JPS58150565A - 環状尿素誘導体の製造方法 - Google Patents
環状尿素誘導体の製造方法Info
- Publication number
- JPS58150565A JPS58150565A JP3179182A JP3179182A JPS58150565A JP S58150565 A JPS58150565 A JP S58150565A JP 3179182 A JP3179182 A JP 3179182A JP 3179182 A JP3179182 A JP 3179182A JP S58150565 A JPS58150565 A JP S58150565A
- Authority
- JP
- Japan
- Prior art keywords
- cyclic urea
- urea derivative
- reaction
- alkylamine
- mol
- 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
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 150000002009 diols Chemical class 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001569 carbon dioxide Substances 0.000 claims description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 18
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 alkylamine salt Chemical class 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- PPNLXDXRZUZRTD-UHFFFAOYSA-N methanamine;methylcarbamic acid Chemical compound NC.CNC(O)=O PPNLXDXRZUZRTD-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 1
- AWHORBWDEKTQAX-UHFFFAOYSA-N 1,3-dipropylurea Chemical compound CCCNC(=O)NCCC AWHORBWDEKTQAX-UHFFFAOYSA-N 0.000 description 1
- FPKCLQHVUJVCLE-UHFFFAOYSA-N 1-methoxyimidazolidin-2-one Chemical compound CON1CCNC1=O FPKCLQHVUJVCLE-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GPUHGQYNYJIMDZ-UHFFFAOYSA-N ethylazanium;n-ethylcarbamate Chemical compound CC[NH3+].CCNC([O-])=O GPUHGQYNYJIMDZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- HOIKXNCMIFKASU-UHFFFAOYSA-N propylazanium;n-propylcarbamate Chemical compound CCC[NH3+].CCCNC([O-])=O HOIKXNCMIFKASU-UHFFFAOYSA-N 0.000 description 1
- KBJXDTIYSSQJAI-UHFFFAOYSA-N propylcarbamic acid Chemical compound CCCNC(O)=O KBJXDTIYSSQJAI-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3179182A JPS58150565A (ja) | 1982-03-02 | 1982-03-02 | 環状尿素誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3179182A JPS58150565A (ja) | 1982-03-02 | 1982-03-02 | 環状尿素誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58150565A true JPS58150565A (ja) | 1983-09-07 |
| JPH0375543B2 JPH0375543B2 (OSRAM) | 1991-12-02 |
Family
ID=12340886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3179182A Granted JPS58150565A (ja) | 1982-03-02 | 1982-03-02 | 環状尿素誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58150565A (OSRAM) |
-
1982
- 1982-03-02 JP JP3179182A patent/JPS58150565A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0375543B2 (OSRAM) | 1991-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yoshida et al. | Novel synthesis of carbamate ester from carbon dioxide, amines, and alkyl halides | |
| US4140716A (en) | Process for making an amide of formic acid and forming nitrodiarylamine therefrom | |
| JP3041703B2 (ja) | カルバミン酸エステルの製法 | |
| JPH04211075A (ja) | アルキレンカーボネートの製造法 | |
| JPS599543B2 (ja) | β−アミノプロピオンアミドの製造方法 | |
| US4499024A (en) | Continuous process for preparing bisfluoroxydifluoromethane | |
| JPS58150565A (ja) | 環状尿素誘導体の製造方法 | |
| EP0013176B2 (en) | Synthesis of lower alkyl amines | |
| CA1249590A (en) | Bicyclic amide acetal production | |
| JPS5941984B2 (ja) | クロロチオ−ル蟻酸エステルの製造方法 | |
| US4866177A (en) | Process for one-step synthesis of amides | |
| JPS624255A (ja) | エチレンシアンヒドリン及びそのエ−テルの共同製法 | |
| US6380420B1 (en) | Process for making fatty acid nitriles and fatty amines by cross-metathesis of normal alpha olefins | |
| EP0395103B1 (en) | Process for preparing perfluoroalkenyl sulfonyl fluorides | |
| JP4090658B2 (ja) | アリールエーテルの製造方法 | |
| US4222959A (en) | Process for the preparation of aromatic formamides | |
| JP3334206B2 (ja) | ２，３，５，６−テトラフルオロアニリンの製造方法 | |
| JPS60172948A (ja) | メタ置換アニリンの製造方法 | |
| AU673458B2 (en) | Process for the preparation of secondary or tertiary amines | |
| JPH0729994B2 (ja) | Ｎ−アルキルアルキレンジアミンの製造方法 | |
| US4097524A (en) | Process for the preparation of formamides | |
| JPH06239787A (ja) | 高純度ベンジル−β−ナフチルエーテルの製造方法 | |
| US6020284A (en) | Preparation of Lucas reagent of enhanced utility and its use in synthesis of cycloaliphatic chlorides | |
| KR900007418B1 (ko) | 인돌류의 제조방법 | |
| EP0129214A1 (en) | Method for the preparation of benzenamines |