CN102267887A - Synthesis process for 1-hydroxycyclohexyl phenyl ketone - Google Patents
Synthesis process for 1-hydroxycyclohexyl phenyl ketone Download PDFInfo
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- CN102267887A CN102267887A CN2011102006329A CN201110200632A CN102267887A CN 102267887 A CN102267887 A CN 102267887A CN 2011102006329 A CN2011102006329 A CN 2011102006329A CN 201110200632 A CN201110200632 A CN 201110200632A CN 102267887 A CN102267887 A CN 102267887A
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Abstract
The invention provides a synthesis process for 1-hydroxycyclohexyl phenyl ketone. The invention is characterized in that: in the synthesis process, cyclohexanecarboxylic acid is used as a raw material and undergoes the reactions of acylation, Friedel-Crafts and alkaline hydrolysis to obtain a crude product of 1-hydroxycyclohexyl phenyl ketone, and the crude product is subjected to refined distillation, crystallization and drying to obtain a finished product of 1-hydroxycyclohexyl phenyl ketone. The synthesis process provided in the invention is more reasonable; no sulfur dioxide gas is emitted in the process; resultant sodium chloride poses little pollution to environment; the yield of the product is high.
Description
Technical field
The present invention relates to a kind of synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone.
Background technology
Prior art for preparing 1-hydroxy-cyclohexyl phenyl ketone synthesis technique is mainly: hexahydrobenzoic acid is through sulfur oxychloride chlorination, cyclohexyl acyl chlorides and benzoyl group generation intermediate phenylcyclohexane ketone, the latter through bromination again hydrolysis be generated as 1-bromine cyclohexyl phenyl ketone.The defective of this technology is the sulfurous gas that produces, and material environmental pollutions such as Sodium Bromide strengthen, and product yield is lower etc.
Summary of the invention
Technical problem to be solved by this invention is at the deficiencies in the prior art, the synthesis technique of the 1-hydroxy-cyclohexyl phenyl ketone of provide that a kind of technology is more reasonable, safety and environmental protection, product yield are higher.
Technical problem to be solved by this invention is to realize by following technical scheme.The present invention is a kind of synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone, is characterized in, its step is as follows:
⑴ acidylate: hexahydrobenzoic acid is added in the reactor, be warmed up to 35 ± 2 ℃, add phosphorus trichloride, 60 ± 2 ℃ of insulations divided and remove inorganic layer after at least 4 hours, got cyclohexanecarbonyl chloride; Wherein, the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 1.8-2.2:1;
⑵ Friedel-Crafts reaction: benzene and catalyzer aluminum chloride are joined in the reactor, after being cooled to 5-10 ℃, drip the cyclohexanecarbonyl chloride that step (1) makes, the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:2.9-3.1:3.16-3.36,15 ± 2 ℃ at least 2.5 hours, obtain the network and the thing of cyclohexyl phenyl ketone and aluminum chloride;
⑶ hydrolysis reaction: be to add in the complex compound in the dilute hydrochloric acid of 1.5-2.5% an amount of mass concentration, stir layering, divide and remove to contain the aluminum chloride water layer, add an amount of washing acid then, to pH〉5 o'clock finish, slough unreacting material benzene by distillation at last, the cyclohexyl phenyl ketone;
⑷ chlorination reaction: the cyclohexyl phenyl ketone is added in the chlorination tank, is warming up to 60 ± 2 ℃, the back feeds chlorine, and reaction finishes, and gets 1-chlorine cyclohexyl phenyl ketone;
⑸ alkaline hydrolysis reaction: by weight 1:0.95-1.10 1-chlorine cyclohexyl phenyl ketone is added in the liquid caustic soda, is stirred to reaction and finishes, add the toluene extraction then, divide to fall water, precipitation reclaims toluene, obtains 1-hydroxy cyclohexyl phenylketone crude product;
⑹ refining: 1-hydroxy cyclohexyl phenylketone crude product is put into rectifying still, and under the lobe pump decompression, the rectifying product is collected cut; The product that rectifying is come out is put in the crystallization kettle, used the petroleum ether dissolution recrystallization again, centrifugation then, the distillation mother liquor steams the reuse of solvent sherwood oil, gets finished product 1-hydroxy cyclohexyl phenylketone after the wet product oven dry.
The optimal technical scheme of the synthesis technique of above-described 1-hydroxy-cyclohexyl phenyl ketone is:
1, in the step (1), the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 2:1.
2, in the step (2), the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:3:3.26.
3, the hydrogen chloride gas of step (2) reaction generation absorbs and recovery set usefulness by three grades of sprays; The chloride tail gas that step (4) reaction produces adopts falling liquid film to add the alkali lye absorption; The hydrogen chloride gas that reaction produces absorbs by three grades of sprays and recovery set is used.
The principal reaction equation of synthesis technique of the present invention is as follows:
⑴ acidylate:
⑵ Fu Ke
⑶ hydrolysis:
⑷ chlorination:
⑸ alkaline hydrolysis:
Compared with prior art, technology of the present invention is more reasonable, and production process does not have sulfur dioxide gas and emits, and the sodium-chlor environmental pollution of generation is less, and product yield is higher.
Embodiment
Below further describe concrete technical scheme of the present invention,, and do not constitute restriction its right so that those skilled in the art understands the present invention further.
Embodiment 1, a kind of synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone, and its step is as follows:
⑴ acidylate: hexahydrobenzoic acid is added in the reactor, be warmed up to 33 ℃, add phosphorus trichloride, 58 ℃ of insulations divided and remove inorganic layer after at least 4 hours, got cyclohexanecarbonyl chloride; Wherein, the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 1.8:1;
⑵ Friedel-Crafts reaction: benzene and catalyzer aluminum chloride are joined in the reactor, after being cooled to 5 ℃, drip the cyclohexanecarbonyl chloride that step (1) makes, the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:2.9:3.16,13 ℃ at least 2.5 hours, obtain the network and the thing of cyclohexyl phenyl ketone and aluminum chloride;
⑶ hydrolysis reaction: be to add in the complex compound in 1.5% the dilute hydrochloric acid an amount of mass concentration, stir layering, divide and remove to contain the aluminum chloride water layer, add an amount of washing acid then, to pH〉5 o'clock finish, slough unreacting material benzene by distillation at last, the cyclohexyl phenyl ketone;
⑷ chlorination reaction: the cyclohexyl phenyl ketone is added in the chlorination tank, is warming up to 58 ℃, the back feeds chlorine, and reaction finishes, and gets 1-chlorine cyclohexyl phenyl ketone;
⑸ alkaline hydrolysis reaction: by weight 1:0.95 1-chlorine cyclohexyl phenyl ketone is added in the liquid caustic soda, is stirred to reaction and finishes, add the toluene extraction then, divide to fall water, precipitation reclaims toluene, obtains 1-hydroxy cyclohexyl phenylketone crude product;
⑹ refining: 1-hydroxy cyclohexyl phenylketone crude product is put into rectifying still, and under the lobe pump decompression, the rectifying product is collected cut; The product that rectifying is come out is put in the crystallization kettle, used the petroleum ether dissolution recrystallization again, centrifugation then, the distillation mother liquor steams the reuse of solvent sherwood oil, gets finished product 1-hydroxy cyclohexyl phenylketone after the wet product oven dry.
Embodiment 2, a kind of synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone, and its step is as follows:
⑴ acidylate: hexahydrobenzoic acid is added in the reactor, be warmed up to 37 ℃, add phosphorus trichloride, 62 ℃ of insulations divided and remove inorganic layer after at least 4 hours, got cyclohexanecarbonyl chloride; Wherein, the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 2.2:1;
⑵ Friedel-Crafts reaction: benzene and catalyzer aluminum chloride are joined in the reactor, after being cooled to 10 ℃, drip the cyclohexanecarbonyl chloride that step (1) makes, the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:3.1:3.36,15 ± 2 ℃ at least 2.5 hours, obtain the network and the thing of cyclohexyl phenyl ketone and aluminum chloride;
⑶ hydrolysis reaction: be to add in the complex compound in 2.5% the dilute hydrochloric acid an amount of mass concentration, stir layering, divide and remove to contain the aluminum chloride water layer, add an amount of washing acid then, to pH〉5 o'clock finish, slough unreacting material benzene by distillation at last, the cyclohexyl phenyl ketone;
⑷ chlorination reaction: the cyclohexyl phenyl ketone is added in the chlorination tank, is warming up to 62 ℃, the back feeds chlorine, and reaction finishes, and gets 1-chlorine cyclohexyl phenyl ketone;
⑸ alkaline hydrolysis reaction: by weight 1:1.10 1-chlorine cyclohexyl phenyl ketone is added in the liquid caustic soda, is stirred to reaction and finishes, add the toluene extraction then, divide to fall water, precipitation reclaims toluene, obtains 1-hydroxy cyclohexyl phenylketone crude product;
⑹ refining: 1-hydroxy cyclohexyl phenylketone crude product is put into rectifying still, and under the lobe pump decompression, the rectifying product is collected cut; The product that rectifying is come out is put in the crystallization kettle, used the petroleum ether dissolution recrystallization again, centrifugation then, the distillation mother liquor steams the reuse of solvent sherwood oil, gets finished product 1-hydroxy cyclohexyl phenylketone after the wet product oven dry.
Embodiment 3, a kind of synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone, and its step is as follows:
⑴ acidylate: hexahydrobenzoic acid is added in the reactor, be warmed up to 35 ℃, add phosphorus trichloride, 60 ℃ of insulations divided and remove inorganic layer after at least 4 hours, got cyclohexanecarbonyl chloride; Wherein, the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 2:1;
⑵ Friedel-Crafts reaction: benzene and catalyzer aluminum chloride are joined in the reactor, after being cooled to 8 ℃, drip the cyclohexanecarbonyl chloride that step (1) makes, the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:3:3.26,15 ℃ at least 2.5 hours, obtain the network and the thing of cyclohexyl phenyl ketone and aluminum chloride;
⑶ hydrolysis reaction: be to add in the complex compound in 2.0% the dilute hydrochloric acid an amount of mass concentration, stir layering, divide and remove to contain the aluminum chloride water layer, add an amount of washing acid then, to pH〉5 o'clock finish, slough unreacting material benzene by distillation at last, the cyclohexyl phenyl ketone;
⑷ chlorination reaction: the cyclohexyl phenyl ketone is added in the chlorination tank, is warming up to 60 ℃, the back feeds chlorine, and reaction finishes, and gets 1-chlorine cyclohexyl phenyl ketone;
⑸ alkaline hydrolysis reaction: by weight 1:1.06 1-chlorine cyclohexyl phenyl ketone is added in the liquid caustic soda, is stirred to reaction and finishes, add the toluene extraction then, divide to fall water, precipitation reclaims toluene, obtains 1-hydroxy cyclohexyl phenylketone crude product;
⑹ refining: 1-hydroxy cyclohexyl phenylketone crude product is put into rectifying still, and under the lobe pump decompression, the rectifying product is collected cut; The product that rectifying is come out is put in the crystallization kettle, used the petroleum ether dissolution recrystallization again, centrifugation then, the distillation mother liquor steams the reuse of solvent sherwood oil, gets finished product 1-hydroxy cyclohexyl phenylketone after the wet product oven dry.
The hydrogen chloride gas that step (2) reaction produces absorbs by three grades of sprays and recovery set is used; The chloride tail gas that step (4) reaction produces adopts falling liquid film to add the alkali lye absorption; The hydrogen chloride gas that reaction produces absorbs by three grades of sprays and recovery set is used.
Claims (4)
1. the synthesis technique of a 1-hydroxy-cyclohexyl phenyl ketone is characterized in that, its step is as follows:
⑴ acidylate: hexahydrobenzoic acid is added in the reactor, be warmed up to 35 ± 2 ℃, add phosphorus trichloride, 60 ± 2 ℃ of insulations divided and remove inorganic layer after at least 4 hours, got cyclohexanecarbonyl chloride; Wherein, the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 1.8-2.2:1;
⑵ Friedel-Crafts reaction: benzene and catalyzer aluminum chloride are joined in the reactor, after being cooled to 5-10 ℃, drip the cyclohexanecarbonyl chloride that step (1) makes, the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:2.9-3.1:3.16-3.36,15 ± 2 ℃ at least 2.5 hours, obtain the network and the thing of cyclohexyl phenyl ketone and aluminum chloride;
⑶ hydrolysis reaction: be to add in the complex compound in the dilute hydrochloric acid of 1.5-2.5% an amount of mass concentration, stir layering, divide and remove to contain the aluminum chloride water layer, add an amount of washing acid then, to pH〉5 o'clock finish, slough unreacting material benzene by distillation at last, the cyclohexyl phenyl ketone;
⑷ chlorination reaction: the cyclohexyl phenyl ketone is added in the chlorination tank, is warming up to 60 ± 2 ℃, the back feeds chlorine, and reaction finishes, and gets 1-chlorine cyclohexyl phenyl ketone;
⑸ alkaline hydrolysis reaction: by weight 1:0.95-1.10 1-chlorine cyclohexyl phenyl ketone is added in the liquid caustic soda, is stirred to reaction and finishes, add the toluene extraction then, divide to fall water, precipitation reclaims toluene, obtains 1-hydroxy cyclohexyl phenylketone crude product;
⑹ refining: 1-hydroxy cyclohexyl phenylketone crude product is put into rectifying still, and under the lobe pump decompression, the rectifying product is collected cut; The product that rectifying is come out is put in the crystallization kettle, used the petroleum ether dissolution recrystallization again, centrifugation then, the distillation mother liquor steams the reuse of solvent sherwood oil, gets finished product 1-hydroxy cyclohexyl phenylketone after the wet product oven dry.
2. the synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone according to claim 1 is characterized in that: in the step (1), the weight ratio of raw material hexahydrobenzoic acid and phosphorus trichloride is 2:1.
3. the synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone according to claim 1 is characterized in that: in the step (2), the weight ratio of benzene, aluminum chloride and cyclohexanecarbonyl chloride is 9:3:3.26.
4. the synthesis technique of 1-hydroxy-cyclohexyl phenyl ketone according to claim 1 is characterized in that: the hydrogen chloride gas that step (2) reaction produces absorbs by three grades of sprays and recovery set is used; The chloride tail gas that step (4) reaction produces adopts falling liquid film to add the alkali lye absorption, and the hydrogen chloride gas that reaction produces is used by three grades of spray absorptions and recovery set.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017101553A1 (en) * | 2015-12-15 | 2017-06-22 | 常州强力先端电子材料有限公司 | Fluorene multifunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
| CN106883114A (en) * | 2015-12-15 | 2017-06-23 | 常州强力先端电子材料有限公司 | A kind of fluorenes class polyfunctionality light trigger and its preparation and application |
| CN108299172A (en) * | 2018-02-13 | 2018-07-20 | 江苏优普生物化学科技股份有限公司 | The synthetic method of photoinitiator 1- hydroxycyclohexyl phenyl ketones |
| CN108911959A (en) * | 2018-07-04 | 2018-11-30 | 大丰鑫源达化工有限公司 | A kind of preparation process of photoinitiator 184 |
| CN108911960A (en) * | 2018-08-07 | 2018-11-30 | 宁夏沃凯珑新材料有限公司 | A kind of preparation method of photoinitiator 1- hydroxycyclohexyl phenyl ketone |
| CN109503343A (en) * | 2018-12-28 | 2019-03-22 | 常州久日化学有限公司 | A kind of preparation method of photoinitiator 184 |
| CN109678691A (en) * | 2019-02-22 | 2019-04-26 | 安达市多森新材料科技有限公司 | A kind of purification process of 1- hydroxycyclohexyl phenyl ketone |
| CN109896942A (en) * | 2017-12-07 | 2019-06-18 | 孙建 | A kind of preparation method of alpha-alcohol ketone photoinitiator |
| CN110294667A (en) * | 2018-03-23 | 2019-10-01 | 江苏英力科技发展有限公司 | A method of preparing cyclohexyl phenyl ketone |
| CN111960934A (en) * | 2020-08-26 | 2020-11-20 | 辽宁科技大学 | Synthesis method of photoinitiator 1-hydroxycyclohexyl phenyl ketone |
| US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
| CN113493372A (en) * | 2020-04-03 | 2021-10-12 | 常州强力先端电子材料有限公司 | Preparation method of photoinitiator |
| CN115838327A (en) * | 2022-12-06 | 2023-03-24 | 常州久日化学有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
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| CN106883114A (en) * | 2015-12-15 | 2017-06-23 | 常州强力先端电子材料有限公司 | A kind of fluorenes class polyfunctionality light trigger and its preparation and application |
| US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
| CN106883114B (en) * | 2015-12-15 | 2019-11-19 | 常州强力先端电子材料有限公司 | A kind of fluorenes class polyfunctionality photoinitiator and its preparation and application |
| WO2017101553A1 (en) * | 2015-12-15 | 2017-06-22 | 常州强力先端电子材料有限公司 | Fluorene multifunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
| US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
| CN109896942A (en) * | 2017-12-07 | 2019-06-18 | 孙建 | A kind of preparation method of alpha-alcohol ketone photoinitiator |
| CN108299172A (en) * | 2018-02-13 | 2018-07-20 | 江苏优普生物化学科技股份有限公司 | The synthetic method of photoinitiator 1- hydroxycyclohexyl phenyl ketones |
| CN110294667A (en) * | 2018-03-23 | 2019-10-01 | 江苏英力科技发展有限公司 | A method of preparing cyclohexyl phenyl ketone |
| CN108911959A (en) * | 2018-07-04 | 2018-11-30 | 大丰鑫源达化工有限公司 | A kind of preparation process of photoinitiator 184 |
| CN108911959B (en) * | 2018-07-04 | 2021-12-10 | 大丰鑫源达化工有限公司 | Preparation process of photoinitiator 184 |
| CN108911960A (en) * | 2018-08-07 | 2018-11-30 | 宁夏沃凯珑新材料有限公司 | A kind of preparation method of photoinitiator 1- hydroxycyclohexyl phenyl ketone |
| CN109503343A (en) * | 2018-12-28 | 2019-03-22 | 常州久日化学有限公司 | A kind of preparation method of photoinitiator 184 |
| CN109503343B (en) * | 2018-12-28 | 2022-07-12 | 常州久日化学有限公司 | Preparation method of photoinitiator 184 |
| CN109678691A (en) * | 2019-02-22 | 2019-04-26 | 安达市多森新材料科技有限公司 | A kind of purification process of 1- hydroxycyclohexyl phenyl ketone |
| CN113493372A (en) * | 2020-04-03 | 2021-10-12 | 常州强力先端电子材料有限公司 | Preparation method of photoinitiator |
| CN113493372B (en) * | 2020-04-03 | 2023-08-08 | 常州强力先端电子材料有限公司 | Preparation method of photoinitiator |
| CN111960934A (en) * | 2020-08-26 | 2020-11-20 | 辽宁科技大学 | Synthesis method of photoinitiator 1-hydroxycyclohexyl phenyl ketone |
| CN115838327A (en) * | 2022-12-06 | 2023-03-24 | 常州久日化学有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
| CN115838327B (en) * | 2022-12-06 | 2024-05-03 | 湖南久日新材料有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
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Application publication date: 20111207 |