CN114634463A - 一种2-巯基苯并噻唑的制备方法 - Google Patents
一种2-巯基苯并噻唑的制备方法 Download PDFInfo
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- CN114634463A CN114634463A CN202011493871.3A CN202011493871A CN114634463A CN 114634463 A CN114634463 A CN 114634463A CN 202011493871 A CN202011493871 A CN 202011493871A CN 114634463 A CN114634463 A CN 114634463A
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- mercaptobenzothiazole
- aniline
- rubber
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- sulfur
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 229920001971 elastomer Polymers 0.000 claims description 6
- 239000005060 rubber Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004073 vulcanization Methods 0.000 claims 3
- 239000004135 Bone phosphate Substances 0.000 claims 1
- 244000043261 Hevea brasiliensis Species 0.000 claims 1
- 229920005549 butyl rubber Polymers 0.000 claims 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- NJWUMLMAYBUQJR-UHFFFAOYSA-N carbamothioylsulfanyltellanyl carbamodithioate Chemical compound NC(=S)S[Te]SC(N)=S NJWUMLMAYBUQJR-UHFFFAOYSA-N 0.000 claims 1
- NBGTWXBPCIHUQD-UHFFFAOYSA-N diethylcarbamodithioic acid;n-ethylethanamine Chemical compound CCNCC.CCN(CC)C(S)=S NBGTWXBPCIHUQD-UHFFFAOYSA-N 0.000 claims 1
- 239000012990 dithiocarbamate Substances 0.000 claims 1
- 229940075933 dithionate Drugs 0.000 claims 1
- 229920002681 hypalon Polymers 0.000 claims 1
- 229920000126 latex Polymers 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229920003052 natural elastomer Polymers 0.000 claims 1
- 229920001194 natural rubber Polymers 0.000 claims 1
- 229920003051 synthetic elastomer Polymers 0.000 claims 1
- 239000005061 synthetic rubber Substances 0.000 claims 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims 1
- 229960002447 thiram Drugs 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 18
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 abstract description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 abstract description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 2
- MACMAADVRVVHBD-VMPITWQZSA-N (e)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=CC=C1O MACMAADVRVVHBD-VMPITWQZSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VLDHWMAJBNWALQ-UHFFFAOYSA-M sodium;1,3-benzothiazol-3-ide-2-thione Chemical compound [Na+].C1=CC=C2SC([S-])=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-M 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07D277/72—2-Mercaptobenzothiazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种2‑巯基苯并噻唑的制备方法，其特征在于：通常是将苯胺、二硫化碳和硫磺在高压釜中直接反应，也可用脂肪胺、二甲基甲酰胺、三噻唑烷和多取甲醛等代替二硫化碳，使苯胺和硫磺在高压下反应。用苯胺为原料的方法，其反应压力都较高，一般在4MPa以上，有高达15MPa，因此也称高压法。
Description
技术领域
本发明涉及一种2-巯基苯并噻唑的制备技术领域，特别涉及以苯胺、邻硝基氯苯和二苯硫脲为原料来制备的方法。
背景技术
2-巯基苯并噻唑用作电镀添加剂时又称酸性镀铜光亮剂，在以硫酸铜为主盐的光亮镀铜时作为铺助光亮剂。还用于制取农药杀真菌剂、氮肥增效剂、切消油和润滑添加剂、照相化学中的有机防灰化剂、金属腐蚀抑制剂等，用作检定金、铋、镉、钴、汞、镍、铅、铊和锌的灵敏试剂及橡胶促进剂，用于制造轮胎、内胎、胶带、胶鞋和其他工业橡胶制品。2-巯基苯并噻唑是除草剂苯噻草胺的中间体，也是橡胶促进剂及其中间体。
发明内容
本发明的目的在于提供一种2-巯基苯并噻唑的制备方法。
本发明采用的技术方案为：
通常是将苯胺、二硫化碳和硫磺在高压釜中直接反应，也可用脂肪胺、二甲基甲酰胺、三噻唑烷和多取甲醛等代替二硫化碳，使苯胺和硫磺在高压下反应。用苯胺为原料的方法，其反应压力都较高，一般在4MPa以上，有高达15MPa，因此也称高压法。
本发明的主要优点是：工艺简单，反应温度低，反应时间短；产品产率高，纯度高。
具体实施方式
为了更详细地说明本发明的特点，下面通过具体的实施实例对本发明作进一步的阐述，而不是限制本发明的范围。
实施例1：
邻硝基氯苯与还原剂硫氢化钠、多硫化钠或硫化氢反应都可还原成邻氨基硫酚。进一步与二硫化碳反应而制得促进剂M。这类方法有的反应时间较长（硫氢化钠约需20h），但都可在常压或较低压力下进行，又称常压法。
实施例2：
以邻氯硝基苯、多硫化钠、二硫化碳为原料，在110～130℃温度、343kPa压力下反应生成2-巯基苯并噻唑钠盐，再用硫酸进行酸化、水洗得产品。也可以用苯胺、二硫化碳与硫磺在200℃左右反应，然后在7.85 MPa压力及250～260℃保温2.5 h，即得2-巯基苯并噻唑，用氢氧化钠溶解成钠盐，再调剂pH值至pH=9，过滤，滤液再在38～40℃进行酸化中和，进行水洗、干燥得产品。
将苯胺，二硫化碳，硫黄依次加入缩合釜中。其投料比为（mol）︰1︰0.96︰0.36。在8.1MPa下加热至260℃左右。2h后缩合反应结束。得2-巯基苯并噻唑粗品。冷却降温，将其转移到中和釜 。加碱液中和，过滤，弃除杂质，滤液转入酸化釜内，加硫酸酸化至pH值为6～7。过滤，滤饼用水洗两次，干燥，粉碎，过筛包装得成品。
Claims (1)
1.一种2-巯基苯并噻唑的制备方法，其特征在于：
2-巯基苯并噻唑作为通用型硫化促进剂，广泛用于各种橡胶，对于天然橡胶和通常以硫磺硫化的合成胶具有硫化促进作用，常与其他促进剂体系并用，如与二硫代秋兰姆和二硫代氨基甲酸碲并用可作丁基胶的硫化促进剂；与三盐基顺丁稀二酸铅并用，可用于浅色耐水的氯磺化聚乙烯胶料，在胶乳中常与二硫代氨基甲酸盐并用，而与二乙基二硫代氨基甲酸二乙胺并用时，可室温硫化。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202011493871.3A CN114634463A (zh) | 2020-12-16 | 2020-12-16 | 一种2-巯基苯并噻唑的制备方法 |
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| CN202011493871.3A CN114634463A (zh) | 2020-12-16 | 2020-12-16 | 一种2-巯基苯并噻唑的制备方法 |
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| Publication Number | Publication Date |
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| CN114634463A true CN114634463A (zh) | 2022-06-17 |
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| CN202011493871.3A Pending CN114634463A (zh) | 2020-12-16 | 2020-12-16 | 一种2-巯基苯并噻唑的制备方法 |
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| Country | Link |
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| CN (1) | CN114634463A (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116478110A (zh) * | 2023-03-28 | 2023-07-25 | 烟台恒鑫化工科技有限公司 | 一种橡胶硫化促进剂制备方法及其应用 |
-
2020
- 2020-12-16 CN CN202011493871.3A patent/CN114634463A/zh active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116478110A (zh) * | 2023-03-28 | 2023-07-25 | 烟台恒鑫化工科技有限公司 | 一种橡胶硫化促进剂制备方法及其应用 |
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Application publication date: 20220617 |