CN110627740A - Novel environment-friendly production method of accelerator CBS without waste salt and wastewater - Google Patents
Novel environment-friendly production method of accelerator CBS without waste salt and wastewater Download PDFInfo
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- CN110627740A CN110627740A CN201910938937.6A CN201910938937A CN110627740A CN 110627740 A CN110627740 A CN 110627740A CN 201910938937 A CN201910938937 A CN 201910938937A CN 110627740 A CN110627740 A CN 110627740A
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- 150000003839 salts Chemical class 0.000 title claims abstract description 27
- 239000002699 waste material Substances 0.000 title claims abstract description 27
- 239000002351 wastewater Substances 0.000 title claims abstract description 27
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 61
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000003756 stirring Methods 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 238000005406 washing Methods 0.000 claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 70
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 239000012295 chemical reaction liquid Substances 0.000 claims description 11
- 229920002472 Starch Polymers 0.000 claims description 9
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 9
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 235000019698 starch Nutrition 0.000 claims description 9
- 239000008107 starch Substances 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 7
- 230000001376 precipitating effect Effects 0.000 description 7
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000013040 rubber vulcanization Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a novel environment-friendly production method of accelerator CBS without generating waste salt and waste water, belonging to the field of fine chemical engineering, which comprises the steps of 1) dissolving a dry product M at 40 ~ 65 ℃ by using an organic solvent, 2) dropwise adding cyclohexylamine while stirring, wherein the molar ratio of the cyclohexylamine to the dry product M is 1:1.0 ~ 1.3.3, 3) dropwise adding hydrogen peroxide diluted by using the organic solvent to a reaction end point, 4) stirring for 20 ~ 60min after the end point, cooling, filtering, washing and drying to obtain a finished product CBS.
Description
Technical Field
The invention relates to the field of fine chemical engineering, in particular to a novel environment-friendly production method of accelerator CBS without waste salt and wastewater.
Background
At present, the main production processes for producing the rubber vulcanization accelerator CBS at home and abroad comprise a sodium hypochlorite method and a sodium hypochlorite and hydrogen peroxide mixed oxidation method.
The sodium hypochlorite method has large potential safety hazard due to the use of raw material chlorine, generates a large amount of high-salinity wastewater, has COD (chemical oxygen demand) of about 30000mg/L, has large treatment difficulty and faces the situation of elimination.
In the mixed oxidation method, 70% of hydrogen peroxide is firstly dripped in the early stage, and 30% of sodium hypochlorite is dripped in the later stage to find the end point, so that in the whole process, although waste salt is reduced by about 60%, the waste salt is still generated, the waste water amount is increased, the COD is higher than that of a sodium hypochlorite method, the treatment difficulty is high, the yield is 93%, and the process still needs to be further improved.
The development of the CBS process which does not generate waste salt and waste water, further improves the yield and is suitable for industrial production has great significance.
Disclosure of Invention
In order to make up for the defects of the prior art and solve the problems that the production of the rubber vulcanization accelerator CBS in the prior art generates a large amount of high-salt wastewater and has low yield, the invention provides a novel environment-friendly production method of the accelerator CBS without generating waste salt wastewater.
The technical scheme of the invention is as follows:
a novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) dissolving the dried product M by using an organic solvent at 40 ~ 65 ℃;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1:1.0 ~ 1.3.3;
3) dropwise adding hydrogen peroxide diluted by an organic solvent to the reaction end point;
4) and stirring for a period of time after finishing, cooling, filtering, washing and drying to obtain the finished product CBS.
Preferably, the organic solvent in step 1) and step 3) is methanol, ethanol or isopropanol.
Further, the organic solvent in step 1) and step 3) is isopropanol. Isopropanol is used as an organic solvent and a hydrogen peroxide diluent, so that the yield is highest, and the product purity is highest; probably because the hydrogen peroxide is stable in the isopropanol, the isopropanol reduces the potential of the hydrogen peroxide, so that the reaction is milder; in addition, isopropanol has low solubility for the target product.
Preferably, in step 1), the concentration of the M solution obtained is 0.4 ~ 0.8.8 mol/L.
Preferably, in the step 2), the molar ratio of the cyclohexylamine to the dry product M is 1:1.0 ~ 1.1.1.
Preferably, in step 3), the method for determining the end point of the reaction is as follows: dropping one drop of ammonium sulfate, one drop of starch solution and one drop of potassium iodide reagent on a dropping plate, and dropping 1-2 reaction liquid into the mixed liquid, wherein the end point is indicated if the reaction liquid turns blue.
Preferably, in step 3), the mass-to-volume ratio of the hydrogen peroxide solution is 8% ~ 12%, that is, the ratio of the mass of the hydrogen peroxide (mass of the solute) to the volume of the water and the organic solvent and (total volume of the solvent).
Further, in the step 3), the mass volume ratio of the hydrogen peroxide is 10%.
Preferably, in the step 4), the temperature is reduced to 20 ~ 30 ℃ and the product is precipitated after the temperature is reduced, and the temperature can also be reduced to a lower temperature, such as 10 ~ 15 ℃, but the temperature is too low to consume energy, and the temperature is reduced to 20 ~ 30 ℃, so that the product loss is little, and the industrial requirement is met.
Preferably, in step 4), ethanol is used for washing.
Preferably, in step 4), stirring is carried out for 20 ~ 60min after the end point.
The invention has the beneficial effects that:
1. the invention adopts an organic solvent (most preferably isopropanol) to dilute the hydrogen peroxide, and the hydrogen peroxide diluted by the organic solvent is used for oxidation reaction, so that the product yield and the product quality both achieve ideal effects; the organic solvent can be recycled, no waste salt and waste water are generated, and the method is a novel clean environment-friendly process and has remarkable environmental benefit.
2. The product yield is more than or equal to 94 percent; the initial melting point is more than or equal to 98 ℃, the free amine is less than or equal to 0.25 percent, and the purity is high.
3. The organic solvent can be recycled, the cost is low, the process is simple, the operation is easy, the industrial production can be completely realized, and the economic benefit is remarkable.
Detailed Description
Example 1:
a novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) completely dissolving 270g of a dry product M at 63 ℃ by using 2.55L of isopropanol solvent;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1;
3) after 158.7g of cyclohexylamine is dripped, isopropanol is adopted to prepare hydrogen peroxide with the mass volume ratio of 8 percent; dropwise adding 8% hydrogen peroxide by mass-volume ratio into the reaction system until the end of the reaction;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 30 ℃, precipitating a product, filtering, washing with isopropanol, and drying to obtain a finished product CBS. The yield of the product was found to be 94.5%, the initial melting point was 98.3 ℃ and the free amine was 0.23%.
Example 2:
a novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) completely dissolving 270g of the dried product M at 57 ℃ by using 3.05L of isopropanol solvent;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.05;
3) after the dropwise addition of 151.1g of cyclohexylamine is finished, preparing hydrogen peroxide with the mass volume ratio of 10% by using isopropanol; dropwise adding hydrogen peroxide with the mass volume ratio of 10% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with isopropanol, and drying to obtain a finished product CBS. The yield of the product was found to be 95.6%, the initial melting point was 98.9 ℃ and the free amine was 0.18%.
And filtering the obtained filtrate and distilling the washing liquid to obtain isopropanol for recycling.
Example 3:
in the step 1), the isopropanol obtained in the distillation of example 2 is used as a solvent.
A novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) the isopropanol solvent obtained by distillation of the filtrate and the washing solution of example 2 was used in an amount of 3.05L, and 270g of the dried product M was completely dissolved at 57 ℃;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.05;
3) after the dropwise addition of 151.1g of cyclohexylamine is finished, preparing hydrogen peroxide with the mass volume ratio of 10% by using isopropanol; dropwise adding hydrogen peroxide with the mass volume ratio of 10% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with isopropanol, and drying to obtain a finished product CBS. The yield of the product was found to be 95.4%, the initial melting point was 98.6 ℃ and the free amine was 0.21%.
Example 4:
in step 1), the isopropanol obtained in example 3 was used as a solvent.
A novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) the isopropanol solvent obtained was distilled over 3.05L of the filtrate and washings from example 3, and 270g of dry M were completely dissolved at 57 ℃;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.05;
3) after the dropwise addition of 151.1g of cyclohexylamine is finished, preparing hydrogen peroxide with the mass volume ratio of 10% by using isopropanol; dropwise adding hydrogen peroxide with the mass volume ratio of 10% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with isopropanol, and drying to obtain a finished product CBS. The yield of the product was found to be 95.2%, the initial melting point was 98.5 ℃ and the free amine was 0.21%.
Example 5:
in step 1), the isopropanol obtained in example 4 was used as the solvent.
A novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) the isopropanol solvent obtained was distilled over 3.05L of the filtrate and washings from example 4, and 270g of dry M were completely dissolved at 57 ℃;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.05;
3) after the dropwise addition of 151.1g of cyclohexylamine is finished, preparing hydrogen peroxide with the mass volume ratio of 10% by using isopropanol; dropwise adding hydrogen peroxide with the mass volume ratio of 10% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with isopropanol, and drying to obtain a finished product CBS. The yield of the product was found to be 95.0%, the initial melting point was 98.3 ℃ and the free amine was 0.23%.
From examples 2, 3, 4 and 5, it can be seen that the recycling of the isopropanol solvent for three times still maintains high yield and purity.
Example 6:
a novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) completely dissolving 270g of a dry product M at 50 ℃ by using 3.55L of isopropanol solvent;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.1;
3) after finishing adding 144.3g of cyclohexylamine, preparing hydrogen peroxide with the mass volume ratio of 12% by using isopropanol; dropwise adding hydrogen peroxide with the mass volume ratio of 12% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with ethanol, and drying to obtain a finished product CBS. The yield of the product was found to be 95.1%, the initial melting point was 98.6 ℃ and the free amine was 0.21%.
Example 7:
a novel environment-friendly production method of accelerator CBS without waste salt wastewater production comprises the following steps:
1) completely dissolving 270g of dry product M at 57 ℃ by using 3.05L of ethanol solvent;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1: 1.05;
3) after the dropwise addition of 151.1g of cyclohexylamine is finished, preparing hydrogen peroxide with the mass volume ratio of 10% by adopting ethanol; dropwise adding hydrogen peroxide with the mass volume ratio of 10% into the reaction system until the reaction end point;
4) dropping a drop of ammonium sulfate, a drop of starch solution and a drop of potassium iodide reagent on a dropping plate, dropping 1-2 reaction liquid into the mixed solution, stirring for 30 min after the end point is reached if the end point is indicated by bluing, cooling to 25 ℃, precipitating a product, filtering, washing with ethanol, and drying to obtain a finished product CBS. The yield of the product was found to be 94.1%, the initial melting point was 98.0 ℃ and the free amine was 0.25%.
From the above examples, it can be seen that when isopropanol is used as a solvent, the product yield and product purity are optimal, probably because the hydrogen peroxide is stable in the isopropanol, the isopropanol lowers the potential of the hydrogen peroxide, so that the reaction is milder; in addition, isopropanol has low solubility for the target product.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; such modifications and substitutions do not depart from the spirit and scope of the present invention, and they should be construed as being included in the following claims and description.
Claims (10)
1. A novel environment-friendly production method of accelerator CBS without waste salt wastewater is characterized by comprising the following steps:
1) dissolving the dried product M by using an organic solvent at 40 ~ 65 ℃;
2) adding cyclohexylamine dropwise while stirring, wherein the molar ratio of cyclohexylamine to the dry product M is 1:1.0 ~ 1.3.3;
3) dropwise adding hydrogen peroxide diluted by an organic solvent to the reaction end point;
4) and stirring for a period of time after finishing, cooling, filtering, washing and drying to obtain the finished product CBS.
2. The novel environment-friendly production method of accelerator CBS without generating waste salt wastewater as claimed in claim 1, wherein: the organic solvent in the step 1) and the step 3) is methanol, ethanol or isopropanol.
3. The novel environment-friendly production method of accelerator CBS without generating waste salt wastewater as claimed in claim 2, wherein: the organic solvent in the step 1) and the step 3) is isopropanol.
4. The novel environment-friendly production method of accelerator CBS without generating waste salt and wastewater as claimed in claim 1 or 8, wherein the concentration of the M solution obtained in step 1) is 0.4 ~ 0.8.8 mol/L.
5. The novel environment-friendly production method of accelerator CBS without generating waste salt and wastewater as claimed in claim 1, wherein in step 2), the molar ratio of cyclohexylamine to dry product M is 1:1.0 ~ 1.1.1.
6. The novel environment-friendly production method of accelerator CBS without generating waste salt and wastewater as claimed in claim 1, wherein in step 3), the method for judging the reaction end point comprises the following steps: dropping one drop of ammonium sulfate, one drop of starch solution and one drop of potassium iodide reagent on a dropping plate, and dropping 1-2 reaction liquid into the mixed liquid, wherein the end point is indicated if the reaction liquid turns blue.
7. The novel environment-friendly production method of the accelerator CBS without generating waste salt and wastewater as claimed in claim 1, wherein in the step 3), the mass volume ratio of the hydrogen peroxide is 8% ~ 12%.
8. The novel environment-friendly production method of accelerator CBS without generating waste salt wastewater as claimed in claim 7, wherein: in the step 3), the mass volume ratio of the hydrogen peroxide is 10%.
9. The novel environment-friendly production method of the accelerator CBS without generating waste salt and wastewater as claimed in claim 1, wherein in the step 4), the temperature is reduced to 20 ~ 30 ℃.
10. A novel process for the environmentally friendly production of accelerator CBS without generating waste salt effluent as claimed in claim 1 or 9, wherein: in step 4), ethanol is used for washing.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117551054A (en) * | 2024-01-11 | 2024-02-13 | 科迈化工股份有限公司 | Method for improving the yield of synthetic sulfenamide accelerators using isopropyl alcohol |
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| CN1872845A (en) * | 2005-05-31 | 2006-12-06 | 中国石油天然气集团公司 | Method and equipment for preparing 2 - benzothiazole sulphenamide |
| CN103508977A (en) * | 2013-09-30 | 2014-01-15 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerator CZ by adopting double-dripping method using hydrogen peroxide as oxidizing agent |
| CN109810075A (en) * | 2019-03-03 | 2019-05-28 | 朝阳天铭工贸有限公司 | A kind of technique of isopropanol method purification DM |
-
2019
- 2019-09-30 CN CN201910938937.6A patent/CN110627740A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013084A1 (en) * | 1991-12-21 | 1993-07-08 | Akzo Nobel N.V. | Process for producing benzothiazolyl-2-sulphenamides |
| CN1872845A (en) * | 2005-05-31 | 2006-12-06 | 中国石油天然气集团公司 | Method and equipment for preparing 2 - benzothiazole sulphenamide |
| CN103508977A (en) * | 2013-09-30 | 2014-01-15 | 科迈化工股份有限公司 | Method for producing rubber vulcanization accelerator CZ by adopting double-dripping method using hydrogen peroxide as oxidizing agent |
| CN109810075A (en) * | 2019-03-03 | 2019-05-28 | 朝阳天铭工贸有限公司 | A kind of technique of isopropanol method purification DM |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117551054A (en) * | 2024-01-11 | 2024-02-13 | 科迈化工股份有限公司 | Method for improving the yield of synthetic sulfenamide accelerators using isopropyl alcohol |
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Application publication date: 20191231 |
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