CN111253337A - Novel process for anhydrous clean production of vulcanization accelerator DM - Google Patents
Novel process for anhydrous clean production of vulcanization accelerator DM Download PDFInfo
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- CN111253337A CN111253337A CN202010243138.XA CN202010243138A CN111253337A CN 111253337 A CN111253337 A CN 111253337A CN 202010243138 A CN202010243138 A CN 202010243138A CN 111253337 A CN111253337 A CN 111253337A
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- reaction
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- pressure
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- introducing oxygen
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000004073 vulcanization Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 238000001035 drying Methods 0.000 claims abstract description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005406 washing Methods 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 9
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims abstract description 9
- FIYYMXYOBLWYQO-UHFFFAOYSA-N ortho-iodylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I(=O)=O FIYYMXYOBLWYQO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004806 packaging method and process Methods 0.000 claims abstract description 9
- XTCBHFKSTRGVMZ-UHFFFAOYSA-N phenyltellanylbenzene Chemical compound C=1C=CC=CC=1[Te]C1=CC=CC=C1 XTCBHFKSTRGVMZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract description 6
- 229920001971 elastomer Polymers 0.000 abstract description 5
- 239000005060 rubber Substances 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical group C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- 238000013040 rubber vulcanization Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- -1 tires Substances 0.000 description 1
- 239000002351 wastewater 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
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/78—Sulfur atoms attached to a second hetero atom to a second sulphur atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A novel process for the anhydrous clean production of a vulcanization accelerator DM belongs to the technical field of production of rubber accelerators, and comprises the following steps in sequence: a, adding 25-35L of one of organic solvents of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate into a reaction kettle, dissolving 2.5-3.5 kg of an accelerator M, simultaneously adding 5-20% of one of catalysts of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid, b introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min, stopping introducing oxygen when the pressure in the kettle begins to increase to 1.5MPa, and c continuing to preserve heat for 1-3 hours; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing for 2-4 times by using a pure organic solvent; f, drying the washed materials, and packaging to obtain the finished product. The invention has the advantages that: the invention thoroughly solves the problem of 'three wastes' treatment in the traditional process, is beneficial to the sustainable development of the enterprise and provides a brand-new idea for the rapid development of the industry.
Description
Technical Field
The invention belongs to the technical field of production of rubber accelerators, and particularly relates to a rubber vulcanization accelerator DM (the chemical name of the vulcanization accelerator DM is dibenzothiazyl disulfide, and the molecular formula of the vulcanization accelerator DM is C14H8N2S4) The production method of (1).
Background
The vulcanization accelerator DM with the chemical name of 2, 2' -dibenzothiazyl disulfide is a general accelerator for natural rubber, synthetic rubber and reclaimed rubber, and is widely used for manufacturing general industrial products such as tires, rubber tubes, rubber shoes, adhesive tapes and the like. At present, the main production processes for producing the rubber vulcanization accelerator DM at home and abroad comprise a sodium nitrite method and a hydrogen peroxide method, the sodium nitrite method is eliminated due to the fact that carcinogenic substances are generated in the oxidation process, most of the hydrogen peroxide methods firstly adopt that a raw material accelerator M (2-mercaptobenzothiazole) reacts with a sodium hydroxide solution to generate M-Na salt, then oxidation is carried out on the M-Na salt and an oxidant prepared from hydrogen peroxide and sulfuric acid, and a large amount of wastewater is generated in the whole procedure. By combining the current situation of the production process of the accelerator DM at home and abroad, a new anhydrous clean production process of the accelerator DM is independently developed from the requirements of cleanness, safety, product quality and the like.
Disclosure of Invention
The invention aims to provide a novel process for the anhydrous clean production of the vulcanization accelerator DM, which has the advantages of high effective content, low cost, environmental protection and short production period.
The purpose of the invention is realized by the following technical scheme:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 25-35L of one of organic solvents of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate into a reaction kettle with a stirrer, dissolving 2.5-3.5 kg of an accelerant M, simultaneously adding 5-20% of one of catalysts of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid, b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting the reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, stopping introducing oxygen when the pressure in the kettle starts to increase to 1.5MPa, and keeping the temperature for 1-3 h; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying and packaging the washed materials to obtain a finished product.
Further:
and washing liquid formed by washing the organic solvent is directly put into a reaction kettle for use, and reaction mother liquor enters a distillation system for recycling.
The drying is carried out in a closed circulation enhanced drying system.
In the invention: ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone, ethyl acetate, diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid are all industrial grade, and the content is more than 98%.
The invention has the beneficial effects that: the novel anhydrous clean production process of the accelerator DM formed by the invention thoroughly solves the problem of treatment of three wastes in the traditional process, is beneficial to sustainable development of the enterprise, and provides a brand-new idea for rapid development of the industry.
In order to make the technical solutions of the present invention better understood and make the above objects, features and advantages of the present invention more comprehensible, the present invention is described in further detail with reference to examples below.
Detailed Description
Example 1:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 25-35L of organic solvent (one of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate) into a 50L reaction kettle with a stirrer to dissolve 2.5-3.5 kg of promoter M, simultaneously adding 5-20% of catalyst (one of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid), b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting the reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, keeping the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
Example 2:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 28-32L of organic solvent (one of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate) into a 50L reaction kettle with a stirrer to dissolve 2.8-3.2 kg of promoter M, simultaneously adding 9-16% of catalyst (one of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid), b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting the reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, keeping the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
Example 3:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 29-31L of organic solvent (one of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate) into a 50L reaction kettle with a stirrer to dissolve 2.9-3.1 kg of promoter M, simultaneously adding 11-14% of catalyst (one of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid), b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting the reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, keeping the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
Example 4:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 26-28L of organic solvent ethanol into a 50L reaction kettle with a stirrer to dissolve 2.6-2.8 kg of promoter M, simultaneously adding 5-9% of catalyst diphenyl tellurium, b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, and c, continuing to keep the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
Example 5:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 29-31L of organic solvent isopropanol into a 50L reaction kettle with a stirrer to dissolve 2.9-3.1 kg of accelerator M, simultaneously adding 10-14% of catalyst nickel chloride, b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, and continuing to keep the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
Example 6:
the new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 32-34L of organic solvent ethyl acetate into a 50L reaction kettle with a stirrer to dissolve 3.2-3.4 kg of accelerator M, simultaneously adding 15-19% of catalyst 2-iodoxybenzoic acid, b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, finishing the reaction (the reaction time is 3-6 h) when the pressure in the kettle starts to increase to 1.5MPa, stopping introducing oxygen, continuing to keep the temperature for 1-3 h, and stopping heat preservation; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying the washed materials in a closed circulation enhanced drying system, and packaging to obtain a finished product DM.
In each example:
the washing liquid is directly put into the reaction kettle for use, and the reaction mother liquid enters a distillation system for recycling.
The organic solvent used in the invention is not limited to ethanol, glycol, isopropanol, dichloromethane, chloroform, acetone, ethyl acetate and other organic solvents; the catalyst is not limited to diphenyl tellurium, nickel chloride, 2-iodoxybenzoic acid, etc.
The above description is only for the specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (3)
1. The new process for the anhydrous clean production of the vulcanization accelerator DM sequentially comprises the following steps: a, adding 25-35L of one of organic solvents of ethanol, ethylene glycol, isopropanol, dichloromethane, chloroform, acetone and ethyl acetate into a reaction kettle with a stirrer, dissolving 2.5-3.5 kg of an accelerant M, simultaneously adding 5-20% of one of catalysts of diphenyl tellurium, nickel chloride and 2-iodoxybenzoic acid, b, introducing steam, heating to 50-100 ℃, slowly introducing oxygen at the speed of 100-300 ml/min for oxidation, starting the reaction when the pressure in the kettle reaches 0.3MPa, keeping the reaction pressure between 0.3-1.5 MPa, stopping introducing oxygen when the pressure in the kettle starts to increase to 1.5MPa, and keeping the temperature for 1-3 h; d, performing hot filtration in a closed container to obtain a crude product DM; e, washing the crude product DM with a pure organic solvent for 2-4 times; f, drying and packaging the washed materials to obtain a finished product.
2. The new process for the anhydrous clean production of vulcanization accelerators DM according to claim 1, characterized in that: and washing liquid formed by washing the organic solvent is directly put into a reaction kettle for use, and reaction mother liquor enters a distillation system for recycling.
3. The new process for the anhydrous clean production of vulcanization accelerators DM according to claim 1, characterized in that: the drying is carried out in a closed circulation enhanced drying system.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010243138.XA CN111253337A (en) | 2020-03-31 | 2020-03-31 | Novel process for anhydrous clean production of vulcanization accelerator DM |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010243138.XA CN111253337A (en) | 2020-03-31 | 2020-03-31 | Novel process for anhydrous clean production of vulcanization accelerator DM |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002088056A (en) * | 2000-09-13 | 2002-03-27 | Sanshin Chem Ind Co Ltd | Oxidation method |
| CN101139338A (en) * | 2007-07-09 | 2008-03-12 | 青岛科技大学 | Preparation of 2,2-disulfo-dibenzopyrene by oxygen process based on 2-mercaptan benzothiazole ammonia salt |
| CN103709121A (en) * | 2013-11-18 | 2014-04-09 | 朝阳天铭工贸有限公司 | Preparation method for pharmaceutical grade 2-mercaptobenzothiazole and derivative DM thereof |
| CN108947932A (en) * | 2018-08-13 | 2018-12-07 | 淄博和美华医药科技有限公司 | A kind of mono- step oxidation technology of fine work DM and method |
-
2020
- 2020-03-31 CN CN202010243138.XA patent/CN111253337A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002088056A (en) * | 2000-09-13 | 2002-03-27 | Sanshin Chem Ind Co Ltd | Oxidation method |
| CN101139338A (en) * | 2007-07-09 | 2008-03-12 | 青岛科技大学 | Preparation of 2,2-disulfo-dibenzopyrene by oxygen process based on 2-mercaptan benzothiazole ammonia salt |
| CN103709121A (en) * | 2013-11-18 | 2014-04-09 | 朝阳天铭工贸有限公司 | Preparation method for pharmaceutical grade 2-mercaptobenzothiazole and derivative DM thereof |
| CN108947932A (en) * | 2018-08-13 | 2018-12-07 | 淄博和美华医药科技有限公司 | A kind of mono- step oxidation technology of fine work DM and method |
Non-Patent Citations (6)
| Title |
|---|
| BRIAN J. EVANS等: "19F NMR Study of the Reaction of p-Fluorobenzenethiol and Disulfide with periodate nd Other Selected Oxidizing Agents", 《J. ORG. CHEM.》 * |
| DEREK H.R. BARTONA等: "TELLURAMINE DERIVATIVES AS SELECTIVE OXIDANTS", 《TETRAHEDRON LETTERS》 * |
| STEVEN V. LEY等: "DIARYL TELLUROXIDES AS NEW MILD OXIDISING REAGENTS", 《TETRAHEDRON》 * |
| THOMAS G. BACK等: ""Aromatic Derivatives and Tellurium Analogues of Cyclic Seleninate Esters and Spirodioxyselenuranes That Act as Glutathione Peroxidase Mimetics"", 《J. ORG. CHEM.》 * |
| 姚启正等: "《药物合成反应》", 30 September 2012, 中国医药科技出版社 * |
| 杨晓玲等: "二硫化二苯并噻唑的催化合成", 《应用化工》 * |
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Application publication date: 20200609 |