CN103787874B - 一种苯甲酰氯的制备工艺 - Google Patents
一种苯甲酰氯的制备工艺 Download PDFInfo
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- CN103787874B CN103787874B CN201410070802.XA CN201410070802A CN103787874B CN 103787874 B CN103787874 B CN 103787874B CN 201410070802 A CN201410070802 A CN 201410070802A CN 103787874 B CN103787874 B CN 103787874B
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- Prior art keywords
- benzoyl chloride
- crude product
- rectifying
- kilograms
- reactor
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 title claims abstract description 106
- 238000005516 engineering process Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims abstract description 61
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000012043 crude product Substances 0.000 claims abstract description 55
- 239000000460 chlorine Substances 0.000 claims abstract description 53
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 48
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000007670 refining Methods 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 47
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 40
- 239000000463 material Substances 0.000 claims description 33
- 238000005660 chlorination reaction Methods 0.000 claims description 30
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 25
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 25
- 238000010792 warming Methods 0.000 claims description 24
- 235000005074 zinc chloride Nutrition 0.000 claims description 20
- 239000011592 zinc chloride Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- ZBOGUDPFEVIZIQ-UHFFFAOYSA-N toluene;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC=C1 ZBOGUDPFEVIZIQ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 11
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 10
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 229960004365 benzoic acid Drugs 0.000 claims description 9
- 238000006298 dechlorination reaction Methods 0.000 claims description 9
- 238000001291 vacuum drying Methods 0.000 claims description 9
- 239000000498 cooling water Substances 0.000 claims description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 7
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- 239000011269 tar Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- 238000003756 stirring Methods 0.000 abstract description 8
- 230000035484 reaction time Effects 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 5
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- -1 acyl chlorides Chemical class 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410070802.XA CN103787874B (zh) | 2014-02-28 | 2014-02-28 | 一种苯甲酰氯的制备工艺 |
Applications Claiming Priority (1)
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CN201410070802.XA CN103787874B (zh) | 2014-02-28 | 2014-02-28 | 一种苯甲酰氯的制备工艺 |
Publications (2)
Publication Number | Publication Date |
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CN103787874A CN103787874A (zh) | 2014-05-14 |
CN103787874B true CN103787874B (zh) | 2015-11-18 |
Family
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Family Applications (1)
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CN201410070802.XA Active CN103787874B (zh) | 2014-02-28 | 2014-02-28 | 一种苯甲酰氯的制备工艺 |
Country Status (1)
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CN (1) | CN103787874B (zh) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104447298B (zh) * | 2014-12-12 | 2016-03-30 | 山东凯盛新材料有限公司 | 苯甲酰氯的制备方法 |
CN104592000B (zh) * | 2014-12-22 | 2017-01-11 | 上海方纶新材料科技有限公司 | 制备氯甲酰基取代苯的清洁工艺 |
CN105175242B (zh) * | 2015-09-14 | 2017-09-05 | 宜都市友源实业有限公司 | 一种三氯甲苯和/或苯甲酰氯废渣的回收利用方法 |
CN106008197A (zh) * | 2016-06-06 | 2016-10-12 | 山东福尔有限公司 | 一种邻氟苯甲酰氯的制备方法 |
CN109553524B (zh) * | 2017-12-28 | 2021-11-09 | 浙江本立科技股份有限公司 | 一种2,4-二氯-5-氟苯甲酰氯的合成方法 |
CN109553525A (zh) * | 2017-12-29 | 2019-04-02 | 浙江本立科技股份有限公司 | 一种取代芳烃甲酰氯的合成方法 |
CN108191646A (zh) * | 2018-01-08 | 2018-06-22 | 江苏振方生物化学有限公司 | 一种回收对氯苯甲酸制对氯苯甲酰氯的制备工艺 |
CN108299150A (zh) * | 2018-01-29 | 2018-07-20 | 江苏佳麦化工有限公司 | 4-正丁基苯甲酰氯的合成方法 |
CN108558599B (zh) * | 2018-03-29 | 2021-01-29 | 浦拉司科技(上海)有限责任公司 | 2-联苯基甲醇的合成工艺 |
CN109721489A (zh) * | 2019-01-22 | 2019-05-07 | 江苏佳麦化工有限公司 | 一种连续滴加三氯苄合成苯甲酰氯的方法 |
CN110256194A (zh) * | 2019-07-30 | 2019-09-20 | 江苏超跃化学有限公司 | 一种烷基芳香烃侧链氯化反应时催化剂自动添加的方法 |
CN112979453A (zh) * | 2019-12-13 | 2021-06-18 | 江西仰立新材料有限公司 | 一种苯甲酰氯类化合物的制备方法 |
CN112759163A (zh) * | 2020-12-31 | 2021-05-07 | 清大国华环境集团股份有限公司 | 苯甲酰氯生产过程中产生的残液的处理方法及处理系统 |
CN112778078A (zh) * | 2021-01-24 | 2021-05-11 | 湖南比德生化科技股份有限公司 | 一种间苯二甲酸酰氯化副产氯化氢制备3-氯-3-甲基丁炔的工艺 |
CN113105302B (zh) * | 2021-03-04 | 2024-01-12 | 老河口华辰化学有限公司 | 一种邻氯甲苯氯化联产邻氯氯苄、邻氯二氯苄和邻氯三氯苄的方法 |
CN114230434B (zh) * | 2021-12-28 | 2024-01-26 | 河南特格纳特科技有限公司 | 一种烷基苯定向氯化生产三氯苄的方法 |
CN114656330B (zh) * | 2022-04-07 | 2024-03-15 | 河南特格纳特科技有限公司 | 一种三氯甲苯的制备方法及其三氯甲苯 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1148587A (zh) * | 1996-05-17 | 1997-04-30 | 常熟市金城化工厂 | 苯甲酰氯的制备方法 |
-
2014
- 2014-02-28 CN CN201410070802.XA patent/CN103787874B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1148587A (zh) * | 1996-05-17 | 1997-04-30 | 常熟市金城化工厂 | 苯甲酰氯的制备方法 |
Non-Patent Citations (1)
Title |
---|
"苯甲酰氯的生产工艺的优化";王建峰 等;《山东化工》;20121231;第41卷(第12期);第13-15页 * |
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Publication number | Publication date |
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CN103787874A (zh) | 2014-05-14 |
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Denomination of invention: A preparation process of benzoyl chloride Effective date of registration: 20220722 Granted publication date: 20151118 Pledgee: Bank of China Limited by Share Ltd. Three Gorges Branch Pledgor: YIDU JOVIAN INDUSTRY CO.,LTD. Registration number: Y2022420000231 |
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Granted publication date: 20151118 Pledgee: Bank of China Limited by Share Ltd. Three Gorges Branch Pledgor: YIDU JOVIAN INDUSTRY CO.,LTD. Registration number: Y2022420000231 |