CA1074333A - Method for synthesizing n-methyl-ureas - Google Patents
Method for synthesizing n-methyl-ureasInfo
- Publication number
- CA1074333A CA1074333A CA267,040A CA267040A CA1074333A CA 1074333 A CA1074333 A CA 1074333A CA 267040 A CA267040 A CA 267040A CA 1074333 A CA1074333 A CA 1074333A
- Authority
- CA
- Canada
- Prior art keywords
- urea
- methyl
- ureas
- formaldehyde
- kgs
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 230000002194 synthesizing effect Effects 0.000 title description 2
- 239000004202 carbamide Substances 0.000 claims abstract description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 4
- 229960004279 formaldehyde Drugs 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 241001572615 Amorphus Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT29962/75A IT1051036B (it) | 1975-12-03 | 1975-12-03 | Procedimento per la sintesi di n metil uree |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1074333A true CA1074333A (en) | 1980-03-25 |
Family
ID=11228764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA267,040A Expired CA1074333A (en) | 1975-12-03 | 1976-12-02 | Method for synthesizing n-methyl-ureas |
Country Status (31)
Country | Link |
---|---|
JP (1) | JPS5271419A (xx) |
AR (1) | AR220673A1 (xx) |
AT (1) | AT350582B (xx) |
AU (1) | AU508607B2 (xx) |
BE (1) | BE849073A (xx) |
BG (1) | BG32846A3 (xx) |
BR (1) | BR7608197A (xx) |
CA (1) | CA1074333A (xx) |
CS (1) | CS193070B2 (xx) |
DD (1) | DD127478A5 (xx) |
DE (1) | DE2654928C3 (xx) |
DK (1) | DK536076A (xx) |
EG (1) | EG12262A (xx) |
ES (1) | ES454228A1 (xx) |
FR (1) | FR2333781A1 (xx) |
GB (1) | GB1517820A (xx) |
HU (1) | HU179578B (xx) |
IE (1) | IE44189B1 (xx) |
IN (1) | IN144718B (xx) |
IT (1) | IT1051036B (xx) |
LU (1) | LU76306A1 (xx) |
MX (1) | MX4021E (xx) |
NL (1) | NL167418C (xx) |
NO (1) | NO147274C (xx) |
PH (1) | PH13011A (xx) |
PL (1) | PL109171B1 (xx) |
PT (1) | PT65922B (xx) |
SE (1) | SE7613630L (xx) |
TR (1) | TR18980A (xx) |
YU (1) | YU292276A (xx) |
ZA (1) | ZA767109B (xx) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0215964B1 (en) * | 1985-09-10 | 1991-01-23 | Kawaken Fine Chemicals Co., Ltd. | Process for preparing cyclic urea derivatives |
US4617400A (en) * | 1985-09-11 | 1986-10-14 | Kawaken Fine Chemicals Co., Ltd. | Process for preparing cyclic urea derivatives |
DE3800083A1 (de) * | 1988-01-05 | 1989-07-13 | Basf Ag | Verfahren zur herstellung von cyclischen n,n'-dimethylharnstoffen |
DE4425696A1 (de) * | 1994-07-20 | 1996-01-25 | Basf Ag | Verfahren zur Herstellung 1,3-disubstituierter Imidazolidinone |
DE19743760A1 (de) * | 1997-10-02 | 1999-04-08 | Basf Ag | Verfahren zur Herstellung von cyclischen Harnstoffderivaten |
-
1975
- 1975-12-03 IT IT29962/75A patent/IT1051036B/it active
-
1976
- 1976-11-26 DK DK536076A patent/DK536076A/da not_active Application Discontinuation
- 1976-11-29 ZA ZA767109A patent/ZA767109B/xx unknown
- 1976-11-29 EG EG76748A patent/EG12262A/xx active
- 1976-11-30 TR TR18980A patent/TR18980A/xx unknown
- 1976-12-01 YU YU02922/76A patent/YU292276A/xx unknown
- 1976-12-01 LU LU76306A patent/LU76306A1/xx unknown
- 1976-12-01 NO NO764100A patent/NO147274C/no unknown
- 1976-12-01 GB GB50196/76A patent/GB1517820A/en not_active Expired
- 1976-12-01 IN IN2141/CAL/76A patent/IN144718B/en unknown
- 1976-12-01 AU AU20145/76A patent/AU508607B2/en not_active Expired
- 1976-12-02 PT PT65922A patent/PT65922B/pt unknown
- 1976-12-02 CA CA267,040A patent/CA1074333A/en not_active Expired
- 1976-12-02 DD DD196085A patent/DD127478A5/xx unknown
- 1976-12-02 AT AT894276A patent/AT350582B/de active
- 1976-12-02 PH PH19190A patent/PH13011A/en unknown
- 1976-12-02 HU HU76SA2998A patent/HU179578B/hu unknown
- 1976-12-02 FR FR7636337A patent/FR2333781A1/fr active Granted
- 1976-12-02 BR BR7608197A patent/BR7608197A/pt unknown
- 1976-12-03 DE DE2654928A patent/DE2654928C3/de not_active Expired
- 1976-12-03 BG BG7634826A patent/BG32846A3/xx unknown
- 1976-12-03 AR AR265719A patent/AR220673A1/es active
- 1976-12-03 PL PL1976194144A patent/PL109171B1/pl unknown
- 1976-12-03 SE SE7613630A patent/SE7613630L/xx not_active Application Discontinuation
- 1976-12-03 CS CS767876A patent/CS193070B2/cs unknown
- 1976-12-03 JP JP51144818A patent/JPS5271419A/ja active Pending
- 1976-12-03 ES ES454228A patent/ES454228A1/es not_active Expired
- 1976-12-03 NL NL7613527.A patent/NL167418C/xx not_active IP Right Cessation
- 1976-12-03 BE BE172980A patent/BE849073A/xx not_active IP Right Cessation
- 1976-12-03 MX MX765185U patent/MX4021E/es unknown
- 1976-12-03 IE IE2665/76A patent/IE44189B1/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKEX | Expiry |