CA1076131A - Method for the transesterification of thiocarbamic acid esters - Google Patents
Method for the transesterification of thiocarbamic acid estersInfo
- Publication number
- CA1076131A CA1076131A CA250,553A CA250553A CA1076131A CA 1076131 A CA1076131 A CA 1076131A CA 250553 A CA250553 A CA 250553A CA 1076131 A CA1076131 A CA 1076131A
- Authority
- CA
- Canada
- Prior art keywords
- grams
- millimols
- transesterification
- trap
- solvent
- 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 11
- 238000005809 transesterification reaction Methods 0.000 title claims abstract description 7
- 150000003560 thiocarbamic acids Chemical class 0.000 title claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- RHLWQEFHFQTKNT-UHFFFAOYSA-N (2z)-1-cyclooctyl-2-diazocyclooctane Chemical compound [N-]=[N+]=C1CCCCCCC1C1CCCCCCC1 RHLWQEFHFQTKNT-UHFFFAOYSA-N 0.000 claims abstract description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 239000012429 reaction media Substances 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- C07C273/1809—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 with formation of the N-C(O)-N moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/26—Polythioesters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (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 |
|---|---|---|---|
| IT22616/75A IT1037577B (it) | 1975-04-23 | 1975-04-23 | Procedimento per la transesterificazione di esteri di acidi tiocarbammici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076131A true CA1076131A (en) | 1980-04-22 |
Family
ID=11198467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA250,553A Expired CA1076131A (en) | 1975-04-23 | 1976-04-20 | Method for the transesterification of thiocarbamic acid esters |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS51128918A (cs) |
| AT (1) | ATA294276A (cs) |
| AU (1) | AU501786B2 (cs) |
| BE (1) | BE841007A (cs) |
| CA (1) | CA1076131A (cs) |
| DE (1) | DE2617918C3 (cs) |
| DK (1) | DK180076A (cs) |
| ES (1) | ES447392A1 (cs) |
| FR (1) | FR2308614A1 (cs) |
| GB (1) | GB1507429A (cs) |
| IE (1) | IE42800B1 (cs) |
| IL (1) | IL49429A0 (cs) |
| IN (1) | IN144588B (cs) |
| IT (1) | IT1037577B (cs) |
| LU (1) | LU74809A1 (cs) |
| NL (1) | NL7604302A (cs) |
| NO (1) | NO761374L (cs) |
| PT (1) | PT65033B (cs) |
| RO (1) | RO69169A (cs) |
| SE (1) | SE431449B (cs) |
| YU (1) | YU100776A (cs) |
| ZA (1) | ZA762148B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410697A (en) * | 1980-01-25 | 1983-10-18 | Reanal Finomvegyszergyar | Process for the preparation of N-aryl-N'-(mono- or di substituted)-urea derivatives |
| US5621132A (en) * | 1992-10-19 | 1997-04-15 | Council Of Scientific And Industrial Research | Process for making alkyl N-alkyl or N-aryl-thiocarbamates |
-
1975
- 1975-04-23 IT IT22616/75A patent/IT1037577B/it active
-
1976
- 1976-04-09 ZA ZA762148A patent/ZA762148B/xx unknown
- 1976-04-15 GB GB15729/76A patent/GB1507429A/en not_active Expired
- 1976-04-16 IL IL49429A patent/IL49429A0/xx unknown
- 1976-04-20 CA CA250,553A patent/CA1076131A/en not_active Expired
- 1976-04-20 AU AU13114/76A patent/AU501786B2/en not_active Expired
- 1976-04-20 YU YU01007/76A patent/YU100776A/xx unknown
- 1976-04-21 ES ES447392A patent/ES447392A1/es not_active Expired
- 1976-04-21 LU LU74809A patent/LU74809A1/xx unknown
- 1976-04-21 DK DK180076A patent/DK180076A/da not_active Application Discontinuation
- 1976-04-22 NO NO761374A patent/NO761374L/no unknown
- 1976-04-22 AT AT762942A patent/ATA294276A/de not_active IP Right Cessation
- 1976-04-22 SE SE7604668A patent/SE431449B/xx unknown
- 1976-04-22 RO RO7685763A patent/RO69169A/ro unknown
- 1976-04-22 FR FR7611954A patent/FR2308614A1/fr active Granted
- 1976-04-22 BE BE166371A patent/BE841007A/xx not_active IP Right Cessation
- 1976-04-22 PT PT65033A patent/PT65033B/pt unknown
- 1976-04-22 NL NL7604302A patent/NL7604302A/xx not_active Application Discontinuation
- 1976-04-23 IE IE866/76A patent/IE42800B1/en unknown
- 1976-04-23 IN IN704/CAL/76A patent/IN144588B/en unknown
- 1976-04-23 JP JP51045612A patent/JPS51128918A/ja active Pending
- 1976-04-23 DE DE2617918A patent/DE2617918C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU74809A1 (cs) | 1977-01-12 |
| NO761374L (cs) | 1976-10-26 |
| FR2308614A1 (fr) | 1976-11-19 |
| DE2617918C3 (de) | 1981-12-24 |
| SE7604668L (sv) | 1976-10-24 |
| IE42800L (en) | 1976-10-23 |
| IN144588B (cs) | 1978-05-20 |
| SE431449B (sv) | 1984-02-06 |
| GB1507429A (en) | 1978-04-12 |
| AU1311476A (en) | 1977-10-27 |
| PT65033A (en) | 1976-05-01 |
| ES447392A1 (es) | 1977-07-01 |
| ZA762148B (en) | 1977-04-27 |
| IT1037577B (it) | 1979-11-20 |
| IE42800B1 (en) | 1980-10-22 |
| IL49429A0 (en) | 1976-06-30 |
| ATA294276A (de) | 1978-06-15 |
| AU501786B2 (en) | 1979-06-28 |
| YU100776A (en) | 1982-10-31 |
| BE841007A (fr) | 1976-10-22 |
| RO69169A (ro) | 1981-04-30 |
| DK180076A (da) | 1976-10-24 |
| NL7604302A (nl) | 1976-10-26 |
| FR2308614B1 (cs) | 1980-04-11 |
| DE2617918A1 (de) | 1976-10-28 |
| JPS51128918A (en) | 1976-11-10 |
| DE2617918B2 (de) | 1981-02-12 |
| PT65033B (en) | 1977-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |