CN111302965A - 一种新型色酚制备工艺 - Google Patents
一种新型色酚制备工艺 Download PDFInfo
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- CN111302965A CN111302965A CN202010248275.2A CN202010248275A CN111302965A CN 111302965 A CN111302965 A CN 111302965A CN 202010248275 A CN202010248275 A CN 202010248275A CN 111302965 A CN111302965 A CN 111302965A
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- CN
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- Prior art keywords
- organic solvent
- water
- naphthol
- product
- preparation process
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000009833 condensation Methods 0.000 claims abstract description 13
- 230000005494 condensation Effects 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- 235000017550 sodium carbonate Nutrition 0.000 claims abstract description 9
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- -1 phosphorous ester Chemical class 0.000 claims description 5
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000000975 dye Substances 0.000 abstract description 3
- 239000005416 organic matter Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical class OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- ZCNGWQCRXUGQCW-UHFFFAOYSA-M sodium;3-hydroxynaphthalene-2-carboxylate Chemical compound [Na+].C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ZCNGWQCRXUGQCW-UHFFFAOYSA-M 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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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
2-羟基-3-萘甲酸 | 苯胺 | 三氯化磷 | 含磷有机物 | 纯碱 | |
对比例1 | 770kg | 445kg | 275kg | ------- | 360kg |
实施例1 | 770kg | 445kg | ------ | 35kg | 44kg |
Claims (5)
Priority Applications (1)
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CN202010248275.2A CN111302965B (zh) | 2020-04-01 | 2020-04-01 | 一种新型色酚制备工艺 |
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CN202010248275.2A CN111302965B (zh) | 2020-04-01 | 2020-04-01 | 一种新型色酚制备工艺 |
Publications (2)
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CN111302965A true CN111302965A (zh) | 2020-06-19 |
CN111302965B CN111302965B (zh) | 2022-10-18 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112023957A (zh) * | 2020-09-24 | 2020-12-04 | 青岛科技大学 | 一种基于b-p-o基团催化剂及其制备色酚的方法 |
CN113651709A (zh) * | 2021-07-27 | 2021-11-16 | 佳化化学(茂名)有限公司 | 一种脂肪酰胺丙基二甲基叔胺及其制备方法和应用 |
CN117003662A (zh) * | 2023-08-04 | 2023-11-07 | 唐山华熠实业股份有限公司 | 一种新型色酚制备工艺 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1436588A (en) * | 1972-08-12 | 1976-05-19 | Hoechst Ag | Manufacture of hydroxybenzanilides |
GB9019792D0 (en) * | 1990-09-11 | 1990-10-24 | Chanelle Chemicals Ltd | Manufacture of a salicylanilide derivative |
CN105753731A (zh) * | 2016-04-27 | 2016-07-13 | 嘉兴科隆化工有限公司 | 一种3-氨基-4-甲氧基苯甲酰苯胺的制备方法 |
CN110540512A (zh) * | 2019-08-09 | 2019-12-06 | 肥城岳海化工有限公司 | 一种合成色酚的处理工艺 |
-
2020
- 2020-04-01 CN CN202010248275.2A patent/CN111302965B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1436588A (en) * | 1972-08-12 | 1976-05-19 | Hoechst Ag | Manufacture of hydroxybenzanilides |
GB9019792D0 (en) * | 1990-09-11 | 1990-10-24 | Chanelle Chemicals Ltd | Manufacture of a salicylanilide derivative |
CN105753731A (zh) * | 2016-04-27 | 2016-07-13 | 嘉兴科隆化工有限公司 | 一种3-氨基-4-甲氧基苯甲酰苯胺的制备方法 |
CN110540512A (zh) * | 2019-08-09 | 2019-12-06 | 肥城岳海化工有限公司 | 一种合成色酚的处理工艺 |
Non-Patent Citations (1)
Title |
---|
C.I.CHIRIAC: "Synthesis of amides by a new direct condensatioin reaction", 《 REVUE ROUMAINE DE CHIMIE》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112023957A (zh) * | 2020-09-24 | 2020-12-04 | 青岛科技大学 | 一种基于b-p-o基团催化剂及其制备色酚的方法 |
CN113651709A (zh) * | 2021-07-27 | 2021-11-16 | 佳化化学(茂名)有限公司 | 一种脂肪酰胺丙基二甲基叔胺及其制备方法和应用 |
CN117003662A (zh) * | 2023-08-04 | 2023-11-07 | 唐山华熠实业股份有限公司 | 一种新型色酚制备工艺 |
CN117003662B (zh) * | 2023-08-04 | 2024-02-23 | 唐山华熠实业股份有限公司 | 一种新型色酚制备工艺 |
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CN111302965B (zh) | 2022-10-18 |
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GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A New Process for Preparing Naphthol Effective date of registration: 20230824 Granted publication date: 20221018 Pledgee: Bank of Cangzhou Limited by Share Ltd. Fengnan branch Pledgor: TANGSHAN HUAYI INDUSTRY HOLDINGS CO.,LTD. Registration number: Y2023990000428 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20221018 Pledgee: Bank of Cangzhou Limited by Share Ltd. Fengnan branch Pledgor: TANGSHAN HUAYI INDUSTRY HOLDINGS CO.,LTD. Registration number: Y2023990000428 |
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PC01 | Cancellation 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: A new process for preparing phenols Granted publication date: 20221018 Pledgee: Bank of Cangzhou Limited by Share Ltd. Fengnan branch Pledgor: TANGSHAN HUAYI INDUSTRY HOLDINGS CO.,LTD. Registration number: Y2024980035015 |