CN102503813B - 一种对苯二甲酸氧化残渣中有机酸和钴锰金属的回收方法 - Google Patents
一种对苯二甲酸氧化残渣中有机酸和钴锰金属的回收方法 Download PDFInfo
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- CN102503813B CN102503813B CN2011102826807A CN201110282680A CN102503813B CN 102503813 B CN102503813 B CN 102503813B CN 2011102826807 A CN2011102826807 A CN 2011102826807A CN 201110282680 A CN201110282680 A CN 201110282680A CN 102503813 B CN102503813 B CN 102503813B
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- Prior art keywords
- acid
- cobalt
- manganese
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- cobalt manganese
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 43
- 230000003647 oxidation Effects 0.000 title claims abstract description 41
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 41
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 38
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 34
- 239000002184 metal Substances 0.000 title claims abstract description 34
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 title claims description 40
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 126
- 239000007787 solid Substances 0.000 claims abstract description 91
- 239000000706 filtrate Substances 0.000 claims abstract description 66
- SORNWENKXWLTOD-UHFFFAOYSA-J C(C(=O)[O-])(=O)[O-].[Mn+2].[Co+2].C(C(=O)[O-])(=O)[O-] Chemical compound C(C(=O)[O-])(=O)[O-].[Mn+2].[Co+2].C(C(=O)[O-])(=O)[O-] SORNWENKXWLTOD-UHFFFAOYSA-J 0.000 claims abstract description 57
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 49
- 238000000926 separation method Methods 0.000 claims abstract description 41
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 40
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 34
- 239000010941 cobalt Substances 0.000 claims abstract description 34
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000007864 aqueous solution Substances 0.000 claims abstract description 33
- 238000001914 filtration Methods 0.000 claims abstract description 31
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229940071125 manganese acetate Drugs 0.000 claims abstract description 24
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims abstract description 24
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims abstract description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 18
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims abstract description 18
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 claims abstract description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 16
- 238000004065 wastewater treatment Methods 0.000 claims abstract description 16
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims abstract description 9
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract 2
- 239000003973 paint Substances 0.000 claims abstract 2
- 238000011084 recovery Methods 0.000 claims description 35
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 31
- 229910020632 Co Mn Inorganic materials 0.000 claims description 23
- 229910020678 Co—Mn Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 16
- ZBICJTQZVYWJPB-UHFFFAOYSA-N [Mn].[Co].[Br] Chemical compound [Mn].[Co].[Br] ZBICJTQZVYWJPB-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000001556 precipitation Methods 0.000 claims description 9
- 239000011572 manganese Substances 0.000 abstract description 24
- 229910052748 manganese Inorganic materials 0.000 abstract description 19
- -1 permanganate Chemical compound 0.000 abstract description 10
- 238000001816 cooling Methods 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 7
- 239000005711 Benzoic acid Substances 0.000 abstract description 3
- 235000010233 benzoic acid Nutrition 0.000 abstract description 3
- NXTZRSCVEDUAGZ-UHFFFAOYSA-J cobalt(2+);manganese(2+);tetrabromide Chemical compound [Mn+2].[Co+2].[Br-].[Br-].[Br-].[Br-] NXTZRSCVEDUAGZ-UHFFFAOYSA-J 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 2
- 229940011182 cobalt acetate Drugs 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 239000012456 homogeneous solution Substances 0.000 abstract 1
- LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000010792 warming Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- 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 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IMXLQXHCHYKEEE-UHFFFAOYSA-N benzene;formic acid Chemical compound OC=O.C1=CC=CC=C1 IMXLQXHCHYKEEE-UHFFFAOYSA-N 0.000 description 5
- 238000004064 recycling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 208000005156 Dehydration Diseases 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000000207 volumetry Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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CN2011102826807A CN102503813B (zh) | 2011-09-22 | 2011-09-22 | 一种对苯二甲酸氧化残渣中有机酸和钴锰金属的回收方法 |
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CN2011102826807A CN102503813B (zh) | 2011-09-22 | 2011-09-22 | 一种对苯二甲酸氧化残渣中有机酸和钴锰金属的回收方法 |
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CN102503813A CN102503813A (zh) | 2012-06-20 |
CN102503813B true CN102503813B (zh) | 2013-12-25 |
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104844445B (zh) * | 2015-03-27 | 2017-06-20 | 中国昆仑工程有限公司 | 从pta薄膜蒸发器下料残渣中回收醋酸的方法 |
CN107828965B (zh) * | 2015-11-27 | 2019-04-23 | 江苏理工学院 | 一种分离回收钴锰废料中钴和锰的方法 |
US10723633B2 (en) * | 2015-12-31 | 2020-07-28 | Bp Corporation North America Inc. | Process for recovering heavy metal ions |
CN105688990B (zh) * | 2016-01-22 | 2019-02-26 | 福建洋屿环保科技股份有限公司 | 一种从pta氧化残渣中再生醋酸钴锰复合催化剂的方法 |
CN107176745A (zh) * | 2016-03-09 | 2017-09-19 | 王仲甫 | 多元羧酸残渣的废水生物处理方法 |
CN106432622B (zh) * | 2016-09-27 | 2019-01-01 | 辽阳合成催化剂有限公司 | 一种含饱和二元酸回收料制备不饱和聚酯树脂的方法 |
CN107803211B (zh) * | 2017-10-28 | 2019-06-28 | 浙江上虞利星化工有限公司 | 一种钴或/和锰溴化物的制备方法 |
CN107617445B (zh) * | 2017-10-28 | 2019-12-27 | 浙江上虞利星化工有限公司 | 利用回收钴锰制备钴锰溴水溶液的方法 |
CN107652177A (zh) * | 2017-10-28 | 2018-02-02 | 浙江上虞利星化工有限公司 | 一种钴或/和锰醋酸盐的制备方法 |
CN107597170B (zh) * | 2017-10-28 | 2019-06-28 | 浙江上虞利星化工有限公司 | 利用回收钴锰制备钴锰溴水溶液的方法 |
CN109592715B (zh) * | 2018-12-21 | 2021-04-20 | 陕西师范大学 | 一种以二水合对苯二甲酸锰为前驱体可控制备不同结构氧化锰的方法 |
CN113292498B (zh) * | 2021-06-16 | 2022-11-25 | 浙江工业大学 | 3-过氧苯甲酸-1-甲基咪唑氯盐及其制备和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4490297A (en) * | 1981-12-24 | 1984-12-25 | Dynamit Nobel Ag | Method for the recovery and reuse of cobalt and/or manganese components of catalysts |
CN101177394A (zh) * | 2006-11-08 | 2008-05-14 | 美琪玛国际股份有限公司 | 粗对苯二甲酸(cta)残渣回收及触媒纯化再生***及方法 |
-
2011
- 2011-09-22 CN CN2011102826807A patent/CN102503813B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4490297A (en) * | 1981-12-24 | 1984-12-25 | Dynamit Nobel Ag | Method for the recovery and reuse of cobalt and/or manganese components of catalysts |
CN101177394A (zh) * | 2006-11-08 | 2008-05-14 | 美琪玛国际股份有限公司 | 粗对苯二甲酸(cta)残渣回收及触媒纯化再生***及方法 |
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Effective date of registration: 20220512 Address after: 312369 No. 15, Weiwu Road, Hangzhou Bay Economic and Technological Development Zone, Shangyu, Shaoxing City, Zhejiang Province Patentee after: ZHEJIANG SHANGYU LIXING CHEMICAL CO.,LTD. Address before: 312369 No. 15 Wei five road, Hangzhou Bay Economic and Technological Development Zone, Shangyu District, Shaoxing, Zhejiang Patentee before: ZHEJIANG SHANGYU LIXING CHEMICAL CO.,LTD. Patentee before: JINAN ZHAOHUI TECHNOLOGY Co.,Ltd. |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 312369 No. 15, Weiwu Road, Hangzhou Bay Economic and Technological Development Zone, Shangyu, Shaoxing City, Zhejiang Province Patentee after: Zhejiang Lixing Technology Co.,Ltd. Address before: 312369 No. 15, Weiwu Road, Hangzhou Bay Economic and Technological Development Zone, Shangyu, Shaoxing City, Zhejiang Province Patentee before: ZHEJIANG SHANGYU LIXING CHEMICAL CO.,LTD. |