JPS5869847A - ポリアルキレンポリアミンの製造法 - Google Patents
ポリアルキレンポリアミンの製造法Info
- Publication number
- JPS5869847A JPS5869847A JP57167741A JP16774182A JPS5869847A JP S5869847 A JPS5869847 A JP S5869847A JP 57167741 A JP57167741 A JP 57167741A JP 16774182 A JP16774182 A JP 16774182A JP S5869847 A JPS5869847 A JP S5869847A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- reactant
- mixture
- carbonic acid
- compound
- 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
- 229920000768 polyamine Polymers 0.000 title claims description 22
- 229920001281 polyalkylene Polymers 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- -1 alkylene amine compound Chemical class 0.000 claims description 20
- 239000000376 reactant Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001569 carbon dioxide Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000005323 carbonate salts Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- FDPBFGVIBGLCBC-UHFFFAOYSA-N OC(O)C=C=C Chemical compound OC(O)C=C=C FDPBFGVIBGLCBC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KLQAVPAIZZTMLH-UHFFFAOYSA-N buta-1,2-diene-1,1-diol Chemical compound CC=C=C(O)O KLQAVPAIZZTMLH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- UZPJNBSMYNQUMW-UHFFFAOYSA-N carbonic acid;ethane-1,2-diamine Chemical compound NCCN.OC(O)=O UZPJNBSMYNQUMW-UHFFFAOYSA-N 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SELYJABLPLKXOY-UHFFFAOYSA-N methyl n,n-dimethylcarbamate Chemical compound COC(=O)N(C)C SELYJABLPLKXOY-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- WVCAATDGXHFREC-UHFFFAOYSA-M potassium;ethyl carbonate Chemical compound [K+].CCOC([O-])=O WVCAATDGXHFREC-UHFFFAOYSA-M 0.000 description 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30722881A | 1981-09-30 | 1981-09-30 | |
| US307228 | 1981-09-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5869847A true JPS5869847A (ja) | 1983-04-26 |
| JPS6338343B2 JPS6338343B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-29 |
Family
ID=23188811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57167741A Granted JPS5869847A (ja) | 1981-09-30 | 1982-09-28 | ポリアルキレンポリアミンの製造法 |
Country Status (4)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61289065A (ja) * | 1985-04-04 | 1986-12-19 | ユニオン、カ−バイド、コ−ポレ−シヨン | 酸素含有ポリアミンの転化 |
| JPS62502753A (ja) * | 1985-03-14 | 1987-10-22 | ザ ル−ブリゾル コ−ポレ−シヨン | 高分子量含窒素縮合物及びこれを含む燃料及び潤滑油 |
| JP2014505029A (ja) * | 2010-12-08 | 2014-02-27 | エボニック デグサ ゲーエムベーハー | 気相に対する液相の高い体積比及び／又は高い圧力での、均一触媒を用いた、第一級アミンを得るための、アンモニアによる第一級アルコールの高選択的な直接アミノ化法 |
| JP2019504845A (ja) * | 2016-02-12 | 2019-02-21 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| JP2019504844A (ja) * | 2016-02-12 | 2019-02-21 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| JP2019506409A (ja) * | 2016-02-12 | 2019-03-07 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| JP2020526535A (ja) * | 2017-07-10 | 2020-08-31 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンまたはその尿素誘導体を調製する方法 |
| JP2020527554A (ja) * | 2017-07-10 | 2020-09-10 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンを作製するためのプロセス |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6078945A (ja) * | 1983-10-06 | 1985-05-04 | Mitsui Toatsu Chem Inc | ジエチレントリアミンの製造法 |
| JPH04215441A (ja) * | 1990-12-13 | 1992-08-06 | Nec Corp | 半導体装置及びその製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51147600A (en) * | 1975-06-02 | 1976-12-17 | Texaco Development Corp | Process for preparing polyalkylene polyamine |
| JPS53135911A (en) * | 1977-05-03 | 1978-11-28 | Bayer Ag | Lower molecular weight c22c33 alkylene polyamine and process for preparing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714259A (en) * | 1970-08-20 | 1973-01-30 | Jefferson Chem Co Inc | Production of linear polyethylene polyamines |
-
1982
- 1982-09-24 CA CA000412122A patent/CA1202328A/en not_active Expired
- 1982-09-28 JP JP57167741A patent/JPS5869847A/ja active Granted
- 1982-09-29 EP EP82108995A patent/EP0075935B1/en not_active Expired
- 1982-09-29 DE DE8282108995T patent/DE3272028D1/de not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51147600A (en) * | 1975-06-02 | 1976-12-17 | Texaco Development Corp | Process for preparing polyalkylene polyamine |
| JPS53135911A (en) * | 1977-05-03 | 1978-11-28 | Bayer Ag | Lower molecular weight c22c33 alkylene polyamine and process for preparing same |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62502753A (ja) * | 1985-03-14 | 1987-10-22 | ザ ル−ブリゾル コ−ポレ−シヨン | 高分子量含窒素縮合物及びこれを含む燃料及び潤滑油 |
| JPS61289065A (ja) * | 1985-04-04 | 1986-12-19 | ユニオン、カ−バイド、コ−ポレ−シヨン | 酸素含有ポリアミンの転化 |
| JP2014505029A (ja) * | 2010-12-08 | 2014-02-27 | エボニック デグサ ゲーエムベーハー | 気相に対する液相の高い体積比及び／又は高い圧力での、均一触媒を用いた、第一級アミンを得るための、アンモニアによる第一級アルコールの高選択的な直接アミノ化法 |
| JP2019504845A (ja) * | 2016-02-12 | 2019-02-21 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| JP2019504844A (ja) * | 2016-02-12 | 2019-02-21 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| JP2019506409A (ja) * | 2016-02-12 | 2019-03-07 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップＡｋｚｏ Ｎｏｂｅｌ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| US10428011B2 (en) | 2016-02-12 | 2019-10-01 | Nouryon Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| JP2020526535A (ja) * | 2017-07-10 | 2020-08-31 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンまたはその尿素誘導体を調製する方法 |
| JP2020527554A (ja) * | 2017-07-10 | 2020-09-10 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンを作製するためのプロセス |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0075935A2 (en) | 1983-04-06 |
| JPS6338343B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-29 |
| DE3272028D1 (de) | 1986-08-21 |
| EP0075935A3 (en) | 1985-03-13 |
| EP0075935B1 (en) | 1986-07-16 |
| CA1202328A (en) | 1986-03-25 |
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