CN104557773A - Method for producing rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through solvent process - Google Patents
Method for producing rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through solvent process Download PDFInfo
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- CN104557773A CN104557773A CN201410784494.7A CN201410784494A CN104557773A CN 104557773 A CN104557773 A CN 104557773A CN 201410784494 A CN201410784494 A CN 201410784494A CN 104557773 A CN104557773 A CN 104557773A
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- dicyclohexyl
- hydrogen peroxide
- methyl alcohol
- solvent
- thick
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- 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
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for producing a rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through a solvent process. According to the method, methyl alcohol serves as a solvent, hydrogen peroxide serves as an oxidizing agent, and unrefined crude mercaptobenzothiazole m serves as the raw material. The method is characterized by comprising the following steps: adding 50-80g of molten crude mercaptobenzothiazole m into a reactor with 45-72g of dicyclohexylamine and 500ml of methyl alcohol, reacting the crude mercaptobenzothiazole m with dicyclohexylamine under the condition with a temperature range of 60-100 DEG C and a rotation rate of 800 rpm, then adding 8-12% of the oxidizing agent hydrogen peroxide at a flow rate of 5ml per minute, simultaneously controlling pH of a reaction solution to be 8-11, controlling the dropwise adding time to be 2 hours, carrying out suction filtration, washing, filtering and drying after the reaction is ended to prepare the rubber accelerator DZ product, wherein the purity of the product reaches over 99%; and the yield of the product reaches over 95%. The method is simple in process and is suitable for industrial production.
Description
Technical field
The present invention relates to the production method of a kind of thiofide N, N-dicyclohexyl-2-[4-morpholinodithio sulphenamide (DZ), belong to rubber vulcanization accelerator DZ production technical field.
Background technology
Along with the development of rubber industry, the R & D and manufacture of vulcanization accelerator more and more comes into one's own.DZ is delayed action accelerator, is the requisite a kind of primary accelerator of current rubber industry.Be specially adapted to radial, there is sulfuration promotion and adhesive effect.Document (scientific and technical information, 2005,7:23) reports the method for large proportioning oxidation style synthesis DZ.Captax, dicyclohexyl amine, Virahol are added in reactor and stirs, make its salify; React as oxygenant with clorox, cooling, suction filtration, washing, filtration, dry product.The dicyclohexyl amine amount that this method uses is large, and the yield of accelerator DZ is not high.Document (China Synthetic Rubber Industry, 1996,19:317) reports the fast synthesis method of accelerator DZ.Captax, dicyclohexyl amine, Virahol are added in reactor and stirs, make its salify; React as oxygenant with hydrogen peroxide, cooling, suction filtration, washing, filtration, dry product.This method accelerator DZ yield is low.What aforesaid method raw material adopted is through exquisite M, and salify temperature is lower, and salify rate is not high, causes DZ yield not high, and the employing of solvent is all Virahol, and production cost is high.
Summary of the invention
A kind of solvent method is the object of the present invention is to provide to produce thiofide N, the method for N-dicyclohexyl-2-[4-morpholinodithio sulphenamide; Take methyl alcohol as solvent, hydrogen peroxide is oxygenant, with the method for thick M raw material production rubber vulcanization accelerator DZ, the method is simple to operate, do not produce a large amount of brine waste, the DZ yield synthesized, quality are all higher, and solvent methanol is lower than the unit price of Virahol one times, so production cost is also low.
For achieving the above object, the present invention is realized by following technical proposals: a kind of is solvent with methyl alcohol, hydrogen peroxide is oxygenant, with the method for thick M for raw material production rubber vulcanization accelerator DZ, the method process comprises: joined by the thick M50-80g of melting in the reactor of existing 45-72 gram dicyclohexyl amine and 500ml methyl alcohol, 60-100 DEG C of scope, rotating speed is under the condition of 800 revs/min, make thick M fully and dicyclohexyl amine react, then add with the flow velocity of 5ml/ minute the oxidant hydrogen peroxide that content is 8-12%, control the pH8-11 of reaction soln simultaneously, time for adding is 2 hours, suction filtration after completion of the reaction, washing, filter, dry rubber accelerator DZ product.
The invention has the advantages that: the method process is simple, and oxygenant uses the hydrogen peroxide do not polluted environment, reaction does not produce a large amount of brine waste, and be solvent with price methyl alcohol inexpensively, the purity of the accelerator DZ synthesized reaches more than 99%.Yield reaches more than 95%.
Embodiment
Embodiment 1:
The thick M50g of melting is joined in the reactor of existing 45 grams of dicyclohexyl amines and 500ml methyl alcohol, 60 DEG C, under rotating speed is the condition of 800 revs/min, make thick M fully and dicyclohexyl amine react, then add with the flow velocity of 5ml/ minute the oxidant hydrogen peroxide that content is 8%, control the pH8-11 of reaction soln simultaneously, time for adding is 2 hours, after completion of the reaction suction filtration, washing, filtration, dry rubber accelerator DZ product.
Embodiment 2:
The thick M65g of melting is joined in the reactor of existing 58.5 grams of dicyclohexyl amines and 500ml methyl alcohol, 80 DEG C, under rotating speed is the condition of 800 revs/min, make thick M fully and dicyclohexyl amine react, then add with the flow velocity of 5ml/ minute the oxidant hydrogen peroxide that content is 10%, control the pH8-11 of reaction soln simultaneously, time for adding is 2 hours, after completion of the reaction suction filtration, washing, filtration, dry rubber accelerator DZ product.
Embodiment 3:
The thick M80g of melting is joined in the reactor of existing 72 grams of dicyclohexyl amines and 500ml methyl alcohol, 100 DEG C, under rotating speed is the condition of 800 revs/min, make thick M fully and dicyclohexyl amine react, then add with the flow velocity of 5ml/ minute the oxidant hydrogen peroxide that content is 12%, control the pH8-11 of reaction soln simultaneously, time for adding is 2 hours, after completion of the reaction suction filtration, washing, filtration, dry rubber accelerator DZ product.
Claims (1)
1. a solvent method produces thiofide N, the method of N-dicyclohexyl-2-[4-morpholinodithio sulphenamide, take methyl alcohol as solvent, hydrogen peroxide is oxygenant, there is no exquisite thick M for raw material, the thick M50-80g of melting is it is characterized in that to join in the reactor of existing 45-72 gram dicyclohexyl amine and 500ml methyl alcohol, 60-100 DEG C of scope, rotating speed is under the condition of 800 revs/min, make thick M fully and dicyclohexyl amine react, then add with the flow velocity of 5ml/ minute the oxidant hydrogen peroxide that content is 8-12%, control the pH8-11 of reaction soln simultaneously, time for adding is 2 hours, suction filtration after completion of the reaction, washing, filter, dry rubber accelerator DZ product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410784494.7A CN104557773A (en) | 2014-12-16 | 2014-12-16 | Method for producing rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through solvent process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410784494.7A CN104557773A (en) | 2014-12-16 | 2014-12-16 | Method for producing rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through solvent process |
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| Publication Number | Publication Date |
|---|---|
| CN104557773A true CN104557773A (en) | 2015-04-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410784494.7A Pending CN104557773A (en) | 2014-12-16 | 2014-12-16 | Method for producing rubber vulcanization accelerator N,N-Dicyclohexyl-2-benzothiazole sulfonamide through solvent process |
Country Status (1)
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| CN (1) | CN104557773A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0314663A1 (en) * | 1987-10-29 | 1989-05-03 | Monsanto Europe S.A./N.V. | Process for the preparation of benzothiazole-2-sulphenamides |
| CN103524454A (en) * | 2013-09-30 | 2014-01-22 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerant DZ by solvent method |
-
2014
- 2014-12-16 CN CN201410784494.7A patent/CN104557773A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0314663A1 (en) * | 1987-10-29 | 1989-05-03 | Monsanto Europe S.A./N.V. | Process for the preparation of benzothiazole-2-sulphenamides |
| CN103524454A (en) * | 2013-09-30 | 2014-01-22 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerant DZ by solvent method |
Non-Patent Citations (2)
| Title |
|---|
| 张越等: "用粗M合成橡胶硫化促进剂DZ", 《化学推进剂与高分子材料》 * |
| 殷树梅等: "一步法合成高品质N,N-二环己基-2-苯并噻唑次磺酰胺新工艺", 《精细石油化工》 * |
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Application publication date: 20150429 |