JP2018531286A - 2−メルカプトベンゾチアゾールの調製方法 - Google Patents
2−メルカプトベンゾチアゾールの調製方法 Download PDFInfo
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- JP2018531286A JP2018531286A JP2018537702A JP2018537702A JP2018531286A JP 2018531286 A JP2018531286 A JP 2018531286A JP 2018537702 A JP2018537702 A JP 2018537702A JP 2018537702 A JP2018537702 A JP 2018537702A JP 2018531286 A JP2018531286 A JP 2018531286A
- Authority
- JP
- Japan
- Prior art keywords
- ionic liquid
- sulfonic acid
- aniline
- acid type
- mercaptobenzothiazole
- 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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 40
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 114
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 76
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 239000002608 ionic liquid Substances 0.000 claims abstract description 43
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 37
- 238000002360 preparation method Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 230000035484 reaction time Effects 0.000 claims description 7
- 238000010924 continuous production Methods 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 238000010923 batch production Methods 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 229910052878 cordierite Inorganic materials 0.000 claims description 3
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 230000008901 benefit Effects 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000011973 solid acid Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000003622 immobilized catalyst Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- 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
- C07D277/72—2-Mercaptobenzothiazole
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/14—Silica and magnesia
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【選択図】 なし
Description
93gのアニリン、76gの二硫化炭素、38.4gの硫黄(三つのモル比は1:1:1.2である)を圧力反応器に投入し、体系に1.86gの非固定化スルホン酸型イミダゾールイオン液体[TSVM]HSO4(アニリンと液体との重量比は100:2である)を添加する。反応温度を250℃に、反応圧力を4.5Mpaに制御して、6h反応させた後、粗生成物融体を得る。
上記粗生成物融体を溶媒としてのトルエンが入れられた結晶化装置に圧入し、排出される硫化水素をアルカリ液で吸収処理し、融体が結晶化された後、洗浄、濾過、乾燥して、2−メルカプトベンゾチアゾール製品を得る。ここで、製品の純度は98%以上で、収率は90%である。
反応温度、反応圧力及び反応時間を変化させた以外は、実施例1と同じ方法で調製し、各実施例の工程条件や製品結果は表に示すとおりである:
各原料のモル比を変化させた以外は、実施例1と同じ方法で調製し、各実施例の原料関係や製品結果は表に示すとおりである:
触媒の種類が異なる以外は、実施例1と同じ方法で調製し、各実施例の触媒種類や製品結果は表に示すとおりである:
Claims (10)
- アニリン法で、スルホン酸型イミダゾールイオン液体を含む触媒の作用で反応させて2−メルカプトベンゾチアゾールを調製することを特徴とする2−メルカプトベンゾチアゾールの調製方法。
- 前記スルホン酸型イミダゾールイオン液体が、[TSVM]HSO4及び/または[MPS]2HSO4であることを特徴とする請求項1に記載の調製方法。
- 前記触媒が、前記スルホン酸型イミダゾールイオン液体を担持するための担体をさらに含むことを特徴とする請求項1または2に記載の調製方法。
- 前記担体が、活性アルミナ、コーディエライトハニカムセラミックス、スルフヒドリル基シリカゲル、イオン交換樹脂、HSZMモレキュラーシーブからなる群から選ばれる1種類または複種類であることを特徴とする請求項3に記載の調製方法。
- 前記スルホン酸型イミダゾールイオン液体と前記担体との間の重量比が0.1〜20:100であることを特徴とする請求項4に記載の調製方法。
- 前記反応の反応温度が200〜280℃で、反応圧力が3.0〜8.0Mpaで、反応時間が2〜12hであることを特徴とする請求項4または5に記載の調製方法。
- 前記反応の反応温度が240〜250℃で、反応圧力が4.5〜5.5Mpaで、反応時間が4〜6hであることを特徴とする請求項6に記載の調製方法。
- 前記アニリン法において、アニリン、二硫化炭素、硫黄を反応原料とし、前記アニリン、前記二硫化炭素、前記硫黄間のモル比が1:1.0〜1.3:1.1〜2であって、且つ前記アニリンと前記スルホン酸型イミダゾールイオン液体との間の重量比が100:1〜5であることを特徴とする請求項1に記載の調製方法。
- 前記アニリン、前記二硫化炭素、前記硫黄間のモル比が1:1.0〜1.1:1.2〜1.5であって、且つ前記アニリンと前記スルホン酸型イミダゾールイオン液体との間の重量比が100:1〜2であることを特徴とする請求項8に記載の調製方法。
- バッチ式または連続式工程で前記2−メルカプトベンゾチアゾールを調製することを特徴とする請求項1に記載の調製方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510649388.2 | 2015-10-09 | ||
CN201510649388.2A CN106565630B (zh) | 2015-10-09 | 2015-10-09 | 2-巯基苯并噻唑的制备方法 |
PCT/CN2015/093613 WO2017059614A1 (zh) | 2015-10-09 | 2015-11-02 | 2-巯基苯并噻唑的制备方法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2018531286A true JP2018531286A (ja) | 2018-10-25 |
JP2018531286A6 JP2018531286A6 (ja) | 2018-12-13 |
JP6524354B2 JP6524354B2 (ja) | 2019-06-05 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2018537702A Active JP6524354B2 (ja) | 2015-10-09 | 2015-11-02 | 2−メルカプトベンゾチアゾールの調製方法 |
Country Status (23)
Country | Link |
---|---|
US (1) | US10106513B2 (ja) |
EP (1) | EP3360867B1 (ja) |
JP (1) | JP6524354B2 (ja) |
KR (1) | KR102118465B1 (ja) |
CN (1) | CN106565630B (ja) |
AU (1) | AU2015411254B2 (ja) |
BR (1) | BR112018007111B1 (ja) |
CA (1) | CA3001053C (ja) |
CO (1) | CO2018004330A2 (ja) |
EA (1) | EA033216B1 (ja) |
EC (1) | ECSP18034973A (ja) |
ES (1) | ES2890659T3 (ja) |
HK (1) | HK1258438A1 (ja) |
IL (1) | IL258520B (ja) |
MX (1) | MX2018004321A (ja) |
MY (1) | MY184092A (ja) |
PE (1) | PE20181436A1 (ja) |
PL (1) | PL3360867T3 (ja) |
PT (1) | PT3360867T (ja) |
RS (1) | RS62393B1 (ja) |
SG (1) | SG11201802900VA (ja) |
WO (1) | WO2017059614A1 (ja) |
ZA (1) | ZA201802897B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109574954A (zh) * | 2017-09-28 | 2019-04-05 | 中国石油化工股份有限公司 | 一种制备2-巯基苯并噻唑的方法 |
CN109232472A (zh) * | 2018-10-24 | 2019-01-18 | 科迈化工股份有限公司 | 硫化促进剂mbt及其制备方法 |
CN109701470B (zh) * | 2019-02-19 | 2021-03-02 | 蔚林新材料科技股份有限公司 | 一种连续合成2-巯基苯并噻唑的塔式微反应装置 |
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JPS5287165A (en) * | 1976-01-14 | 1977-07-20 | Sanshin Kagaku Kogyo Kk | Purifying method of crude 22mercapt benzo thiazole |
JPH0559027A (ja) * | 1990-09-07 | 1993-03-09 | Akzo Nv | 2−メルカプト−ベンゾチアゾールの製法 |
WO1997046544A1 (en) * | 1996-06-03 | 1997-12-11 | Akzo Nobel N.V. | Acid catalysed process for preparing 2-mercaptobenzothiazole and derivatives thereof |
CN101508675A (zh) * | 2009-03-26 | 2009-08-19 | 浙江工业大学 | 新型双磺酸型烷基咪唑类离子液体及其制备方法和应用 |
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CN101717377A (zh) * | 2009-11-16 | 2010-06-02 | 天津市科迈化工有限公司 | 橡胶硫化促进剂mbt大规模高压合成方法 |
CN102070562A (zh) * | 2010-12-21 | 2011-05-25 | 天津大学 | 2-巯基苯并噻唑的制备方法 |
CN102304099A (zh) * | 2011-07-11 | 2012-01-04 | 南开大学 | 2-巯基苯并噻唑类衍生物的合成方法改进 |
CN103408506A (zh) * | 2013-08-23 | 2013-11-27 | 宝月(天津)环保工程有限公司 | 一种制备2-硫醇基苯并噻唑及其制备方法 |
CN104098528A (zh) * | 2014-08-05 | 2014-10-15 | 内蒙古工业大学 | 铜催化二硫化碳合成2-巯基苯并噻唑类衍生物的方法 |
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US5367082A (en) * | 1990-09-07 | 1994-11-22 | Akzo N.V. | Process for the preparation of 2-mercaptobenzothiazole |
US6222041B1 (en) * | 2000-02-24 | 2001-04-24 | Uniroyal Chemical Company, Inc. | Method for the production of 2-mercaptobenzothiazole |
JP4889867B2 (ja) * | 2001-03-13 | 2012-03-07 | 株式会社カネカ | 末端にアルケニル基を有するビニル系重合体の製造方法、ビニル系重合体および硬化性組成物 |
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2015
- 2015-10-09 CN CN201510649388.2A patent/CN106565630B/zh active Active
- 2015-11-02 JP JP2018537702A patent/JP6524354B2/ja active Active
- 2015-11-02 EA EA201890877A patent/EA033216B1/ru not_active IP Right Cessation
- 2015-11-02 KR KR1020187013002A patent/KR102118465B1/ko active IP Right Grant
- 2015-11-02 MX MX2018004321A patent/MX2018004321A/es unknown
- 2015-11-02 ES ES15905712T patent/ES2890659T3/es active Active
- 2015-11-02 AU AU2015411254A patent/AU2015411254B2/en active Active
- 2015-11-02 BR BR112018007111-0A patent/BR112018007111B1/pt active IP Right Grant
- 2015-11-02 WO PCT/CN2015/093613 patent/WO2017059614A1/zh active Application Filing
- 2015-11-02 PE PE2018000531A patent/PE20181436A1/es unknown
- 2015-11-02 PL PL15905712T patent/PL3360867T3/pl unknown
- 2015-11-02 CA CA3001053A patent/CA3001053C/en active Active
- 2015-11-02 MY MYPI2018000489A patent/MY184092A/en unknown
- 2015-11-02 EP EP15905712.4A patent/EP3360867B1/en active Active
- 2015-11-02 RS RS20211173A patent/RS62393B1/sr unknown
- 2015-11-02 SG SG11201802900VA patent/SG11201802900VA/en unknown
- 2015-11-02 PT PT159057124T patent/PT3360867T/pt unknown
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2018
- 2018-04-06 IL IL258520A patent/IL258520B/en active IP Right Grant
- 2018-04-09 US US15/948,321 patent/US10106513B2/en active Active
- 2018-04-24 CO CONC2018/0004330A patent/CO2018004330A2/es unknown
- 2018-05-03 ZA ZA2018/02897A patent/ZA201802897B/en unknown
- 2018-05-07 EC ECIEPI201834973A patent/ECSP18034973A/es unknown
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2019
- 2019-01-07 HK HK19100200.5A patent/HK1258438A1/zh unknown
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5287165A (en) * | 1976-01-14 | 1977-07-20 | Sanshin Kagaku Kogyo Kk | Purifying method of crude 22mercapt benzo thiazole |
JPH0559027A (ja) * | 1990-09-07 | 1993-03-09 | Akzo Nv | 2−メルカプト−ベンゾチアゾールの製法 |
WO1997046544A1 (en) * | 1996-06-03 | 1997-12-11 | Akzo Nobel N.V. | Acid catalysed process for preparing 2-mercaptobenzothiazole and derivatives thereof |
CN101638396A (zh) * | 2008-08-01 | 2010-02-03 | 河南省开仑化工有限责任公司 | 一种橡胶硫化促进剂2-硫醇基苯骈噻唑的生产工艺 |
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EP3360867B1 (en) | 2021-09-01 |
EP3360867A4 (en) | 2019-06-19 |
EP3360867A1 (en) | 2018-08-15 |
EA033216B1 (ru) | 2019-09-30 |
PE20181436A1 (es) | 2018-09-12 |
BR112018007111A2 (pt) | 2018-12-11 |
HK1258438A1 (zh) | 2019-11-15 |
ES2890659T3 (es) | 2022-01-21 |
CA3001053A1 (en) | 2017-04-13 |
PL3360867T3 (pl) | 2021-12-27 |
MY184092A (en) | 2021-03-17 |
US20180222875A1 (en) | 2018-08-09 |
AU2015411254B2 (en) | 2019-01-17 |
MX2018004321A (es) | 2018-08-15 |
CA3001053C (en) | 2023-06-20 |
AU2015411254A1 (en) | 2018-05-17 |
CN106565630B (zh) | 2020-06-26 |
SG11201802900VA (en) | 2018-05-30 |
US10106513B2 (en) | 2018-10-23 |
ECSP18034973A (es) | 2018-07-31 |
CN106565630A (zh) | 2017-04-19 |
KR20180105633A (ko) | 2018-09-28 |
PT3360867T (pt) | 2021-09-29 |
WO2017059614A1 (zh) | 2017-04-13 |
KR102118465B1 (ko) | 2020-06-03 |
BR112018007111B1 (pt) | 2021-11-03 |
ZA201802897B (en) | 2021-04-28 |
EA201890877A1 (ru) | 2018-11-30 |
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