CN1403434A - Prepn process of 5-chloro-2,3-dihydro-1-indenone - Google Patents
Prepn process of 5-chloro-2,3-dihydro-1-indenone Download PDFInfo
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- CN1403434A CN1403434A CN 02138331 CN02138331A CN1403434A CN 1403434 A CN1403434 A CN 1403434A CN 02138331 CN02138331 CN 02138331 CN 02138331 A CN02138331 A CN 02138331A CN 1403434 A CN1403434 A CN 1403434A
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- Prior art keywords
- chloro
- indenone
- chloride
- bihydrogen
- preparation
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- 238000000034 method Methods 0.000 title claims description 10
- MEDSHTHCZIOVPU-UHFFFAOYSA-N 5-chloro-2,3-dihydroinden-1-one Chemical compound ClC1=CC=C2C(=O)CCC2=C1 MEDSHTHCZIOVPU-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- AYFJBHFMQODYBC-UHFFFAOYSA-N 3-chloro-1-(4-chlorophenyl)propan-1-one Chemical compound ClCCC(=O)C1=CC=C(Cl)C=C1 AYFJBHFMQODYBC-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- -1 yield 45% Chemical compound 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the preparation process of one kind of chemical product, and is the preparation process of 5-chloro-2,3-dihydro-1-indenone. The preparation process of 5-chloro-2,3-dihydro-1 indenone includes the reaction between 3-chloropropionyl chloride and benzene chloride to produce 3,4'-dichlorophenyl propanone; and the cyclization of the 3,4'-dichlorophenyl propanone. The present invention has high yield, high product quality and less material corrosion, and its effluent may be used in preparing one kind of water treating agent to reduce environmental pollution.
Description
Technical field
The present invention relates to a kind of chemical products preparation method, especially the 5-chloro-2, the preparation method of 3-bihydrogen-1-indenone.
Background technology
5-chloro-2,3-bihydrogen-1-indenone are a kind of important medicine intermediates, and its English name is: 5-chloro-1-indanone, CAS NO:42348-86-7.At present, this product synthetic mainly contains following two kinds of methods:
One, French Patent FR 2784986 introduces, 3-chlorpromazine chloride and Benzene Chloride are made catalyzer at excessive trifluoromethanesulfonic acid, in 120 ℃ react 3,4 '-dichloropropiophenone, yield 45%, 3,4 '-dichloropropiophenone is made catalyzer at excessive trifluoromethanesulfonic acid, in 90 ℃ of reactions, gets 5-chloro-2, the 3-bihydrogen-1-indenone, yield 98%.This method uses trifluoromethanesulfonic acid to make catalyzer, and trifluoromethanesulfonic acid has intensive corrodibility, can cause serious burn, easily injure operator's health, simultaneously, a large amount of trifluoromethanesulfonic acids is difficult to handle the equipment corrosion height, in addition, 3, the yield of 4 '-dichloropropiophenone is low too.
Two, introduce among world patent WO 2000043342 and the French Patent FR 2788764, at N
2Protection down, Benzene Chloride is mixed with the 3-chlorpromazine chloride and is cooled to 0 ℃, adding hydrofluoric acid and boron trifluoride are made catalyzer, cyclization becomes 5-chloro-2 under vitriol oil effect again, the 3-bihydrogen-1-indenone.This method exists the energy consumption height, pollutes drawbacks such as big, operation inconvenience, aftertreatment difficulty.
Summary of the invention
In order to overcome existing 5-chloro-2, the preparation method's of 3-bihydrogen-1-indenone deficiency the invention provides a kind of 5-chloro-2, and the preparation method of 3-bihydrogen-1-indenone is pollution-free substantially, and is little to environmental influence, can realize suitability for industrialized production.
The technical solution adopted for the present invention to solve the technical problems is: a kind of 5-chloro-2, and the preparation method of 3-bihydrogen-1-indenone has following technical process: a, equipment preparation, and agitator, thermometer and drain are set in reactor; B, 3, the preparation of 4 '-dichloropropiophenone adds Benzene Chloride, aluminum chloride in reactor, cooling begins to drip the 3-chlorpromazine chloride, in the dropping process, the controlled temperature scope is-5 ℃～90 ℃, drips Bi Baowen, and chromatogram tracking no longer descends to the content of Benzene Chloride, the reaction feed liquid is slowly added in the solution of hydrochloric acid and frozen water composition, cooling, suction filtration get crude product, and be refining with organic solvent again, drying, get 3,4 '-dichloropropiophenone; C, 5-chloro-2, the preparation of 3-bihydrogen-1-indenone adds 3 in reactor, 4 '-dichloropropiophenone, aluminum chloride and salt heat to 80 ℃～250 ℃ and react, and reaction process adopts chromatogram tracking, after reaction was finished, cooling joined in hydrochloric acid and the mixture of ice and water then, cooling, suction filtration, refining with organic solvent, suction filtration, drying gets 5-chloro-2, the 3-bihydrogen-1-indenone.
Further: the input ratio of 3-chlorpromazine chloride, aluminum chloride and Benzene Chloride is (mol ratio) in the described b step, 3-chlorpromazine chloride: aluminum chloride: Benzene Chloride, 1: (0.75～2.2): (1.1～2.0); In the described c step 3, the input ratio of 4 '-dichloropropiophenone, aluminum chloride and salt is (mol ratio), 3, and 4 '-dichloropropiophenone: aluminum chloride: salt, 1: (1.1～5.5): (0.2～4.5).
Further: the input ratio of 3-chlorpromazine chloride, aluminum chloride and Benzene Chloride is (mol ratio) in the described b step, 3-chlorpromazine chloride: aluminum chloride: Benzene Chloride, 1: (0.9～1.45): (1.5～1.95); In the described c step 3, the input ratio of 4 '-dichloropropiophenone, aluminum chloride and salt is (mol ratio), 3, and 4 '-dichloropropiophenone: aluminum chloride: salt, 1: (3.0～5.0): (3.2～4.0).
Again further: the controlled temperature scope is 15 ℃～65 ℃ in the described b step; The controlled temperature scope is 120 ℃～185 ℃ in the described c step.
Again further: the controlled temperature scope is 25 ℃～55 ℃ in the described b step; The controlled temperature scope is 175 ℃～180 ℃ in the described c step.
Also further: dripping complete soaking time in the described b step is 2 hours.The reaction times is 4 hours in the described c step.
Again further: weight ratio is 1 in described hydrochloric acid and the mixture of ice and water: (20～35).
Again further: in the described b step in hydrochloric acid and the mixture of ice and water weight ratio be 1: 25.In the described c step in hydrochloric acid and the mixture of ice and water weight ratio be 1: 30.
The invention has the beneficial effects as follows, easy and simple to handle, with low cost, product yield height, Functionality, quality and appealing design, the corrodibility of raw material is little, after the hydrogenchloride water that discharges in the reaction absorbs, cover is used in the follow-up hydrolysis, and waste water can be used to prepare a kind of water conditioner---polymerize aluminum chloride, will be reduced to inferior limit to the influence of environment.
Embodiment
5-chloro-2, the preparation of 3-bihydrogen-1-indenone has following technical process:
1, in the reactor of 1000ml, agitator is set, thermometer and drain (tail gas absorption), add 480g Benzene Chloride (content 99%), the 300g aluminum chloride, be cooled to 25 ℃, beginning Dropwise 35 0g3-chlorpromazine chloride (content＞98%), in the dropping process, the controlled temperature scope is 25 ℃～55 ℃, drips Bi Baowen 2 hours, and chromatogram tracking no longer descends to the content of Benzene Chloride, the reaction feed liquid is slowly added in the solution of 80g hydrochloric acid and 2000g frozen water composition, cooling, suction filtration gets crude product, and is refining with organic solvent again, dry 3,4 '-dichloropropiophenone, content is more than 99%, and yield is more than 87%.
2, agitator, thermometer and drain (tail gas absorption) are set in the reactor of 5000ml, add 85g3,4 '-dichloropropiophenone (content＞99%), 275g aluminum chloride and 85g salt (industrial purified salt) heat to 175 ℃～180 ℃ reactions 4 hours, are cooled to 90 ℃ then, join in 40g hydrochloric acid and the 1200g mixture of ice and water, cooling, suction filtration, refining with organic solvent, suction filtration, dry 5-chloro-2,3-bihydrogen-1-indenone, the faint yellow solid of getting, mp, 96 ℃～97 ℃, content＞99%, yield is more than 66%.
Claims (10)
1. 5-chloro-2, the preparation method of 3-bihydrogen-1-indenone is characterized in that having following technical process:
A, equipment are prepared, and agitator, thermometer and drain are set in reactor;
B, 3, the preparation of 4 '-dichloropropiophenone adds Benzene Chloride, aluminum chloride in reactor, cooling begins to drip the 3-chlorpromazine chloride, in the dropping process, the controlled temperature scope is-5 ℃～90 ℃, drips Bi Baowen, and chromatogram tracking no longer descends to the content of Benzene Chloride, the reaction feed liquid is slowly added in the solution of hydrochloric acid and frozen water composition, cooling, suction filtration get crude product, and be refining with organic solvent again, drying, get 3,4 '-dichloropropiophenone;
C, 5-chloro-2, the preparation of 3-bihydrogen-1-indenone adds 3 in reactor, 4 '-dichloropropiophenone, aluminum chloride and salt heat to 80 ℃～250 ℃ and react, and reaction process adopts chromatogram tracking, after reaction was finished, cooling joined in hydrochloric acid and the mixture of ice and water then, cooling, suction filtration, refining with organic solvent, suction filtration, drying gets 5-chloro-2, the 3-bihydrogen-1-indenone.
2. 5-chloro-2 according to claim 1, the preparation method of 3-bihydrogen-1-indenone, it is characterized in that: the input ratio of 3-chlorpromazine chloride, aluminum chloride and Benzene Chloride is (mol ratio) in the described b step, 3-chlorpromazine chloride: aluminum chloride: Benzene Chloride, 1: (0.75～2.2): (1.1～2.0); In the described c step 3, the input ratio of 4 '-dichloropropiophenone, aluminum chloride and salt is (mol ratio), 3, and 4 '-dichloropropiophenone: aluminum chloride: salt, 1: (1.1～5.5): (0.2～4.5).
3. 5-chloro-2 according to claim 2, the preparation method of 3-bihydrogen-1-indenone, it is characterized in that: the input ratio of 3-chlorpromazine chloride, aluminum chloride and Benzene Chloride is (mol ratio) in the described b step, 3-chlorpromazine chloride: aluminum chloride: Benzene Chloride, 1: (0.9～1.45): (1.5～1.95); In the described c step 3, the input ratio of 4 '-dichloropropiophenone, aluminum chloride and salt is (mol ratio), 3, and 4 '-dichloropropiophenone: aluminum chloride: salt, 1: (3.0～5.0): (3.2～4.0).
4. 5-chloro-2 according to claim 1, the preparation method of 3-bihydrogen-1-indenone is characterized in that: the controlled temperature scope is 15 ℃～65 ℃ in the described b step; The controlled temperature scope is 120 ℃～185 ℃ in the described c step.
5. 5-chloro-2 according to claim 4, the preparation method of 3-bihydrogen-1-indenone is characterized in that: the controlled temperature scope is 25 ℃～55 ℃ in the described b step; The controlled temperature scope is 175 ℃～180 ℃ in the described c step.
6. 5-chloro-2 according to claim 1, the preparation method of 3-bihydrogen-1-indenone is characterized in that: dripping complete soaking time in the described b step is 2 hours.
7. 5-chloro-2 according to claim 1, the preparation method of 3-bihydrogen-1-indenone is characterized in that: the reaction times is 4 hours in the described c step.
8. 5-chloro-2 according to claim 1, the preparation method of 3-bihydrogen-1-indenone is characterized in that: weight ratio is 1 in described hydrochloric acid and the mixture of ice and water: (20～35).
9. according to claim 1 or 8 described 5-chloro-2, the preparation method of 3-bihydrogen-1-indenone is characterized in that: in the described b step in hydrochloric acid and the mixture of ice and water weight ratio be 1: 25.
10. according to claim 1 or 8 described 5-chloro-2, the preparation method of 3-bihydrogen-1-indenone is characterized in that: in the described c step in hydrochloric acid and the mixture of ice and water weight ratio be 1: 30.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02138331 CN1403434A (en) | 2002-09-20 | 2002-09-20 | Prepn process of 5-chloro-2,3-dihydro-1-indenone |
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| Application Number | Priority Date | Filing Date | Title |
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| CN 02138331 CN1403434A (en) | 2002-09-20 | 2002-09-20 | Prepn process of 5-chloro-2,3-dihydro-1-indenone |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597226A (en) * | 2008-06-03 | 2009-12-09 | 上海药明康德新药开发有限公司 | The synthetic method of 6-hydroxyl-1-indone |
| CN102491886A (en) * | 2011-12-01 | 2012-06-13 | 上海化工研究院 | Method for synthetizing indanone compound |
| CN103012086A (en) * | 2011-09-26 | 2013-04-03 | 江西阿尔法高科药业有限公司 | Method for preparing 2,3-dihydro-1-indanone and derivative thereof |
| CN103601625A (en) * | 2013-11-26 | 2014-02-26 | 姜堰市科研精细化工有限公司 | Method for producing 5-chloro-1-indanone |
| CN105732377A (en) * | 2016-01-29 | 2016-07-06 | 将辉兰 | Synthetic method of medicine intermediate namely indenone compound |
| CN108558627A (en) * | 2018-05-04 | 2018-09-21 | 山西大学 | A method of preparing 5- hydroxide radical-1-indenones |
| CN109293488A (en) * | 2018-11-14 | 2019-02-01 | 四平市精细化学品有限公司 | A kind of preparation method of 5-chloro-1-indanone |
| CN109534971A (en) * | 2018-11-05 | 2019-03-29 | 宿迁市科莱博生物化学有限公司 | 5- chlorine indone process units and its production method |
| CN112457179A (en) * | 2020-12-04 | 2021-03-09 | 阜新睿光氟化学有限公司 | Preparation method of 5-chloro-1-indanone |
| CN112939756A (en) * | 2021-03-03 | 2021-06-11 | 上海鼎素精细化工有限公司 | Improved process for preparing 5-chloro-indanone |
| CN113651784A (en) * | 2021-08-30 | 2021-11-16 | 大连新阳光材料科技有限公司 | Synthetic method of 3,3',4,4' -biphenyl tetracarboxylic dianhydride |
| CN115436507A (en) * | 2022-08-18 | 2022-12-06 | 山东京博生物科技有限公司 | Method for detecting content of 3,4' -dichloropropiophenone |
| CN117430489A (en) * | 2023-09-27 | 2024-01-23 | 山东京博生物科技有限公司 | A kind of preparation method of 5-chloro-1-indanone |
-
2002
- 2002-09-20 CN CN 02138331 patent/CN1403434A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597226A (en) * | 2008-06-03 | 2009-12-09 | 上海药明康德新药开发有限公司 | The synthetic method of 6-hydroxyl-1-indone |
| CN103012086A (en) * | 2011-09-26 | 2013-04-03 | 江西阿尔法高科药业有限公司 | Method for preparing 2,3-dihydro-1-indanone and derivative thereof |
| CN103012086B (en) * | 2011-09-26 | 2015-11-18 | 江西阿尔法高科药业有限公司 | One prepares the method for 2,3-bihydrogen-1-indenone and derivative thereof |
| CN102491886A (en) * | 2011-12-01 | 2012-06-13 | 上海化工研究院 | Method for synthetizing indanone compound |
| CN102491886B (en) * | 2011-12-01 | 2014-10-01 | 上海化工研究院 | A kind of synthetic method of indanone compound |
| CN103601625A (en) * | 2013-11-26 | 2014-02-26 | 姜堰市科研精细化工有限公司 | Method for producing 5-chloro-1-indanone |
| CN105732377A (en) * | 2016-01-29 | 2016-07-06 | 将辉兰 | Synthetic method of medicine intermediate namely indenone compound |
| CN105732377B (en) * | 2016-01-29 | 2018-07-27 | 南京波普生物医药研发有限公司 | A kind of synthetic method of pharmaceutical intermediate indanone compounds |
| CN108558627A (en) * | 2018-05-04 | 2018-09-21 | 山西大学 | A method of preparing 5- hydroxide radical-1-indenones |
| CN109534971A (en) * | 2018-11-05 | 2019-03-29 | 宿迁市科莱博生物化学有限公司 | 5- chlorine indone process units and its production method |
| CN109534971B (en) * | 2018-11-05 | 2021-12-28 | 宿迁市科莱博生物化学有限公司 | 5-chloro-indanone production device and production method thereof |
| CN109293488A (en) * | 2018-11-14 | 2019-02-01 | 四平市精细化学品有限公司 | A kind of preparation method of 5-chloro-1-indanone |
| CN109293488B (en) * | 2018-11-14 | 2022-05-27 | 四平市精细化学品有限公司 | Preparation method of 5-chloro-2, 3-dihydro-1-indanone |
| CN112457179A (en) * | 2020-12-04 | 2021-03-09 | 阜新睿光氟化学有限公司 | Preparation method of 5-chloro-1-indanone |
| CN112939756A (en) * | 2021-03-03 | 2021-06-11 | 上海鼎素精细化工有限公司 | Improved process for preparing 5-chloro-indanone |
| CN113651784A (en) * | 2021-08-30 | 2021-11-16 | 大连新阳光材料科技有限公司 | Synthetic method of 3,3',4,4' -biphenyl tetracarboxylic dianhydride |
| CN115436507A (en) * | 2022-08-18 | 2022-12-06 | 山东京博生物科技有限公司 | Method for detecting content of 3,4' -dichloropropiophenone |
| CN117430489A (en) * | 2023-09-27 | 2024-01-23 | 山东京博生物科技有限公司 | A kind of preparation method of 5-chloro-1-indanone |
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