CN1644578A - Ab型聚对苯撑苯并二噁唑新单体及其制备与应用 - Google Patents
Ab型聚对苯撑苯并二噁唑新单体及其制备与应用 Download PDFInfo
- Publication number
- CN1644578A CN1644578A CN 200410093359 CN200410093359A CN1644578A CN 1644578 A CN1644578 A CN 1644578A CN 200410093359 CN200410093359 CN 200410093359 CN 200410093359 A CN200410093359 A CN 200410093359A CN 1644578 A CN1644578 A CN 1644578A
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- Prior art keywords
- benzoxazole
- nitro
- methoxycarbonyl phenyl
- amide
- hydroxy
- Prior art date
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- 239000000178 monomer Substances 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 31
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000007670 refining Methods 0.000 claims abstract description 17
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- -1 polyparaphenylene Polymers 0.000 claims description 67
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 54
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 44
- VXFGTUHRHMFGMQ-UHFFFAOYSA-N 4-amino-6-nitrobenzene-1,3-diol;hydrochloride Chemical compound Cl.NC1=CC([N+]([O-])=O)=C(O)C=C1O VXFGTUHRHMFGMQ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 20
- 239000012043 crude product Substances 0.000 claims description 19
- 239000002994 raw material Substances 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- GNBWUEAMCSHHMO-UHFFFAOYSA-N methyl 2-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(Cl)=O GNBWUEAMCSHHMO-UHFFFAOYSA-N 0.000 claims description 14
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000006068 polycondensation reaction Methods 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 208000005156 Dehydration Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 150000002916 oxazoles Chemical class 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 6
- SENSPHQXKYKAHQ-UHFFFAOYSA-N 4-amino-6-nitro-1,3-benzenediol Chemical compound NC1=CC([N+]([O-])=O)=C(O)C=C1O SENSPHQXKYKAHQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000003610 charcoal Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- BJJVGZDKLGAJCZ-UHFFFAOYSA-N 1,4-dioxane;2-(2-hydroxyethoxy)ethanol Chemical compound C1COCCO1.OCCOCCO BJJVGZDKLGAJCZ-UHFFFAOYSA-N 0.000 claims description 2
- MBXIRNHACKAGPA-UHFFFAOYSA-N 4,6-dinitroresorcinol Chemical compound OC1=CC(O)=C([N+]([O-])=O)C=C1[N+]([O-])=O MBXIRNHACKAGPA-UHFFFAOYSA-N 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- 238000007738 vacuum evaporation Methods 0.000 claims description 2
- RVGQBABONQZPBI-UHFFFAOYSA-N methyl 2-phenyl-1,3-benzoxazole-4-carboxylate Chemical compound N=1C=2C(C(=O)OC)=CC=CC=2OC=1C1=CC=CC=C1 RVGQBABONQZPBI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000010792 warming Methods 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 229960001755 resorcinol Drugs 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000013016 damping Methods 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 229940095102 methyl benzoate Drugs 0.000 description 4
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 150000003504 terephthalic acids Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HYMVXXQIUSYBLL-UHFFFAOYSA-N methyl 4-(5-amino-6-hydroxy-1,3-benzoxazol-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=CC(N)=C(O)C=C2O1 HYMVXXQIUSYBLL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SPIFDSWFDKNERT-UHFFFAOYSA-N nickel;hydrate Chemical compound O.[Ni] SPIFDSWFDKNERT-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | ANR·HCl/g(纯度%) | MBC/g(MBC/ANR摩尔比) | 溶剂名称/用量(ml) | PPA/ANR·HCl质量比 | 温度/时间℃/h) | 产量(g) | 收率(%) | 纯度(%) |
2 | ANR/1.00(92.52) | 1.17(1.08) | 二乙二醇二甲醚/30 | 与ANR比3.65 | 120 /2160 /4 | 0.87 | 47.10(精) | 95.22(精) |
3 | 15.02(93.27) | 13.47(1.0) | 乙二醇甲醚乙酸酯/100 | 2.46 | 120 /2145 /5 | 14.05 | 61.49 | 88.56 |
4 | 13.53(93.50) | 12.16(1.0) | 乙二醇甲醚乙酸酯/125 | 2.80 | 120 /2145 /5 | 15.45 | 75.06 | 89.12 |
5 | 10.33(93.96) | 9.33(1.0) | 二乙二醇二甲醚/100 | 1.81 | 120 /2160 /4 | 11.09 | 70.60 | 90.02 |
6 | 15.32(93.27) | 13.74(1.0) | 二乙二醇二甲醚/125 | 3.12 | 120 /2150 /4 | 19.91 | 85.44 | 87.32 |
7 | 3.10(93.96) | 2.98(1.06) | 二乙二醇二甲醚/55 | 1.94 | 120 /2150 /4 | 1.53 | 32.44 | 90.80 |
8 | 10.00(93.96) | 9.61(1.06) | 二乙二醇二甲醚/80 | 2.23 | 120 /2150 /4 | 9.85 | 64.75 | 89.63 |
实施例 | 粗品纯度(%) | 精制溶剂及用量(ml) | C用量(%) | 纯度(%) | 收率(%) | 产品颜色 |
9 | 88.56 | 二氧六环10ml/1g粗品 | 10.0 | 96.91 | 54.96 | 亮黄色粉末 |
10 | 90.05 | 乙酸20ml/1g粗品 | 4.0 | 96.82 | 61.20 | 淡黄色结晶 |
11 | 87.32 | 乙酸16ml/1g粗品 | 4.0 | 96.98 | 61.69 | 淡黄色结晶 |
12 | 89.63 | 乙酸14ml/1g粗品 | 10.0 | 97.20 | 51.12 | 亮黄色结晶 |
13 | 89.96 | DMF16ml/1g粗品 | 10.0 | 92.13 | 80.21 | 棕色粉末 |
实施例 | NHAB(g) | 纯度(%) | 催化剂(%) | H2(MPa) | 温度(℃) | 时间(h) | 收率(%) | 纯度(%) | 备注 |
15 | 5.00 | 97.20 | 10%Pd/C | 0.3 | 60 | 7 | 93.84 | 95.36 | 有废气生成 |
16 | 10.0 | 89.12 | 10%Pd/C | 0.3 | 35 | 2 | 51.96 | 92.76 | 粗品为原料 |
17 | 4.03 | 95.70 | 5%Pd/Al2O3 | 0.3 | 60 | 2 | 84.01 | 94.64 | 吸H2 15min |
18 | 5.00 | 96.58 | 5%Pd/Al2O3 | 0.3 | 50 | 1.5 | 81.19 | 96.42 | 有废气生成 |
19 | 8.50 | 49.57 | 5%Pd/Al2O3 | 0.3 | 65 | 1 | 25.59 | 91.68 | 有废气生成 |
对比例 | NHAB/g(纯度%) | 还原剂/用量g | 催化剂(%) | 溶剂 | 温度(℃) | 时间(h) | 收率(%) | 纯度(%) | 备注 |
1 | 1.40(96.58) | SnCl22H2O/2.76 | 盐酸 | 60 | 7 | 38.10 | 88.84 | 较差 | |
2 | 1.00(95.70) | 水合肼/1.98 | RaneyNi | 水 | 60 | 2 | 19.64 | 82.59 | 无效 |
3 | 1.00(95.70) | 水合肼/1.00 | Fe2+/C | 乙醇 | 78 | 1.5 | 33.51 | 86.17 | 基本无效 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 200410093359 CN1275950C (zh) | 2004-12-18 | 2004-12-18 | Ab型聚对苯撑苯并二噁唑单体及其制备与应用 |
Applications Claiming Priority (1)
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CN 200410093359 CN1275950C (zh) | 2004-12-18 | 2004-12-18 | Ab型聚对苯撑苯并二噁唑单体及其制备与应用 |
Publications (2)
Publication Number | Publication Date |
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CN1644578A true CN1644578A (zh) | 2005-07-27 |
CN1275950C CN1275950C (zh) | 2006-09-20 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101914204A (zh) * | 2010-06-17 | 2010-12-15 | 大连理工大学 | 基于含二氮杂萘酮联苯结构二羟基二胺的聚苯并噁唑及其制备方法 |
CN102977045A (zh) * | 2012-11-28 | 2013-03-20 | 浙江工业大学 | 4-(5-氨基-6-羟基苯并噁唑-2-基)苯甲酸铵及其制备与应用 |
CN103204805A (zh) * | 2012-12-21 | 2013-07-17 | 浙江工业大学 | Ab型pbz单体的关键中间体及其制备方法 |
CN103881092A (zh) * | 2014-04-17 | 2014-06-25 | 哈尔滨工业大学 | 以2-(对甲酰氯基苯基)-5-氨基-6-羟基苯并噁唑为原料制备pbo聚合物的方法 |
CN109912422A (zh) * | 2019-03-29 | 2019-06-21 | 山东润博生物科技有限公司 | 一种4,6-二硝基间苯二酚的制备方法 |
CN110256221A (zh) * | 2019-05-13 | 2019-09-20 | 宜昌苏鹏科技有限公司 | 一种2-烷基蒽醌的合成方法 |
-
2004
- 2004-12-18 CN CN 200410093359 patent/CN1275950C/zh not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101914204A (zh) * | 2010-06-17 | 2010-12-15 | 大连理工大学 | 基于含二氮杂萘酮联苯结构二羟基二胺的聚苯并噁唑及其制备方法 |
CN101914204B (zh) * | 2010-06-17 | 2012-09-12 | 大连理工大学 | 基于含二氮杂萘酮联苯结构二羟基二胺的聚苯并噁唑及其制备方法 |
CN102977045A (zh) * | 2012-11-28 | 2013-03-20 | 浙江工业大学 | 4-(5-氨基-6-羟基苯并噁唑-2-基)苯甲酸铵及其制备与应用 |
CN103204805A (zh) * | 2012-12-21 | 2013-07-17 | 浙江工业大学 | Ab型pbz单体的关键中间体及其制备方法 |
CN103881092A (zh) * | 2014-04-17 | 2014-06-25 | 哈尔滨工业大学 | 以2-(对甲酰氯基苯基)-5-氨基-6-羟基苯并噁唑为原料制备pbo聚合物的方法 |
CN103881092B (zh) * | 2014-04-17 | 2016-08-24 | 哈尔滨工业大学 | 以2-(对甲酰氯基苯基)-5-氨基-6-羟基苯并噁唑为原料制备pbo聚合物的方法 |
CN109912422A (zh) * | 2019-03-29 | 2019-06-21 | 山东润博生物科技有限公司 | 一种4,6-二硝基间苯二酚的制备方法 |
CN110256221A (zh) * | 2019-05-13 | 2019-09-20 | 宜昌苏鹏科技有限公司 | 一种2-烷基蒽醌的合成方法 |
CN110256221B (zh) * | 2019-05-13 | 2022-04-29 | 宜昌苏鹏科技有限公司 | 一种2-烷基蒽醌的合成方法 |
Also Published As
Publication number | Publication date |
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CN1275950C (zh) | 2006-09-20 |
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