CN103351282A - 一种4-氯-3,5-二甲基苯酚的制备方法 - Google Patents
一种4-氯-3,5-二甲基苯酚的制备方法 Download PDFInfo
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- CN103351282A CN103351282A CN201310286303XA CN201310286303A CN103351282A CN 103351282 A CN103351282 A CN 103351282A CN 201310286303X A CN201310286303X A CN 201310286303XA CN 201310286303 A CN201310286303 A CN 201310286303A CN 103351282 A CN103351282 A CN 103351282A
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- xylenol
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- 238000000034 method Methods 0.000 title abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 100
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 46
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 230000009466 transformation Effects 0.000 claims description 40
- 238000009835 boiling Methods 0.000 claims description 10
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 7
- 229960003280 cupric chloride Drugs 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 abstract description 13
- 238000007254 oxidation reaction Methods 0.000 abstract description 11
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000003049 inorganic solvent Substances 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 238000001514 detection method Methods 0.000 description 14
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 12
- 238000013019 agitation Methods 0.000 description 11
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 11
- 238000012544 monitoring process Methods 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 238000005070 sampling Methods 0.000 description 10
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000539 dimer Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000003206 sterilizing agent Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- UPLPHRJJTCUQAY-WIRWPRASSA-N 2,3-thioepoxy madol Chemical compound C([C@@H]1CC2)[C@@H]3S[C@@H]3C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 UPLPHRJJTCUQAY-WIRWPRASSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Abstract
Description
项目 | 反应时间 | MX% | OC% | DC% | PC% | 二聚物2(%) | 选择性 | 转化率 |
实施例1 | 12小时 | 15.34 | 2.2 | 0.2 | 81.55 | 0.1 | 96.44 | 84.56 |
实施例2 | 12小时 | 15.11 | 2.07 | 0.23 | 81.95 | 0.12 | 96.53 | 84.89 |
实施例3 | 12小时 | 15.31 | 2.01 | 0.3 | 81.56 | 0.1 | 96.3 | 84.69 |
实施例4 | 12小时 | 16.38 | 3.07 | 0.51 | 79.27 | 0.18 | 94.8 | 83.62 |
项目 | 时间 | MX% | OC% | DC% | PC% | 二聚物2% |
实施例5 | 15小时 | 10.11 | 3.2 | 1.01 | 81.23 | 3.21 |
实施例6 | 10小时 | 24.82 | 1.51 | 0.21 | 71.85 | 0 |
实施例7 | 5小时 | 49.65 | 1.03 | 0.12 | 47.73 | 0 |
项目 | 时间 | MX% | OC% | DC% | PC% | 二聚物2% |
实施例8 | 8小时 | 14.51 | 3.31 | 1.15 | 80.03 | 0.21 |
实施例9 | 20小时 | 14.02 | 3.05 | 1.09 | 80.35 | 0.74 |
Claims (7)
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104744221A (zh) * | 2015-04-13 | 2015-07-01 | 中国科学院青岛生物能源与过程研究所 | 一种对氯苯酚化合物的制备方法 |
CN105037104A (zh) * | 2015-06-02 | 2015-11-11 | 铜陵市恒兴化工有限责任公司 | 一种4-氯-3,5-二甲基苯酚的制备方法 |
CN111517922A (zh) * | 2020-04-28 | 2020-08-11 | 万华化学集团股份有限公司 | 一种制备4-氯-3,5-二甲基苯酚的方法 |
CN114805033A (zh) * | 2022-05-23 | 2022-07-29 | 陕西煤业化工技术研究院有限责任公司 | 一种氯代苯酚类化合物的合成方法 |
CN115433060A (zh) * | 2022-10-31 | 2022-12-06 | 青岛科技大学 | 一种单氯代苯酚化合物的制备方法 |
CN115583869A (zh) * | 2022-09-13 | 2023-01-10 | 安徽海华科技集团有限公司 | 一种酚类化合物选择性氧化氯化方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102199075A (zh) * | 2011-04-02 | 2011-09-28 | 湖南利洁生物化工有限公司 | 一种1-羟基-3,5-二甲基-4-氯苯的制备方法 |
-
2013
- 2013-07-09 CN CN201310286303.XA patent/CN103351282B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102199075A (zh) * | 2011-04-02 | 2011-09-28 | 湖南利洁生物化工有限公司 | 一种1-羟基-3,5-二甲基-4-氯苯的制备方法 |
Non-Patent Citations (2)
Title |
---|
张兵: "高沸点热敏物系中4-氯-3,5-二甲基苯酚的分离提纯", 《中国优秀硕士学位论文全文数据库工程科技I辑》, 15 May 2013 (2013-05-15), pages 016 - 175 * |
魏文珑等: "对氯间二甲酚的合成研究", 《应用化工》, vol. 36, no. 11, 30 November 2007 (2007-11-30), pages 1066 - 1068 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104744221A (zh) * | 2015-04-13 | 2015-07-01 | 中国科学院青岛生物能源与过程研究所 | 一种对氯苯酚化合物的制备方法 |
CN105037104A (zh) * | 2015-06-02 | 2015-11-11 | 铜陵市恒兴化工有限责任公司 | 一种4-氯-3,5-二甲基苯酚的制备方法 |
CN111517922A (zh) * | 2020-04-28 | 2020-08-11 | 万华化学集团股份有限公司 | 一种制备4-氯-3,5-二甲基苯酚的方法 |
CN111517922B (zh) * | 2020-04-28 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备4-氯-3,5-二甲基苯酚的方法 |
CN114805033A (zh) * | 2022-05-23 | 2022-07-29 | 陕西煤业化工技术研究院有限责任公司 | 一种氯代苯酚类化合物的合成方法 |
CN115583869A (zh) * | 2022-09-13 | 2023-01-10 | 安徽海华科技集团有限公司 | 一种酚类化合物选择性氧化氯化方法 |
CN115583869B (zh) * | 2022-09-13 | 2024-04-23 | 安徽海华科技集团有限公司 | 一种酚类化合物选择性氧化氯化方法 |
CN115433060A (zh) * | 2022-10-31 | 2022-12-06 | 青岛科技大学 | 一种单氯代苯酚化合物的制备方法 |
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