CN102408329A - 2,4-二羟基苯甲酸的制备方法 - Google Patents
2,4-二羟基苯甲酸的制备方法 Download PDFInfo
- Publication number
- CN102408329A CN102408329A CN201110312780XA CN201110312780A CN102408329A CN 102408329 A CN102408329 A CN 102408329A CN 201110312780X A CN201110312780X A CN 201110312780XA CN 201110312780 A CN201110312780 A CN 201110312780A CN 102408329 A CN102408329 A CN 102408329A
- Authority
- CN
- China
- Prior art keywords
- resorcinol
- alcohol
- preparation
- sodium
- solution
- 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 17
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 title abstract description 11
- 229940114055 beta-resorcylic acid Drugs 0.000 title abstract 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 33
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 14
- 239000011734 sodium Substances 0.000 claims abstract description 13
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 13
- KAVGXOKHWPNOAL-UHFFFAOYSA-N benzene-1,3-diol;sodium Chemical compound [Na].OC1=CC=CC(O)=C1 KAVGXOKHWPNOAL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 10
- 238000011084 recovery Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 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 claims abstract description 5
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 235000011089 carbon dioxide Nutrition 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- -1 sodium alkoxide Chemical class 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000002440 industrial waste Substances 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 11
- 229960001755 resorcinol Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | S | R1 | m1,g | m2,g | T,℃ | P.MPa | t,h | Y,% | P,% |
2 | 乙醇 | 乙醇钠 | 10.2 | 15 | 80 | 10 | 4 | 82.4 | 98 |
3 | 丙醇 | 丙醇钠 | 13 | 12 | 50 | 8.5 | 3 | 78.3 | 98 |
4 | 丁醇 | 丁醇钠 | 15 | 17 | 100 | 15 | 5 | 87.1 | 97 |
5 | 乙醇 | 乙醇钠 | 9 | 16 | 80 | 10 | 4 | 83.5 | 97 |
6 | 丙醇 | 丙醇钠 | 12 | 14 | 60 | 8.5 | 3 | 80.2 | 98 |
7 | 丁醇 | 丁醇钠 | 14 | 18 | 100 | 15 | 5 | 87.9 | 97 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110312780.XA CN102408329B (zh) | 2011-10-17 | 2011-10-17 | 2,4-二羟基苯甲酸的制备方法 |
Applications Claiming Priority (1)
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---|---|---|---|
CN201110312780.XA CN102408329B (zh) | 2011-10-17 | 2011-10-17 | 2,4-二羟基苯甲酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102408329A true CN102408329A (zh) | 2012-04-11 |
CN102408329B CN102408329B (zh) | 2014-04-23 |
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CN201110312780.XA Active CN102408329B (zh) | 2011-10-17 | 2011-10-17 | 2,4-二羟基苯甲酸的制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN102408329B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109096086A (zh) * | 2018-09-28 | 2018-12-28 | 石家庄绿田科技有限公司 | 一种2,6-二羟基苯甲酸的制备方法 |
CN114437338A (zh) * | 2022-01-24 | 2022-05-06 | 吉林省聚科高新材料有限公司 | 一种聚醚醚酮的合成方法 |
CN115322108A (zh) * | 2022-08-05 | 2022-11-11 | 河南大学 | 胆碱2, 6-二羟基苯甲酸离子液体、合成方法及作为镁空气电池电解液添加剂的应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1442518A1 (ru) * | 1986-12-29 | 1988-12-07 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Способ получени метилового эфира 3,6-диметил-2,4-дигидроксибензойной кислоты |
US4996354A (en) * | 1988-09-21 | 1991-02-26 | Basf Aktiengesellschaft | Preparation of 2,4-dihydroxybenzoic acid |
EP0436379A2 (en) * | 1989-12-27 | 1991-07-10 | Kolon Industries Inc. | A process for preparation of an aromatic carboxylic acid |
KR930002964B1 (ko) * | 1990-10-20 | 1993-04-16 | 주식회사 코오롱 | 살리실산 유도체의 제조방법 |
CN1394843A (zh) * | 2002-03-15 | 2003-02-05 | 中国科学院上海有机化学研究所 | 同时生产2,4-二羟基苯甲酸和2,6-二羟基苯甲酸的无溶剂合成新工艺 |
CN102211995A (zh) * | 2011-05-09 | 2011-10-12 | 杭州方迪科技有限公司 | 一种2,6-二羟基苯甲酸的制备方法 |
-
2011
- 2011-10-17 CN CN201110312780.XA patent/CN102408329B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1442518A1 (ru) * | 1986-12-29 | 1988-12-07 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Способ получени метилового эфира 3,6-диметил-2,4-дигидроксибензойной кислоты |
US4996354A (en) * | 1988-09-21 | 1991-02-26 | Basf Aktiengesellschaft | Preparation of 2,4-dihydroxybenzoic acid |
EP0436379A2 (en) * | 1989-12-27 | 1991-07-10 | Kolon Industries Inc. | A process for preparation of an aromatic carboxylic acid |
KR930002964B1 (ko) * | 1990-10-20 | 1993-04-16 | 주식회사 코오롱 | 살리실산 유도체의 제조방법 |
CN1394843A (zh) * | 2002-03-15 | 2003-02-05 | 中国科学院上海有机化学研究所 | 同时生产2,4-二羟基苯甲酸和2,6-二羟基苯甲酸的无溶剂合成新工艺 |
CN102211995A (zh) * | 2011-05-09 | 2011-10-12 | 杭州方迪科技有限公司 | 一种2,6-二羟基苯甲酸的制备方法 |
Non-Patent Citations (2)
Title |
---|
《Organic Syntheses》 19431231 M.Nierenstein beta-resorcylic acid 第557页 1-6 第2卷, * |
M.NIERENSTEIN: "β-resorcylic acid", 《ORGANIC SYNTHESES》, vol. 2, 31 December 1943 (1943-12-31), pages 557 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109096086A (zh) * | 2018-09-28 | 2018-12-28 | 石家庄绿田科技有限公司 | 一种2,6-二羟基苯甲酸的制备方法 |
CN114437338A (zh) * | 2022-01-24 | 2022-05-06 | 吉林省聚科高新材料有限公司 | 一种聚醚醚酮的合成方法 |
CN115322108A (zh) * | 2022-08-05 | 2022-11-11 | 河南大学 | 胆碱2, 6-二羟基苯甲酸离子液体、合成方法及作为镁空气电池电解液添加剂的应用 |
CN115322108B (zh) * | 2022-08-05 | 2023-05-12 | 河南大学 | 胆碱2, 6-二羟基苯甲酸离子液体、合成方法及作为镁空气电池电解液添加剂的应用 |
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Publication number | Publication date |
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CN102408329B (zh) | 2014-04-23 |
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Effective date of registration: 20160223 Address after: 200436 322, 1363, 1345, 323, Hu Tai Road, Shanghai, Zhabei District Patentee after: SHANGHAI HONGYUAN XINCHUANG MATERIAL TECHNOLOGY CO., LTD. Patentee after: Zhejiang Hongsheng Chemical Research Limited Patentee after: Zhejiang Longsheng Chemicals Co., Ltd. Address before: 201206 31F01-3102 new Jinqiao Building, room 28, new Jinqiao Road, Shanghai, Pudong New Area Patentee before: Shanghai Annuo Aromatic Amine Chemical Co., Ltd. Patentee before: Zhejiang Hongsheng Chemical Research Limited Patentee before: Zhejiang Amino-Chem Co., Ltd. Patentee before: Zhejiang Longsheng Group Co., Ltd. |