CN104761451B - 丙酸甲酯的制备方法 - Google Patents
丙酸甲酯的制备方法 Download PDFInfo
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- CN104761451B CN104761451B CN201510127023.3A CN201510127023A CN104761451B CN 104761451 B CN104761451 B CN 104761451B CN 201510127023 A CN201510127023 A CN 201510127023A CN 104761451 B CN104761451 B CN 104761451B
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- CN
- China
- Prior art keywords
- propanoic acid
- exchange resin
- gel
- esterification
- catalyst
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 229940017219 methyl propionate Drugs 0.000 title claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 57
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 54
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 54
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 52
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 51
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000011347 resin Substances 0.000 claims abstract description 48
- 229920005989 resin Polymers 0.000 claims abstract description 48
- 238000005886 esterification reaction Methods 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 35
- 230000032050 esterification Effects 0.000 claims abstract description 35
- 230000002378 acidificating effect Effects 0.000 claims abstract description 34
- 230000000694 effects Effects 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 19
- 229920001577 copolymer Polymers 0.000 abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 19
- 239000001257 hydrogen Substances 0.000 abstract description 19
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract description 19
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 4
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 48
- 239000000126 substance Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 19
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000004364 calculation method Methods 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000011148 porous material Substances 0.000 description 6
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000011831 acidic ionic liquid Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- -1 alkyl imidazolium cation Chemical compound 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GEMITLJMEMBDKW-UHFFFAOYSA-N hydrogen sulfate;1h-imidazol-3-ium Chemical compound C1=CNC=N1.OS(O)(=O)=O GEMITLJMEMBDKW-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AJTWAFXXIGBVRF-UHFFFAOYSA-N pyridine;sulfo hydrogen sulfate Chemical compound C1=CC=NC=C1.OS(=O)(=O)OS(O)(=O)=O AJTWAFXXIGBVRF-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 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
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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Priority Applications (1)
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CN201510127023.3A CN104761451B (zh) | 2012-12-20 | 2012-12-20 | 丙酸甲酯的制备方法 |
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CN201510127023.3A CN104761451B (zh) | 2012-12-20 | 2012-12-20 | 丙酸甲酯的制备方法 |
CN201210557811.2A CN102976939B (zh) | 2012-12-20 | 2012-12-20 | 丙酸酯的制备方法 |
Related Parent Applications (1)
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CN201210557811.2A Division CN102976939B (zh) | 2012-12-20 | 2012-12-20 | 丙酸酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN104761451A CN104761451A (zh) | 2015-07-08 |
CN104761451B true CN104761451B (zh) | 2016-08-17 |
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CN201210557811.2A Active CN102976939B (zh) | 2012-12-20 | 2012-12-20 | 丙酸酯的制备方法 |
CN201510126780.9A Active CN104788311B (zh) | 2012-12-20 | 2012-12-20 | 丙酸正丙酯的制备方法 |
CN201510127023.3A Active CN104761451B (zh) | 2012-12-20 | 2012-12-20 | 丙酸甲酯的制备方法 |
CN201510126543.2A Active CN104761450B (zh) | 2012-12-20 | 2012-12-20 | 丙酸乙酯的制备方法 |
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CN201210557811.2A Active CN102976939B (zh) | 2012-12-20 | 2012-12-20 | 丙酸酯的制备方法 |
CN201510126780.9A Active CN104788311B (zh) | 2012-12-20 | 2012-12-20 | 丙酸正丙酯的制备方法 |
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Families Citing this family (2)
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CN109970555A (zh) * | 2018-12-28 | 2019-07-05 | 深圳光华伟业股份有限公司 | 电子级丙酸正丙酯的制备方法 |
CN113248376B (zh) * | 2021-07-15 | 2021-10-01 | 山东海科新源材料科技股份有限公司 | 电子级丙酸酯的制备方法及其所得产品和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6274749B1 (en) * | 1997-07-29 | 2001-08-14 | Hoechst Research & Technology Gmbh & Co. Kg | High-temperature resistant sulfonated aromatic polyether ketone cation exchangers and sulfonated poly (phenylene sulfide) cation exchangers as catalysts at reaction temperature above 150° C |
CN101219398A (zh) * | 2007-01-09 | 2008-07-16 | 罗门哈斯公司 | 用于非均相酸催化的方法 |
CN102320962A (zh) * | 2011-07-18 | 2012-01-18 | 邢台旭阳煤化工有限公司 | 一种催化合成丙酸甲酯的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4528395A (en) * | 1983-08-15 | 1985-07-09 | American Cyanamid Co. | Process for esterifying 3,5-di-tert-butyl-4-hydroxybenzoic acid |
CN1059199C (zh) * | 1997-04-28 | 2000-12-06 | 国营吴江香料厂 | 丙酸乙酯生产工艺 |
JP4160087B2 (ja) * | 2006-07-11 | 2008-10-01 | 株式会社日本触媒 | アクリル酸エステルの製造方法 |
CN101560152B (zh) * | 2009-05-27 | 2012-05-23 | 南京工业大学 | 一种合成丙酸酯的方法 |
US20110065943A1 (en) * | 2009-09-16 | 2011-03-17 | Rajiv Manohar Banavali | Method for selective esterification of free fatty acids in triglycerides |
-
2012
- 2012-12-20 CN CN201210557811.2A patent/CN102976939B/zh active Active
- 2012-12-20 CN CN201510126780.9A patent/CN104788311B/zh active Active
- 2012-12-20 CN CN201510127023.3A patent/CN104761451B/zh active Active
- 2012-12-20 CN CN201510126543.2A patent/CN104761450B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6274749B1 (en) * | 1997-07-29 | 2001-08-14 | Hoechst Research & Technology Gmbh & Co. Kg | High-temperature resistant sulfonated aromatic polyether ketone cation exchangers and sulfonated poly (phenylene sulfide) cation exchangers as catalysts at reaction temperature above 150° C |
CN101219398A (zh) * | 2007-01-09 | 2008-07-16 | 罗门哈斯公司 | 用于非均相酸催化的方法 |
CN102320962A (zh) * | 2011-07-18 | 2012-01-18 | 邢台旭阳煤化工有限公司 | 一种催化合成丙酸甲酯的方法 |
Non-Patent Citations (1)
Title |
---|
大孔磺酸树脂负载AlCl3固体超强酸催化剂的制备;赵小军等;《化学工业与工程》;200006;第17卷(第3期);第169-173页 * |
Also Published As
Publication number | Publication date |
---|---|
CN102976939A (zh) | 2013-03-20 |
CN104788311B (zh) | 2016-10-19 |
CN104761450B (zh) | 2016-08-24 |
CN102976939B (zh) | 2015-03-25 |
CN104788311A (zh) | 2015-07-22 |
CN104761450A (zh) | 2015-07-08 |
CN104761451A (zh) | 2015-07-08 |
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Effective date of registration: 20190619 Address after: 272211 New Material Industrial Park, Huji Town, Jinxiang County, Jining City, Shandong Province Patentee after: Shandong Songsheng New Materials Co.,Ltd. Address before: 213181 No. 28 Yinshan Road, Xixia Shu Industrial Park, Xinbei District, Changzhou City, Jiangsu Province Patentee before: CHANGZHOU SONGSHENG PERFUMERY Co.,Ltd. |
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Effective date of registration: 20200929 Address after: 213181, No. 28, silver mountain road, Xixia villa Industrial Park, Xinbei District, Jiangsu, Changzhou Patentee after: CHANGZHOU SONGSHENG PERFUMERY Co.,Ltd. Address before: 272211 New Material Industrial Park, Huji Town, Jinxiang County, Jining City, Shandong Province Patentee before: Shandong Songsheng New Materials Co.,Ltd. |
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Effective date of registration: 20201028 Address after: Room 301, unit B, building 24, century Pearl Garden, Zhonglou District, Changzhou City, Jiangsu Province Patentee after: Xu Songhao Address before: 213181, No. 28, silver mountain road, Xixia villa Industrial Park, Xinbei District, Jiangsu, Changzhou Patentee before: CHANGZHOU SONGSHENG PERFUMERY Co.,Ltd. |
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Effective date of registration: 20201216 Address after: 272211 New Material Industrial Park, Huji Town, Jinxiang County, Jining City, Shandong Province Patentee after: Shandong Songsheng New Materials Co.,Ltd. Address before: 213001 Room 301, unit B, building 24, century Pearl Garden, Zhonglou District, Changzhou City, Jiangsu Province Patentee before: Xu Songhao |
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Denomination of invention: Preparation method of methyl propionate Effective date of registration: 20231208 Granted publication date: 20160817 Pledgee: Industrial and Commercial Bank of China Limited Jinxiang sub branch Pledgor: Shandong Songsheng New Materials Co.,Ltd. Registration number: Y2023980070251 |
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