SU921464A3 - Способ получени сложных эфиров тиокарбаминовой кислоты - Google Patents
Способ получени сложных эфиров тиокарбаминовой кислоты Download PDFInfo
- Publication number
- SU921464A3 SU921464A3 SU772517657A SU2517657A SU921464A3 SU 921464 A3 SU921464 A3 SU 921464A3 SU 772517657 A SU772517657 A SU 772517657A SU 2517657 A SU2517657 A SU 2517657A SU 921464 A3 SU921464 A3 SU 921464A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- catalyst
- chloride
- reaction
- general formula
- publ
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000002148 esters Chemical class 0.000 title abstract description 6
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 title description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims abstract description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 5
- 239000008346 aqueous phase Substances 0.000 claims abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 3
- -1 thiocarbamic acid ester Chemical class 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- 230000008092 positive effect Effects 0.000 claims 3
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101150053899 RSH1 gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- OWRABTHGOKNUDV-UHFFFAOYSA-N n,n-dipropylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)CCC OWRABTHGOKNUDV-UHFFFAOYSA-N 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72028476A | 1976-09-03 | 1976-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU921464A3 true SU921464A3 (ru) | 1982-04-15 |
Family
ID=24893423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772517657A SU921464A3 (ru) | 1976-09-03 | 1977-09-02 | Способ получени сложных эфиров тиокарбаминовой кислоты |
Country Status (22)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147715A (en) * | 1978-03-23 | 1979-04-03 | Stauffer Chemical Company | Thiocarbamate preparation utilizing quaternary ammonium salt catalysts |
| JPS60136502A (ja) * | 1983-12-05 | 1985-07-20 | ストウフアー・ケミカル・カンパニー | 除草組成物および雑草抑制方法 |
| KR102467113B1 (ko) * | 2019-11-20 | 2022-11-14 | 미쓰비시 덴키 빌딩 솔루션즈 가부시키가이샤 | 판정 장치, 판정 방법 및 기록 매체에 저장된 판정 프로그램 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2983747A (en) * | 1958-07-28 | 1961-05-09 | Stauffer Chemical Co | Process for making thiolcarbamates |
-
1977
- 1977-08-26 DE DE19772738628 patent/DE2738628A1/de not_active Withdrawn
- 1977-08-26 CA CA285,552A patent/CA1103665A/en not_active Expired
- 1977-08-29 FR FR7726182A patent/FR2363551A1/fr active Granted
- 1977-08-30 BR BR7705777A patent/BR7705777A/pt unknown
- 1977-08-31 CH CH1062077A patent/CH636605A5/de not_active IP Right Cessation
- 1977-09-01 DK DK390277A patent/DK390277A/da not_active Application Discontinuation
- 1977-09-01 IL IL52868A patent/IL52868A/xx unknown
- 1977-09-01 CS CS570777A patent/CS207480B1/cs unknown
- 1977-09-01 DD DD7700200853A patent/DD132432A5/xx unknown
- 1977-09-02 PL PL1977200632A patent/PL108414B1/pl unknown
- 1977-09-02 IT IT50870/77A patent/IT1091119B/it active
- 1977-09-02 BE BE2056207A patent/BE858348A/xx not_active IP Right Cessation
- 1977-09-02 HU HU77SA3059A patent/HU175829B/hu unknown
- 1977-09-02 NL NL7709711A patent/NL7709711A/xx not_active Application Discontinuation
- 1977-09-02 ES ES462081A patent/ES462081A1/es not_active Expired
- 1977-09-02 SU SU772517657A patent/SU921464A3/ru active
- 1977-09-02 AR AR269075A patent/AR219718A1/es active
- 1977-09-02 IN IN1360/CAL/77A patent/IN145874B/en unknown
- 1977-09-02 ZA ZA00775331A patent/ZA775331B/xx unknown
- 1977-09-02 AU AU28508/77A patent/AU508898B2/en not_active Expired
- 1977-09-02 GB GB36761/77A patent/GB1538643A/en not_active Expired
- 1977-09-03 JP JP52105400A patent/JPS6058748B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1103665A (en) | 1981-06-23 |
| IN145874B (enrdf_load_stackoverflow) | 1979-01-13 |
| DE2738628A1 (de) | 1978-03-09 |
| CS207480B1 (en) | 1981-07-31 |
| PL200632A1 (pl) | 1978-05-22 |
| AR219718A1 (es) | 1980-09-15 |
| GB1538643A (en) | 1979-01-24 |
| NL7709711A (nl) | 1978-03-07 |
| IL52868A (en) | 1980-06-30 |
| CH636605A5 (en) | 1983-06-15 |
| FR2363551B1 (enrdf_load_stackoverflow) | 1983-09-23 |
| AU2850877A (en) | 1979-03-08 |
| AU508898B2 (en) | 1980-04-03 |
| BR7705777A (pt) | 1978-06-06 |
| IT1091119B (it) | 1985-06-26 |
| BE858348A (nl) | 1978-03-02 |
| HU175829B (hu) | 1980-10-28 |
| DK390277A (da) | 1978-03-04 |
| JPS6058748B2 (ja) | 1985-12-21 |
| DD132432A5 (de) | 1978-09-27 |
| PL108414B1 (en) | 1980-04-30 |
| JPS5334722A (en) | 1978-03-31 |
| IL52868A0 (en) | 1977-11-30 |
| FR2363551A1 (fr) | 1978-03-31 |
| ZA775331B (en) | 1978-07-26 |
| ES462081A1 (es) | 1978-12-01 |
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