CA1097676A - Production industrielle de n-alkylacarbamates - Google Patents
Production industrielle de n-alkylacarbamatesInfo
- Publication number
- CA1097676A CA1097676A CA293,294A CA293294A CA1097676A CA 1097676 A CA1097676 A CA 1097676A CA 293294 A CA293294 A CA 293294A CA 1097676 A CA1097676 A CA 1097676A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- formula
- alkyl
- chloride
- naphthyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- -1 carbamyl chlorides Chemical class 0.000 claims description 15
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 6
- LPCJHUPMQKSPDC-UHFFFAOYSA-N 3,5-diethylphenol Chemical compound CCC1=CC(O)=CC(CC)=C1 LPCJHUPMQKSPDC-UHFFFAOYSA-N 0.000 description 6
- 229940054025 carbamate anxiolytics Drugs 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 4
- 150000004780 naphthols Chemical class 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HUNDISMVCBSIKO-UHFFFAOYSA-N (3,5-diethylphenyl) n-methylcarbamate Chemical compound CCC1=CC(CC)=CC(OC(=O)NC)=C1 HUNDISMVCBSIKO-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- JGFZITGNFAVSKU-UHFFFAOYSA-N 3,5-dimethyl-4-(methylsulfanyl)phenol Chemical compound CSC1=C(C)C=C(O)C=C1C JGFZITGNFAVSKU-UHFFFAOYSA-N 0.000 description 1
- ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 description 1
- ZDUIHRJGDMTBEX-UHFFFAOYSA-N 3-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC(O)=C1 ZDUIHRJGDMTBEX-UHFFFAOYSA-N 0.000 description 1
- SZBIKNXBDIVHKY-UHFFFAOYSA-N 4-(dimethylamino)-3-methylphenol Chemical compound CN(C)C1=CC=C(O)C=C1C SZBIKNXBDIVHKY-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical class CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772702372 DE2702372A1 (de) | 1977-01-21 | 1977-01-21 | Verfahren zur herstellung von n-alkylcarbamaten |
| DEP2702372.9 | 1977-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097676A true CA1097676A (fr) | 1981-03-17 |
Family
ID=5999198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,294A Expired CA1097676A (fr) | 1977-01-21 | 1977-12-16 | Production industrielle de n-alkylacarbamates |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5392714A (fr) |
| BE (1) | BE863017A (fr) |
| CA (1) | CA1097676A (fr) |
| DD (1) | DD133793A5 (fr) |
| DE (1) | DE2702372A1 (fr) |
| FR (1) | FR2378002A1 (fr) |
| GB (1) | GB1594422A (fr) |
| HU (1) | HU175440B (fr) |
| IL (1) | IL53600A0 (fr) |
| IT (1) | IT1103262B (fr) |
| NL (1) | NL7800740A (fr) |
| SU (1) | SU860694A1 (fr) |
| ZA (1) | ZA78364B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6015771A (en) * | 1998-05-22 | 2000-01-18 | Bayer Aktiengesellschaft | Thermally-responsive record material |
| US6294502B1 (en) | 1998-05-22 | 2001-09-25 | Bayer Aktiengesellschaft | Thermally-responsive record material |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191325971A (en) * | 1913-11-12 | 1914-03-05 | Bruno Beckmann Chem Fab G M B | Improved Manufacture of Carbamic Acid Ester of alpha-dichlorhydrin. |
| CH383945A (de) * | 1960-04-14 | 1964-11-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Arylcarbamaten und deren Verwendung zur Insektenbekämpfung |
| GB1054673A (fr) * | 1962-08-23 | |||
| GB1042203A (en) * | 1963-04-09 | 1966-09-14 | Robert J Geary | Substituted phenyl carbamates and their use as plant growth regulants |
-
1977
- 1977-01-21 DE DE19772702372 patent/DE2702372A1/de not_active Withdrawn
- 1977-12-13 IL IL53600A patent/IL53600A0/xx unknown
- 1977-12-16 CA CA293,294A patent/CA1097676A/fr not_active Expired
-
1978
- 1978-01-09 JP JP60578A patent/JPS5392714A/ja active Pending
- 1978-01-16 SU SU782566402A patent/SU860694A1/ru active
- 1978-01-18 IT IT47692/78A patent/IT1103262B/it active
- 1978-01-18 BE BE184400A patent/BE863017A/fr unknown
- 1978-01-19 DD DD7800203306A patent/DD133793A5/xx unknown
- 1978-01-20 FR FR7801658A patent/FR2378002A1/fr not_active Withdrawn
- 1978-01-20 NL NL7800740A patent/NL7800740A/xx not_active Application Discontinuation
- 1978-01-20 HU HU78BA3617A patent/HU175440B/hu unknown
- 1978-01-20 ZA ZA00780364A patent/ZA78364B/xx unknown
- 1978-01-20 GB GB2348/78A patent/GB1594422A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2378002A1 (fr) | 1978-08-18 |
| IT7847692A0 (it) | 1978-01-18 |
| IT1103262B (it) | 1985-10-14 |
| JPS5392714A (en) | 1978-08-15 |
| SU860694A1 (ru) | 1981-08-30 |
| BE863017A (fr) | 1978-07-18 |
| DE2702372A1 (de) | 1978-07-27 |
| ZA78364B (en) | 1979-01-31 |
| NL7800740A (nl) | 1978-07-25 |
| IL53600A0 (en) | 1978-03-10 |
| GB1594422A (en) | 1981-07-30 |
| DD133793A5 (de) | 1979-01-24 |
| HU175440B (hu) | 1980-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |