JPH0555498B2 - - Google Patents
Info
- Publication number
- JPH0555498B2 JPH0555498B2 JP62253867A JP25386787A JPH0555498B2 JP H0555498 B2 JPH0555498 B2 JP H0555498B2 JP 62253867 A JP62253867 A JP 62253867A JP 25386787 A JP25386787 A JP 25386787A JP H0555498 B2 JPH0555498 B2 JP H0555498B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkanolamine
- ethyleneimine
- gas
- catalyst
- 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
- 239000007789 gas Substances 0.000 claims description 36
- -1 aziridine compound Chemical class 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 23
- 238000006297 dehydration reaction Methods 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000002994 raw material Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 22
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 19
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000002516 radical scavenger Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 239000002912 waste gas Substances 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000001541 aziridines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- CSWPOLMVXVBCSV-UHFFFAOYSA-N 2-ethylaziridine Chemical compound CCC1CN1 CSWPOLMVXVBCSV-UHFFFAOYSA-N 0.000 description 1
- 241000511343 Chondrostoma nasus Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical group [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25386787A JPH0196167A (ja) | 1987-10-09 | 1987-10-09 | アジリジン化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25386787A JPH0196167A (ja) | 1987-10-09 | 1987-10-09 | アジリジン化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0196167A JPH0196167A (ja) | 1989-04-14 |
| JPH0555498B2 true JPH0555498B2 (fr) | 1993-08-17 |
Family
ID=17257234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25386787A Granted JPH0196167A (ja) | 1987-10-09 | 1987-10-09 | アジリジン化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0196167A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003321444A (ja) * | 2002-04-24 | 2003-11-11 | Nippon Shokubai Co Ltd | アジリジン類およびｎ−ビニルアミド類の製造方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4759129B2 (ja) * | 2000-11-06 | 2011-08-31 | 株式会社日本触媒 | アジリジン化合物の製造方法および気相反応方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5010593A (fr) * | 1973-04-16 | 1975-02-03 | ||
| JPS62149337A (ja) * | 1985-12-23 | 1987-07-03 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
| JPS62152539A (ja) * | 1985-12-27 | 1987-07-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
| JPS62152543A (ja) * | 1985-12-27 | 1987-07-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
-
1987
- 1987-10-09 JP JP25386787A patent/JPH0196167A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5010593A (fr) * | 1973-04-16 | 1975-02-03 | ||
| JPS62149337A (ja) * | 1985-12-23 | 1987-07-03 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
| JPS62152539A (ja) * | 1985-12-27 | 1987-07-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
| JPS62152543A (ja) * | 1985-12-27 | 1987-07-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | アルカノ−ルアミン類の気相分子内脱水反応用触媒 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003321444A (ja) * | 2002-04-24 | 2003-11-11 | Nippon Shokubai Co Ltd | アジリジン類およびｎ−ビニルアミド類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0196167A (ja) | 1989-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |