CN114085132B - 一种2,6-二羟基甲苯的制备方法 - Google Patents
一种2,6-二羟基甲苯的制备方法 Download PDFInfo
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- CN114085132B CN114085132B CN202111457233.0A CN202111457233A CN114085132B CN 114085132 B CN114085132 B CN 114085132B CN 202111457233 A CN202111457233 A CN 202111457233A CN 114085132 B CN114085132 B CN 114085132B
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- China
- Prior art keywords
- kettle
- dihydroxytoluene
- cooling
- phosphoric acid
- diaminotoluene
- Prior art date
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- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 48
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000001816 cooling Methods 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 23
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 17
- 239000010410 layer Substances 0.000 claims abstract description 17
- 238000000605 extraction Methods 0.000 claims abstract description 14
- 239000012044 organic layer Substances 0.000 claims abstract description 14
- 238000005185 salting out Methods 0.000 claims abstract description 13
- 230000007062 hydrolysis Effects 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000008213 purified water Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 238000007670 refining Methods 0.000 claims abstract description 7
- 238000005086 pumping Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 18
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims description 13
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 claims description 13
- 235000019837 monoammonium phosphate Nutrition 0.000 claims description 13
- 239000012452 mother liquor Substances 0.000 claims description 12
- 238000005070 sampling Methods 0.000 claims description 12
- 210000003298 dental enamel Anatomy 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 229960002089 ferrous chloride Drugs 0.000 claims description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- 229940032296 ferric chloride Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 230000008901 benefit Effects 0.000 abstract description 7
- 238000002844 melting Methods 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 6
- 238000004090 dissolution Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 238000004321 preservation Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- NHMJKYVPXYBHSL-UHFFFAOYSA-N 3-hydroxy-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(O)CCCC1=O NHMJKYVPXYBHSL-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
- C07C37/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen by substitution of a NH2 group
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
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CN202111457233.0A CN114085132B (zh) | 2021-12-02 | 2021-12-02 | 一种2,6-二羟基甲苯的制备方法 |
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CN114085132A CN114085132A (zh) | 2022-02-25 |
CN114085132B true CN114085132B (zh) | 2023-10-24 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104341275A (zh) * | 2014-10-24 | 2015-02-11 | 盐城市鼎烨化工有限公司 | 一种2,6-二羟基甲苯的合成方法 |
CN107262150A (zh) * | 2017-06-06 | 2017-10-20 | 青岛科技大学 | 一种间苯二胺水解用负载型固体酸催化剂的制备方法 |
CN111620761A (zh) * | 2020-06-02 | 2020-09-04 | 湖北仙盛科技股份有限公司 | 一种2,6-二羟基甲苯的合成方法 |
CN112679322A (zh) * | 2021-01-22 | 2021-04-20 | 浙江工业大学 | 一种超临界co2催化制备2,6-二羟基甲苯的方法 |
-
2021
- 2021-12-02 CN CN202111457233.0A patent/CN114085132B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104341275A (zh) * | 2014-10-24 | 2015-02-11 | 盐城市鼎烨化工有限公司 | 一种2,6-二羟基甲苯的合成方法 |
CN107262150A (zh) * | 2017-06-06 | 2017-10-20 | 青岛科技大学 | 一种间苯二胺水解用负载型固体酸催化剂的制备方法 |
CN111620761A (zh) * | 2020-06-02 | 2020-09-04 | 湖北仙盛科技股份有限公司 | 一种2,6-二羟基甲苯的合成方法 |
CN112679322A (zh) * | 2021-01-22 | 2021-04-20 | 浙江工业大学 | 一种超临界co2催化制备2,6-二羟基甲苯的方法 |
Non-Patent Citations (1)
Title |
---|
杜彬斌.2,6-二羟基甲苯合成工艺研究.中国优秀博硕士学位论文全文数据库(硕士) 工程科技Ⅰ辑.2010,B016-23. * |
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Effective date of registration: 20230316 Address after: 441000 Leiyan Avenue, Leihe Development Park, Yicheng city, Xiangyang City, Hubei Province Applicant after: Hubei teteng New Material Technology Co.,Ltd. Applicant after: HUBEI University OF ARTS AND SCIENCE Address before: 441000 Leiyan Avenue, Leihe Development Park, Yicheng city, Xiangyang City, Hubei Province Applicant before: Hubei teteng New Material Technology Co.,Ltd. |
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Address after: 441053 Luzhong Road, Xiangcheng District, Xiangyang, Hubei Province, No. 296 Applicant after: HUBEI University OF ARTS AND SCIENCE Applicant after: Hubei teteng New Material Technology Co.,Ltd. Address before: 441000 Leiyan Avenue, Leihe Development Park, Yicheng city, Xiangyang City, Hubei Province Applicant before: Hubei teteng New Material Technology Co.,Ltd. Applicant before: HUBEI University OF ARTS AND SCIENCE |
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