CN105152906A - 一种联产3,5-二甲基苯甲酸和均苯三甲酸的方法 - Google Patents
一种联产3,5-二甲基苯甲酸和均苯三甲酸的方法 Download PDFInfo
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- CN105152906A CN105152906A CN201510632424.4A CN201510632424A CN105152906A CN 105152906 A CN105152906 A CN 105152906A CN 201510632424 A CN201510632424 A CN 201510632424A CN 105152906 A CN105152906 A CN 105152906A
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- Prior art keywords
- acid
- oxidation reactor
- reaction
- general formula
- trimethylbenzene
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 title claims abstract description 124
- 238000000034 method Methods 0.000 title claims abstract description 67
- UMVOQQDNEYOJOK-UHFFFAOYSA-N 3,5-dimethylbenzoic acid Chemical compound CC1=CC(C)=CC(C(O)=O)=C1 UMVOQQDNEYOJOK-UHFFFAOYSA-N 0.000 title abstract 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims abstract description 90
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 162
- 230000003647 oxidation Effects 0.000 claims description 149
- 238000006243 chemical reaction Methods 0.000 claims description 98
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 66
- 239000000047 product Substances 0.000 claims description 62
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 36
- 239000000706 filtrate Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- -1 transition metal salt Chemical class 0.000 claims description 18
- WIAPFNDQWLOVKC-UHFFFAOYSA-N 1,3,5-trimethylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)(C(O)=O)C1 WIAPFNDQWLOVKC-UHFFFAOYSA-N 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 16
- 239000007791 liquid phase Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000012065 filter cake Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000003039 volatile agent Substances 0.000 claims description 11
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 239000012265 solid product Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 229910052748 manganese Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 5
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 5
- 241001330002 Bambuseae Species 0.000 claims description 5
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 5
- 239000011425 bamboo Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- MKACMVMZUIQKNY-UHFFFAOYSA-N 2-hydroxy-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(=O)C2=C1 MKACMVMZUIQKNY-UHFFFAOYSA-N 0.000 claims description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 5
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 description 28
- 230000009466 transformation Effects 0.000 description 28
- 239000011572 manganese Substances 0.000 description 22
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- NBEFMISJJNGCIZ-UHFFFAOYSA-N 3,5-dimethylbenzaldehyde Chemical class CC1=CC(C)=CC(C=O)=C1 NBEFMISJJNGCIZ-UHFFFAOYSA-N 0.000 description 7
- 239000013067 intermediate product Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IQWWTJDRVBWBEL-UHFFFAOYSA-N (3,5-dimethylphenyl)methanol Chemical compound CC1=CC(C)=CC(CO)=C1 IQWWTJDRVBWBEL-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000001223 reverse osmosis Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 description 2
- 238000002288 cocrystallisation Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 239000002893 slag Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl 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
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201510632424.4A CN105152906B (zh) | 2015-09-29 | 2015-09-29 | 一种联产3,5‑二甲基苯甲酸和均苯三甲酸的方法 |
Applications Claiming Priority (1)
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CN201510632424.4A CN105152906B (zh) | 2015-09-29 | 2015-09-29 | 一种联产3,5‑二甲基苯甲酸和均苯三甲酸的方法 |
Publications (2)
Publication Number | Publication Date |
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CN105152906A true CN105152906A (zh) | 2015-12-16 |
CN105152906B CN105152906B (zh) | 2017-07-28 |
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Family Applications (1)
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CN201510632424.4A Active CN105152906B (zh) | 2015-09-29 | 2015-09-29 | 一种联产3,5‑二甲基苯甲酸和均苯三甲酸的方法 |
Country Status (1)
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CN (1) | CN105152906B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107540520A (zh) * | 2016-06-29 | 2018-01-05 | 中国科学院大连化学物理研究所 | 一种由频那醇制备均苯四甲酸或偏苯三甲酸的方法 |
CN113318471A (zh) * | 2021-07-08 | 2021-08-31 | 山东友道化学有限公司 | 二甲苯氧化反应液的处理方法及系统 |
Citations (7)
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CN1333200A (zh) * | 2001-07-18 | 2002-01-30 | 湖南大学 | 选择性氧化二甲苯成甲基苯甲醛、甲基苯甲醇和甲基苯甲酸的方法 |
CN1572766A (zh) * | 2003-06-20 | 2005-02-02 | 三菱瓦斯化学株式会社 | 高纯度芳香族多羧酸的制造方法 |
JP2005534687A (ja) * | 2002-07-30 | 2005-11-17 | エスケー ケミカルズ カンパニー リミテッド | トリメリット酸の製造方法 |
CN101362687A (zh) * | 2008-10-08 | 2009-02-11 | 湖南大学 | 空气氧化对二甲苯制备对苯二甲酸的方法和设备 |
CN102146029A (zh) * | 2010-02-04 | 2011-08-10 | 中国石油化工股份有限公司 | 一种均三甲苯连续氧化制备均苯三甲酸的方法 |
CN102336658A (zh) * | 2011-07-29 | 2012-02-01 | 安徽泰达新材料股份有限公司 | 一种3,5-二甲基苯甲酸的生产方法 |
CN102924266A (zh) * | 2012-10-26 | 2013-02-13 | 中国石油化工股份有限公司 | 由混合二甲苯共氧化的催化剂体系制备苯二甲酸的方法 |
-
2015
- 2015-09-29 CN CN201510632424.4A patent/CN105152906B/zh active Active
Patent Citations (7)
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CN1333200A (zh) * | 2001-07-18 | 2002-01-30 | 湖南大学 | 选择性氧化二甲苯成甲基苯甲醛、甲基苯甲醇和甲基苯甲酸的方法 |
JP2005534687A (ja) * | 2002-07-30 | 2005-11-17 | エスケー ケミカルズ カンパニー リミテッド | トリメリット酸の製造方法 |
CN1572766A (zh) * | 2003-06-20 | 2005-02-02 | 三菱瓦斯化学株式会社 | 高纯度芳香族多羧酸的制造方法 |
CN101362687A (zh) * | 2008-10-08 | 2009-02-11 | 湖南大学 | 空气氧化对二甲苯制备对苯二甲酸的方法和设备 |
CN102146029A (zh) * | 2010-02-04 | 2011-08-10 | 中国石油化工股份有限公司 | 一种均三甲苯连续氧化制备均苯三甲酸的方法 |
CN102336658A (zh) * | 2011-07-29 | 2012-02-01 | 安徽泰达新材料股份有限公司 | 一种3,5-二甲基苯甲酸的生产方法 |
CN102924266A (zh) * | 2012-10-26 | 2013-02-13 | 中国石油化工股份有限公司 | 由混合二甲苯共氧化的催化剂体系制备苯二甲酸的方法 |
Non-Patent Citations (1)
Title |
---|
NARUHISA HIRAI,ET AL.: "Aerobic oxidation of trimethylbenzenes catalyzed by N,Nˊ,N〞-trihydroxyisocyanuric acid (THICA) as a key catalyst", 《TETRAHEDRON》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107540520A (zh) * | 2016-06-29 | 2018-01-05 | 中国科学院大连化学物理研究所 | 一种由频那醇制备均苯四甲酸或偏苯三甲酸的方法 |
CN107540520B (zh) * | 2016-06-29 | 2020-04-07 | 中国科学院大连化学物理研究所 | 一种由频那醇制备均苯四甲酸或偏苯三甲酸的方法 |
CN113318471A (zh) * | 2021-07-08 | 2021-08-31 | 山东友道化学有限公司 | 二甲苯氧化反应液的处理方法及系统 |
CN113318471B (zh) * | 2021-07-08 | 2024-05-31 | 山东友道化学有限公司 | 二甲苯氧化反应液的处理方法及系统 |
Also Published As
Publication number | Publication date |
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CN105152906B (zh) | 2017-07-28 |
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