JPS5946263A - トリチオカルボン酸ジエステルの製造法 - Google Patents
トリチオカルボン酸ジエステルの製造法Info
- Publication number
- JPS5946263A JPS5946263A JP58111966A JP11196683A JPS5946263A JP S5946263 A JPS5946263 A JP S5946263A JP 58111966 A JP58111966 A JP 58111966A JP 11196683 A JP11196683 A JP 11196683A JP S5946263 A JPS5946263 A JP S5946263A
- Authority
- JP
- Japan
- Prior art keywords
- producing
- acid diester
- formula
- trithiocarboxylic
- phase transfer
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000002253 acid Substances 0.000 title claims description 10
- 150000005690 diesters Chemical class 0.000 title claims 5
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- -1 cycloaliphatic Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- FTJHYGJLHCGQHQ-UHFFFAOYSA-N 2-bromooctane Chemical compound CCCCCCC(C)Br FTJHYGJLHCGQHQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NSOICZUELLNOCM-UHFFFAOYSA-N CCCCCCCC[C](CCCCCCCC)CCCCCCCC Chemical compound CCCCCCCC[C](CCCCCCCC)CCCCCCCC NSOICZUELLNOCM-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- FJCYOJUAUCXOQJ-UHFFFAOYSA-N bis(octylsulfanyl)methanethione Chemical compound CCCCCCCCSC(=S)SCCCCCCCC FJCYOJUAUCXOQJ-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- WNIMPVMSRDFHTD-UHFFFAOYSA-N methanetrithiol Chemical compound SC(S)S WNIMPVMSRDFHTD-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000000276 sedentary effect Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22010/82A IT1159071B (it) | 1982-06-23 | 1982-06-23 | Processo per la preparazione di diesteri dell'acido tritiocarbonico |
| IT22010A/82 | 1982-06-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5946263A true JPS5946263A (ja) | 1984-03-15 |
| JPS6147831B2 JPS6147831B2 (en]) | 1986-10-21 |
Family
ID=11190135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58111966A Granted JPS5946263A (ja) | 1982-06-23 | 1983-06-23 | トリチオカルボン酸ジエステルの製造法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4868322A (en]) |
| EP (1) | EP0097626B1 (en]) |
| JP (1) | JPS5946263A (en]) |
| AT (1) | ATE19063T1 (en]) |
| DE (1) | DE3362908D1 (en]) |
| IT (1) | IT1159071B (en]) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006290759A (ja) * | 2005-04-07 | 2006-10-26 | Chisso Corp | カーボネート結合基を有する液晶性化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
| JP2007145841A (ja) * | 2005-11-29 | 2007-06-14 | E I Du Pont De Nemours & Co | トリチオカーボネート類の合成 |
| JP2010202572A (ja) * | 2009-03-03 | 2010-09-16 | Ube Ind Ltd | トリチオカーボネート化合物及びその製法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6354329U (en]) * | 1986-09-29 | 1988-04-12 | ||
| US5342629A (en) * | 1991-06-28 | 1994-08-30 | Union Oil Company Of California | Preservation of wood chips |
| WO1996011165A1 (en) * | 1994-10-11 | 1996-04-18 | Entek Corporation | Process for synthesizing thiocarbonates |
| US7038062B2 (en) * | 2004-07-01 | 2006-05-02 | The Goodyear Tire & Rubber Company | Synthesis of cyclic trithiocarbonates from epoxides |
| FR2893025B1 (fr) * | 2005-11-10 | 2010-12-03 | Arkema | Procede de preparation d'esters de type trithiocarbonate sans odeur ou a odeur attenuee |
| US7230063B1 (en) * | 2005-12-22 | 2007-06-12 | The Goodyear Tire & Rubber Company | Functional trithiocarbonate RAFT agents |
| CN104262217B (zh) * | 2014-09-25 | 2016-04-06 | 陕西师范大学 | 三硫代碳酸-二（五氟苄基）酯及其制备方法和应用 |
| CN105294524B (zh) * | 2015-11-11 | 2017-10-20 | 陕西师范大学 | 二硫代羧酸五氟苄基酯及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468651C3 (de) * | 1963-06-05 | 1973-12-20 | Dr. Spiess Gmbh, 6719 Kleinkarlbach | Verfahren zur Herstellung von Thiol- und Thionverbindungen sowie Thio- und Dithiocarbonsäuren |
| US4341715A (en) * | 1980-10-06 | 1982-07-27 | Phillips Petroleum Company | S-Allyl-S'-n-butyl-trithiocarbonate |
-
1982
- 1982-06-23 IT IT22010/82A patent/IT1159071B/it active
-
1983
- 1983-06-22 AT AT83830123T patent/ATE19063T1/de not_active IP Right Cessation
- 1983-06-22 DE DE8383830123T patent/DE3362908D1/de not_active Expired
- 1983-06-22 EP EP83830123A patent/EP0097626B1/en not_active Expired
- 1983-06-23 JP JP58111966A patent/JPS5946263A/ja active Granted
-
1988
- 1988-06-28 US US07/212,135 patent/US4868322A/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006290759A (ja) * | 2005-04-07 | 2006-10-26 | Chisso Corp | カーボネート結合基を有する液晶性化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
| JP2007145841A (ja) * | 2005-11-29 | 2007-06-14 | E I Du Pont De Nemours & Co | トリチオカーボネート類の合成 |
| JP2010202572A (ja) * | 2009-03-03 | 2010-09-16 | Ube Ind Ltd | トリチオカーボネート化合物及びその製法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6147831B2 (en]) | 1986-10-21 |
| ATE19063T1 (de) | 1986-04-15 |
| US4868322A (en) | 1989-09-19 |
| IT1159071B (it) | 1987-02-25 |
| IT8222010A0 (it) | 1982-06-23 |
| EP0097626A1 (en) | 1984-01-04 |
| DE3362908D1 (en) | 1986-05-15 |
| EP0097626B1 (en) | 1986-04-09 |
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