CH492682A - Verfahren zur Herstellung von neuen Carbamaten - Google Patents
Verfahren zur Herstellung von neuen CarbamatenInfo
- Publication number
- CH492682A CH492682A CH1078965A CH1078965A CH492682A CH 492682 A CH492682 A CH 492682A CH 1078965 A CH1078965 A CH 1078965A CH 1078965 A CH1078965 A CH 1078965A CH 492682 A CH492682 A CH 492682A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenol
- substituted
- formula
- amine
- reacted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 alkali metal salt Chemical class 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- AAHHJSWMPOIMTL-UHFFFAOYSA-N 2-(1,3-oxathiolan-2-yl)phenol Chemical compound OC1=CC=CC=C1C1SCCO1 AAHHJSWMPOIMTL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDTJZIUGKIQWPI-UHFFFAOYSA-N 2-(1,3-dithiolan-2-yl)phenol Chemical compound OC1=CC=CC=C1C1SCCS1 BDTJZIUGKIQWPI-UHFFFAOYSA-N 0.000 description 2
- GASSLYMVJDEQDQ-UHFFFAOYSA-N 2-[bis(2-hydroxyethylsulfanyl)methyl]phenol Chemical compound OCCSC(SCCO)C1=CC=CC=C1O GASSLYMVJDEQDQ-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- BKJDNXPECIOMDK-UHFFFAOYSA-N 2-(1,3-dithian-2-yl)phenol Chemical compound OC1=CC=CC=C1C1SCCCS1 BKJDNXPECIOMDK-UHFFFAOYSA-N 0.000 description 1
- VVMDOOIVBRONTJ-UHFFFAOYSA-N 3-(1,3-dithiolan-2-yl)phenol Chemical compound OC1=CC=CC(C2SCCS2)=C1 VVMDOOIVBRONTJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ODODCXUTOYPTDB-UHFFFAOYSA-N OC(=O)N(C)C1=CC=CC(C2SCCS2)=C1 Chemical compound OC(=O)N(C)C1=CC=CC(C2SCCS2)=C1 ODODCXUTOYPTDB-UHFFFAOYSA-N 0.000 description 1
- KPWXCMRERKCSDF-UHFFFAOYSA-N OC(=O)N(C)C1=CC=CC=C1C1SC(CO)CS1 Chemical compound OC(=O)N(C)C1=CC=CC=C1C1SC(CO)CS1 KPWXCMRERKCSDF-UHFFFAOYSA-N 0.000 description 1
- KYEXPBWBHGARRZ-UHFFFAOYSA-N OC(=O)N(C)C1=CC=CC=C1C1SCCCS1 Chemical compound OC(=O)N(C)C1=CC=CC=C1C1SCCCS1 KYEXPBWBHGARRZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KAYRXNLQJHAJFX-UHFFFAOYSA-N methyl-[2-(1,3-oxathiolan-2-yl)phenyl]carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1C1SCCO1 KAYRXNLQJHAJFX-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1529669A CH504159A (de) | 1964-10-08 | 1965-07-30 | Schädlingsbekämpfungsmittel |
| CH1078965A CH492682A (de) | 1964-10-08 | 1965-07-30 | Verfahren zur Herstellung von neuen Carbamaten |
| ES0318236A ES318236A1 (es) | 1964-10-08 | 1965-10-07 | Procedimiento para la preparacion de carbamatos. |
| JP6157765A JPS498850B1 (enrdf_load_stackoverflow) | 1964-10-08 | 1965-10-08 | |
| JP5737672A JPS5121976B1 (enrdf_load_stackoverflow) | 1964-10-08 | 1972-06-10 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1311364A CH468977A (de) | 1964-10-08 | 1964-10-08 | Verfahren zur Herstellung von neuen Carbamaten |
| CH1078965A CH492682A (de) | 1964-10-08 | 1965-07-30 | Verfahren zur Herstellung von neuen Carbamaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH492682A true CH492682A (de) | 1970-06-30 |
Family
ID=25707298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1078965A CH492682A (de) | 1964-10-08 | 1965-07-30 | Verfahren zur Herstellung von neuen Carbamaten |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JPS498850B1 (enrdf_load_stackoverflow) |
| CH (1) | CH492682A (enrdf_load_stackoverflow) |
| ES (1) | ES318236A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59166174A (ja) * | 1983-02-04 | 1984-09-19 | 美津濃株式会社 | スキ−板 |
| EP0209569B1 (en) * | 1985-01-07 | 1994-09-21 | FLOREANI, Adrian J. | Snow ski |
-
1965
- 1965-07-30 CH CH1078965A patent/CH492682A/de not_active IP Right Cessation
- 1965-10-07 ES ES0318236A patent/ES318236A1/es not_active Expired
- 1965-10-08 JP JP6157765A patent/JPS498850B1/ja active Pending
-
1972
- 1972-06-10 JP JP5737672A patent/JPS5121976B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES318236A1 (es) | 1966-04-16 |
| JPS5121976B1 (enrdf_load_stackoverflow) | 1976-07-06 |
| JPS498850B1 (enrdf_load_stackoverflow) | 1974-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |