JPH01157938A - Production of diemthylaminoethanol - Google Patents
Production of diemthylaminoethanolInfo
- Publication number
- JPH01157938A JPH01157938A JP31539087A JP31539087A JPH01157938A JP H01157938 A JPH01157938 A JP H01157938A JP 31539087 A JP31539087 A JP 31539087A JP 31539087 A JP31539087 A JP 31539087A JP H01157938 A JPH01157938 A JP H01157938A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ethylene oxide
- dimethylamine
- yield
- circulating
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 56
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000007788 liquid Substances 0.000 claims abstract description 15
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960002887 deanol Drugs 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 abstract description 22
- 239000002994 raw material Substances 0.000 abstract description 21
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 7
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 239000002250 absorbent Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000005187 foaming Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 52
- 125000005265 dialkylamine group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ジメチルアミノエタノール(以下[DMOH
Jと称す)の製造法に関する。さらに詳しくは、本発明
はジメチルアミンと酸化エチレンからジメチルアミノエ
タノールを製造するに当たり、反応生成液を反応溶媒と
して循環させながら該循環液に原料のジアミンおよび酸
化エチレンを連続的に供給して反応させる連続的な製造
方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides dimethylaminoethanol (hereinafter [DMOH
J). More specifically, in producing dimethylaminoethanol from dimethylamine and ethylene oxide, the reaction product liquid is circulated as a reaction solvent, and the raw materials diamine and ethylene oxide are continuously supplied to the circulating liquid and reacted. Concerning continuous manufacturing methods.
DMOHは、カチオン系高分子凝集剤の原料、また溶剤
、界面活性剤、塗料、ガス吸収剤、ウレタン発泡触媒等
の原料等として利用されており、工業上有用な物質であ
る。DMOH is an industrially useful substance that is used as a raw material for cationic polymer flocculants, and as a raw material for solvents, surfactants, paints, gas absorbents, urethane foaming catalysts, and the like.
従来、ジメチルアミンと酸化エチレンとを反応させDM
OHを製造する方法は公知である。Conventionally, dimethylamine and ethylene oxide were reacted to produce DM.
Methods for producing OH are known.
例えば、W、 H,Horne & R,L、 5hn
er、 J、 Am、 Chem、 Soc、。For example, W, H, Horne & R, L, 5hn
er, J, Am, Chem, Soc,.
2925 (1932)によると、アルコール類を反応
溶媒として使用し、ジアルキルアミンと酸化エチレンと
のモル比を1=1.3として反応させたとき収率が75
%となり最良な成績を与えると報告している。2925 (1932), when alcohols are used as reaction solvents and the molar ratio of dialkylamine and ethylene oxide is 1=1.3, the yield is 75.
% and give the best results.
しかし、アルコール類を反応溶媒として使用すると副生
成物が増大しく例えばメタノールを溶媒とすると溶媒自
身が酸化エチレンと反応し、エチレングリコールモノメ
チルエーテルを副生ずる)好ましくない。However, when alcohols are used as a reaction solvent, by-products increase, and for example, when methanol is used as a solvent, the solvent itself reacts with ethylene oxide, producing ethylene glycol monomethyl ether as a by-product).
また、特開昭61−100550号公報には液相半回分
法によりジアルキルアミンの溶媒液に酸化エチレンを連
続的に供給しジアルキルアミン二酸化エチレンのモル比
が2〜3:1に達した時点で反応を終了する方法が開示
されている。この方法は、反応系においてジアルキルア
ミンの存在がDMOHの量よりも常に大きい状態で反応
を終了させる方法である。すなわち、ジアルキルアミン
と酸化エチレンとの反応終了時に多量のジアルキルアミ
ンを残留させて合成反応を行わせる方法である。In addition, JP-A-61-100550 discloses that ethylene oxide is continuously supplied to a dialkylamine solvent solution by a liquid phase semi-batch method, and when the molar ratio of dialkylamine ethylene dioxide reaches 2 to 3:1, A method of terminating the reaction is disclosed. In this method, the reaction is terminated in a state where the presence of dialkylamine in the reaction system is always greater than the amount of DMOH. That is, this is a method in which a large amount of dialkylamine remains at the end of the reaction between dialkylamine and ethylene oxide to carry out the synthesis reaction.
(例えば、公報第2頁左下欄参照)
しかしながらこの方法では、DMOHの空時収率が高く
なく、装置的にも大量のジアルキルアミンを前置し長時
間を要して反応させる装置が必要であり、さらに収率以
外に選択率も必ずしも高くなく経済的な方法とは言い難
い。(For example, see the bottom left column of page 2 of the publication.) However, this method does not have a high space-time yield of DMOH, and requires equipment that requires a large amount of dialkylamine in advance and a long reaction time. Furthermore, in addition to the yield, the selectivity is not necessarily high and it is difficult to say that it is an economical method.
一方、反応溶媒を使用することなく連続法によりDMO
Hを製造する方法もまた公知である。On the other hand, DMO was prepared by a continuous method without using a reaction solvent.
Methods for producing H are also known.
例えば英国特許第1479747号では、反応生成物の
1〜50wt%を循環させ、原料ジアミンおよび酸化エ
チレンを連続的に供給して100℃前後の反応温度、加
圧下に反応させる方法が開示されている。しかし、DM
OHの収率は実施例によれば約93%(モル)(対酸化
エチレン)であり工業的′には未だ十分ではない。For example, British Patent No. 1479747 discloses a method in which 1 to 50 wt% of the reaction product is circulated, raw material diamine and ethylene oxide are continuously supplied, and the reaction is carried out at a reaction temperature of around 100° C. under pressure. . However, DM
According to the examples, the yield of OH is about 93% (mol) (based on ethylene oxide), which is still not sufficient for industrial use.
c問題点を解決するための手段〕
本発明者らは、従来の方法におけるこれらの課題を解決
すべく種々の検討を行い、本発明を為した。c. Means for Solving the Problems] The present inventors conducted various studies to solve these problems in conventional methods, and accomplished the present invention.
すなわち、本発明は、ジメチルアミンと酸化エチレンか
らジメチルアミノエタノールを製造するに当たり、反応
生成液を循環させながら該循環液中にジメチルアミンお
よび酸化エチレンを、循環液量に対して1/80容量か
ら1/200容量の量で連続的に供給することを特徴と
するジメチルアミノエタノールの製造法である。That is, the present invention, in producing dimethylaminoethanol from dimethylamine and ethylene oxide, circulates the reaction product liquid and adds dimethylamine and ethylene oxide to the circulating liquid from 1/80 volume to the circulating liquid volume. This is a method for producing dimethylaminoethanol, characterized in that it is continuously supplied in an amount of 1/200 volume.
本゛発明によると、ジメチルアミンと酸化エチレンとか
らDMOHを従来になく選択性良く、高収率で得ること
ができ、かつ−船釣な反応溶媒を使用しないため目的物
のDMOHの分離精製も効率的に行うことができる。例
えば、ジメチルアミン過剰で酸化エチレンと反応させた
反応生成液を循環させながら、該循環液量に対して1/
90の量のジメチルアミン$よび酸化エチレン(モル比
2.0)混合物を連続的に供給して、反応温度150℃
で反応させ99.4モル%の収率でDMOHを得ること
ができる。しかも得られた生成物中には副生物は殆ど含
まれていない。According to the present invention, it is possible to obtain DMOH from dimethylamine and ethylene oxide with better selectivity and higher yield than ever before, and also because it does not use an expensive reaction solvent, it is also possible to separate and purify the target DMOH. It can be done efficiently. For example, while circulating a reaction product liquid that has been reacted with ethylene oxide with an excess of dimethylamine,
A mixture of dimethylamine $90 and ethylene oxide (molar ratio 2.0) was continuously fed, and the reaction temperature was 150°C.
DMOH can be obtained with a yield of 99.4 mol%. Furthermore, the obtained product contains almost no by-products.
本発明は、先に記述した様にDMOH液を循環させなが
ら該循環液に原料ジメチルアミンおよび酸化エチレンを
連続的に供給して反応させる方法であるが、該循環液に
対する供給する原料は、通常1/80〜1/200容量
の量である。供給する原料の量が循環液量に対して17
80容量よりも多いと副生物の生成が多くなり、反応選
択率が悪く、また1/200容量よりも少ないと空時収
率が良くない。原料の供給量は上記の範囲で実質的に副
生物の生成を抑制し、比較的収率良く目的物DMOHを
得ることができるが、さらには1/80〜1/150容
量が収率の点からより好適である。これを循環液の循環
比で表すと、下記式からγ=80〜200.好ましくは
80〜150となる。As described above, the present invention is a method of continuously supplying and reacting raw materials dimethylamine and ethylene oxide to the circulating liquid while circulating the DMOH liquid, but the raw materials to be supplied to the circulating liquid are usually The amount is 1/80 to 1/200 of the capacity. The amount of raw material supplied is 17% relative to the amount of circulating fluid.
If the volume is more than 80, by-products will be produced in large quantities, resulting in poor reaction selectivity, and if it is less than 1/200 volume, the space-time yield will be poor. The amount of raw material supplied within the above range can substantially suppress the production of by-products and obtain the target product DMOH with a relatively good yield, but 1/80 to 1/150 volume is the point of yield. It is more suitable. Expressing this in terms of the circulation ratio of the circulating fluid, γ=80 to 200. Preferably it is 80-150.
循環比(γ)=〔循環量(m’/hr)] / [原料
(DMA十 8口) (m’/hr))
ただし、DMA=ジメチルアミン、
BO: 酸化エチレン
原料供給量=反応液抜き出し量とし、反応液の比重を0
.82とする。Circulation ratio (γ) = [Circulation amount (m'/hr)] / [Raw material (DMA 18 ports) (m'/hr)) Where, DMA = dimethylamine, BO: Ethylene oxide raw material supply amount = Reaction liquid withdrawal The specific gravity of the reaction solution is 0.
.. 82.
本発明の方法は、上記の様に反応生成液の循環量を多く
し、原料の供給量を小さくして反応させる方法であるが
、これ以外にジメチルアミンと酸化エチレンとのモル比
、および反応温度もまた本発明の方法を有利に実施する
上で重−な要件の一つである。ジメチルアミンと酸化エ
チレンとの仕込モル比は、酸化エチレンに対するジメチ
ルアミンの量が大きくなるに伴い副生物の生成が減少す
るのでモル比はジメチルアミンの量が過剰であることが
望ましいが余りに多くても経済的に不利であるので、本
発明の方法を有利に実施するには、一般的にはジメチル
アミン/酸化エチレン(モル比)として1.5以上、1
.5〜3.0が好適である。The method of the present invention is a method in which the reaction is carried out by increasing the circulation rate of the reaction product liquid and decreasing the supply rate of the raw materials as described above, but the molar ratio of dimethylamine and ethylene oxide and the reaction Temperature is also one of the important requirements for carrying out the process of the invention advantageously. Regarding the molar ratio of dimethylamine and ethylene oxide, it is preferable that the amount of dimethylamine is in excess because as the amount of dimethylamine relative to ethylene oxide increases, the production of by-products will decrease. Therefore, in order to carry out the method of the present invention advantageously, the dimethylamine/ethylene oxide (molar ratio) is generally 1.5 or more, 1.
.. 5 to 3.0 is suitable.
反応温度は、高い方が酸化エチレンの反応率およびDM
OH収率が大きく好ましいが、余りにも高温では反応し
たDMOHの分解が起こりかえって収率の低下を招くこ
とにもなり好ましくない。The higher the reaction temperature, the higher the reaction rate of ethylene oxide and the DM
Although it is preferable that the OH yield is large, it is not preferable that the temperature is too high because the reacted DMOH may be decomposed, resulting in a decrease in the yield.
したがって、一般的には100〜200℃で実施される
が、本発明の方法を有利に実施するには、140〜18
0℃の温度が望ましい。Therefore, although it is generally carried out at a temperature of 100 to 200 °C, the method of the invention is advantageously carried out at a temperature of 140 to 18 °C.
A temperature of 0°C is preferred.
本発明の反応において、反応圧力は特に特定されないが
、密閉系での反応であるから仕込原料モル比、反応温度
などにより自ずと定まる。例えばジメチルアミン/酸化
エチレンのモル比が2.0、反応温度150℃のとき、
反応圧力は約20kg/cm2Gである。In the reaction of the present invention, the reaction pressure is not particularly specified, but since the reaction is a closed system, it is naturally determined by the molar ratio of the raw materials to be charged, the reaction temperature, etc. For example, when the molar ratio of dimethylamine/ethylene oxide is 2.0 and the reaction temperature is 150°C,
The reaction pressure is about 20 kg/cm2G.
また、反応時間は短いと酸化エチレンの反応率が低く好
ましくなく、逆に長すぎると経済的に不利であり、通常
は10〜60分の範囲が望ましい。Furthermore, if the reaction time is too short, the reaction rate of ethylene oxide will be low, which is undesirable, while if it is too long, it will be economically disadvantageous, and a range of 10 to 60 minutes is usually desirable.
以上の様に本発明の方法は、従来になく選択性良く、高
収率でジメチルアミンと酸化エチレンとからDMOHを
得ることができ、かつ一般的な反応溶媒を使用しないた
め目的物のDMOHの分離精製も効率的に行うことがで
き、工業的に優れた方法である。As described above, the method of the present invention can obtain DMOH from dimethylamine and ethylene oxide with unprecedented selectivity and high yield, and since it does not use a common reaction solvent, the target product DMOH can be obtained. Separation and purification can also be carried out efficiently, making it an excellent method from an industrial perspective.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
尚、実施例においては、循環機能を持つ密閉型反応器を
使用し、予め合成したDMOHを循環させながら、ジメ
チルアミンと酸化エチレンとの所定量を連続的に供給し
、反応液を循環しながらその一部を系外に抜き出しなが
ら反応させた。In the examples, a closed reactor with a circulation function was used, and predetermined amounts of dimethylamine and ethylene oxide were continuously supplied while circulating DMOH synthesized in advance, and while circulating the reaction solution. A part of it was extracted from the system and reacted.
実施例 1
反応液の循環量を1.6 m3/hrとし、7.58
kg/hrのジメチルアミンと5.04 kg/hrの
酸化エチレン(モル比;1,5)(循環液量に対する原
料の供給量、 1/104)を連続的に供給し、原料の
供給量に見合う量の反応液を反応器の一部から系外に抜
き出しながら反応温度150℃で反応させた。DMOH
の収率は96.5モル%(対酸化エチレン)であった。Example 1 The circulation rate of the reaction solution was 1.6 m3/hr, and the reaction rate was 7.58 m3/hr.
kg/hr of dimethylamine and 5.04 kg/hr of ethylene oxide (molar ratio: 1.5) (raw material supply amount relative to circulating fluid volume, 1/104) were continuously supplied, and the raw material supply amount The reaction was carried out at a reaction temperature of 150° C. while extracting a corresponding amount of the reaction liquid out of the system from a part of the reactor. DMOH
The yield was 96.5 mol% (based on ethylene oxide).
反応時の反応圧力的21 kg/cm’Gであった。The reaction pressure during the reaction was 21 kg/cm'G.
抜き出した反応液の組成は表に示す通りである。The composition of the extracted reaction solution is shown in the table.
実施例 2
反応液の循環量を1.2 m3/hrとし、7.40
kg/hrのジメチルアミンと3.6 kg/hrの酸
化エチレン(モル比;2.0)(循環液量に対する原料
の供給量1/90 )を連続的に供給した以外は実施例
1と同様に実施した。DMOHの収率は99.4モル%
(対酸化エチレン)であった。なお、反応時の反応圧力
的21 kg/cm2Gであった。反応液の組成は表に
示す通りである。Example 2 The circulation rate of the reaction solution was 1.2 m3/hr, and the reaction rate was 7.40 m3/hr.
Same as Example 1 except that kg/hr dimethylamine and 3.6 kg/hr ethylene oxide (molar ratio: 2.0) (raw material supply amount 1/90 with respect to circulating fluid amount) were continuously supplied. It was carried out in The yield of DMOH is 99.4 mol%
(vs. ethylene oxide). The reaction pressure during the reaction was 21 kg/cm2G. The composition of the reaction solution is shown in the table.
比較例 1
実施例と同様な反応器を使用し、反応液の循環量を1.
2 m3/hrとし、7.80 kg/hrのジメチル
アミンと5.20 kg/hrの酸化エチレン(モル比
;1.5)(循環液量に対する原料の供給量、1/76
)を連続的に供給した以外は実施例1と同様に実施した
。Comparative Example 1 A reactor similar to that of Example was used, and the circulation amount of the reaction solution was set to 1.
2 m3/hr, 7.80 kg/hr of dimethylamine and 5.20 kg/hr of ethylene oxide (molar ratio: 1.5) (raw material supply amount relative to circulating fluid volume, 1/76
The same procedure as in Example 1 was carried out except that ) was continuously supplied.
DMOHの収率は94.6モル%(対酸化エチレン)で
あった。なお反応時の反応圧力的21 kg/cm2G
であった。反応液の組成は表に示す通りである。The yield of DMOH was 94.6 mol% (based on ethylene oxide). The reaction pressure during the reaction was 21 kg/cm2G.
Met. The composition of the reaction solution is shown in the table.
比較例 2
反応液の循環量を1.6 m3/hrとし、7.60
kg/hrのジメチルアミンと5.30 kg/hrの
酸化エチレン(モル比;1.4)(循環液量に対する原
料の供給量、 1/102)を連続的に供給し、反応温
度134℃として反応させた以外は実施例1と同様に実
施した。Comparative Example 2 The circulation rate of the reaction solution was 1.6 m3/hr, and the reaction rate was 7.60 m3/hr.
kg/hr of dimethylamine and 5.30 kg/hr of ethylene oxide (molar ratio: 1.4) (feeding amount of raw materials relative to circulating fluid volume, 1/102) were continuously supplied, and the reaction temperature was set at 134°C. The same procedure as in Example 1 was carried out except for the reaction.
DMOHの収率は87.0モル%(対酸化エチレン)で
あった。なお、反応時の反応圧力的15kg 7cm2
Gであった反応液の組成は表に示す通りである。The yield of DMOH was 87.0 mol% (based on ethylene oxide). In addition, the reaction pressure during the reaction is 15 kg 7 cm2
The composition of the reaction solution G is as shown in the table.
比較例 3
反応液の循環量を1.6 m3/hrとし、7.90
kg/hrのジメチルアミンと7.10 kg/hrの
酸化エチレン(モル比;1.1)(循環液量に対する原
料の供給量、1/88)を連続的に供給し、反応温度1
50℃として反応させた以外は実施例1と同様に実施し
た。Comparative Example 3 The circulation rate of the reaction solution was 1.6 m3/hr, and the reaction rate was 7.90 m3/hr.
kg/hr of dimethylamine and 7.10 kg/hr of ethylene oxide (molar ratio: 1.1) (feeding amount of raw material to circulating liquid amount, 1/88) were continuously supplied, and the reaction temperature was 1/2.
The same procedure as in Example 1 was carried out except that the reaction temperature was 50°C.
DMOHの収率は78.2モル%(対酸化エチレン)で
あった。なお反応時の反応圧力的20kg 7cm2G
であった。反応液の組成は表に示す通りである。The yield of DMOH was 78.2 mol% (based on ethylene oxide). In addition, the reaction pressure during the reaction is 20kg 7cm2G
Met. The composition of the reaction solution is shown in the table.
表(反応液の組成等) 手続補正書 昭和63年2 月19 日Table (composition of reaction solution, etc.) Procedural amendment February 19, 1988
Claims (1)
ノールを製造するに当たり、反応生成液を循環させなが
ら該循環液中にジメチルアミンおよび酸化エチレンを、
循環液量に対して1/80容量から1/200容量の量
で連続的に供給することを特徴とするジメチルアミノエ
タノールの製造法In producing dimethylaminoethanol from dimethylamine and ethylene oxide, while circulating the reaction product liquid, dimethylamine and ethylene oxide are added to the circulating liquid.
A method for producing dimethylaminoethanol, characterized in that it is continuously supplied in an amount of 1/80 to 1/200 volume relative to the amount of circulating liquid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31539087A JP2508773B2 (en) | 1987-12-15 | 1987-12-15 | Method for producing dimethylaminoethanol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP31539087A JP2508773B2 (en) | 1987-12-15 | 1987-12-15 | Method for producing dimethylaminoethanol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01157938A true JPH01157938A (en) | 1989-06-21 |
JP2508773B2 JP2508773B2 (en) | 1996-06-19 |
Family
ID=18064821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP31539087A Expired - Lifetime JP2508773B2 (en) | 1987-12-15 | 1987-12-15 | Method for producing dimethylaminoethanol |
Country Status (1)
Country | Link |
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JP (1) | JP2508773B2 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04120632A (en) * | 1990-09-11 | 1992-04-21 | Nec Gumma Ltd | Logic analyzer |
DE4414879C2 (en) * | 1994-04-28 | 1998-10-29 | Basf Ag | Process for the preparation of color stable dialkylaminoethanol |
EP1219592A1 (en) * | 2000-12-19 | 2002-07-03 | Nippon Shokubai Co., Ltd. | Method for production of alkanolamine and apparatus therefor |
US6566556B2 (en) | 2000-12-19 | 2003-05-20 | Nippon Shokubai Co., Ltd. | Method for production of alkanolamine and apparatus therefor |
WO2012080409A1 (en) | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialkylethanolamine having high colour stability |
US8791302B2 (en) | 2010-12-17 | 2014-07-29 | Basf Se | Process for preparing an N,N-dialky-ethanolamine having high color stability |
CN115894261A (en) * | 2022-12-23 | 2023-04-04 | 山东蓝湾新材料有限公司 | Industrial preparation method of N, N-dimethylethanolamine |
CN115957697A (en) * | 2023-01-10 | 2023-04-14 | 山东蓝湾新材料有限公司 | A kind of reaction kettle for dimethylethanolamine production and production method thereof |
-
1987
- 1987-12-15 JP JP31539087A patent/JP2508773B2/en not_active Expired - Lifetime
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04120632A (en) * | 1990-09-11 | 1992-04-21 | Nec Gumma Ltd | Logic analyzer |
DE4414879C2 (en) * | 1994-04-28 | 1998-10-29 | Basf Ag | Process for the preparation of color stable dialkylaminoethanol |
EP1219592A1 (en) * | 2000-12-19 | 2002-07-03 | Nippon Shokubai Co., Ltd. | Method for production of alkanolamine and apparatus therefor |
US6566556B2 (en) | 2000-12-19 | 2003-05-20 | Nippon Shokubai Co., Ltd. | Method for production of alkanolamine and apparatus therefor |
WO2012080409A1 (en) | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialkylethanolamine having high colour stability |
US8791302B2 (en) | 2010-12-17 | 2014-07-29 | Basf Se | Process for preparing an N,N-dialky-ethanolamine having high color stability |
CN115894261A (en) * | 2022-12-23 | 2023-04-04 | 山东蓝湾新材料有限公司 | Industrial preparation method of N, N-dimethylethanolamine |
CN115894261B (en) * | 2022-12-23 | 2024-05-03 | 山东蓝湾新材料有限公司 | Industrial preparation method of N, N-dimethylethanolamine |
CN115957697A (en) * | 2023-01-10 | 2023-04-14 | 山东蓝湾新材料有限公司 | A kind of reaction kettle for dimethylethanolamine production and production method thereof |
Also Published As
Publication number | Publication date |
---|---|
JP2508773B2 (en) | 1996-06-19 |
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