JPS6232746B2 - - Google Patents
Info
- Publication number
- JPS6232746B2 JPS6232746B2 JP53150939A JP15093978A JPS6232746B2 JP S6232746 B2 JPS6232746 B2 JP S6232746B2 JP 53150939 A JP53150939 A JP 53150939A JP 15093978 A JP15093978 A JP 15093978A JP S6232746 B2 JPS6232746 B2 JP S6232746B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- conduit
- column
- continuously
- thiocarbamate
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000005804 alkylation reaction Methods 0.000 claims description 11
- 230000029936 alkylation Effects 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 8
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 7
- 239000000376 reactant Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 230000006203 ethylation Effects 0.000 description 4
- 238000006200 ethylation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical class CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- OAVZKNPXSOCTMP-UHFFFAOYSA-N cyclohexyl(ethyl)carbamothioic s-acid Chemical compound CCN(C(S)=O)C1CCCCC1 OAVZKNPXSOCTMP-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- NCPDPTXSMJDCIH-UHFFFAOYSA-N dipropylcarbamothioic s-acid Chemical compound CCCN(C(S)=O)CCC NCPDPTXSMJDCIH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- -1 polymethylene group Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15093978A JPS5579362A (en) | 1978-12-05 | 1978-12-05 | Method of manufacturing substituted thiocarbamate in continuous cycle and apparatus therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15093978A JPS5579362A (en) | 1978-12-05 | 1978-12-05 | Method of manufacturing substituted thiocarbamate in continuous cycle and apparatus therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5579362A JPS5579362A (en) | 1980-06-14 |
| JPS6232746B2 true JPS6232746B2 (hu) | 1987-07-16 |
Family
ID=15507708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15093978A Granted JPS5579362A (en) | 1978-12-05 | 1978-12-05 | Method of manufacturing substituted thiocarbamate in continuous cycle and apparatus therefor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5579362A (hu) |
-
1978
- 1978-12-05 JP JP15093978A patent/JPS5579362A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5579362A (en) | 1980-06-14 |
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