 JPH085867 B2 JP H085867B2
- Authority
- JP
- Japan
- Prior art keywords
- dmi
- imidazolidinone
- dimethyl
- urea
- solvent
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 239000004202 carbamide Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 claims description 10
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003880 polar aprotic solvent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- MTHNHFGCXFFGEM-UHFFFAOYSA-N 1-[2-(carbamoylamino)propyl]-1-methylurea Chemical compound NC(=O)NC(C)CN(C)C(N)=O MTHNHFGCXFFGEM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KLGOMEZYSOZCCB-UHFFFAOYSA-N n,n'-bis(prop-2-enyl)ethane-1,2-diamine Chemical compound C=CCNCCNCC=C KLGOMEZYSOZCCB-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】 産業上の利用分野 本発明は1,3−ジメチル−２−イミダゾリジノン（以下D
MIと略記）の製造方法に関する。TECHNICAL FIELD The present invention relates to 1,3-dimethyl-2-imidazolidinone (hereinafter referred to as D
Abbreviated as MI).
DMIは極性非プロトン溶媒として極めて有用な物質で
ある。特にポリアミド類、ポリ塩化ビニル、ポリビニル
アルコール、ポリスチレン、ポリウレタン、フエノール
樹脂などの高分子化合物に優れた溶媒であり、また無機
塩類の多くのものと錯塩を形成して溶解し、多くの有機
反応の溶媒としても用いられる有用な物質である。DMI is a very useful substance as a polar aprotic solvent. In particular, it is an excellent solvent for high molecular compounds such as polyamides, polyvinyl chloride, polyvinyl alcohol, polystyrene, polyurethane, and phenol resins. It also forms complex salts with many inorganic salts and dissolves them, and it can be used for many organic reactions. It is a useful substance that is also used as a solvent.
従来の技術 DMIの製造方法は多数提案されている。Conventional Technology Many methods for manufacturing DMI have been proposed.
例えば、エチレンジアミンと尿素を反応させて２−イ
ミダゾリジノンを得、これにホルマリンを付加させた反
応生成物をトリクロロ酢酸、ギ酸などで還元してN,N′
−ジメチル化させる方法、またこの還元方法を改良して
貴金属触媒を使用し、酸性下に水素添加する方法、さら
にN,N′−ジメチルエチレンジアミンから、これとホス
ゲンもしくはトリクロロメチルクロロホーメートをホス
ゲンに分解しながら反応する方法などが知られている。For example, ethylenediamine and urea are reacted to obtain 2-imidazolidinone, and the reaction product obtained by adding formalin to this is reduced with trichloroacetic acid, formic acid or the like to produce N, N ′.
-A method for dimethylation, a method for improving this reduction method by using a noble metal catalyst to carry out hydrogenation under acidic conditions, and from N, N'-dimethylethylenediamine to phosgene or trichloromethylchloroformate to phosgene. A method of reacting while decomposing is known.
また、本発明方法と類似の方法として、N,N′−ジア
リルエチレンジアミンと尿素より1,3−ジアリル−２−
イミダゾリジノンを40％の収率で得たとの報告〔J.Hete
rocyclic Chem.（1971）,8,509〕も公知である。さら
に、N,N′−ジメチルエチレンジアミンと尿素を加熱反
応させた場合、中間体として1,1′−ジメチル−1,1′−
ジメチレンビスウレア を生成し、これを約300℃に加熱してDMIを35％の収率で
得たとの報告がなされている〔J.C.S.（Perkin Tran
s.）2.（1981）,317〕。In addition, as a method similar to the method of the present invention, 1,3-diallyl-2-diamine from N, N'-diallylethylenediamine and urea is used.
Reported that imidazolidinone was obtained in a yield of 40% [J. Hete
rocyclic Chem. (1971), 8,509] is also known. Furthermore, when N, N'-dimethylethylenediamine and urea are reacted by heating, 1,1'-dimethyl-1,1'-
Dimethylene bis-urea Was produced and heated to about 300 ° C. to obtain DMI with a yield of 35% [JCS (Perkin Tran
s.) 2. (1981), 317].
発明が解決しようとする問題点 N,N′−ジメチルエチレンジアミンと尿素よりDMIを製
造する方法はこの様に公知であるが、収率が極めて低
く、到底満足できるものではなかった。Problems to be Solved by the Invention Although a method for producing DMI from N, N′-dimethylethylenediamine and urea is known as described above, the yield is extremely low, and it is not completely satisfactory.
このような理由で、従来この尿素を使用する方法はエ
チレンジアミンとの反応において２−イミダゾリジノン
を製造する方法に適用され、前述の如く、引き続きホル
マリンとの生成物を還元する事によりDMIが製造されて
いた。従って、直接N,N′−ジメチルエチレンジアミン
と尿素より収率良くDMIを製造できるならば極めて簡素
なプロセスとなる。For this reason, conventionally, the method using urea is applied to the method for producing 2-imidazolidinone in the reaction with ethylenediamine, and as described above, DMI is produced by continuously reducing the product with formalin. It had been. Therefore, if DMI can be directly produced in good yield from N, N'-dimethylethylenediamine and urea, the process becomes extremely simple.
問題を解決するための手段 本発明者等はN,N′−ジメチルエチレンジアミンと尿
素とを反応させ、高収率でDMIを得る製造方法につき鋭
意検討した結果、極性非プロトン溶媒の存在下、180℃
以上で反応させることによりその目的が達せられること
を見い出し、本発明を完成した。Means for Solving the ProblemThe present inventors have conducted extensive studies on a production method of reacting N, N′-dimethylethylenediamine and urea to obtain DMI in a high yield, and in the presence of a polar aprotic solvent, 180 ℃
The present invention has been completed by finding that the object can be achieved by the above reaction.
本発明方法においては180℃以上、好ましくは200〜26
0℃で反応させることにより高収率でDMIが得られる。18
0℃以下では反応速度が小さく、中間体である1,1′−ジ
メチル−1,1′−ジメチレンビスウレアが残存し、300℃
付近では加熱方法の点で問題がある。In the method of the present invention, 180 ° C or higher, preferably 200 to 26
By reacting at 0 ° C, DMI can be obtained in high yield. 18
At 0 ° C or lower, the reaction rate is low, and the intermediate 1,1′-dimethyl-1,1′-dimethylenebisurea remains at 300 ° C.
There is a problem in the heating method in the vicinity.
本発明方法において使用される溶媒としては、炭化水
素及びハロゲン化炭化水素は適さず、極性溶媒を使用す
る。好ましい溶媒としてはN,N′−ジメチルホルムアミ
ド、N,N′−ジメチルアセトアミド、テトラメチル尿
素、ジメチルスルホキシド、ヘキサメチルホスホルアミ
ド、スルホラン、メチルイソブチルケトン、ニトロベン
ゼン、テトラヒドロフラン、ジオキサン、DMI等極性非
プロトン溶媒が良い。また沸点が低い場合、過大な耐圧
装置が必要となる為、180℃以上の沸点を有する溶媒が
好ましく、特に収率及び溶媒分離の煩雑さを避ける意味
からDMIを溶媒とするのが好ましい。Hydrocarbons and halogenated hydrocarbons are not suitable as the solvent used in the method of the present invention, and polar solvents are used. Preferred solvents are N, N'-dimethylformamide, N, N'-dimethylacetamide, tetramethylurea, dimethyl sulfoxide, hexamethylphosphoramide, sulfolane, methyl isobutyl ketone, nitrobenzene, tetrahydrofuran, dioxane, polar aproton such as DMI. Good solvent. Further, when the boiling point is low, an excessively high pressure resistance device is required. Therefore, a solvent having a boiling point of 180 ° C. or higher is preferable, and DMI is preferably used as the solvent in order to avoid the yield and the complexity of solvent separation.
本発明方法においては、このような極性非プロトン溶
媒を用いることにより、比較的低い温度でマイルドな反
応が実施できて高収率でDMIが得られる。In the method of the present invention, by using such a polar aprotic solvent, a mild reaction can be carried out at a relatively low temperature and DMI can be obtained in a high yield.
仕込まれるN,N′−ジメチルエチレンジアミンと尿素
の量比は通常、1.0:0.5〜1.0:2.5のモル比で選ばれる。
しかしながらN,N′−ジメチルエチレンジアミンに対し
等モル以上の尿素を使用する場合はシアヌル酸が多量副
生し、DMIを取出す場合の操作も煩雑となる。従って、
好ましくは1.0:0.6〜1.0:1.2のモル比を反応させるのが
良い。The amount ratio of N, N'-dimethylethylenediamine and urea to be charged is usually selected in a molar ratio of 1.0: 0.5 to 1.0: 2.5.
However, when urea is used in an equimolar amount or more with respect to N, N'-dimethylethylenediamine, a large amount of cyanuric acid is by-produced, and the operation for extracting DMI becomes complicated. Therefore,
It is preferable to react at a molar ratio of 1.0: 0.6 to 1.0: 1.2.
本発明方法の通常の態様を述べれば、還流冷却器、温
度計、及び機械的撹拌機を備えた反応器中にN,N′−ジ
メチルエチレンジアミン、尿素及び溶媒を加える。昇温
して140℃以下で反応後、引き続き180℃以上に昇温して
反応させる。反応終了液は蒸留等によってDMIを取出す
ことができる。特に、DMIを溶媒とした場合、蒸留時溶
媒との分離が必要でなく、極めて簡素化されたプロセス
となる。In general terms of the process of the invention, N, N'-dimethylethylenediamine, urea and solvent are added to a reactor equipped with a reflux condenser, thermometer, and mechanical stirrer. After heating to 140 ° C or lower, the temperature is raised to 180 ° C or higher to react. DMI can be removed from the reaction-completed liquid by distillation or the like. In particular, when DMI is used as a solvent, it is not necessary to separate it from the solvent at the time of distillation, and the process is extremely simplified.
以下実施例を挙げさらに詳細に説明する。 Examples will be described below in more detail.
実施例１ 500mlのステンレス製オートクレーブ内に、N,N′−ジ
メチルエチレンジアミン88.1g（1.0モル）、尿素60.1g
（1.0モル）及びDMI100.0gを仕込んだ。反応温度210℃
迄約30分で昇温し、その温度で３時間反応させた。系内
圧力は最高14.5kg/cm2Ｇ迄達した。反応終了後蒸留し
て、約2/3程DMIを留出した後釜液中に析出した結晶物を
過し、引き続き液を蒸留することにより、ガスクロ
マトグラフイーによる純度99.5％のDMI留分192.7gを得
た（収率80.8％）。蒸留後の釜残は一部DMIを含んだシ
アヌル酸であった。Example 1 88.1 g (1.0 mol) of N, N'-dimethylethylenediamine and 60.1 g of urea were placed in a 500 ml stainless steel autoclave.
(1.0 mol) and DMI100.0g were prepared. Reaction temperature 210 ℃
The temperature was raised to about 30 minutes, and the reaction was carried out at that temperature for 3 hours. The system pressure reached a maximum of 14.5 kg / cm 2 G. After the reaction was completed, the mixture was distilled, and about 2/3 of the DMI was distilled off.After passing through the crystallized product in the kettle liquid, the liquid was continuously distilled to obtain a DMI fraction with a purity of 99.5% by gas chromatography of 192.7 g. Was obtained (yield 80.8%). The residue after distillation was cyanuric acid containing some DMI.
実施例２〜８ DMIの替りに各種溶媒を使用し、実施例１と全く同様
にして反応、処理して表の通りの結果を得た。Examples 2 to 8 Various solvents were used instead of DMI, and the reaction and treatment were carried out in the same manner as in Example 1 to obtain the results shown in the table.
Claims (3)
との反応により1,3−ジメチル−２−イミダゾリジノン
を製造するに際し、極性非プロトン溶媒の存在下180℃
以上で反応させることを特徴とする1,3−ジメチル−２
−イミダゾリジノンの製造方法。1. When 1,3-dimethyl-2-imidazolidinone is produced by the reaction of N, N'-dimethylethylenediamine and urea, 180 ° C. in the presence of a polar aprotic solvent.
1,3-dimethyl-2 characterized by reacting as above
-Method for producing imidazolidinone.
−イミダゾリジノンである特許請求の範囲第（１）項記
載の方法。2. The polar aprotic solvent is 1,3-dimethyl-2.
-A method according to claim (1) which is imidazolidinone.
囲第（１）項記載の方法。3. The method according to claim 1, wherein the reaction temperature is 200 to 260 ° C.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60069044A JPH085867B2 (en) | 1985-04-03 | 1985-04-03 | Method for producing 1,3-dimethyl-2-imidazolidinone |
| US06/846,564 US4731453A (en) | 1985-04-03 | 1986-03-31 | Process for producing 1, 3-dialkyl-2-imidazolidinone |
| CA000505558A CA1264761A (en) | 1985-04-03 | 1986-04-01 | Process for producing 1, 3-dialkyl-2-imidazolidinone |
| KR1019860002532A KR870001929B1 (en) | 1985-04-03 | 1986-04-03 | Method for preparing 1,3-dialkyl-2-imidazolidinone |
| IN246/MAS/86A IN167189B (en) | 1985-04-03 | 1986-04-03 | |
| EP86104563A EP0198345B1 (en) | 1985-04-03 | 1986-04-03 | Process for producing 1,3-dialkyl-2-imidazolidinone |
| DE8686104563T DE3673049D1 (en) | 1985-04-03 | 1986-04-03 | METHOD FOR PRODUCING 1,3-DIALKYL-2-IMIDAZOLIDINONE. |
| IN822/MAS/89A IN170558B (en) | 1985-04-03 | 1989-11-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60069044A JPH085867B2 (en) | 1985-04-03 | 1985-04-03 | Method for producing 1,3-dimethyl-2-imidazolidinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61229866A JPS61229866A (en) | 1986-10-14 |
| JPH085867B2 true JPH085867B2 (en) | 1996-01-24 |
Family
ID=13391189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60069044A Expired - Lifetime JPH085867B2 (en) | 1985-04-03 | 1985-04-03 | Method for producing 1,3-dimethyl-2-imidazolidinone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH085867B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0992497B1 (en) | 1998-10-09 | 2003-12-17 | Mitsui Chemicals, Inc. | Manufactoring process for 1,3-Dialkyl-2-imidazolinones |
| JP4541468B2 (en) * | 1998-10-09 | 2010-09-08 | 三井化学株式会社 | 1,3-dialkyl-2-imidazolidinone and process for producing the same |
| CN120695474B (en) * | 2025-08-07 | 2026-04-17 | 湖北荆州华邦化学有限公司 | 1, 3-Dimethyl imidazolinone purification device and process based on coupling cooling |
-
1985
- 1985-04-03 JP JP60069044A patent/JPH085867B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61229866A (en) | 1986-10-14 |
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