JPH02111765A - Production of dimorpholinodiethyl ether compound - Google Patents
Production of dimorpholinodiethyl ether compoundInfo
- Publication number
- JPH02111765A JPH02111765A JP63263433A JP26343388A JPH02111765A JP H02111765 A JPH02111765 A JP H02111765A JP 63263433 A JP63263433 A JP 63263433A JP 26343388 A JP26343388 A JP 26343388A JP H02111765 A JPH02111765 A JP H02111765A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- raney cobalt
- component
- formula
- diethylene glycol
- 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
- -1 dimorpholinodiethyl ether compound Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000010941 cobalt Substances 0.000 claims abstract description 12
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000000243 solution Substances 0.000 abstract description 6
- 229910052782 aluminium Inorganic materials 0.000 abstract description 5
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229910000531 Co alloy Inorganic materials 0.000 abstract description 2
- 239000012670 alkaline solution Substances 0.000 abstract description 2
- 229910002058 ternary alloy Inorganic materials 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 230000003213 activating effect Effects 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical class C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 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
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、ジモルホリノジエチルエーテル化合物の製造
方法に関するものである。ジモルホリノジエチルエーテ
ル化合物は、ポリウレタン重合用触媒として広く利用さ
れている有用な化合物である。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for producing a dimorpholino diethyl ether compound. Dimorpholino diethyl ether compounds are useful compounds that are widely used as catalysts for polyurethane polymerization.
従」ロケ道」（
ジモルホリノジエチルエーテル化合物に関しては様々な
文献が提出されているが、ジエチレングリコールを原料
とする製造方法に関するものは、下記の２件である。Various documents have been submitted regarding dimorpholino diethyl ether compounds, but the following two are related to production methods using diethylene glycol as a raw material.
（１） ニッケル触媒の存在下にモルホリンとジエチ
レングリコールをオートクレーブ中、水素加圧下に反応
させる方法、（特開昭４７−４１９３号公題を
るなめの手段
報）
＋２） リン含有化合物の触媒量存在下に、二級アミ
ン化合物とジオール化合物を２５０〜３５０℃の温度お
よび加圧下に反応させる方法、（特開昭５１−１４６４
０３号公報）
明が解゛しようと る課題
リン含有化合物を触媒とする方法は、２５０℃以上の高
温と２０気圧以上の高圧を必要とする為腐食など装置上
の問題が多く、その上側生成物が多いので分離精製に手
間がかかる欠点がある。また、ラネーニッケル触媒を使
用する方法は、オートクレーブ中で通常の水素化反応と
同様に処理できるが、反応選択率が甚だ悪く、目的物の
収率は１２％前後にすぎないため工業化するには満足で
きる方法ではない。(1) A method of reacting morpholine and diethylene glycol under hydrogen pressure in an autoclave in the presence of a nickel catalyst (as reported in JP-A No. 47-4193 by Runname) +2) Presence of a catalytic amount of a phosphorus-containing compound Below, a method of reacting a secondary amine compound and a diol compound at a temperature of 250 to 350°C and under pressure is described (Japanese Patent Application Laid-Open No. 51-1464).
(No. 03 Publication) Problems that Akira is trying to solve The method using a phosphorus-containing compound as a catalyst requires a high temperature of 250°C or higher and a high pressure of 20 atmospheres or higher, which causes many equipment problems such as corrosion. It has the disadvantage that separation and purification is time-consuming because there are a lot of substances. In addition, the method using a Raney nickel catalyst can be treated in an autoclave in the same way as a normal hydrogenation reaction, but the reaction selectivity is extremely poor and the yield of the target product is only around 12%, which is not satisfactory for industrialization. There's no way to do it.
本発明は、以上のような状況に諾み、目的物の収率の向
上と操作性の両面において工業化するに足る新たなジモ
ルホリノジエチルエーテル化合物の製造方法を提供する
ものである。In view of the above-mentioned circumstances, the present invention provides a new method for producing a dimorpholino diethyl ether compound that is suitable for industrialization in terms of both improved yield of the desired product and operability.
基を表し、互いに同一もしくは異なっても良い）で示さ
れるジモルホリノジエチルエーテル化合物を製造するに
際し、
一般式（Ｉ［＞及び−服代（ＩＩＩ）
Ｒ。When producing a dimorpholino diethyl ether compound represented by the general formula (I[> and -Fukudai (III) R.
（式中、Ｒ、、Ｒ２，Ｒ３，Ｒ４は前記に同じ）で示さ
れるモルホリン化合物とジエチレングリコールをラネー
コバルト触媒の存在下に縮合させることを特徴とする一
般式（Ｉ）で示されるジモルホリノジエチルエーテル化
合物の製造方法である。Dimorpholinodiethyl represented by the general formula (I), characterized by condensing a morpholine compound represented by (wherein R, , R2, R3, R4 are the same as above) and diethylene glycol in the presence of a Raney cobalt catalyst. This is a method for producing an ether compound.
本発明で製造される化合物を具体的に例示すれば、４．
４′−ジモルホリノジエチルエーテル、４．４”−ジ（
２，６−ジメチルモルホリノ）ジエチルエーテル、４．
４°−ジ（３，５−ジメチルモルホリノ、）ジエチルエ
ーテル、４．４′−ジ（３，６−ジメチルモルホリノ）
ジエチルエーテル、４−（３，５−ジメチルモルホリノ
）−４゜−（３，６−ジメチルモルホリノ）ジエチルエ
ーテルなどであり、これら単独または二種以上の混合物
はいずれもポリウレタン重合用の触媒として有用なもの
である。Specific examples of the compounds produced in the present invention include 4.
4'-dimorpholinodiethyl ether, 4.4''-di(
2,6-dimethylmorpholino)diethyl ether, 4.
4°-di(3,5-dimethylmorpholino,) diethyl ether, 4,4'-di(3,6-dimethylmorpholino)
diethyl ether, 4-(3,5-dimethylmorpholino)-4゜-(3,6-dimethylmorpholino)diethyl ether, etc., and these alone or a mixture of two or more are useful as catalysts for polyurethane polymerization. It is something.
本発明で使用されるラネーコバルト触媒は、コバルト成
分３０〜５０％、アルミニウム成分７０〜５０％からな
るラネーコバルト合金をアルカリ溶液中に投入してアル
ミニウム成分を溶出させ活性化した後、水洗したもので
あり、通常の市販品が使用できる。コバルトとアルミニ
ウムの他に第３成分として、マンガン、モリブデン、鉛
、ニッケル、鉄などを少量添加した三元合金型のラネー
コバルト触媒も本発明に使用できる。ラネーコバルト触
媒の本発反応における使用量は、ジエチレングリコール
に対して５〜７０重量％、好ましくは１０〜５０重量％
が良い。The Raney cobalt catalyst used in the present invention is prepared by putting a Raney cobalt alloy consisting of 30 to 50% cobalt and 70 to 50% aluminum into an alkaline solution to elute and activate the aluminum component, and then washing with water. Therefore, ordinary commercially available products can be used. A ternary alloy type Raney cobalt catalyst in which a small amount of manganese, molybdenum, lead, nickel, iron, etc. is added as a third component in addition to cobalt and aluminum can also be used in the present invention. The amount of Raney cobalt catalyst used in the main reaction is 5 to 70% by weight, preferably 10 to 50% by weight based on diethylene glycol.
is good.
ジエチレングリコールとモルホリン化合物の反応比率は
、モルホリン化合物を理論量よりも過剰に用いるのが好
まし゛く、モル比で２５倍以上用いると良い結果を与え
る。Regarding the reaction ratio between diethylene glycol and the morpholine compound, it is preferable to use the morpholine compound in excess of the theoretical amount, and a molar ratio of 25 times or more gives good results.
本発明の反応は、無溶媒で充分実施できる。また、水、
アルコール類、エステル類、エーテル類および炭化水素
類などの溶媒の存在下でも実施できる。The reaction of the present invention can be fully carried out without a solvent. Also, water,
It can also be carried out in the presence of solvents such as alcohols, esters, ethers and hydrocarbons.
本発明の一実施態様を述べれば、オートクレーブにジエ
チレングリコールと過剰量のモルホリン化合物およびラ
ネーコバルト触媒を仕込み、水素圧５〜１５０ ｋｇ／
ｃｍ２、好ましくは１０〜５０ｋｇ／ｃｍ２、反応温度
１００〜２７０℃、好ましくは１５０〜２５０℃の反応
条件で十数時間ないし数十時間反応させる０本発明の反
応時間は、反応温度を高めに設定すれば短縮することが
できる。しかし、その場合目的物の若干の収率低下は避
けられず、低温度で長時間反応させるのとどちらが良い
かは、状況によって選択することができる０例えば、１
７０℃の反応温度で７０時間以上反応させた場合は、仕
込みジエチレングリコールを基準とする反応収率で目的
物を９０％以上得ることができる０反応終了後は、触媒
を濾過して反応液を減圧蒸留すれば高純度の目的物を得
ることができる。In one embodiment of the present invention, diethylene glycol, an excess amount of morpholine compound, and a Raney cobalt catalyst are charged into an autoclave, and the hydrogen pressure is 5 to 150 kg/
cm2, preferably 10 to 50 kg/cm2, reaction temperature 100 to 270°C, preferably 150 to 250°C for ten or more hours to several tens of hours.The reaction time of the present invention is set at a higher reaction temperature. You can shorten it by doing so. However, in this case, a slight decrease in the yield of the target product is unavoidable, and whether it is better to react at low temperature for a long time can be selected depending on the situation.
If the reaction is carried out at a reaction temperature of 70°C for 70 hours or more, the desired product can be obtained with a reaction yield of 90% or more based on the charged diethylene glycol. After the reaction is complete, filter the catalyst and reduce the pressure of the reaction solution. Distillation allows you to obtain the target product with high purity.
以下、実施例により本発明を更に具体的に例示するが、
これらは本発明の説明のものであって、本発明を限定す
るものではない。Hereinafter, the present invention will be illustrated more specifically with reference to Examples.
These are illustrative of the invention and are not intended to limit it.
１克邑
実施例 １
２００１オートクレーブに２．６−ジメチルモルホリン
３４．５ｇ（０，３モル）、ジエチレングリコール１０
．６ｇ（０，１モル）およびラネーコバルト触媒５ｇ
（’０ＤＨＴ−６０Ｊ ：川研ファインケミカル株式会
社製）を入れ、水素置換後水素初圧１０ ｋｇ／ｃｍ２
を充填し、１７０℃で７６時間攪拌した０反応後冷却し
て触媒を濾過した後、ガスクロマトグラフィーによって
定量した。その結果２６−ジメチルモルホリノジエチル
エーテルの収率は、９３．８％であった。また、本反応
液を減圧下に蒸留して沸点１５８〜１６０℃／ １．５
ｍｍＨｇの目的物留分２５．７ｇ（純度９９％）を得
た。1 Example 1 2001 34.5 g (0.3 mol) of 2,6-dimethylmorpholine and 10 diethylene glycol in an autoclave
．． 6 g (0,1 mol) and 5 g Raney cobalt catalyst
('0DHT-60J: manufactured by Kawaken Fine Chemicals Co., Ltd.) and the initial hydrogen pressure after hydrogen replacement was 10 kg/cm2.
After the reaction, which was stirred at 170° C. for 76 hours, the reaction mixture was cooled and the catalyst was filtered, followed by quantitative determination by gas chromatography. As a result, the yield of 26-dimethylmorpholinodiethyl ether was 93.8%. In addition, this reaction solution was distilled under reduced pressure to obtain a boiling point of 158-160°C/1.5
25.7 g (purity 99%) of the target product fraction of mmHg was obtained.
実施例 ２
実施例１と同様に原料をオートクレーブに仕込み、反応
温度を２００℃として１５時間攪拌した。Example 2 In the same manner as in Example 1, raw materials were charged into an autoclave, and the reaction temperature was set to 200° C. and stirred for 15 hours.
反応終了後のガスクロマトグラフィーによる分析結果よ
り、２．６−ジメチルモルホリノジエチルエーテルの収
率は８６．７％であった。また、触媒を濾過した反応液
を精留して２．６−ジメチルモルホリノジエチルエーテ
ル２３．７ｇ＜純度９９％）を得た。The yield of 2.6-dimethylmorpholinodiethyl ether was 86.7% based on the analysis results by gas chromatography after the reaction was completed. Further, the reaction solution from which the catalyst had been filtered was rectified to obtain 23.7 g of 2,6-dimethylmorpholinodiethyl ether (purity: 99%).
実施例 ３
実施例１において２．６−ジメチルモルホリンの代わり
に３．５−ジメチルモルホリンと３．６−ジメチルモル
ホリンの混合物（約７５ ： ２５＞３４．５ｇ（０，
３モル）を用いた他は同様に行い２００°Ｃで６０時間
攪拌した６反応後冷却して触媒を濾過した後、反応液を
精留して沸点１６１〜１６４℃／ １．５ ｍｍＨ）Ｈ
の留分のジメチルモルホリノジエチルエーテル（３，５
一体と３．６一体の混合物） ２０．１ ｇを得た。ガ
スクロマトグラフィーによる純度は９５％、収率は６７
％であった。Example 3 In Example 1, a mixture of 3.5-dimethylmorpholine and 3.6-dimethylmorpholine (approximately 75:25>34.5 g (0,
After the reaction, the reaction solution was cooled and the catalyst was filtered, and the reaction solution was rectified to give a boiling point of 161-164°C/1.5 mmH)H.
Dimethylmorpholinodiethyl ether (3,5
20.1 g of a mixture of 3.6 and 3.6 pieces were obtained. Purity by gas chromatography: 95%, yield: 67%
%Met.
北Ｊレケカ」し
本発明により従来低数率でしか得られながったジモルホ
リノジエチルエーテル化合物を高収率で得ることができ
るようになり、しがも工業的規模での生産が容易になる
。According to the present invention, it is now possible to obtain dimorpholino diethyl ether compounds in high yields, which could only be obtained in low numbers in the past, and production on an industrial scale has become easier. Become.
特許出願人 川研ファインケミカル株式会社特許出願人
サンアプロ株式会社Patent applicant: Kawaken Fine Chemical Co., Ltd. Patent applicant: Sun-Apro Co., Ltd.
Claims (1)
たはメチル基を表し、互いに同一もしくは異なっても良
い）で示されるジモルホリノジエチルエーテル化合物を
製造するに際し、 一般式（II）及び一般式（III） ▲数式、化学式、表等があります▼（II） ▲数式、化学式、表等があります▼（III） （式中、Ｒ＿１、Ｒ＿２、Ｒ＿３、Ｒ＿４は前記に同じ
）で示されるモルホリン化合物とジエチレングリコール
をラネーコバルト触媒の存在下に縮合させることを特徴
とする一般式（ I ）で示されるジモルホリノジエチル
エーテル化合物の製造方法。[Claims] 1. General formula (I) ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R_1, R_2, R_3, R_4 represent a hydrogen atom or a methyl group, and are the same or different from each other) When producing the dimorpholino diethyl ether compound represented by general formula (II) and general formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) (wherein R_1, R_2, R_3, R_4 are the same as above) and diethylene glycol are condensed in the presence of a Raney cobalt catalyst. A method for producing a morpholino diethyl ether compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63263433A JP2639496B2 (en) | 1988-10-19 | 1988-10-19 | Method for producing dimorpholino diethyl ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63263433A JP2639496B2 (en) | 1988-10-19 | 1988-10-19 | Method for producing dimorpholino diethyl ether compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02111765A true JPH02111765A (en) | 1990-04-24 |
| JP2639496B2 JP2639496B2 (en) | 1997-08-13 |
Family
ID=17389437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63263433A Expired - Lifetime JP2639496B2 (en) | 1988-10-19 | 1988-10-19 | Method for producing dimorpholino diethyl ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2639496B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0735067A1 (en) * | 1995-03-31 | 1996-10-02 | Huntsman Corporation | Dimorpholinodiethylether having improved isocyanate stability |
| US7405327B2 (en) | 2004-05-13 | 2008-07-29 | Basf Aktiengesellschaft | Method for the continuous production of an amine |
-
1988
- 1988-10-19 JP JP63263433A patent/JP2639496B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0735067A1 (en) * | 1995-03-31 | 1996-10-02 | Huntsman Corporation | Dimorpholinodiethylether having improved isocyanate stability |
| US7405327B2 (en) | 2004-05-13 | 2008-07-29 | Basf Aktiengesellschaft | Method for the continuous production of an amine |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2639496B2 (en) | 1997-08-13 |
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