CN104387269A - 一种2,3,5-三甲基氢醌二烷酸酯的制备方法 - Google Patents
一种2,3,5-三甲基氢醌二烷酸酯的制备方法 Download PDFInfo
- Publication number
- CN104387269A CN104387269A CN201410625114.5A CN201410625114A CN104387269A CN 104387269 A CN104387269 A CN 104387269A CN 201410625114 A CN201410625114 A CN 201410625114A CN 104387269 A CN104387269 A CN 104387269A
- Authority
- CN
- China
- Prior art keywords
- auxiliary agent
- content
- magnetic
- solid acid
- acid 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- HSVDVWLWYPSVEF-UHFFFAOYSA-N carboxy hydrogen carbonate 2,3,5-trimethylbenzene-1,4-diol Chemical compound C(=O)(O)OC(=O)O.CC1=C(O)C=C(C(=C1C)O)C HSVDVWLWYPSVEF-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000011973 solid acid Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 238000006462 rearrangement reaction Methods 0.000 claims abstract description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 13
- 239000012065 filter cake Substances 0.000 claims description 12
- 229910052742 iron Inorganic materials 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- -1 carboxylic acid halides Chemical class 0.000 claims description 7
- 230000010355 oscillation Effects 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 238000003828 vacuum filtration Methods 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 229910000859 α-Fe Inorganic materials 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910000314 transition metal oxide Inorganic materials 0.000 claims description 3
- DHBIJBUUMSDQMR-UHFFFAOYSA-N 1,4-dioxane prop-2-enoic acid Chemical group O1CCOCC1.C(C=C)(=O)O DHBIJBUUMSDQMR-UHFFFAOYSA-N 0.000 claims description 2
- 229910017840 NH 3 Inorganic materials 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910001566 austenite Inorganic materials 0.000 claims description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- 150000004767 nitrides Chemical class 0.000 claims description 2
- 229910052755 nonmetal Inorganic materials 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 230000008569 process Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000005426 magnetic field effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000002572 peristaltic effect Effects 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- JXLWCZWBHZGUEE-UHFFFAOYSA-N (4-acetyloxy-2,3,5-trimethylphenyl) acetate Chemical compound CC(=O)OC1=CC(C)=C(OC(C)=O)C(C)=C1C JXLWCZWBHZGUEE-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- AYJXHIDNNLJQDT-UHFFFAOYSA-N 2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical compound CC1=CC(=O)CC(C)(C)C1=O AYJXHIDNNLJQDT-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- IWAOTYDFIQQFPL-UHFFFAOYSA-N acetic acid;2,3,5-trimethylbenzene-1,4-diol Chemical class CC(O)=O.CC(O)=O.CC1=CC(O)=C(C)C(C)=C1O IWAOTYDFIQQFPL-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004821 distillation Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000007885 magnetic separation Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000005408 paramagnetism Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410625114.5A CN104387269B (zh) | 2014-11-07 | 2014-11-07 | 一种2,3,5-三甲基氢醌二烷酸酯的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410625114.5A CN104387269B (zh) | 2014-11-07 | 2014-11-07 | 一种2,3,5-三甲基氢醌二烷酸酯的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104387269A true CN104387269A (zh) | 2015-03-04 |
CN104387269B CN104387269B (zh) | 2016-01-20 |
Family
ID=52605248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410625114.5A Active CN104387269B (zh) | 2014-11-07 | 2014-11-07 | 一种2,3,5-三甲基氢醌二烷酸酯的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104387269B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109705082A (zh) * | 2018-12-19 | 2019-05-03 | 万华化学集团股份有限公司 | 一种制备维生素e乙酸酯的方法 |
CN109970553A (zh) * | 2019-04-03 | 2019-07-05 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
CN111675612A (zh) * | 2020-06-16 | 2020-09-18 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1186065A (zh) * | 1996-12-27 | 1998-07-01 | 大赛璐化学工业株式会社 | 制备三甲基对苯二酚双酯的方法 |
JPH1149710A (ja) * | 1997-08-01 | 1999-02-23 | Nippon Petrochem Co Ltd | トリメチルハイドロキノン類の製造法 |
JPH11255707A (ja) * | 1998-03-10 | 1999-09-21 | Nippon Petrochem Co Ltd | トリメチルハイドロキノン類の製造法 |
-
2014
- 2014-11-07 CN CN201410625114.5A patent/CN104387269B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1186065A (zh) * | 1996-12-27 | 1998-07-01 | 大赛璐化学工业株式会社 | 制备三甲基对苯二酚双酯的方法 |
JPH1149710A (ja) * | 1997-08-01 | 1999-02-23 | Nippon Petrochem Co Ltd | トリメチルハイドロキノン類の製造法 |
JPH11255707A (ja) * | 1998-03-10 | 1999-09-21 | Nippon Petrochem Co Ltd | トリメチルハイドロキノン類の製造法 |
Non-Patent Citations (1)
Title |
---|
李适等: "磁性固体酸的设计制备及其催化应用", 《化学进展》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109705082A (zh) * | 2018-12-19 | 2019-05-03 | 万华化学集团股份有限公司 | 一种制备维生素e乙酸酯的方法 |
CN109705082B (zh) * | 2018-12-19 | 2021-04-20 | 万华化学集团股份有限公司 | 一种制备维生素e乙酸酯的方法 |
CN109970553A (zh) * | 2019-04-03 | 2019-07-05 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
CN109970553B (zh) * | 2019-04-03 | 2021-09-03 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
CN111675612A (zh) * | 2020-06-16 | 2020-09-18 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
CN111675612B (zh) * | 2020-06-16 | 2023-03-03 | 万华化学集团股份有限公司 | 一种制备2,3,5-三甲基氢醌二酯的方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104387269B (zh) | 2016-01-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104387269B (zh) | 一种2,3,5-三甲基氢醌二烷酸酯的制备方法 | |
EP3805196B1 (en) | Preparation method for high optical indoxacarb intermediate | |
Ghodke et al. | Solvent free synthesis of coumarins using environment friendly solid acid catalysts | |
CN108047042A (zh) | 一种使用超重力技术合成2,3,5-三甲基氢醌二酯的方法 | |
CN102631930A (zh) | 一种糠醛气相加氢制糠醇的催化剂及其制备方法 | |
CN104910035A (zh) | 一种以负载固体碱催化合成羟烷基酰胺的方法 | |
Osiglio et al. | Alcohol acetylation with acetic acid using borated zirconia as catalyst | |
Hajipour et al. | Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions | |
Ghayem et al. | ZnFe2O4@ Fe3O4 nanocatalyst for the synthesis of the 1, 8-dioxooctahydroxanthene: antioxidant and antimicrobial studies | |
CN110152647A (zh) | 一种催化剂及其制备方法和应用 | |
Ghasemi et al. | The synergistic effect of copper chromite spinel nanoparticles (CuCr 2 O 4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids | |
CN110152648A (zh) | 锡催化剂的制备方法、锡催化剂及其应用 | |
CN111054384A (zh) | 有机液体储氢材料脱氢的催化剂及其制备方法 | |
CN102091637A (zh) | 一种用于合成香兰素的多相催化剂及其制备方法 | |
CN106140235B (zh) | 一种负载型正丁烷氧化制顺酐催化剂及其制备方法 | |
CN106492862B (zh) | 一种用于制备顺酐的催化剂及其制备方法 | |
Alavi et al. | Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions | |
CN114029072A (zh) | 一种固体超强酸催化剂及用其制备对甲氧基肉桂酸异辛酯的方法 | |
WO2007069656A1 (ja) | 重合性ヒドロキシジアマンチルエステル化合物の製造方法 | |
CN108929240B (zh) | 一种2-羟基-5-氨基苯甲酸的制备方法 | |
CN103613538B (zh) | 一种2,2,4-三甲基-1,2-二氢化喹啉聚合体的催化合成工艺 | |
Bodaghifard et al. | Inorganic-organic hybrid nanomaterial (Fe3O4@ SiO2-AQ): A retrievable heterogeneous catalyst for the green synthesis of 4H-chromenes | |
CN112574043A (zh) | 一种碱性红中间体3-乙基氨基对甲基苯酚的生产工艺 | |
CN102000613B (zh) | 一种铁系催化剂失活再生的方法 | |
CN109320415A (zh) | 一种zsm-5分子筛催化剂在制备硬脂酸甲酯中的应用 |
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 | ||
C56 | Change in the name or address of the patentee | ||
CP02 | Change in the address of a patent holder |
Address after: 264002 Yantai economic and Technological Development Zone, Shandong, Tian Shan Road, No. 17 Patentee after: Wanhua Chemical Group Co.,Ltd. Address before: 264002 Yantai City, Shandong province Zhifu District No. 7 Patentee before: Wanhua Chemical Group Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231218 Address after: 264006 No. 59, Chongqing Street, Yantai Economic and Technological Development Zone, Shandong Province Patentee after: Wanhua Chemical Group Nutrition Technology Co.,Ltd. Address before: 264002 17 Tianshan Road, Yantai economic and Technological Development Zone, Shandong Patentee before: Wanhua Chemical Group Co.,Ltd. |