CN104557769A - Production method of rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfenamide - Google Patents
Production method of rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfenamide Download PDFInfo
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- CN104557769A CN104557769A CN201410783828.9A CN201410783828A CN104557769A CN 104557769 A CN104557769 A CN 104557769A CN 201410783828 A CN201410783828 A CN 201410783828A CN 104557769 A CN104557769 A CN 104557769A
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- reaction
- dicyclohexyl
- production method
- hydrogen peroxide
- accelerator
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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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a production method of a rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfonamide. The production method comprises the following steps: adding 50-80g of molten coarse M to a reaction which containing 45-72g of dicyclohexylamine and 500ml of isopropanol, reacting the coarse M with the dicyclohexylamine thoroughly under the conditions of a temperature within the range of 60-100 DEG C and the rotating speed of 800r/min, next, adding the oxidizing agent hydrogen peroxide with the concentration of 8-12% at the flow rate of 5ml/min, wherein the pH of the reaction solution is controlled to be 8-11 and dropwise adding time is 2 hours; and after the reaction is finished, performing suction filtration, water washing, filtering and drying to obtain the product rubber accelerator DZ. The method is simple in process; the oxidizing agent is hydrogen peroxide having no pollution to the environment; the method can be put into industrialization easily; no lots of saline wastewater is generated during the reaction; a proper amount of dicyclohexylamine is used; the synthesized DZ is high in yield and good in quality.
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.Patent (patent No. 200810053774.5) the method process delivered on July 8th, 2008 comprises: join in stills for air blowing by Virahol and dicyclohexyl amine, under the condition stirred, dicyclohexyl amine is fully dissolved in Virahol, add sulfuric acid again, control pH value simultaneously, then drip M-Na salt, drip oxidizing agent sodium hypochlorite simultaneously, pH value is controlled, after completion of the reaction suction filtration, washing, filtration, dry rubber accelerator DZ product in reaction process.Although the DZ quality that the method for this patent obtains reaches 99%, yield does not have concrete numerical value, and operation needs three kinds of raw materials to drip simultaneously, operation more complicated.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 salify rate is not high, and accelerator DZ yield is low.Aforesaid method all can produce the waste water of a large amount of contains sodium sulfate, sodium chloride salt, to environment.
Summary of the invention
The object of the present invention is to provide a kind of with the production method of thiofide N, N-dicyclohexyl-2-[4-morpholinodithio sulphenamide; The method is simple to operate, does not produce a large amount of brine waste, and dicyclohexyl amine consumption is appropriate, and the DZ yield synthesized, quality are all higher.
For achieving the above object, the present invention is realized by following technical proposals: a kind of take hydrogen peroxide as oxygenant, with the method for thick M for raw material production rubber vulcanization accelerator DZ, it is characterized in that comprising following process:
The thick M50-80g of melting is joined in the reactor of existing 45-72 gram dicyclohexyl amine and 500ml Virahol, under 60-100 DEG C of scope, rotating speed are 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 concentration is 8-12%, 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.
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, is easy to industrialization, and the dicyclohexyl amine of use is appropriate, and 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 Virahol, 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 concentration 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 Virahol, 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 concentration 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 Virahol, 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 concentration 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 thiofide N, the production method of N-dicyclohexyl-2-[4-morpholinodithio sulphenamide, 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 Virahol, 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 concentration 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 |
|---|---|---|---|
| CN201410783828.9A CN104557769A (en) | 2014-12-16 | 2014-12-16 | Production method of rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfenamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410783828.9A CN104557769A (en) | 2014-12-16 | 2014-12-16 | Production method of rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfenamide |
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| Publication Number | Publication Date |
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| CN104557769A true CN104557769A (en) | 2015-04-29 |
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| CN201410783828.9A Pending CN104557769A (en) | 2014-12-16 | 2014-12-16 | Production method of rubber vulcanization accelerator N,N-dicyclohexyl-2-benzothiazole sulfenamide |
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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 |
| CN102391206A (en) * | 2011-09-20 | 2012-03-28 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerator DZ |
-
2014
- 2014-12-16 CN CN201410783828.9A patent/CN104557769A/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 |
| CN102391206A (en) * | 2011-09-20 | 2012-03-28 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerator DZ |
Non-Patent Citations (2)
| Title |
|---|
| 张越: "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 |