CN104725204B - 磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 - Google Patents
磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 Download PDFInfo
- Publication number
- CN104725204B CN104725204B CN201510077926.5A CN201510077926A CN104725204B CN 104725204 B CN104725204 B CN 104725204B CN 201510077926 A CN201510077926 A CN 201510077926A CN 104725204 B CN104725204 B CN 104725204B
- Authority
- CN
- China
- Prior art keywords
- anthraquinone
- sulfonated graphene
- catalyst
- benzoic acid
- alkyl
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 abstract description 62
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 31
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 238000000034 method Methods 0.000 abstract description 22
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract description 18
- 150000004056 anthraquinones Chemical class 0.000 abstract description 18
- 239000005711 Benzoic acid Substances 0.000 abstract description 17
- 235000010233 benzoic acid Nutrition 0.000 abstract description 17
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 abstract description 15
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 7
- 239000000376 reactant Substances 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000002779 inactivation Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- JZFDKGFWNSQAHU-UHFFFAOYSA-N 2-(4-ethylbenzoyl)benzoic acid Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JZFDKGFWNSQAHU-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229910002804 graphite Inorganic materials 0.000 description 6
- 239000010439 graphite Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- -1 2- ethyl Chemical group 0.000 description 3
- VNUUCYDAIBOFMG-UHFFFAOYSA-N 2-(4-butylbenzoyl)benzoic acid Chemical compound C1=CC(CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O VNUUCYDAIBOFMG-UHFFFAOYSA-N 0.000 description 3
- RDQYZLXSZLXNJY-UHFFFAOYSA-N 2-(4-pentylbenzoyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O RDQYZLXSZLXNJY-UHFFFAOYSA-N 0.000 description 3
- IOAUOQJJKWICQR-UHFFFAOYSA-N 2-(4-propylbenzoyl)benzoic acid Chemical compound C1=CC(CCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O IOAUOQJJKWICQR-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ICQOWIXIHDDXDI-UHFFFAOYSA-N 2-(4-methylbenzoyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1C(O)=O ICQOWIXIHDDXDI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical compound C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000011964 heteropoly acid Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- SGHGTABSBRRVLL-UHFFFAOYSA-N 2-butylanthracene Chemical group C1=CC=CC2=CC3=CC(CCCC)=CC=C3C=C21 SGHGTABSBRRVLL-UHFFFAOYSA-N 0.000 description 1
- ZXAGXLDEMUNQSH-UHFFFAOYSA-N 2-ethylanthracene Chemical group C1=CC=CC2=CC3=CC(CC)=CC=C3C=C21 ZXAGXLDEMUNQSH-UHFFFAOYSA-N 0.000 description 1
- JXXZUIVXBOMDIF-UHFFFAOYSA-N C(=O)O.CC1=CC=C(C(=O)C2=C(C=CC=C2)NC2=C(C(=O)O)C=CC=C2)C=C1 Chemical compound C(=O)O.CC1=CC=C(C(=O)C2=C(C=CC=C2)NC2=C(C(=O)O)C=CC=C2)C=C1 JXXZUIVXBOMDIF-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | 原料 | 原料转化率(%) | 蒽醌选择性(%) |
1 | 2-(4’-甲基苯甲酰基)苯甲酸 | 92 | 90 |
2 | 2-(4’-乙基苯甲酰基)苯甲酸 | 95 | 99 |
3 | 2-(4’-丙基苯甲酰基)苯甲酸 | 90 | 92 |
4 | 2-(4’-丁基苯甲酰基)苯甲酸 | 92 | 93 |
5 | 2-(4’-戊基苯甲酰基)苯甲酸 | 89 | 90 |
实施例 | 原料 | 原料转化率(%) | 蒽醌选择性(%) |
6 | 2-(4’-甲基苯甲酰基)苯甲酸 | 82 | 90 |
7 | 2-(4’-乙基苯甲酰基)苯甲酸 | 89 | 97 |
8 | 2-(4’-丙基苯甲酰基)苯甲酸 | 80 | 92 |
9 | 2-(4’-丁基苯甲酰基)苯甲酸 | 81 | 93 |
10 | 2-(4’-戊基苯甲酰基)苯甲酸 | 82 | 90 |
实施例 | 催化剂 | 反应温度(℃) | 原料转化率(%) | 蒽醌选择性(%) |
11 | 1 | 200 | 89 | 92 |
12 | 1 | 250 | 95 | 99 |
13 | 1 | 300 | 96 | 99 |
14 | 1 | 350 | 96 | 97 |
15 | 2 | 200 | 82 | 98 |
16 | 2 | 250 | 89 | 97 |
17 | 2 | 300 | 90 | 97 |
18 | 2 | 350 | 93 | 95 |
实施例 | 催化剂 | 反应时间(h) | 原料转化率(%) | 蒽醌选择性(%) |
19 | 1 | 0.5 | 88 | 99 |
20 | 1 | 0.75 | 95 | 99 |
21 | 1 | 1 | 96 | 99 |
22 | 1 | 2 | 97 | 95 |
23 | 2 | 0.5 | 80 | 99 |
24 | 2 | 0.75 | 87 | 97 |
25 | 2 | 1 | 90 | 97 |
26 | 2 | 2 | 95 | 90 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510077926.5A CN104725204B (zh) | 2015-02-14 | 2015-02-14 | 磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510077926.5A CN104725204B (zh) | 2015-02-14 | 2015-02-14 | 磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104725204A CN104725204A (zh) | 2015-06-24 |
CN104725204B true CN104725204B (zh) | 2017-02-01 |
Family
ID=53449690
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510077926.5A Active CN104725204B (zh) | 2015-02-14 | 2015-02-14 | 磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104725204B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106045838B (zh) * | 2016-06-04 | 2019-02-01 | 江阴市长江化工有限公司 | 2-乙基蒽醌的合成装置及工艺 |
CN106905270A (zh) * | 2017-03-16 | 2017-06-30 | 南开大学 | 一种生产5‑羟甲基糠醛的工艺 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1315768C (zh) * | 2004-11-24 | 2007-05-16 | 大连理工大学 | 一种2-烷基蒽醌的合成方法 |
CN103896772A (zh) * | 2014-03-06 | 2014-07-02 | 大连大学 | 一种催化酯化甘油制备甘油酯的方法 |
-
2015
- 2015-02-14 CN CN201510077926.5A patent/CN104725204B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN104725204A (zh) | 2015-06-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107602368B (zh) | 两步法制备2-戊基蒽醌的方法 | |
CN107746372A (zh) | 一种2‑乙基蒽醌的生产工艺 | |
US2461740A (en) | Process of making organic acids from carbonaceous material | |
CN106966884B (zh) | 一种蒽氧化制备蒽醌的方法 | |
CN106831315B (zh) | 一种氯乙烷的连续化生产方法 | |
CN103319379B (zh) | 一种蒽醌类化合物的合成工艺 | |
CN102816093B (zh) | 甲硫醇氧化法生产二甲基二硫的方法 | |
CN104725204B (zh) | 磺化石墨烯催化剂用于2‑烷基蒽醌生产的方法 | |
CN104193657B (zh) | 一种环保型对-(β-羟乙基砜硫酸酯)苯胺的合成方法 | |
CN108940327A (zh) | 一种硫碳基固体酸催化剂的制备方法 | |
CN106745245B (zh) | 一种焦锑酸钠和偏锑酸钠的制备方法 | |
CN111253261A (zh) | 一种3,5-二硝基苯甲酸的制备方法 | |
CN110270371B (zh) | 一种木质素基固体酸催化苄基化反应方法 | |
CN104803837B (zh) | 一种碱脱硅改性的Hβ分子筛催化乙苯与苯酐反应一步法制备2-乙基蒽醌的方法 | |
CN106631783A (zh) | 一种乙酸正丁酯的制备方法 | |
CN101492368B (zh) | 一种苯甲酸的生产方法 | |
CN109503437A (zh) | 2-硝基-4-甲砜基苯甲酸的制备方法 | |
CN115636746A (zh) | 一种高值化综合利用煤制乙二醇甲酸甲酯废液的工艺方法 | |
CN107098802B (zh) | 基于Beta沸石的2-烷基蒽醌制备方法 | |
CN113292407A (zh) | 一种固体超强酸催化合成蒽缔蒽酮的生产方法 | |
CN1519193A (zh) | 一种四丁基脲在过氧化氢生产中的应用 | |
WO2018004461A1 (en) | One-step approach to 2,5-diformylfuran from carbohydrates by a molybdenum-based catalyst | |
US1834621A (en) | Catalytic reduction of carbonyl compounds | |
CN109894135B (zh) | 掺氮炭黑负载钯铋合金催化剂及其制备方法和应用 | |
CN112608291A (zh) | 一种氧化制顺酐水相催化加氢联产丁二酸的方法 |
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 | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20201021 Address after: 5 / F, building H5, Jining innovation Valley, No.9 Haichuan Road, Rencheng District, Zaozhuang City, Shandong Province Patentee after: Shandong Zhongke New Material Research Institute Co., Ltd Address before: 314000, No. 1, No. 778, Asia Pacific Road, Nanhu District, Jiaxing, Jiaxing, No. 9, north of Building No. 2, Zhejiang Patentee before: JIAXING RUNBO CHEMICAL TECHNOLOGY Co.,Ltd. |
|
CP02 | Change in the address of a patent holder | ||
CP02 | Change in the address of a patent holder |
Address after: 272071 5th floor, building H5, Jining innovation Valley, No.9 Haichuan Road, Rencheng District, Jining City, Shandong Province Patentee after: Shandong Zhongke New Material Research Institute Co., Ltd Address before: 272071 5th floor, building H5, Jining innovation Valley, No.9 Haichuan Road, Rencheng District, Zaozhuang City, Shandong Province Patentee before: Shandong Zhongke New Material Research Institute Co., Ltd |