CN106631759B - A kind of system and method producing methacrylic acid coproducing methyl methacrylaldehyde - Google Patents
A kind of system and method producing methacrylic acid coproducing methyl methacrylaldehyde Download PDFInfo
- Publication number
- CN106631759B CN106631759B CN201611128699.5A CN201611128699A CN106631759B CN 106631759 B CN106631759 B CN 106631759B CN 201611128699 A CN201611128699 A CN 201611128699A CN 106631759 B CN106631759 B CN 106631759B
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- CN
- China
- Prior art keywords
- methacrolein
- tower
- methacrylic acid
- chilling
- gas
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- 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.)
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 76
- ACWQBUSCFPJUPN-UHFFFAOYSA-N 2-methylbut-2-enal Chemical compound CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 13
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims abstract description 228
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 62
- 239000002253 acid Substances 0.000 claims abstract description 61
- 230000003647 oxidation Effects 0.000 claims abstract description 60
- 238000010521 absorption reaction Methods 0.000 claims abstract description 55
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000010828 elution Methods 0.000 claims abstract description 50
- 238000011084 recovery Methods 0.000 claims abstract description 28
- 238000009834 vaporization Methods 0.000 claims abstract description 23
- 230000008016 vaporization Effects 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000012535 impurity Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002245 particle Substances 0.000 claims abstract description 7
- 239000007789 gas Substances 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 230000003197 catalytic effect Effects 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 23
- 238000000605 extraction Methods 0.000 claims description 20
- 239000012071 phase Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 239000012530 fluid Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- 238000004064 recycling Methods 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000012856 packing Methods 0.000 claims description 9
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 7
- 239000007792 gaseous phase Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229910052750 molybdenum Inorganic materials 0.000 claims description 6
- 239000011733 molybdenum Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000011964 heteropoly acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 239000010808 liquid waste Substances 0.000 claims 1
- 238000004056 waste incineration Methods 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 4
- 208000012839 conversion disease Diseases 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- -1 feedstock preheater Chemical compound 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000002745 absorbent Effects 0.000 description 6
- 239000002250 absorbent Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201611128699.5A CN106631759B (en) | 2016-12-09 | 2016-12-09 | A kind of system and method producing methacrylic acid coproducing methyl methacrylaldehyde |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201611128699.5A CN106631759B (en) | 2016-12-09 | 2016-12-09 | A kind of system and method producing methacrylic acid coproducing methyl methacrylaldehyde |
Publications (2)
Publication Number | Publication Date |
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CN106631759A CN106631759A (en) | 2017-05-10 |
CN106631759B true CN106631759B (en) | 2019-02-15 |
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Family Applications (1)
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CN201611128699.5A Active CN106631759B (en) | 2016-12-09 | 2016-12-09 | A kind of system and method producing methacrylic acid coproducing methyl methacrylaldehyde |
Country Status (1)
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CN (1) | CN106631759B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3681855B1 (en) * | 2017-09-11 | 2021-08-11 | Dow Global Technologies LLC | Method for recovery of methacrolein and methanol from methacrolein dimethylacetal |
CN110551013A (en) * | 2018-05-30 | 2019-12-10 | 中国石油集团东北炼化工程有限公司吉林设计院 | energy recovery method of acrolein refining process |
CN110551008B (en) * | 2018-05-30 | 2022-07-19 | 中石油吉林化工工程有限公司 | Tail gas recycling method in acrolein production process |
JP6574294B1 (en) * | 2018-09-11 | 2019-09-11 | 住友化学株式会社 | Methacrylic acid production equipment |
JP6611390B1 (en) * | 2018-11-14 | 2019-11-27 | 住友化学株式会社 | Methacrylic acid production equipment |
JP6611391B1 (en) * | 2018-11-14 | 2019-11-27 | 住友化学株式会社 | Methacrylic acid production equipment |
CN109232232B (en) * | 2018-11-19 | 2021-06-22 | 平湖石化有限责任公司 | Refining method of acrylic acid |
CN112439300A (en) * | 2019-09-05 | 2021-03-05 | 中石油吉林化工工程有限公司 | Tail gas treatment system and tail gas treatment method for preparing acrylic acid |
CN111138266B (en) * | 2019-11-18 | 2023-07-14 | 中国寰球工程有限公司 | Method and device for preparing acrylic acid or methacrylic acid |
CN111116335B (en) * | 2019-11-25 | 2023-05-23 | 中国寰球工程有限公司 | Process for preparing acrolein or methacrolein |
CN111217697B (en) * | 2020-01-13 | 2022-08-05 | 万华化学集团股份有限公司 | Method for preparing methacrylic acid by gas phase oxidation of C4 compound |
CN115368231B (en) * | 2022-09-19 | 2024-04-09 | 万华化学集团股份有限公司 | Continuous production process of methacrylic acid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101844973A (en) * | 2010-06-01 | 2010-09-29 | 上海华谊丙烯酸有限公司 | Method for absorbing and separating methacrolein |
CN105001072A (en) * | 2015-07-21 | 2015-10-28 | 中国化学赛鼎宁波工程有限公司 | Propylene-to-acrylic acid oxidation absorption system and method thereof |
-
2016
- 2016-12-09 CN CN201611128699.5A patent/CN106631759B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101844973A (en) * | 2010-06-01 | 2010-09-29 | 上海华谊丙烯酸有限公司 | Method for absorbing and separating methacrolein |
CN105001072A (en) * | 2015-07-21 | 2015-10-28 | 中国化学赛鼎宁波工程有限公司 | Propylene-to-acrylic acid oxidation absorption system and method thereof |
Non-Patent Citations (2)
Title |
---|
异丁烯空气氧化法制取MMA(旭硝子法);无;《化工新型材料科技资料》;19791231;第12-15页 |
甲基丙烯醛气液相平衡数据测定及应用;钱志刚等,;《上海化工》;20120101;第37卷(第7期);第7-10页 |
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Publication number | Publication date |
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CN106631759A (en) | 2017-05-10 |
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Effective date of registration: 20170822 Address after: 315040, Lane 999, Lane 1, R & D Park, national hi tech Zone, Zhejiang, Ningbo Applicant after: Sedin Ningbo Engineering Co., Ltd. Applicant after: Shandong Yidali Chemical Co., Ltd. Applicant after: Heze HOLLEY New Material Co Ltd Address before: 315040, Lane 999, Lane 1, R & D Park, national hi tech Zone, Zhejiang, Ningbo Applicant before: Sedin Ningbo Engineering Co., Ltd. |
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Effective date of registration: 20191128 Address after: 274000 555 Haihe Road, Heze Development Zone, Shandong Co-patentee after: Heze HOLLEY New Material Co Ltd Patentee after: Shandong Yidali Chemical Co., Ltd. Address before: 315040, Lane 999, Lane 1, R & D Park, national hi tech Zone, Zhejiang, Ningbo Co-patentee before: Shandong Yidali Chemical Co., Ltd. Patentee before: Sedin Ningbo Engineering Co., Ltd. Co-patentee before: Heze HOLLEY New Material Co Ltd |
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Effective date of registration: 20191223 Address after: No. 333, Haihe Road, Heze Development Zone, 274000 Shandong Province Patentee after: Heze HOLLEY New Material Co Ltd Address before: 274000 555 Haihe Road, Heze Development Zone, Shandong Co-patentee before: Heze HOLLEY New Material Co Ltd Patentee before: Shandong Yidali Chemical 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: No. 333, Haihe Road, Heze Development Zone, 274000 Shandong Province Patentee after: Qixiang Huali New Material Co., Ltd Address before: No. 333, Haihe Road, Heze Development Zone, 274000 Shandong Province Patentee before: HEZE HUALI NEW MATERIAL Co.,Ltd. |