CN103755613A - Preparation method of rubber vulcanization accelerator zinc dibenzyl dithiocarbamate - Google Patents
Preparation method of rubber vulcanization accelerator zinc dibenzyl dithiocarbamate Download PDFInfo
- Publication number
- CN103755613A CN103755613A CN201410009894.0A CN201410009894A CN103755613A CN 103755613 A CN103755613 A CN 103755613A CN 201410009894 A CN201410009894 A CN 201410009894A CN 103755613 A CN103755613 A CN 103755613A
- Authority
- CN
- China
- Prior art keywords
- preparation
- dibenzylamine
- product
- reaction
- zinc
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000013040 rubber vulcanization Methods 0.000 title claims abstract description 11
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 title claims abstract description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011787 zinc oxide Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 31
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 20
- 239000013543 active substance Substances 0.000 claims description 11
- SKLFNNLCTLZUOV-UHFFFAOYSA-N dibenzylcarbamodithioic acid;zinc Chemical compound [Zn].C=1C=CC=CC=1CN(C(=S)S)CC1=CC=CC=C1 SKLFNNLCTLZUOV-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 2
- LNCUBODYXWFYEE-UHFFFAOYSA-N N-benzyl-1-phenylmethanamine 1,2-xylene Chemical group C=1(C(=CC=CC1)C)C.C(C1=CC=CC=C1)NCC1=CC=CC=C1 LNCUBODYXWFYEE-UHFFFAOYSA-N 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- -1 dibenzyl dithio zinc formate Chemical compound 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- YKVABMCSVUSETE-UHFFFAOYSA-N dibenzylcarbamodithioic acid;sodium Chemical compound [Na].C=1C=CC=CC=1CN(C(=S)S)CC1=CC=CC=C1 YKVABMCSVUSETE-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of a rubber vulcanization accelerator zinc dibenzyl dithiocarbamate. The method comprises the following steps: adding a solution of dibenzylamine-xylene mixture into a container, and adding a surfactant, a catalyst and zinc oxide; heating to certain temperature, and dropwise adding carbon disulfide into the mixture; stirring and reacting for certain time, and filtering out the product zinc dibenzyl dithiocarbamate from the reaction mixture; adding water into the filtered product for azeotropic distillation with the water to obtain a high-purity product. The method is simple to operate; compared with the traditional preparation method, the reaction conditions are not harsh, the product has high purity, and the solvent is recycled to facilitate environmental protection; more importantly, by adding the catalyst, the reaction time is greatly shortened, and the reaction period is reduced.
Description
(1) technical field:
The invention belongs to thiofide field, relate to a kind of preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc.
(2) technical background:
Zinc dibenzyldithiocarbamate can be abbreviated as: ZBEC, and its structural formula is:
This product is the very fast ultraaccelerator of a kind of speed, be applicable to natural gum and synthetical glue, this product is a kind of safe secondary amine dithiocarbamatetype accelerator, use this product not emit Carcinogenic Nitrosamines, in all zinc salt of dithiocarbamate class promotor, ZBEC has the longest scorching quality, has fabulous anti-early stage sulfo-effect in latex.Its sulfurate activity temperature is lower, operates safelyr, and the uses such as alternative ZDBC, ZDEC, PZ, are the good promoting agents of thiazole accelerator.While using this product, the use level of zinc oxide and Sulfur is general, and lipid acid can be used can.It can directly add sizing material, also can make dispersion and add latex.The industrial general method for making of zinc dibenzyldithiocarbamate is: dibenzylamine, sodium hydroxide react with dithiocarbonic anhydride and generates dibenzyl aminodithioformic acid sodium solution, in zinc sulfate or zinc oxide reaction, generate zinc dithiocarbamate again, the method produces a large amount of containing inorganic salt waste water.DE4102337 discloses a kind of preparation method of zinc dibenzyldithiocarbamate, though the method is used organic solution to drink zinc oxide, has got rid of the generation of inorganic salt, and reaction needed 24h, steams after organic solution, washes product with water, produces a large amount of waste water.DE10017103 discloses a kind of preparation method of dibenzyl dithio zinc formate: dibenzylamine and zinc carbonate generate complex compound, then react with dithiocarbonic anhydride and sodium hydroxide, generates dibenzyl dithio zinc formate, still produces a large amount of brine wastes.
(3) summary of the invention:
The present invention, for making up the deficiencies in the prior art, provides a kind of preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc.
The present invention is achieved through the following technical solutions:
The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc of the present invention, comprise the following steps: the solution that adds dibenzylamine, xylene mixture in container, add tensio-active agent simultaneously, add catalyzer and zinc oxide, while being raised to certain temperature, dithiocarbonic anhydride is added drop-wise in mixture, stirring reaction, after the regular hour, filters out product zinc dibenzyldithiocarbamate from reaction mixture; Filter rear product Jia Shui and water component distillation again, make high purity ZBEC product.
In reparation technology of the present invention, in the reaction times, temperature of reaction, adds the amount of dibenzylamine, dimethylbenzene, and the amount of catalyzer, zinc oxide all can affect the generation of product, according to optimum scheme choice of the present invention.
Mol ratio in the present invention: dibenzylamine: dithiocarbonic anhydride=1:0.9-1.2.
Dibenzylamine: zinc oxide=1:0.4-0.6.
In the present invention in dibenzylamine: the consumption of catalyzer is the 2-12% of dibenzylamine quality.
The amount of tensio-active agent is the 1-2% of dibenzylamine quality.
The amount of dimethylbenzene is 4-6 times of dibenzylamine quality.
Reaction times is 4-6 hour, and temperature of reaction is 25-60 ℃.
Tensio-active agent is anionic surfactant sodium dodecylbenzene sulfonate.
Catalyzer is lower molecular weight lipid acid.
While filtering rear product Jia Shui and water component distillation, the dimethylbenzene distilling out and water are recycled.
The invention has the beneficial effects as follows, simple to operate, with preparation method's comparison in the past, reaction conditions is not harsh, and product purity is high, and gold-plating goes out thing solvent xylene and water can recycle, and non-wastewater discharge is beneficial to environmental protection.Use zinc oxide not produce inorganic salt, and the most important thing is, add catalyzer greatly to shorten the reaction times, reduce reaction time.
(4) embodiment:
Embodiment 1:
The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc of the present invention, comprise the following steps: in the four-hole boiling flask of 500ml that has thermometer, agitator, chuck and control temperature, add 200g dimethylbenzene, 50g dibenzylamine, 0.5g tensio-active agent, 17.4gCS
2, 8.3gZnO, 6g catalyzer, drips dithiocarbonic anhydride while being warming up to 25 ℃, stirring reaction 6h.Then cooling is filtered, and filtration product adds water azeotropic and steams dimethylbenzene, and remained drying obtains product ZBEC.Product yield 98.1%, 183 ℃ of fusing points, zinc content 10.17%.
Tensio-active agent is anionic surfactant sodium dodecylbenzene sulfonate.
Catalyzer is a kind of in formic acid, acetic acid, propionic acid.
While filtering rear product Jia Shui and water component distillation, the dimethylbenzene distilling out and water recoverable.
Embodiment 2:
The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc of the present invention, comprise the following steps: in the four-hole boiling flask of 500ml that has thermometer, agitator, chuck and control temperature, add 240g dimethylbenzene, 50g dibenzylamine, 0.7g tensio-active agent, 21.0gCS
2, 10gZnO, 4g catalyzer, drips dithiocarbonic anhydride while being warming up to 40 ℃, stirring reaction 5h.Then cooling is filtered, and filtration product adds water azeotropic and steams dimethylbenzene, and remained drying obtains product ZBEC.Product yield 97.9%, 183 ℃ of fusing points, zinc content 10.87%.
All the other are identical with embodiment 1.
Embodiment 3:
The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc of the present invention, comprise the following steps: in the four-hole boiling flask of 500ml that has thermometer, agitator, chuck and control temperature, add 280g dimethylbenzene, 50g dibenzylamine, 0.8g tensio-active agent, 21.5gCS
2, 11.9gZnO, 2g catalyzer, drips dithiocarbonic anhydride while being warming up to 35 ℃, stirring reaction 5.5h.Then cooling is filtered, and filtration product adds water azeotropic and steams dimethylbenzene, and remained drying obtains product ZBEC.Product yield 97.8%, 183 ℃ of fusing points, zinc content 10.98%.
All the other are identical with embodiment 1.
Embodiment 4:
The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc of the present invention, comprise the following steps: in the four-hole boiling flask of 500ml that has thermometer, agitator, chuck and control temperature, add 300g dimethylbenzene, 50g dibenzylamine, 1g tensio-active agent, 23gCS
2, 12.3gZnO, 1g catalyzer, drips dithiocarbonic anhydride while being warming up to 60 ℃, stirring reaction 4h.Then cooling is filtered, and filtration product adds water azeotropic and steams dimethylbenzene, and remained drying obtains product ZBEC.Product yield 98.1%, 183 ℃ of fusing points, zinc content 11.3%.
All the other are identical with embodiment 1.
Claims (6)
1. the preparation method of a rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc, it is characterized in that: comprise the following steps: the solution that adds dibenzylamine, xylene mixture in container, add tensio-active agent simultaneously, add catalyzer and zinc oxide, while being raised to certain temperature, dithiocarbonic anhydride is added drop-wise in mixture, stirring reaction, after the regular hour, filters out product zinc dibenzyldithiocarbamate from reaction mixture; Filter rear product Jia Shui and water component distillation again, make high purity product.
2. preparation method according to claim 1, is characterized in that: tensio-active agent is anionic surfactant sodium dodecylbenzene sulfonate.
3. preparation method according to claim 2, is characterized in that: mol ratio is, dibenzylamine: dithiocarbonic anhydride=1:0.9-1.2; Dibenzylamine: zinc oxide=1:0.4-0.6; Catalyzer is the 2-12% of dibenzylamine quality; Tensio-active agent is the 1-2% of dibenzylamine quality; Dimethylbenzene is 4-6 times of dibenzylamine quality.
4. according to the preparation method described in any one in claim 1-3, it is characterized in that: the reaction times is 4-6 hour, temperature of reaction is 25-60 ℃.
5. according to the preparation method described in any one in claim 1-3, it is characterized in that: catalyzer is lower molecular weight lipid acid.
6. according to the preparation method described in any one in claim 1-3, it is characterized in that: while filtering rear product Jia Shui and water component distillation, the dimethylbenzene distilling out and water are recycled.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410009894.0A CN103755613B (en) | 2014-01-09 | 2014-01-09 | The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410009894.0A CN103755613B (en) | 2014-01-09 | 2014-01-09 | The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103755613A true CN103755613A (en) | 2014-04-30 |
CN103755613B CN103755613B (en) | 2016-03-02 |
Family
ID=50522975
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410009894.0A Expired - Fee Related CN103755613B (en) | 2014-01-09 | 2014-01-09 | The preparation method of rubber vulcanization accelerator dibenzyl aminodithioformic acid zinc |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103755613B (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016001582A1 (en) * | 2014-07-03 | 2016-01-07 | Mlpc International | Method for producing metal dithiocarbamates |
WO2016083733A1 (en) | 2014-11-25 | 2016-06-02 | Mlpc International | Method for producing zinc dithiocarbamates |
CN106588726A (en) * | 2016-12-12 | 2017-04-26 | 江苏连连化学股份有限公司 | Method for preparing rubber vulcanization accelerator zinc N-ethyl-N-phenyldithiocarbamate through one-step method |
CN106588727A (en) * | 2016-12-12 | 2017-04-26 | 江苏连连化学股份有限公司 | Method for preparing rubber vulcanization accelerator zinc N-ethyl-N-phenyldithiocarbamate via one-step process |
CN108147985A (en) * | 2017-12-20 | 2018-06-12 | 蔚林新材料科技股份有限公司 | The preparation method of zinc dibutyl dithiocarbamate |
CN114213297A (en) * | 2021-12-01 | 2022-03-22 | 蔚林新材料科技股份有限公司 | Method for continuously synthesizing rubber vulcanization accelerator EZ |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859787A (en) * | 1987-04-30 | 1989-08-22 | C. F. Spiess & Sohn Gmbh & Co. | Process for the preparation of dialkyldithiocarbamates of multivalent metals |
DE4102337A1 (en) * | 1991-01-26 | 1992-07-30 | Metallgesellschaft Ag | Zinc bis-di:benzyl:thiocarbamate prodn. - by direct reaction of di:benzylamine with carbon di:sulphide and zinc oxide in azeotrope-forming solvent, in presence of anionic emulsifier |
CN101955452A (en) * | 2010-04-29 | 2011-01-26 | 濮阳蔚林化工股份有限公司 | Method for preparing zinc dibenzyl dithiocarbamate (ZBDC) thiofide |
CN102276509A (en) * | 2011-06-03 | 2011-12-14 | 鹤壁联昊化工有限公司 | One-step method for preparing rubber promoter zinc dibenzyl dithiocarbamate |
-
2014
- 2014-01-09 CN CN201410009894.0A patent/CN103755613B/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859787A (en) * | 1987-04-30 | 1989-08-22 | C. F. Spiess & Sohn Gmbh & Co. | Process for the preparation of dialkyldithiocarbamates of multivalent metals |
DE4102337A1 (en) * | 1991-01-26 | 1992-07-30 | Metallgesellschaft Ag | Zinc bis-di:benzyl:thiocarbamate prodn. - by direct reaction of di:benzylamine with carbon di:sulphide and zinc oxide in azeotrope-forming solvent, in presence of anionic emulsifier |
CN101955452A (en) * | 2010-04-29 | 2011-01-26 | 濮阳蔚林化工股份有限公司 | Method for preparing zinc dibenzyl dithiocarbamate (ZBDC) thiofide |
CN102276509A (en) * | 2011-06-03 | 2011-12-14 | 鹤壁联昊化工有限公司 | One-step method for preparing rubber promoter zinc dibenzyl dithiocarbamate |
Non-Patent Citations (1)
Title |
---|
杨鑫莉等: "橡胶硫化促进剂Pz的合成", 《广西化工》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016001582A1 (en) * | 2014-07-03 | 2016-01-07 | Mlpc International | Method for producing metal dithiocarbamates |
FR3023289A1 (en) * | 2014-07-03 | 2016-01-08 | Mlpc Internat | PROCESS FOR THE PREPARATION OF METAL DITHIOCARBAMATES |
WO2016083733A1 (en) | 2014-11-25 | 2016-06-02 | Mlpc International | Method for producing zinc dithiocarbamates |
CN106588726A (en) * | 2016-12-12 | 2017-04-26 | 江苏连连化学股份有限公司 | Method for preparing rubber vulcanization accelerator zinc N-ethyl-N-phenyldithiocarbamate through one-step method |
CN106588727A (en) * | 2016-12-12 | 2017-04-26 | 江苏连连化学股份有限公司 | Method for preparing rubber vulcanization accelerator zinc N-ethyl-N-phenyldithiocarbamate via one-step process |
CN106588727B (en) * | 2016-12-12 | 2018-09-11 | 江苏连连化学股份有限公司 | The method that one-step method prepares thiofide N- ethyl, N-phenyl zinc dithiocarbamates |
CN106588726B (en) * | 2016-12-12 | 2018-09-11 | 江苏连连化学股份有限公司 | The method that one-step method prepares thiofide N- ethyl, N-phenyl zinc dithiocarbamates |
CN108147985A (en) * | 2017-12-20 | 2018-06-12 | 蔚林新材料科技股份有限公司 | The preparation method of zinc dibutyl dithiocarbamate |
CN114213297A (en) * | 2021-12-01 | 2022-03-22 | 蔚林新材料科技股份有限公司 | Method for continuously synthesizing rubber vulcanization accelerator EZ |
Also Published As
Publication number | Publication date |
---|---|
CN103755613B (en) | 2016-03-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103755613A (en) | Preparation method of rubber vulcanization accelerator zinc dibenzyl dithiocarbamate | |
CN110372551B (en) | Preparation method of 3-mercaptopropionic acid | |
CN102838558A (en) | Method for preparing rubber accelerator DM (2,2'-dithiobis(benzothiazole)) from 2-mercaptobenzothiazole coarse product as raw material | |
CN102827102A (en) | Refinement method of rubber vulcanization accelerator MBT (2-mercaptobenzthiazole) | |
CN105524014A (en) | Purification method of rubber vulcanization accelerator 2-mercaptobenzothiazole | |
CN102295592A (en) | Preparation method of rubber vulcanization accelerator zinc dimethyldithiocarbamate | |
CN105541906B (en) | A kind of purification process of glufosinate-ammonium | |
CN104311505A (en) | Purification method of 2-mercaptobenzothiazole serving as rubber vulcanization accelerator M | |
CN105541683A (en) | Method for preparing tetrathioperoxydicarbamic acid | |
CN103130657A (en) | Synthetic method of 2-chloro-4-aminophenol | |
CN101863785A (en) | Environmental-protection preparation method of betaine hydrochloride | |
CN103896307A (en) | Method for refining coke oven gas desulfurization waste liquid salt extraction product ammonium sulfate again | |
CN103739534B (en) | The synthetic method of rubber accelerator tetrabenzylthiuram disulfide | |
CN102993114B (en) | A kind of production method of 1H-TETRAZOLE-5-acetic acid | |
CN103058899A (en) | Synthetic method for methyl-sulfuryl benzaldehyde | |
CN105037215B (en) | A kind of environment protection method of high yield dioxygen oxidation method synthesis accelerant DPG | |
CN104829509A (en) | Preparation method of rubber vulcanization accelerator | |
CN103524450A (en) | Synthetic method for accelerator DZ by using methanol as solvent | |
CN101759658A (en) | Method for purifying low-content thiofide MBT through ethyl alcohol recrystallization | |
CN105503677A (en) | Preparation method of environment-friendly and efficient sulfurization crosslinking agent 1,6-bis(N,N-dibenzyl carbamyl disulfide) hexane | |
CN109651211A (en) | A method of preparing 2,3- sodium dimercaptopropane sulfonate | |
CN103833563B (en) | A kind of method improving iminodiethanoic acid yield | |
CN104163802B (en) | The preparation method of thiazolamine-4-ethyl formate | |
CN102816095B (en) | Preparation method for organic thiosulfate | |
CN102936231B (en) | Synthesis of rubber accelerator NS via plasma one-step oxidation method |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160302 |
|
CF01 | Termination of patent right due to non-payment of annual fee |