CN108002984B - 从萘连续制备(α、β)萘酚钠的生产***及方法 - Google Patents
从萘连续制备(α、β)萘酚钠的生产***及方法 Download PDFInfo
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- CN108002984B CN108002984B CN201710825467.3A CN201710825467A CN108002984B CN 108002984 B CN108002984 B CN 108002984B CN 201710825467 A CN201710825467 A CN 201710825467A CN 108002984 B CN108002984 B CN 108002984B
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- naphthalene
- combined
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 358
- 238000000034 method Methods 0.000 title claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 55
- AJXVJQAPXVDFBT-UHFFFAOYSA-M sodium;naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=CC([O-])=CC=C21 AJXVJQAPXVDFBT-UHFFFAOYSA-M 0.000 title claims abstract description 25
- 239000003513 alkali Substances 0.000 claims abstract description 95
- 238000006243 chemical reaction Methods 0.000 claims abstract description 66
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 65
- 238000011084 recovery Methods 0.000 claims abstract description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 230000004927 fusion Effects 0.000 claims abstract description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 145
- 239000007788 liquid Substances 0.000 claims description 77
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 57
- 239000000463 material Substances 0.000 claims description 54
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 44
- 230000008569 process Effects 0.000 claims description 32
- DGVVJWXRCWCCOD-UHFFFAOYSA-N naphthalene;hydrate Chemical compound O.C1=CC=CC2=CC=CC=C21 DGVVJWXRCWCCOD-UHFFFAOYSA-N 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 20
- 239000007921 spray Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 11
- 239000011552 falling film Substances 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 2
- 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 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-M naphthalen-1-olate Chemical compound C1=CC=C2C([O-])=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-M 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000002351 wastewater Substances 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 9
- 238000010924 continuous production Methods 0.000 abstract description 6
- 125000004122 cyclic group Chemical group 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000005416 organic matter Substances 0.000 abstract description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 45
- 239000000047 product Substances 0.000 description 23
- 230000001276 controlling effect Effects 0.000 description 15
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 230000008901 benefit Effects 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 230000001105 regulatory effect Effects 0.000 description 10
- 150000001720 carbohydrates Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000007664 blowing Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 230000007613 environmental effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 6
- 239000003345 natural gas Substances 0.000 description 6
- 238000010669 acid-base reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- FCPGLSSNBUVLLD-UHFFFAOYSA-N naphthalen-1-ol;sodium Chemical compound [Na].C1=CC=C2C(O)=CC=CC2=C1 FCPGLSSNBUVLLD-UHFFFAOYSA-N 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004134 energy conservation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- ZBNNKSSSCSTNNK-UHFFFAOYSA-M sodium;naphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=CC=CC2=C1 ZBNNKSSSCSTNNK-UHFFFAOYSA-M 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000007499 fusion processing Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 230000017105 transposition Effects 0.000 description 2
- VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical class CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 1
- ONZWNZGVZFLMNZ-UHFFFAOYSA-N 1-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C([NH3+])=C(S([O-])(=O)=O)C=CC2=C1 ONZWNZGVZFLMNZ-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- KSTGSVANFMJGGB-UHFFFAOYSA-N 2-ethylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CC)=CC=C21 KSTGSVANFMJGGB-UHFFFAOYSA-N 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ZNYPFGRLOVXIFH-UHFFFAOYSA-N naphthalen-2-ol;sodium Chemical compound [Na].C1=CC=CC2=CC(O)=CC=C21 ZNYPFGRLOVXIFH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
Images
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
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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CN201710825467.3A CN108002984B (zh) | 2017-09-14 | 2017-09-14 | 从萘连续制备(α、β)萘酚钠的生产***及方法 |
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CN201710825467.3A CN108002984B (zh) | 2017-09-14 | 2017-09-14 | 从萘连续制备(α、β)萘酚钠的生产***及方法 |
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CN108002984B true CN108002984B (zh) | 2021-02-19 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1513824A (zh) * | 2003-08-18 | 2004-07-21 | 常州市华达化工厂 | 联产甲萘酚和乙萘酚的制备方法 |
CN1557807A (zh) * | 2004-01-18 | 2004-12-29 | 阳 李 | 在乙萘酚生产中2-萘磺酸钠盐制备的改进工艺 |
CN1958567A (zh) * | 2006-10-17 | 2007-05-09 | 江苏华达化工集团有限公司 | 一种1-萘磺酸和1-萘磺酸钠盐的制备方法 |
CN104016835A (zh) * | 2014-06-24 | 2014-09-03 | 湖北鑫慧化工有限公司 | 一种2-萘酚磺化碱熔优化生产工艺 |
CN104193593A (zh) * | 2014-09-26 | 2014-12-10 | 青岛奥盖克化工股份有限公司 | 一种液相碱熔法生产2-萘酚的环保制备工艺 |
CN104693009A (zh) * | 2015-03-04 | 2015-06-10 | 肖刚学 | 萘磺化产物直接碱熔联产1-萘酚和2-萘酚的方法 |
-
2017
- 2017-09-14 CN CN201710825467.3A patent/CN108002984B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1513824A (zh) * | 2003-08-18 | 2004-07-21 | 常州市华达化工厂 | 联产甲萘酚和乙萘酚的制备方法 |
CN1557807A (zh) * | 2004-01-18 | 2004-12-29 | 阳 李 | 在乙萘酚生产中2-萘磺酸钠盐制备的改进工艺 |
CN1958567A (zh) * | 2006-10-17 | 2007-05-09 | 江苏华达化工集团有限公司 | 一种1-萘磺酸和1-萘磺酸钠盐的制备方法 |
CN104016835A (zh) * | 2014-06-24 | 2014-09-03 | 湖北鑫慧化工有限公司 | 一种2-萘酚磺化碱熔优化生产工艺 |
CN104193593A (zh) * | 2014-09-26 | 2014-12-10 | 青岛奥盖克化工股份有限公司 | 一种液相碱熔法生产2-萘酚的环保制备工艺 |
CN104693009A (zh) * | 2015-03-04 | 2015-06-10 | 肖刚学 | 萘磺化产物直接碱熔联产1-萘酚和2-萘酚的方法 |
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Denomination of invention: Continuous preparation from naphthalene( a b) Production system and method of naphthol sodium Effective date of registration: 20210809 Granted publication date: 20210219 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2021500000036 |
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Denomination of invention: Production system and method for continuous preparation of (a, b) sodium naphthol from naphthalene Effective date of registration: 20220811 Granted publication date: 20210219 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2022500000056 |
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Denomination of invention: Continuous preparation from naphthalene( a b) Production system and method of sodium naphthol Effective date of registration: 20230317 Granted publication date: 20210219 Pledgee: Chongqing chemical medicine holding (Group) Co.,Ltd. Pledgor: Chongqing Unisplendour Chemical Co.,Ltd. Registration number: Y2023500000020 |