JPH0558618B2 - - Google Patents
Info
- Publication number
- JPH0558618B2 JPH0558618B2 JP61011503A JP1150386A JPH0558618B2 JP H0558618 B2 JPH0558618 B2 JP H0558618B2 JP 61011503 A JP61011503 A JP 61011503A JP 1150386 A JP1150386 A JP 1150386A JP H0558618 B2 JPH0558618 B2 JP H0558618B2
- Authority
- JP
- Japan
- Prior art keywords
- propanediol
- amino
- reaction
- catalyst
- hydrogen
- 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 - Fee Related
Links
- 239000003054 catalyst Substances 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 12
- KEQUNHIAUQQPAC-UHFFFAOYSA-N Dihydroxyacetone (dimer) Chemical compound OCC1(O)COC(O)(CO)CO1 KEQUNHIAUQQPAC-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 4
- 229940120503 dihydroxyacetone Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 3
- YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical compound OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- -1 nitro alcohols Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DOGCTUGYGZGSFX-UHFFFAOYSA-N 1-aminopropane-1,3-diol Chemical compound NC(O)CCO DOGCTUGYGZGSFX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は2−アミノ−1,3−プロパンジオー
ルの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing 2-amino-1,3-propanediol.
さらに詳しくは、ジヒドロキシアセトンダイマ
ーとアンモニアとを溶媒の存在下、水素化触媒を
用いて反応することを特徴とする2−アミノ−
1,3−プロパンジオールの製造法である。本発
明により得られた2−アミノ−1,3−プロパン
ジオールは医薬中間体、特にX線造影剤の原料と
して有用なものである。 More specifically, the 2-amino-
This is a method for producing 1,3-propanediol. 2-Amino-1,3-propanediol obtained according to the present invention is useful as a raw material for pharmaceutical intermediates, especially X-ray contrast agents.
(従来技術並びに本発明が解決しようとする問題
点)
2−アミノ−1,3−プロパンジオールを得る
方法としては、2−ニトロ−1,3−プロパンジ
オールを接触水素化還元するヨーロツパ特許第
71037記載の方法が知られている。該方法によれ
は、溶媒としてメタノールを用い塩化アンモニウ
ムの存在下、5%パラジウムカーボン触媒を用い
て、2−ニトロ−1,3−プロパンジオールNa
塩を還元して2−アミノ−1,3−プロパンジオ
ールを得ている。しかしながら、該方法では使用
する原料2−ニトロ−1,3−プロパンジオール
が他のニトロアルコール類と同様に熱的に非常に
不安定であり、比較的低温でも激しい分解が生
じ、場合によつては爆発する危険性があることが
知られている。特にアルカリ塩ではそれが顕著で
ある。このようなことから、上記方法では原料の
安定性に問題があり、工業的規模の製造法には適
さない。又他の方法としてはドイツ特許公報第
2829916号記載の方法がある。該方法はジヒドロ
キシアセトンモノマーとアンモニアとを溶媒の存
在下、水素化触媒を用いて接触水素還元して2−
アミノ−1,3−プロパンジオールを得ている。
しかしながら該方法は、その実施例をみると触媒
としてラネーニツケル触媒を使用する場合、100
〜200Kg/cm2の高圧を必要とし、触媒量も原料に
対し60%以上と多量に使用しており、溶媒量も原
料の約3倍と多い。又パラジウム触媒、白金触媒
を使用する例も記載されており、これら貴金属触
媒を用いると3Kg/cm2の低圧で反応が進行してい
る。しかし、これら貴金属触媒は最も汎用される
ラネーニツケルやラネーコバルト等の触媒に較べ
非常に高価であり、使用量も多いことから、貴金
属触媒の使用は有利とは言えない。これらのこと
から、上記方法は工業的規模の製造法としては充
分とは言えず又収率の記載がないため経済的メリ
ツトは不明である。さらにジヒドロキシアセトン
モノマーは工業的に得難く入手が困難であり、こ
れを使用することには問題がある。(Prior art and problems to be solved by the present invention) As a method for obtaining 2-amino-1,3-propanediol, the European Patent No.
The method described in No. 71037 is known. According to this method, 2-nitro-1,3-propanediol Na
2-Amino-1,3-propanediol is obtained by reducing the salt. However, in this method, the raw material 2-nitro-1,3-propanediol used is very thermally unstable like other nitro alcohols, and severe decomposition occurs even at relatively low temperatures, and in some cases is known to be explosive. This is especially noticeable with alkali salts. For this reason, the above method has a problem with the stability of the raw materials and is not suitable for industrial scale production. Another method is the German Patent Publication No.
There is a method described in No. 2829916. This method involves catalytic hydrogen reduction of dihydroxyacetone monomer and ammonia using a hydrogenation catalyst in the presence of a solvent to obtain 2-
Amino-1,3-propanediol is obtained.
However, in the example of this method, when Raney nickel catalyst is used as a catalyst, 100%
A high pressure of ~200Kg/cm 2 is required, a large amount of catalyst is used, more than 60% of the raw material, and the amount of solvent is about three times that of the raw material. Examples using palladium catalysts and platinum catalysts are also described, and when these noble metal catalysts are used, the reaction proceeds at a low pressure of 3 kg/cm 2 . However, these noble metal catalysts are much more expensive than the most widely used catalysts such as Raney nickel and Raney cobalt, and the amount used is large, so the use of noble metal catalysts cannot be said to be advantageous. For these reasons, the above method cannot be said to be sufficient as a production method on an industrial scale, and the economic merit is unclear since there is no description of the yield. Furthermore, dihydroxyacetone monomer is difficult to obtain industrially, and there are problems in using it.
(問題を解決するための手段)
本発明は斯る現状に鑑み、2−アミノ−1,3
−プロパンジオールを工業的に有利に製造する方
法を開発すべく鋭意研究を重ねた結果、人手の容
易なジヒドロキシアセトンダイマーから収率良
く、2−アミノ−1,3−プロパンジオールを得
る方法を確立した。(Means for solving the problem) In view of the current situation, the present invention provides 2-amino-1,3
- As a result of intensive research to develop an industrially advantageous method for producing propanediol, we established a method for obtaining 2-amino-1,3-propanediol in good yield from dihydroxyacetone dimer, which is easy to do manually. did.
ジヒドロキシアセトンダイマーの構造式は
であり、その構造式からは目的物である2−アミ
ノ−1,3−プロパンジオールを得ることは予測
されにくい。しかし、ジヒドロキシアセトンダイ
マーを水等の溶媒に溶解させ、この溶液をアンモ
ニアと水素化触媒の共存下接触水素化還元を行な
うと、おどろくべきことに2−アミノ−1,3−
プロパンジオールを得ることを見いだし、本発明
を完成するに至つた。、即ち、本発明は溶媒の存
在下、ジヒドロキシアセトンダイマーとアンモニ
アとを水素化触媒を用いて接触水素化還元するこ
とを特徴とする2−アミノ−1,3−プロパンジ
オールの製造法に係る。本発明に使用される溶媒
はジヒドロキシアセトンダイマーを溶解するもの
であればよく、例えば水、メタノール、エタノー
ル、ジオキサン等であり、特に好ましいのは水で
ある。溶媒量としては、ジヒドロキシアセトンダ
イマーを溶解させるのに必要な最小量でよく、経
済性を考慮すると、原料と同量〜5倍(重量比)
が好ましい。使用するアンモニア量としては、ジ
ヒドロキシアセトンダイマーに対し、2倍〜10倍
モルが適当であり、好ましくは4倍モル〜6倍モ
ルである。本発明に使用される水素化触媒として
はもつとも汎用されるラネーニツケル、ラネーコ
バルト等であり、その使用量は原料に対し5〜30
%(重量比)が好ましい。 The structural formula of dihydroxyacetone dimer is Therefore, it is difficult to predict that the target product, 2-amino-1,3-propanediol, will be obtained from the structural formula. However, when dihydroxyacetone dimer is dissolved in a solvent such as water and this solution is subjected to catalytic hydrogenation reduction in the coexistence of ammonia and a hydrogenation catalyst, surprisingly, 2-amino-1,3-
They discovered that propanediol can be obtained and completed the present invention. That is, the present invention relates to a method for producing 2-amino-1,3-propanediol, which is characterized by subjecting dihydroxyacetone dimer and ammonia to catalytic hydrogenation reduction using a hydrogenation catalyst in the presence of a solvent. The solvent used in the present invention may be any solvent as long as it dissolves the dihydroxyacetone dimer, such as water, methanol, ethanol, dioxane, etc., and water is particularly preferred. The amount of solvent should be the minimum amount necessary to dissolve the dihydroxyacetone dimer, and considering economic efficiency, it should be the same amount as the raw material to 5 times (weight ratio)
is preferred. The amount of ammonia to be used is suitably 2 to 10 times the mole of dihydroxyacetone dimer, preferably 4 to 6 times by mole. Hydrogenation catalysts used in the present invention include Raney nickel and Raney cobalt, which are commonly used.
% (weight ratio) is preferred.
反応温度としては通常40〜150℃好ましくは60
〜100℃である。 The reaction temperature is usually 40 to 150℃, preferably 60℃.
~100℃.
反応圧力は高くても差し支えないが、100Kg/
cm2以下で充分であり、20〜40Kg/cm2の範囲が実用
的である。 The reaction pressure can be high, but 100Kg/
cm 2 or less is sufficient, and a range of 20 to 40 Kg/cm 2 is practical.
本発明に従えば、水素化は1〜5時間で反応が
完結する。反応液からの後処理方法については特
に限定はなく、どんな方法でもよいが、例えば反
応終了後触媒を別し、その液を蒸留により分
離精製を行なえば容易に高純度の2−アミノ−
1,3−プロパンジオールが得られる。収率とし
ては、81〜86%と非常に高い値を得ることができ
る。ジヒドロキシアセトンモノマーを使用して同
様の反応を行なつた場合、2−アミノ−1,3−
プロパンジオールの収率は68%とダイマー使用の
場合より低く、本発明が収率的に非常に有利であ
ることがわかる。 According to the present invention, the hydrogenation reaction is completed in 1 to 5 hours. There is no particular limitation on the method of post-treatment of the reaction solution, and any method may be used. For example, if the catalyst is separated after the reaction is completed and the solution is separated and purified by distillation, highly pure 2-amino-
1,3-propanediol is obtained. A very high yield of 81 to 86% can be obtained. When a similar reaction is performed using dihydroxyacetone monomer, 2-amino-1,3-
The yield of propanediol was 68%, which is lower than when using a dimer, which shows that the present invention is very advantageous in terms of yield.
(発明の効果)
第一に比較的入手容易なジヒドロキシアセトン
ダイマーを用いることができる。(Effects of the Invention) First, dihydroxyacetone dimer, which is relatively easily available, can be used.
第二に収率が81〜86%と高い。 Second, the yield is high at 81-86%.
第三に溶媒、触媒、アンモニアの使用量が少な
い。 Thirdly, the amount of solvent, catalyst, and ammonia used is small.
第四に沸点が近似の不純物が生成しないため、
簡単な蒸留により高純度の目的物を得ることがで
きる。 Fourth, impurities with similar boiling points are not generated, so
A highly pure target product can be obtained by simple distillation.
このように本発明は非常に工業的に有利な製造
法である。 As described above, the present invention is a very industrially advantageous manufacturing method.
(実施例)
以下実施例により説明するが本発明はこれに限
定されるものではない。(Example) The present invention will be explained below using examples, but the present invention is not limited thereto.
実施例 1
内容積1000mlのステンレス製電磁撹拌式オート
クレーブにジヒドロキシアセトンダイマー200g、
25%アンモニア水溶液378g、通常の方法で展開
して得たラネーニツケル触媒30gを入れ、それに
水素を導入して圧力を30Kg/cm2、温度90℃にて水
素添加反応を行なつた。反応が進行するにつれ水
素圧力は減少するので逐次水素を追加した。2時
間30分で水素吸収はなくなり反応が完結した。室
温まで冷却後、水素及びアンモニアを追い出し触
媒を別後、蒸留を行ない2mmHgで沸点130〜
132℃の2−アミノ−1,3−プロパンジオール
174g(収率86%、GC純度90%)を得た。Example 1 200 g of dihydroxyacetone dimer was placed in a stainless steel electromagnetic stirring autoclave with an internal volume of 1000 ml.
378 g of a 25% ammonia aqueous solution and 30 g of Raney nickel catalyst obtained by developing in a conventional manner were charged, hydrogen was introduced thereto, and a hydrogenation reaction was carried out at a pressure of 30 Kg/cm 2 and a temperature of 90°C. As the reaction progressed, the hydrogen pressure decreased, so hydrogen was added successively. After 2 hours and 30 minutes, hydrogen absorption disappeared and the reaction was completed. After cooling to room temperature, hydrogen and ammonia are expelled, the catalyst is separated, and distillation is performed to obtain a boiling point of 130 ~ 2 mmHg.
2-amino-1,3-propanediol at 132℃
174 g (yield 86%, GC purity 90%) was obtained.
実施例 2
実施例1において、ラネーニツケル触媒のかわ
りにラネーコバルト触媒15gを入れそれに水素を
導入して圧力を30Kg/cm2、温度90℃にて水素添加
反応を行なつた。2時間で水素吸収はなくなり反
応が完結した。室温まで冷却後、水素及びアンモ
ニアを追い出し触媒を別後、蒸留を行ない2−
アミノ−1,3−プロパンジオール164g(収率
81%)を得た。Example 2 In Example 1, 15 g of Raney cobalt catalyst was substituted for the Raney nickel catalyst, hydrogen was introduced thereto, and a hydrogenation reaction was carried out at a pressure of 30 Kg/cm 2 and a temperature of 90°C. After 2 hours, hydrogen absorption disappeared and the reaction was completed. After cooling to room temperature, hydrogen and ammonia are removed and the catalyst is separated, followed by distillation.
Amino-1,3-propanediol 164g (yield
81%).
実施例 3
内容積1000mlのステンレス製電磁撹拌式オート
クレーブにジヒドロキシアセトンダイマー100g、
15%アンモニアメタノール溶液378g、通常の方
法で展開して得られたラネーニツケル触媒15gを
入れ、それに水素を導入して圧力を30Kg/cm2、温
度90℃にて水素添加反応を行なつた。Example 3 100 g of dihydroxyacetone dimer was placed in a stainless steel electromagnetic stirring autoclave with an internal volume of 1000 ml.
378 g of a 15% ammonia methanol solution and 15 g of Raney nickel catalyst obtained by development in a conventional manner were charged, hydrogen was introduced thereto, and a hydrogenation reaction was carried out at a pressure of 30 kg/cm 2 and a temperature of 90°C.
2時間で水素吸収はなくなり反応が完結した。
室温まで冷却後、水素及びアンモニアを追い出し
触媒を別後、蒸留を行ない、2−アミノ−1,
3−プロパンジオール86g(収率85%)を得た。 After 2 hours, hydrogen absorption disappeared and the reaction was completed.
After cooling to room temperature, hydrogen and ammonia are removed and the catalyst is separated, followed by distillation to obtain 2-amino-1,
86 g (yield: 85%) of 3-propanediol was obtained.
比較例 1
実施例3においてジヒドロキシアセトンダイマ
ーのかわりに、ジヒドロキシアセトンモノマーを
用い他は実施例3と同様に反応を行なつた。Comparative Example 1 The reaction was carried out in the same manner as in Example 3, except that a dihydroxyacetone monomer was used instead of the dihydroxyacetone dimer.
1時間50分で水素吸収はなくなり反応が完結し
た。同様の後処理を行ない、2−アミノ−1,3
−プロパンジオール69g(収率68%)を得た。 After 1 hour and 50 minutes, hydrogen absorption disappeared and the reaction was completed. After similar post-treatment, 2-amino-1,3
-Propanediol 69g (yield 68%) was obtained.
Claims (1)
ンダイマーとアンモニアとを水素化触媒を用いて
水素で接触還元することを特徴とする2−アミノ
−1,3−プロパンジオールの製造法。1. A method for producing 2-amino-1,3-propanediol, which comprises catalytically reducing dihydroxyacetone dimer and ammonia with hydrogen using a hydrogenation catalyst in the presence of water or an organic solvent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61011503A JPS62169751A (en) | 1986-01-21 | 1986-01-21 | Production of 2-amino-1,3-propanediol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61011503A JPS62169751A (en) | 1986-01-21 | 1986-01-21 | Production of 2-amino-1,3-propanediol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62169751A JPS62169751A (en) | 1987-07-25 |
JPH0558618B2 true JPH0558618B2 (en) | 1993-08-27 |
Family
ID=11779823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61011503A Granted JPS62169751A (en) | 1986-01-21 | 1986-01-21 | Production of 2-amino-1,3-propanediol |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62169751A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4412065A1 (en) * | 1994-04-11 | 1995-10-19 | Pfeifer & Langen | Process for the preparation of hydroxyamines |
US5998669A (en) * | 1998-09-17 | 1999-12-07 | Abbott Laboratories | Process for production of 2-amino-1,3-propanediol |
KR100286570B1 (en) * | 1999-03-09 | 2001-03-15 | 남창우 | Process for the production of SERINOL (2-amino-1,3-propanediol) |
-
1986
- 1986-01-21 JP JP61011503A patent/JPS62169751A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS62169751A (en) | 1987-07-25 |
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Legal Events
Date | Code | Title | Description |
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LAPS | Cancellation because of no payment of annual fees |