DE1518824A1 - Sulfonylarylharnstoffe und Verfahren zu ihrer Herstellung - Google Patents
Sulfonylarylharnstoffe und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1518824A1 DE1518824A1 DE19651518824 DE1518824A DE1518824A1 DE 1518824 A1 DE1518824 A1 DE 1518824A1 DE 19651518824 DE19651518824 DE 19651518824 DE 1518824 A DE1518824 A DE 1518824A DE 1518824 A1 DE1518824 A1 DE 1518824A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- alkyl
- alkylhydroxylamines
- atoms
- 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 12
- 238000002360 preparation method Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkyl isocyanates Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000007971 urates Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- 241001461123 Matrona Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0045945 | 1965-05-03 | ||
| DEF0045946 | 1965-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1518824A1 true DE1518824A1 (de) | 1969-01-23 |
Family
ID=25976750
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518824 Pending DE1518824A1 (de) | 1965-05-03 | 1965-05-03 | Sulfonylarylharnstoffe und Verfahren zu ihrer Herstellung |
| DE19651542778 Pending DE1542778A1 (de) | 1965-05-03 | 1965-05-03 | Mittel zur Bekaempfung von Unkraeutern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651542778 Pending DE1542778A1 (de) | 1965-05-03 | 1965-05-03 | Mittel zur Bekaempfung von Unkraeutern |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE680411A (enrdf_load_stackoverflow) |
| DE (2) | DE1518824A1 (enrdf_load_stackoverflow) |
| ES (1) | ES326225A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1120667A (enrdf_load_stackoverflow) |
| IL (1) | IL25663A (enrdf_load_stackoverflow) |
| NL (1) | NL6605709A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9016984D0 (en) * | 1990-08-02 | 1990-09-19 | Ici Plc | Aniline derivatives |
-
1965
- 1965-05-03 DE DE19651518824 patent/DE1518824A1/de active Pending
- 1965-05-03 DE DE19651542778 patent/DE1542778A1/de active Pending
-
1966
- 1966-04-28 NL NL6605709A patent/NL6605709A/xx unknown
- 1966-04-29 IL IL2566366A patent/IL25663A/xx unknown
- 1966-04-30 ES ES0326225A patent/ES326225A1/es not_active Expired
- 1966-05-03 GB GB1958166A patent/GB1120667A/en not_active Expired
- 1966-05-03 BE BE680411D patent/BE680411A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL25663A (en) | 1970-02-19 |
| NL6605709A (enrdf_load_stackoverflow) | 1966-11-04 |
| GB1120667A (en) | 1968-07-24 |
| ES326225A1 (es) | 1967-07-01 |
| BE680411A (enrdf_load_stackoverflow) | 1966-11-03 |
| DE1542778A1 (de) | 1970-07-23 |
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