DE2212766A1 - Verfahren zur Herstellung von fluessigen Thiocarbaminsaeureestern - Google Patents
Verfahren zur Herstellung von fluessigen ThiocarbaminsaeureesternInfo
- Publication number
- DE2212766A1 DE2212766A1 DE19722212766 DE2212766A DE2212766A1 DE 2212766 A1 DE2212766 A1 DE 2212766A1 DE 19722212766 DE19722212766 DE 19722212766 DE 2212766 A DE2212766 A DE 2212766A DE 2212766 A1 DE2212766 A1 DE 2212766A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- reaction product
- phosgene
- acid ester
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 21
- 239000007788 liquid Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003560 thiocarbamic acids Chemical class 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 33
- -1 chlorothioformic acid ester Chemical class 0.000 claims description 25
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- WARIWGPBHKPYON-UHFFFAOYSA-N Ethiolate Chemical compound CCSC(=O)N(CC)CC WARIWGPBHKPYON-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 238000011160 research Methods 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 230000001133 acceleration Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims 2
- GRSBAMVBFWRBBH-UHFFFAOYSA-N o-ethyl chloromethanethioate Chemical compound CCOC(Cl)=S GRSBAMVBFWRBBH-UHFFFAOYSA-N 0.000 claims 2
- ZCQWPWOIQCHISE-UHFFFAOYSA-N CC[S+]=C(N)[O-] Chemical class CC[S+]=C(N)[O-] ZCQWPWOIQCHISE-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100232409 Drosophila melanogaster icln gene Proteins 0.000 description 1
- 241000982822 Ficus obtusifolia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 101100232415 Schizosaccharomyces pombe (strain 972 / ATCC 24843) saf5 gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- NVZRLFKNPMVIEV-UHFFFAOYSA-N o-ethyl n,n-diethylcarbamothioate Chemical compound CCOC(=S)N(CC)CC NVZRLFKNPMVIEV-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
- C07C329/04—Esters of monothiocarbonic acids
- C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00125794A US3804873A (en) | 1971-03-18 | 1971-03-18 | Process for manufacturing a liquid thiocarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2212766A1 true DE2212766A1 (de) | 1972-11-23 |
Family
ID=22421452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722212766 Pending DE2212766A1 (de) | 1971-03-18 | 1972-03-16 | Verfahren zur Herstellung von fluessigen Thiocarbaminsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3804873A (OSRAM) |
| JP (1) | JPS5341124B2 (OSRAM) |
| BR (1) | BR7201501D0 (OSRAM) |
| CA (1) | CA966499A (OSRAM) |
| DE (1) | DE2212766A1 (OSRAM) |
| FR (1) | FR2129706A5 (OSRAM) |
| GB (1) | GB1372629A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR219067A1 (es) * | 1976-03-29 | 1980-07-31 | Stauffer Chemical Co | Nuevos compuestos herbicidas derivados de s-metil sustituido tiocarbamato y sulfoxidos de los mismos |
-
1971
- 1971-03-18 US US00125794A patent/US3804873A/en not_active Expired - Lifetime
-
1972
- 1972-03-06 CA CA136,490A patent/CA966499A/en not_active Expired
- 1972-03-09 GB GB1095672A patent/GB1372629A/en not_active Expired
- 1972-03-16 DE DE19722212766 patent/DE2212766A1/de active Pending
- 1972-03-16 FR FR7209152A patent/FR2129706A5/fr not_active Expired
- 1972-03-16 BR BR1501/72A patent/BR7201501D0/pt unknown
- 1972-03-17 JP JP2670572A patent/JPS5341124B2/ja not_active Expired
-
1973
- 1973-03-30 US US00346501A patent/US3808253A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5341124B2 (OSRAM) | 1978-10-31 |
| US3808253A (en) | 1974-04-30 |
| FR2129706A5 (OSRAM) | 1972-10-27 |
| CA966499A (en) | 1975-04-22 |
| GB1372629A (en) | 1974-11-06 |
| BR7201501D0 (pt) | 1974-12-31 |
| US3804873A (en) | 1974-04-16 |
| JPS4848422A (OSRAM) | 1973-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |