CN106608891A - 一种含取代基的邻羟基苯甲酸铬的制备方法 - Google Patents
一种含取代基的邻羟基苯甲酸铬的制备方法 Download PDFInfo
- Publication number
- CN106608891A CN106608891A CN201611129017.2A CN201611129017A CN106608891A CN 106608891 A CN106608891 A CN 106608891A CN 201611129017 A CN201611129017 A CN 201611129017A CN 106608891 A CN106608891 A CN 106608891A
- Authority
- CN
- China
- Prior art keywords
- chromium
- substituent group
- oxybenzoic acid
- containing substituent
- preparation
- 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
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- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- XGRZWVWRMKAQNU-UHFFFAOYSA-K 2-carboxyphenolate;chromium(3+) Chemical compound [Cr+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O XGRZWVWRMKAQNU-UHFFFAOYSA-K 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 229910001430 chromium ion Inorganic materials 0.000 claims abstract description 28
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 75
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 63
- 239000012046 mixed solvent Substances 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 239000000047 product Substances 0.000 claims description 52
- 239000011651 chromium Substances 0.000 claims description 49
- 229910052804 chromium Inorganic materials 0.000 claims description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 42
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 238000012545 processing Methods 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- 239000012467 final product Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229940055042 chromic sulfate Drugs 0.000 claims description 18
- 229910000356 chromium(III) sulfate Inorganic materials 0.000 claims description 18
- 239000011696 chromium(III) sulphate Substances 0.000 claims description 18
- 235000015217 chromium(III) sulphate Nutrition 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- PYXSPTLIBJZHQW-UHFFFAOYSA-K chromium(3+);propanoate Chemical compound [Cr+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O PYXSPTLIBJZHQW-UHFFFAOYSA-K 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 14
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 5
- 239000003495 polar organic solvent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 5
- 238000005406 washing Methods 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 4
- 150000001844 chromium Chemical class 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 235000012721 chromium Nutrition 0.000 description 41
- 239000000706 filtrate Substances 0.000 description 40
- 238000012360 testing method Methods 0.000 description 25
- 238000001514 detection method Methods 0.000 description 20
- 238000001914 filtration Methods 0.000 description 18
- 238000005070 sampling Methods 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000004675 formic acid derivatives Chemical class 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 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 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- 235000007831 chromium(III) chloride Nutrition 0.000 description 3
- AHXGRMIPHCAXFP-UHFFFAOYSA-L chromyl dichloride Chemical class Cl[Cr](Cl)(=O)=O AHXGRMIPHCAXFP-UHFFFAOYSA-L 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical group OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- MJYOVTMTZXJGNG-UHFFFAOYSA-N 2-butylperoxybenzoic acid Chemical compound CCCCOOC1=CC=CC=C1C(O)=O MJYOVTMTZXJGNG-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- -1 3- nitro -5- butoxy oxybenzoic acids Chemical class 0.000 description 1
- IAQNJTPPIHLAJV-UHFFFAOYSA-N 3-butan-2-yloxybenzoic acid Chemical class CCC(C)OC1=CC=CC(C(O)=O)=C1 IAQNJTPPIHLAJV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- LXMQZGGLHVSEBA-UHFFFAOYSA-N chromium;trihydrate Chemical compound O.O.O.[Cr] LXMQZGGLHVSEBA-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Treatment Of Metals (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
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CN201611129017.2A CN106608891B (zh) | 2016-12-09 | 2016-12-09 | 一种含取代基的邻羟基苯甲酸铬的制备方法 |
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CN201611129017.2A CN106608891B (zh) | 2016-12-09 | 2016-12-09 | 一种含取代基的邻羟基苯甲酸铬的制备方法 |
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CN106608891A true CN106608891A (zh) | 2017-05-03 |
CN106608891B CN106608891B (zh) | 2018-09-21 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0941983A1 (en) * | 1998-03-13 | 1999-09-15 | Toyo Ink Manufacturing Co., Ltd. | Toner for developing electrostatic latent image, charge control agent for use in the toner, and process for preparing the charge control agent |
JP2003202707A (ja) * | 2002-01-07 | 2003-07-18 | Toyo Ink Mfg Co Ltd | 静電荷像現像用トナー |
CN103387493A (zh) * | 2013-07-05 | 2013-11-13 | 天津市化学试剂研究所 | 一种水杨酸铬的制备方法 |
CN103694362A (zh) * | 2013-12-19 | 2014-04-02 | 青岛农业大学 | 超声波辅助复合氧化剂合成氧化玉米淀粉的方法及合成物 |
CN104030918A (zh) * | 2014-06-20 | 2014-09-10 | 天津市合成材料工业研究所有限公司 | 金属络合-(3,5-二叔丁基水杨酸)的制备方法 |
CN105694524A (zh) * | 2016-01-28 | 2016-06-22 | 江苏盛吉化工有限公司 | 一种酸性黑172的制备方法 |
-
2016
- 2016-12-09 CN CN201611129017.2A patent/CN106608891B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0941983A1 (en) * | 1998-03-13 | 1999-09-15 | Toyo Ink Manufacturing Co., Ltd. | Toner for developing electrostatic latent image, charge control agent for use in the toner, and process for preparing the charge control agent |
JP2003202707A (ja) * | 2002-01-07 | 2003-07-18 | Toyo Ink Mfg Co Ltd | 静電荷像現像用トナー |
CN103387493A (zh) * | 2013-07-05 | 2013-11-13 | 天津市化学试剂研究所 | 一种水杨酸铬的制备方法 |
CN103694362A (zh) * | 2013-12-19 | 2014-04-02 | 青岛农业大学 | 超声波辅助复合氧化剂合成氧化玉米淀粉的方法及合成物 |
CN104030918A (zh) * | 2014-06-20 | 2014-09-10 | 天津市合成材料工业研究所有限公司 | 金属络合-(3,5-二叔丁基水杨酸)的制备方法 |
CN105694524A (zh) * | 2016-01-28 | 2016-06-22 | 江苏盛吉化工有限公司 | 一种酸性黑172的制备方法 |
Non-Patent Citations (2)
Title |
---|
MADIHA H. SOLIMAN ET AL.: "Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) new complexes of 5-aminosalicylic acid: Spectroscopic, thermal characterization and biological activity studies", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND》 * |
刘春生: "CI酸性棕28的合成研究", 《染料与染色》 * |
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Address after: 530001 No.7, beierli, Wangzhou Road, XiXiangTang District, Nanning City, Guangxi Zhuang Autonomous Region Patentee after: GUANGXI RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Address before: 530001 No.7, beierli, Wangzhou Road, XiXiangTang District, Nanning City, Guangxi Zhuang Autonomous Region Patentee before: Guangxi Research Institute of Chemical Industry |
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