CN101402552A - Method for producing m-cresol with direct hydrolyzation - Google Patents
Method for producing m-cresol with direct hydrolyzation Download PDFInfo
- Publication number
- CN101402552A CN101402552A CNA2008102351007A CN200810235100A CN101402552A CN 101402552 A CN101402552 A CN 101402552A CN A2008102351007 A CNA2008102351007 A CN A2008102351007A CN 200810235100 A CN200810235100 A CN 200810235100A CN 101402552 A CN101402552 A CN 101402552A
- Authority
- CN
- China
- Prior art keywords
- meta
- cresol
- extraction
- aminotoluene
- hydrolysis
- 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
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 title claims description 74
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000605 extraction Methods 0.000 claims abstract description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 37
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 37
- 239000007864 aqueous solution Substances 0.000 claims abstract description 31
- 230000007062 hydrolysis Effects 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000007670 refining Methods 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract 4
- 229940100630 metacresol Drugs 0.000 claims description 72
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 238000011084 recovery Methods 0.000 claims description 31
- 239000007788 liquid Substances 0.000 claims description 26
- 238000006386 neutralization reaction Methods 0.000 claims description 24
- 238000007701 flash-distillation Methods 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- 235000019270 ammonium chloride Nutrition 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 16
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 12
- 239000000284 extract Substances 0.000 claims description 12
- 239000003337 fertilizer Substances 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract description 10
- 235000010288 sodium nitrite Nutrition 0.000 abstract description 5
- 239000001117 sulphuric acid Substances 0.000 abstract description 5
- 235000011149 sulphuric acid Nutrition 0.000 abstract description 5
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 14
- 239000000413 hydrolysate Substances 0.000 abstract 3
- 238000002156 mixing Methods 0.000 abstract 3
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 3
- 230000003472 neutralizing effect Effects 0.000 abstract 2
- 239000003518 caustics Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 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 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Fertilizers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008102351007A CN101402552B (en) | 2008-11-13 | 2008-11-13 | Method for producing m-cresol with direct hydrolyzation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008102351007A CN101402552B (en) | 2008-11-13 | 2008-11-13 | Method for producing m-cresol with direct hydrolyzation |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101402552A true CN101402552A (en) | 2009-04-08 |
CN101402552B CN101402552B (en) | 2011-11-16 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008102351007A Active CN101402552B (en) | 2008-11-13 | 2008-11-13 | Method for producing m-cresol with direct hydrolyzation |
Country Status (1)
Country | Link |
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CN (1) | CN101402552B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101941890A (en) * | 2010-09-02 | 2011-01-12 | 江苏淮河化工有限公司 | Method and device for preparing metacresol |
CN102838457A (en) * | 2012-09-20 | 2012-12-26 | 山东潍坊润丰化工有限公司 | Synthesis method of 2, 5-dichlorophenol |
CN103044205A (en) * | 2012-12-08 | 2013-04-17 | 浙江鼎龙科技有限公司 | Preparation method of 3-methyl-4-isopropylphenol |
CN107721822A (en) * | 2017-09-18 | 2018-02-23 | 江苏迈达新材料股份有限公司 | A kind of method and system for industrializing continuous production paracresol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1223565C (en) * | 2003-01-06 | 2005-10-19 | 唐师法 | Preparation process of meta-cresol |
CN101125800A (en) * | 2007-09-28 | 2008-02-20 | 中北大学 | Technique for preparing m-cresol |
CN101591223A (en) * | 2008-05-30 | 2009-12-02 | 南京理工大学 | The direct hydrolysis meta-aminotoluene prepares the method for meta-cresol |
-
2008
- 2008-11-13 CN CN2008102351007A patent/CN101402552B/en active Active
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101941890A (en) * | 2010-09-02 | 2011-01-12 | 江苏淮河化工有限公司 | Method and device for preparing metacresol |
CN101941890B (en) * | 2010-09-02 | 2014-06-11 | 江苏淮河化工有限公司 | Method and device for preparing metacresol |
CN102838457A (en) * | 2012-09-20 | 2012-12-26 | 山东潍坊润丰化工有限公司 | Synthesis method of 2, 5-dichlorophenol |
CN103044205A (en) * | 2012-12-08 | 2013-04-17 | 浙江鼎龙科技有限公司 | Preparation method of 3-methyl-4-isopropylphenol |
CN107721822A (en) * | 2017-09-18 | 2018-02-23 | 江苏迈达新材料股份有限公司 | A kind of method and system for industrializing continuous production paracresol |
Also Published As
Publication number | Publication date |
---|---|
CN101402552B (en) | 2011-11-16 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for producing m-cresol with direct hydrolyzation Effective date of registration: 20181227 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: 2018320000382 |
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Date of cancellation: 20191212 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: 2018320000382 |
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Denomination of invention: Method for producing m-cresol with direct hydrolyzation Effective date of registration: 20191213 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2019320000354 |
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Date of cancellation: 20200902 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2019320000354 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Production of m-Cresol by direct hydrolysis Effective date of registration: 20200903 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2020980005697 |
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Date of cancellation: 20210824 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2020980005697 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for producing m-Cresol by direct hydrolysis Effective date of registration: 20210825 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2021980008261 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220822 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2021980008261 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for producing m-cresol by direct hydrolysis Effective date of registration: 20220823 Granted publication date: 20111116 Pledgee: Bank of China Limited Huai'an Qingjiangpu Branch Pledgor: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Registration number: Y2022980013394 |
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Address after: 223002 Huaian City, Jiangsu province Qingpu District West Road No. 40 Patentee after: Jiangsu Kesheng Intelligent Equipment Co.,Ltd. Country or region after: China Address before: 223002 Huaian City, Jiangsu province Qingpu District West Road No. 40 Patentee before: JIANGSU KESHENG CHEMICAL MACHINERY Co.,Ltd. Country or region before: China |