SE406321B - Sett att framstella alifatiskt och cykloalifatiskt 1,3-disubstituerade symmetriska tiourinemnen - Google Patents
Sett att framstella alifatiskt och cykloalifatiskt 1,3-disubstituerade symmetriska tiourinemnenInfo
- Publication number
- SE406321B SE406321B SE7102668A SE266871A SE406321B SE 406321 B SE406321 B SE 406321B SE 7102668 A SE7102668 A SE 7102668A SE 266871 A SE266871 A SE 266871A SE 406321 B SE406321 B SE 406321B
- Authority
- SE
- Sweden
- Prior art keywords
- reaction
- activated carbon
- carbon
- sulfur
- amine
- Prior art date
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 38
- YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 150000003585 thioureas Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000012990 dithiocarbamate Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000004659 dithiocarbamates Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DCYNAHFAQKMWDW-UHFFFAOYSA-N azane;carbamodithioic acid Chemical compound N.NC(S)=S DCYNAHFAQKMWDW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical class N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical compound NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 description 1
- VJDVTCMMFZCKKG-UHFFFAOYSA-N 1,1-ditert-butylthiourea Chemical compound CC(C)(C)N(C(N)=S)C(C)(C)C VJDVTCMMFZCKKG-UHFFFAOYSA-N 0.000 description 1
- KAJICSGLHKRDLN-UHFFFAOYSA-N 1,3-dicyclohexylthiourea Chemical compound C1CCCCC1NC(=S)NC1CCCCC1 KAJICSGLHKRDLN-UHFFFAOYSA-N 0.000 description 1
- AMZQAMADELMUOH-UHFFFAOYSA-N 1,3-dihexadecylthiourea Chemical compound CCCCCCCCCCCCCCCCNC(=S)NCCCCCCCCCCCCCCCC AMZQAMADELMUOH-UHFFFAOYSA-N 0.000 description 1
- CYYJFWJNIQDCLT-UHFFFAOYSA-N 1,3-dihexylthiourea Chemical compound CCCCCCNC(=S)NCCCCCC CYYJFWJNIQDCLT-UHFFFAOYSA-N 0.000 description 1
- AUXGIIVHLRLBSG-UHFFFAOYSA-N 1,3-dipropylthiourea Chemical compound CCCNC(=S)NCCC AUXGIIVHLRLBSG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical class SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/14—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702015010 DE2015010C3 (de) | 1970-03-28 | Verfahren zur Herstellung von aliphatisch und cycloaliphatisch 13-disubstituierten Thioharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE406321B true SE406321B (sv) | 1979-02-05 |
Family
ID=5766569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7102668A SE406321B (sv) | 1970-03-28 | 1971-03-02 | Sett att framstella alifatiskt och cykloalifatiskt 1,3-disubstituerade symmetriska tiourinemnen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3708496A (ja) |
| JP (1) | JPS5335057B1 (ja) |
| AT (1) | AT299235B (ja) |
| BE (1) | BE763637A (ja) |
| CH (1) | CH543491A (ja) |
| ES (1) | ES388700A1 (ja) |
| FI (1) | FI54102C (ja) |
| FR (1) | FR2084907A5 (ja) |
| GB (1) | GB1304487A (ja) |
| LU (1) | LU62701A1 (ja) |
| NL (1) | NL7102543A (ja) |
| SE (1) | SE406321B (ja) |
| ZA (1) | ZA71441B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3835145A (en) * | 1972-09-11 | 1974-09-10 | Sterling Drug Inc | 2- and 3-pyridylisothiocyanates |
| DE3821464A1 (de) * | 1988-06-25 | 1989-12-28 | Degussa | Verfahren zur herstellung substituierter organyloxysilylfunktioneller, cyclischer thioharnstoffe und diese verbindungen |
| CN102731357B (zh) * | 2012-07-04 | 2014-02-12 | 山东汇海医药化工有限公司 | 高纯度n,n′-二环己基硫脲的制备方法 |
| CN114702421B (zh) * | 2022-04-15 | 2023-06-30 | 鹤壁中昊新材料科技有限公司 | 一种以伯胺为原材料合成1，3-二取代对称性硫脲的制备方法 |
-
1971
- 1971-01-22 ZA ZA710441A patent/ZA71441B/xx unknown
- 1971-02-17 CH CH231171A patent/CH543491A/de not_active IP Right Cessation
- 1971-02-19 AT AT143071A patent/AT299235B/de not_active IP Right Cessation
- 1971-02-24 FI FI536/71A patent/FI54102C/fi active
- 1971-02-25 NL NL7102543A patent/NL7102543A/xx not_active Application Discontinuation
- 1971-02-27 ES ES388700A patent/ES388700A1/es not_active Expired
- 1971-03-02 LU LU62701D patent/LU62701A1/xx unknown
- 1971-03-02 SE SE7102668A patent/SE406321B/sv unknown
- 1971-03-02 BE BE763637A patent/BE763637A/xx unknown
- 1971-03-19 FR FR7109759A patent/FR2084907A5/fr not_active Expired
- 1971-03-25 US US00128120A patent/US3708496A/en not_active Expired - Lifetime
- 1971-03-26 JP JP1732571A patent/JPS5335057B1/ja active Pending
- 1971-04-19 GB GB2508871*A patent/GB1304487A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA71441B (en) | 1971-10-27 |
| FR2084907A5 (ja) | 1971-12-17 |
| US3708496A (en) | 1973-01-02 |
| JPS5335057B1 (ja) | 1978-09-25 |
| CH543491A (de) | 1973-10-31 |
| GB1304487A (ja) | 1973-01-24 |
| DE2015010B2 (de) | 1977-05-18 |
| FI54102C (fi) | 1978-10-10 |
| BE763637A (fr) | 1971-08-02 |
| DE2015010A1 (de) | 1971-11-25 |
| LU62701A1 (ja) | 1971-08-20 |
| ES388700A1 (es) | 1973-05-16 |
| AT299235B (de) | 1972-06-12 |
| NL7102543A (ja) | 1971-09-30 |
| FI54102B (fi) | 1978-06-30 |
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