CN103772153B - 4-氯-3-甲酚的合成方法及其*** - Google Patents
4-氯-3-甲酚的合成方法及其*** Download PDFInfo
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- CN103772153B CN103772153B CN201410000130.5A CN201410000130A CN103772153B CN 103772153 B CN103772153 B CN 103772153B CN 201410000130 A CN201410000130 A CN 201410000130A CN 103772153 B CN103772153 B CN 103772153B
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- reaction
- end volatiles
- reboiler
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- sulfuryl chloride
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- HKHXLHGVIHQKMK-UHFFFAOYSA-N 2-chloro-m-cresol Chemical class CC1=CC=CC(O)=C1Cl HKHXLHGVIHQKMK-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000010189 synthetic method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 239000000047 product Substances 0.000 claims abstract description 36
- 239000003039 volatile agent Substances 0.000 claims abstract description 35
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 30
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229940100630 metacresol Drugs 0.000 claims abstract description 28
- 230000007704 transition Effects 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 11
- 238000001953 recrystallisation Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- 238000006386 neutralization reaction Methods 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000013517 stratification Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000005660 chlorination reaction Methods 0.000 abstract description 5
- 230000009466 transformation Effects 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical class CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 8
- OUADMZZEIRSDSG-NKFUZKMXSA-N C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](CO)[C@@]2(OC)[C@@H]2[C@H]1N2 Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](CO)[C@@]2(OC)[C@@H]2[C@H]1N2 OUADMZZEIRSDSG-NKFUZKMXSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000010959 commercial synthesis reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- SMFHPCZZAAMJJO-UHFFFAOYSA-N 2-chloro-5-methylphenol Chemical class CC1=CC=C(Cl)C(O)=C1 SMFHPCZZAAMJJO-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
PCMC | MC | DCMC | OCMC | 选择性 | 收率 |
88.53 | 9.21 | 1.65 | 0.04 | 97.51% | 88.53% |
PCMC | MC | DCMC | OCMC | 其他杂质总和 | 选择性 | 收率 |
76.13 | 3.66 | 12.12 | 3.24 | 3.93 | 79.02% | 76.13% |
实施例 | PCMC | MC | DCMC | OCMC | 选择性 | 收率 |
3 | 87.12 | 10.13 | 1.77 | 0 | 96.94% | 87.12% |
4 | 51.06 | 47.96 | 0.59 | 0 | 98.11% | 51.06% |
PCMC | MC | DCMC | OCMC |
88.16 | 9.87 | 1.54 | 0 |
PCMC(吨) | 前馏分(吨) | 过渡组分(吨) | 收率 |
1.1 | 0.15 | 0.10 | 91.44 |
Claims (3)
Priority Applications (1)
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CN201410000130.5A CN103772153B (zh) | 2014-01-02 | 2014-01-02 | 4-氯-3-甲酚的合成方法及其*** |
Applications Claiming Priority (1)
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CN201410000130.5A CN103772153B (zh) | 2014-01-02 | 2014-01-02 | 4-氯-3-甲酚的合成方法及其*** |
Publications (2)
Publication Number | Publication Date |
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CN103772153A CN103772153A (zh) | 2014-05-07 |
CN103772153B true CN103772153B (zh) | 2015-09-09 |
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CN201410000130.5A Active CN103772153B (zh) | 2014-01-02 | 2014-01-02 | 4-氯-3-甲酚的合成方法及其*** |
Country Status (1)
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CN (1) | CN103772153B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104045521B (zh) * | 2014-06-27 | 2016-06-15 | 江苏焕鑫新材料股份有限公司 | 一种对氯间甲酚绿色合成工艺 |
CN115466166B (zh) * | 2022-10-31 | 2023-02-03 | 山东新和成维生素有限公司 | 一种低温合成4-氯-3,5-二甲基苯酚的方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9705493D0 (en) * | 1997-03-17 | 1997-05-07 | Univ Wales Swansea The | Chlorination of aromatic compounds and catalysts therefor |
CN100560554C (zh) * | 2007-01-10 | 2009-11-18 | 胡汉忠 | 对氯代烷基苯酚的工业化制备方法 |
CN101225025B (zh) * | 2008-02-13 | 2010-09-29 | 上海华谊丙烯酸有限公司 | 一种分离苯酚羟基化反应液中邻/对苯二酚的方法 |
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Address after: 410000 Ningxiang County, Hunan City, Changsha Province Patentee after: HUNAN LIJIE BIOCHEMICAL Co.,Ltd. Address before: 410000 1 South, Ningxiang Economic Development Zone, Hunan, Changsha Patentee before: HUNAN LIJIE BIOCHEMICAL Co.,Ltd. Address after: 410600 Ningxiang County, Hunan City, Changsha Province Patentee after: HUNAN LIJIE BIOLOGICAL GROUP CO.,LTD. Address before: 410000 Ningxiang County, Hunan City, Changsha Province Patentee before: HUNAN LIJIE BIOCHEMICAL Co.,Ltd. |
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Denomination of invention: Synthesis method of 4-chloro-3-cresol and system thereof Effective date of registration: 20160902 Granted publication date: 20150909 Pledgee: Bank of Beijing Limited by Share Ltd. Changsha branch Pledgor: HUNAN LIJIE BIOLOGICAL GROUP CO.,LTD. Registration number: 2016430000032 |
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Effective date of registration: 20181022 Address after: 415000 Hai de Lu, Qixing nun village, de Shan town, Changde economic and Technological Development Zone, Changde, Hunan Patentee after: Hunan crown bio chemical technology Co.,Ltd. Address before: 410600 Ningxiang County, Changsha, Hunan Patentee before: HUNAN LIJIE BIOLOGICAL GROUP CO.,LTD. |
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Denomination of invention: Synthesis method of 4-chloro-3-cresol and system thereof Effective date of registration: 20181203 Granted publication date: 20150909 Pledgee: Zhejiang Yangfan Holding Co.,Ltd. Pledgor: Hunan crown bio chemical technology Co.,Ltd. Registration number: 2018430000117 |
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Date of cancellation: 20200401 Granted publication date: 20150909 Pledgee: Zhejiang Yangfan Holding Co.,Ltd. Pledgor: Hunan crown bio chemical technology Co.,Ltd. Registration number: 2018430000117 |
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Denomination of invention: Synthesis method and system of 4-chloro-3-cresol Effective date of registration: 20230807 Granted publication date: 20150909 Pledgee: Changsha Xiangjiang Asset Management Co.,Ltd. Pledgor: Hunan crown bio chemical technology Co.,Ltd. Registration number: Y2023980050807 |