CN104447208A - Method for reclaiming triphenyl carbinol from waste liquor from production of olmesartan medoxomil - Google Patents
Method for reclaiming triphenyl carbinol from waste liquor from production of olmesartan medoxomil Download PDFInfo
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- CN104447208A CN104447208A CN201410710229.4A CN201410710229A CN104447208A CN 104447208 A CN104447208 A CN 104447208A CN 201410710229 A CN201410710229 A CN 201410710229A CN 104447208 A CN104447208 A CN 104447208A
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- triphenylcarbinol
- waste liquid
- olmesartan medoxomill
- production waste
- method reclaiming
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
Abstract
The invention relates to a method for reclaiming triphenyl carbinol from waste liquor from production of olmesartan medoxomil, belonging to the technical field of reclaiming of triphenyl carbinol. The method comprises the following steps of: adding activated carbon into waste liquor from production of olmesartan medoxomil, decolorizing, filtering by pressing, reducing the pressure of a filtrate to reclaim a solvent, adding a diluted acid into the solution subjected to pressure reduction for solvent reclamation to crystallize, centrifugally separating to obtain crude triphenyl carbinol, recrystallizing the crude triphenyl carbinol with a solvent, and post-processing to obtain the fine triphenyl carbinol. The process provided by the invention is stale, can not cause pollution to environment, is low in cost and high in reclamation rate and is suitable for industrial production, and the reaction condition is easy to control.
Description
Technical field
The present invention relates to a kind of method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid, belong to triphenylcarbinol recovery technology field.
Background technology
Olmesartan medoxomill is that one is used for the treatment of hypertensive chemicals.The main method of current production olmesartan medoxomill is with imidazolyl carboxylic acid ester for starting raw material, reacts obtained triphenyl Olmesartan ethyl ester with N-(trityl group)-5-(4 '-3-bromomethylbiphenyl-2-base) tetrazole; Triphenyl Olmesartan ethyl ester and potassium hydroxide effect, generate triphenyl Olmesartan acid potassium; Triphenyl Olmesartan acid potassium and 4-chloromethyl-5-methyl isophthalic acid, 3-dioxole-2-reactive ketone obtains triphenyl olmesartan medoxomill.Triphenyl olmesartan medoxomill acts on acid; slough trityl-protecting group and generate triphenylcarbinol and olmesartan medoxomill; after centrifugation olmesartan medoxomill, triphenylcarbinol is stayed in waste liquid becomes mixed waste liquor with other materials; do not carry out separation and purification and reclaim comprehensive utilization; not only pollution is caused to environment, and cause certain wasting of resources.
Summary of the invention
The object of the present invention is to provide a kind of method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid, its process stabilizing, reaction conditions are easy to control, environmentally safe, cost is low, the rate of recovery is high, be easy to industrialization.
The method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid of the present invention, comprises the following steps:
(1) in olmesartan medoxomill production waste liquid, add gac, decolouring, press filtration, then carry out decompression and solvent recovery to filtrate, then in the solution after decompression and solvent recovery, add diluted acid crystallization, centrifugation obtains triphenylcarbinol crude product;
(2) step (1) gained triphenylcarbinol crude product solvent is carried out recrystallization, then obtain the fine work of triphenylcarbinol through last handling process.
In step (1), it is the centrifugal waste liquid preparing olmesartan medoxomill crude product operation that described olmesartan medoxomill produces waste liquid, and the mass percentage that olmesartan medoxomill produces triphenylcarbinol in waste liquid is 15 ~ 20%.
In step (1), the mass ratio of described triphenylcarbinol and gac is 1:0.02 ~ 0.1, and bleaching temperature is 50 ~ 80 DEG C, preferably 60 ~ 70 DEG C; Bleaching time is 20 ~ 40min, preferred 30min.
In step (1), described press filtration temperature is 50 ~ 80 DEG C, and press filtration pressure is 0.1 ~ 0.3MPa; Vacuum tightness >=-0.06Mpa during decompression, temperature is 50 ~ 60 DEG C.
In step (1), described diluted acid is salt aqueous acid, and the mass percentage of hydrochloric acid is 2 ~ 5%; The mass ratio of triphenylcarbinol and diluted acid is 1:3 ~ 6, preferably 4 ~ 5; Tc is 10 ~ 25 DEG C, and crystallization time is 30 ~ 60min; Time centrifugal, rotating speed is 1000 ~ 3000r/min, and centrifugation time is 20 ~ 40min, preferred 30min.
In step (2), solvent for use is the mixing solutions of first alcohol and water, and the mass ratio of first alcohol and water is 1:2 ~ 5, preferably 3 ~ 4; The mass ratio of triphenylcarbinol crude product and solvent is 1:3 ~ 6, preferably 4 ~ 5.
In step (2), described recrystallization process is dissolving, press filtration and crystallization.Solvent temperature is 50 ~ 70 DEG C, preferably 60 ~ 65 DEG C; Dissolution time is 20 ~ 40min, preferred 30min; Press filtration temperature is 50 ~ 70 DEG C, preferably 60 ~ 65 DEG C; The pressure of press filtration is 0.1 ~ 0.3Mpa; Tc is 5 ~ 15 DEG C, and crystallization time is 30 ~ 60min.
In step (2), described last handling process is centrifugal and vacuum-drying, and time centrifugal, rotating speed is 1000 ~ 3000r/min, and centrifugation time is 20 ~ 40min, preferred 30min; Vacuum tightness >=-0.08MPa, drying temperature is 50 ~ 80 DEG C, preferably 60 ~ 70 DEG C; Time of drying is 3 ~ 6h.
Compared with prior art, the present invention has following beneficial effect:
The present invention is simple to operate, processing condition are gentle, are easy to control, products obtained therefrom purity high (HPLC content is more than 99.0%), yield high (more than 94.8%), solve olmesartan medoxomill thoroughly and produce in waste liquid that triphenylcarbinol is to the pollution problem of environment, the olmesartan medoxomill simultaneously in waste liquid obtains recycling and purifying, decreases the three wastes, achieve recycling economy, reduce production cost, process stabilizing, be applicable to suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention is further illustrated, but do not limit enforcement of the present invention.
Raw materials usedly be commercially available prod.
Embodiment 1
(1) in 2000L reactor, add 1200kg produce waste liquid containing the olmesartan medoxomill of 20wt% triphenylcarbinol, open and stir, add 4.8kg gac, be warming up to 50 DEG C and stir decolouring 40min, (temperature is 50 DEG C in press filtration, pressure is 0.2 ± 0.1MPa), filtrate reduced in volume (vacuum tightness >=-0.06Mpa, temperature is 55 ± 5 DEG C) after recycling design, concentrated solution is depressed into stirring and crystallizing in the crystallization kettle filling 1440kg2wt% aqueous hydrochloric acid while hot, decrease temperature crystalline to 10 DEG C, insulation crystallization 30min, centrifugal, washing, dry 237.5kg triphenylcarbinol crude product, yield is 98.96%,
(2) in refining reaction still, 237.5kg methyl alcohol and 1187.5kg purified water is added, 237.5kg triphenylcarbinol crude product is added under stirring, be warming up to 70 DEG C, (temperature is 70 DEG C in press filtration after stirring and dissolving 40min, pressure is 0.2 ± 0.1MPa), filtrate cooling stirring and crystallizing, in 15 DEG C of insulation crystallization 60min, blowing is centrifugal, wash with water, discharging after drying, in vacuum tightness >=-0.08MPa, at temperature 80 DEG C, dry 3 hours, obtained triphenylcarbinol fine work 227.3kg, yield is 95.71%, HPLC content is 99.43%, quality product meets quality standard.
Embodiment 2
(1) in 2000L reactor, add 1300kg produce waste liquid containing the olmesartan medoxomill of 18.5wt% triphenylcarbinol, open and stir, add 24kg gac, be warming up to 80 DEG C and stir decolouring 20min, (temperature is 80 DEG C in press filtration, pressure is 0.2 ± 0.1MPa), filtrate reduced in volume (vacuum tightness >=-0.06Mpa, temperature is 55 ± 5 DEG C) after recycling design, concentrated solution is depressed into stirring and crystallizing in the crystallization kettle filling 720kg 5wt% aqueous hydrochloric acid while hot, decrease temperature crystalline to 25 DEG C, insulation crystallization 60min, centrifugal, wash with water, dry 238.2kg triphenylcarbinol crude product, yield is 99.04%,
(2) in refining reaction still, 238.2kg methyl alcohol and 476.4kg purified water is added, 238.2kg triphenylcarbinol crude product is added under stirring, be warming up to 50 DEG C, (temperature is 50 DEG C in press filtration after stirring and dissolving 20min, pressure is 0.2 ± 0.1MPa), filtrate cooling stirring and crystallizing, in 5 DEG C of insulation crystallization 30min, blowing is centrifugal, washing, discharging after drying, under vacuum tightness >=-0.08MPa, temperature 50 C, dry 6 hours, obtained triphenylcarbinol fine work 225.9kg, yield is 94.84%, HPLC content is 99.61%, and quality product meets quality standard.
Embodiment 3
(1) in 2000L reactor, add 1412kg produce waste liquid containing the olmesartan medoxomill of 17wt% triphenylcarbinol, open and stir, add 12kg gac, be warming up to 70 DEG C and stir decolouring 30min, (temperature is 70 DEG C in press filtration, pressure is 0.2 ± 0.1MPa), filtrate reduced in volume (vacuum tightness >=-0.06Mpa, temperature is 55 ± 5 DEG C) after recycling design, concentrated solution is depressed into stirring and crystallizing in the crystallization kettle filling 960kg4wt% aqueous hydrochloric acid while hot, decrease temperature crystalline to 20 DEG C, insulation crystallization 50min, centrifugal, washing, dry 237.8kg triphenylcarbinol crude product, yield is 99.07%,
(2) in refining reaction still, 237.8kg methyl alcohol and 951.2kg purified water is added, 237.8kg triphenylcarbinol crude product is added under stirring, be warming up to 65 DEG C, (temperature is 65 DEG C in press filtration after stirring and dissolving 30min, pressure is 0.2 ± 0.1MPa), filtrate cooling stirring and crystallizing, in 12 DEG C of insulation crystallization 50min, blowing is centrifugal, washing, discharging after drying, under vacuum tightness >=-0.08Mpa, temperature 60 C, dry 5 hours, obtained triphenylcarbinol fine work 226.5kg, yield is 95.25%, HPLC content is 99.37%, and quality product meets quality standard.
Embodiment 4
(1) in 2000L reactor, add 1600kg produce waste liquid containing the olmesartan medoxomill of 15wt% triphenylcarbinol, open and stir, add 16.8kg gac, be warming up to 60 DEG C and stir decolouring 30min, (temperature is 60 DEG C in press filtration, pressure is 0.2 ± 0.1MPa), filtrate reduced in volume (vacuum tightness >=-0.06Mpa, temperature is 55 ± 5 DEG C) after recycling design, concentrated solution is depressed into stirring and crystallizing in the crystallization kettle filling 1200kg 3wt% aqueous hydrochloric acid while hot, decrease temperature crystalline to 15 DEG C, insulation crystallization 40min, centrifugal, washing, dry 237.6kg triphenylcarbinol crude product, yield is 99.0%,
(2) in refining reaction still, 237.6kg methyl alcohol and 712.8kg purified water is added, 237.6kg triphenylcarbinol crude product is added under stirring, be warming up to 60 DEG C, (temperature is 60 DEG C in press filtration after stirring and dissolving 25min, pressure is 0.2 ± 0.1MPa), filtrate cooling stirring and crystallizing, in 8 DEG C of insulation crystallization 40min, blowing is centrifugal, washing, discharging after drying, under vacuum tightness >=-0.08MPa, temperature 70 C, dry 4 hours, obtained triphenylcarbinol fine work 226.9kg, yield is 95.5%, HPLC content is 99.29%, and quality product meets quality standard.
Claims (10)
1. produce from olmesartan medoxomill the method reclaiming triphenylcarbinol waste liquid, it is characterized in that comprising the following steps:
(1) in olmesartan medoxomill production waste liquid, add gac, decolouring, press filtration, then carry out decompression and solvent recovery to filtrate, then in the solution after decompression and solvent recovery, add diluted acid crystallization, centrifugation obtains triphenylcarbinol crude product;
(2) step (1) gained triphenylcarbinol crude product solvent is carried out recrystallization, then obtain triphenylcarbinol fine work through last handling process.
2. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1, it is characterized in that: in step (1), the mass percentage that olmesartan medoxomill produces triphenylcarbinol in waste liquid is 15 ~ 20%.
3. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1 and 2, it is characterized in that: in step (1), the mass ratio of triphenylcarbinol and gac is 1:0.02 ~ 0.1, and bleaching temperature is 50 ~ 80 DEG C, and bleaching time is 20 ~ 40min.
4. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1 and 2, it is characterized in that: in step (1), press filtration temperature is 50 ~ 80 DEG C, and press filtration pressure is 0.1 ~ 0.3MPa; Vacuum tightness >=-0.06Mpa during decompression, temperature is 50 ~ 60 DEG C.
5. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1 and 2, it is characterized in that: in step (1), diluted acid is salt aqueous acid, and the mass percentage of hydrochloric acid is 2 ~ 5%; The mass ratio of triphenylcarbinol and diluted acid is 1:3 ~ 6.
6. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1 and 2, it is characterized in that: in step (1), Tc is 10 ~ 25 DEG C, and crystallization time is 30 ~ 60min.
7. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1, it is characterized in that: in step (2), solvent for use is the mixing solutions of first alcohol and water, and the mass ratio of first alcohol and water is 1:2 ~ 5; The mass ratio of triphenylcarbinol crude product and solvent is 1:3 ~ 6.
8. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1, is characterized in that: in step (2), and recrystallization process is dissolving, press filtration and crystallization.
9. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1 or 8, it is characterized in that: in step (2), solvent temperature is 50 ~ 70 DEG C, and dissolution time is 20 ~ 40min; Press filtration temperature is 50 ~ 70 DEG C, and pressure is 0.1 ~ 0.3Mpa; Tc is 5 ~ 15 DEG C, and crystallization time is 30 ~ 60min.
10. the method reclaiming triphenylcarbinol from olmesartan medoxomill production waste liquid according to claim 1, it is characterized in that: in step (2), last handling process is centrifugal and vacuum-drying; Vacuum tightness >=-0.08MPa, drying temperature is 50 ~ 80 DEG C, and time of drying is 3 ~ 6h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410710229.4A CN104447208B (en) | 2014-11-28 | 2014-11-28 | The method reclaiming triphenylcarbinol waste liquid is produced from olmesartan medoxomil |
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| CN201410710229.4A CN104447208B (en) | 2014-11-28 | 2014-11-28 | The method reclaiming triphenylcarbinol waste liquid is produced from olmesartan medoxomil |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102459243A (en) * | 2009-05-20 | 2012-05-16 | 兰贝克赛实验室有限公司 | Process for the preparation of olmesartan medoxomil |
| CN102584804A (en) * | 2011-12-13 | 2012-07-18 | 浙江华海药业股份有限公司 | Process for preparing olmesartan medoxomil with trityl olmesartan medoxomil deprotection base |
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- 2014-11-28 CN CN201410710229.4A patent/CN104447208B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102459243A (en) * | 2009-05-20 | 2012-05-16 | 兰贝克赛实验室有限公司 | Process for the preparation of olmesartan medoxomil |
| CN102584804A (en) * | 2011-12-13 | 2012-07-18 | 浙江华海药业股份有限公司 | Process for preparing olmesartan medoxomil with trityl olmesartan medoxomil deprotection base |
Non-Patent Citations (1)
| Title |
|---|
| 韩薇薇等: "奥美沙坦酯及其关键中间体的合成方法", 《化学试剂》, vol. 35, no. 8, 31 December 2013 (2013-12-31), pages 711 - 716 * |
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| CN104447208B (en) | 2016-08-24 |
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