CN104447208B - The method reclaiming triphenylcarbinol waste liquid is produced from olmesartan medoxomil - Google Patents
The method reclaiming triphenylcarbinol waste liquid is produced from olmesartan medoxomil Download PDFInfo
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- CN104447208B CN104447208B CN201410710229.4A CN201410710229A CN104447208B CN 104447208 B CN104447208 B CN 104447208B CN 201410710229 A CN201410710229 A CN 201410710229A CN 104447208 B CN104447208 B CN 104447208B
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- triphenylcarbinol
- waste liquid
- olmesartan medoxomil
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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 present invention relates to a kind of method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid, belong to triphenylcarbinol recovery technology field.The present invention is to produce to olmesartan medoxomil to add activated carbon in waste liquid, decolouring, filter pressing, then filtrate carries out decompression and solvent recovery, then adds diluted acid crystallization in the solution after decompression and solvent recovery, is centrifugally separating to obtain triphenylcarbinol crude product；Gained triphenylcarbinol crude product solvent is carried out recrystallization, is then passed through last handling process and prepares the fine work of triphenylcarbinol.Present invention process is stable, reaction condition is easily controllable, environmentally safe, low cost, the response rate high, be prone to industrialization.
Description
Technical field
The present invention relates to a kind of method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid, belong to triphenylcarbinol and reclaim
Technical field.
Background technology
Olmesartan medoxomil is a kind of chemicals for treating hypertension.The main method producing olmesartan medoxomil at present is with miaow
Triazole carboxylic acid's ester is initiation material, reacts with N-(trityl group)-5-(4 '-3-bromomethylbiphenyl-2-base) tetrazole and prepares triphenyl Austria
Mei Shatan ethyl ester；Triphenyl Olmesartan ethyl ester and potassium hydroxide effect, generate triphenyl Olmesartan acid potassium；Triphenyl Aomei
Husky smooth acid potassium prepares triphenyl olmesartan medoxomil with 4-chloromethyl-5-methyl-1,3-dioxy heterocyclic pentene-2-reactive ketone.Triphenyl Aomei
Husky smooth ester and acid effect, slough trityl-protecting group and generate triphenylcarbinol and olmesartan medoxomil, be performing centrifugal separation on Olmesartan
Become mixed waste liquor with other materials during waste liquid stayed by triphenylcarbinol after ester, do not carry out isolated and purified and reclaim comprehensive utilization,
Not only environment is caused pollution, and causes certain wasting of resources.
Summary of the invention
It is an object of the invention to provide a kind of method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid, its technique is steady
Determine, reaction condition is easily controllable, environmentally safe, low cost, the response rate high, be prone to industrialization.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid of the present invention, comprises the following steps:
(1) produce addition activated carbon in waste liquid, decolouring, filter pressing to olmesartan medoxomil, then filtrate carried out decompression and solvent recovery,
Then solution after decompression and solvent recovery add diluted acid crystallization, is centrifugally separating to obtain triphenylcarbinol crude product；
(2) step (1) gained triphenylcarbinol crude product solvent is carried out recrystallization, be then passed through last handling process and prepare three
The fine work of phenyl methanol.
In step (1), it is the centrifugal waste liquid preparing olmesartan medoxomil crude product operation that described olmesartan medoxomil produces waste liquid, Aomei
It is 15～20% that husky smooth ester produces the weight/mass percentage composition of triphenylcarbinol in waste liquid.
In step (1), described triphenylcarbinol is 1:0.02～0.1 with the mass ratio of activated carbon, and bleaching temperature is 50～80 DEG C,
Preferably 60～70 DEG C；Bleaching time is 20～40min, preferably 30min.
In step (1), described filter pressing temperature is 50～80 DEG C, and filter pressing pressure is 0.1～0.3MPa；Vacuum during decompression
>=-0.06Mpa, temperature is 50～60 DEG C.
In step (1), described diluted acid is salt aqueous acid, and the weight/mass percentage composition of hydrochloric acid is 2～5%；Triphenylcarbinol with
The mass ratio of diluted acid is 1:3～6, preferably 4～5；Crystallization temperature 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, preferably 30min.
In step (2), solvent for use is the mixed solution of first alcohol and water, and the mass ratio of first alcohol and water is 1:2～5, preferably 3～
4；Triphenylcarbinol crude product is 1:3～6 with the mass ratio of solvent, preferably 4～5.
In step (2), described recrystallization process is dissolving, filter pressing and crystallization.Solution temperature is 50～70 DEG C, preferably 60～
65℃；Dissolution time is 20～40min, preferably 30min；Filter pressing temperature is 50～70 DEG C, preferably 60～65 DEG C；The pressure of filter pressing
Power is 0.1～0.3Mpa；Crystallization temperature 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, from
The heart time is 20～40min, preferably 30min；Vacuum >=-0.08MPa, baking temperature is 50～80 DEG C, preferably 60～70 DEG C；
Drying time is 3～6h.
Compared with prior art, the method have the advantages that
The present invention is simple to operate, and process conditions are gentle, it is easy to control, and products obtained therefrom purity is high (HPLC content is more than 99.0%),
Yield is high (more than 94.8%), solves olmesartan medoxomil thoroughly and produces the triphenylcarbinol pollution problem to environment in waste liquid,
Olmesartan medoxomil in waste liquid has obtained recycling and purification simultaneously, decreases the three wastes, it is achieved that recycling economy, reduces life
Produce cost, process stabilizing, be suitable for industrialized production.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is further illustrated, but is not limiting as the enforcement of the present invention.
Raw materials used it is commercially available prod.
Embodiment 1
(1) in 2000L reactor, add the 1200kg olmesartan medoxomil containing 20wt% triphenylcarbinol and produce waste liquid, open
Stirring, add 4.8kg activated carbon, be warming up to 50 DEG C stirring decolouring 40min, filter pressing (temperature is 50 DEG C, and pressure is 0.2 ± 0.1MPa),
After filtrate reduced in volume (vacuum >=-0.06Mpa, temperature is 55 ± 5 DEG C) recycling design, concentrated solution is depressed into while hot and fills 1440kg
Stirring and crystallizing in the crystallization kettle of 2wt% aqueous hydrochloric acid solution, decrease temperature crystalline to 10 DEG C, insulation crystallization 30min, centrifugal, washing, dry
Dry 237.5kg triphenylcarbinol crude product, yield is 98.96%；
(2) adding 237.5kg methanol and 1187.5kg purified water in refining reaction still, stirring is lower adds 237.5kg triphenyl
Methanol crude product, is warming up to 70 DEG C, filter pressing after stirring and dissolving 40min (temperature is 70 DEG C, and pressure is 0.2 ± 0.1MPa), filtrate
Cooling stirring and crystallizing, in 15 DEG C of insulation crystallization 60min, blowing is centrifuged, washes with water, and discharging after drying, in vacuum
At >=-0.08MPa, temperature 80 DEG C, being dried 3 hours, prepare triphenylcarbinol fine work 227.3kg, yield is 95.71%, HPLC
Content is 99.43%, and product quality meets quality standard.
Embodiment 2
(1) in 2000L reactor, add the 1300kg olmesartan medoxomil containing 18.5wt% triphenylcarbinol and produce waste liquid, open
Opening stirring, add 24kg activated carbon, be warming up to 80 DEG C of stirring decolouring 20min, (temperature is 80 DEG C, and pressure is in filter pressing
0.2 ± 0.1MPa), after filtrate reduced in volume (vacuum >=-0.06Mpa, temperature is 55 ± 5 DEG C) recycling design, concentrated solution is taken advantage of
Hot pressing crystallizes 60min to stirring and crystallizing in the crystallization kettle fill 720kg 5wt% aqueous hydrochloric acid solution, decrease temperature crystalline to 25 DEG C, insulation,
Being centrifuged, wash with water, be dried to obtain 238.2kg triphenylcarbinol crude product, yield is 99.04%；
(2) adding 238.2kg methanol and 476.4kg purified water in refining reaction still, stirring is lower adds 238.2kg triphenyl
Methanol crude product, is warming up to 50 DEG C, filter pressing after stirring and dissolving 20min (temperature is 50 DEG C, and 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, in vacuum >=-0.08MPa,
Under temperature 50 C, being dried 6 hours, prepare triphenylcarbinol fine work 225.9kg, yield is 94.84%, and HPLC content is 99.61%,
Product quality meets quality standard.
Embodiment 3
(1) in 2000L reactor, add the 1412kg olmesartan medoxomil containing 17wt% triphenylcarbinol and produce waste liquid, open
Stirring, add 12kg activated carbon, be warming up to 70 DEG C stirring decolouring 30min, filter pressing (temperature is 70 DEG C, and pressure is 0.2 ± 0.1MPa),
After filtrate reduced in volume (vacuum >=-0.06Mpa, temperature is 55 ± 5 DEG C) recycling design, concentrated solution is depressed into while hot and fills 960kg
Stirring and crystallizing in the crystallization kettle of 4wt% aqueous hydrochloric acid solution, decrease temperature crystalline to 20 DEG C, insulation crystallization 50min, centrifugal, washing, dry
Dry 237.8kg triphenylcarbinol crude product, yield is 99.07%；
(2) adding 237.8kg methanol and 951.2kg purified water in refining reaction still, stirring is lower adds 237.8kg triphenyl
Methanol crude product, is warming up to 65 DEG C, filter pressing after stirring and dissolving 30min (temperature is 65 DEG C, and 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, in vacuum >=-0.08Mpa,
Under temperature 60 C, being dried 5 hours, prepare triphenylcarbinol fine work 226.5kg, yield is 95.25%, and HPLC content is 99.37%,
Product quality meets quality standard.
Embodiment 4
(1) in 2000L reactor, add the 1600kg olmesartan medoxomil containing 15wt% triphenylcarbinol and produce waste liquid, open
Stirring, adds 16.8kg activated carbon, is warming up to 60 DEG C of stirring decolouring 30min, and (temperature is 60 DEG C, and pressure is in filter pressing
0.2 ± 0.1MPa), after filtrate reduced in volume (vacuum >=-0.06Mpa, temperature is 55 ± 5 DEG C) recycling design, concentrated solution is taken advantage of
Hot pressing crystallizes 40min to stirring and crystallizing in the crystallization kettle fill 1200kg 3wt% aqueous hydrochloric acid solution, decrease temperature crystalline to 15 DEG C, insulation,
Centrifugal, washing, is dried to obtain 237.6kg triphenylcarbinol crude product, and yield is 99.0%；
(2) adding 237.6kg methanol and 712.8kg purified water in refining reaction still, stirring is lower adds 237.6kg triphenyl
Methanol crude product, is warming up to 60 DEG C, filter pressing after stirring and dissolving 25min (temperature is 60 DEG C, and 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, in vacuum >=-0.08MPa,
Under temperature 70 C, being dried 4 hours, prepare triphenylcarbinol fine work 226.9kg, yield is 95.5%, and HPLC content is 99.29%,
Product quality meets quality standard.
Claims (7)
1. one kind produces, from olmesartan medoxomil, the method reclaiming triphenylcarbinol waste liquid, it is characterised in that comprise the following steps:
(1) produce addition activated carbon in waste liquid, decolouring, filter pressing to olmesartan medoxomil, then filtrate carried out decompression and solvent recovery,
Then solution after decompression and solvent recovery add diluted acid crystallization, is centrifugally separating to obtain triphenylcarbinol crude product；Olmesartan medoxomil
Producing the weight/mass percentage composition of triphenylcarbinol in waste liquid is 15～20%；Triphenylcarbinol is 1 with the mass ratio of activated carbon:
0.02～0.1；Diluted acid is salt aqueous acid, and the weight/mass percentage composition of hydrochloric acid is 2～5%；Triphenylcarbinol and the quality of diluted acid
Ratio is 1:3～6；
(2) step (1) gained triphenylcarbinol crude product solvent is carried out recrystallization, be then passed through last handling process and prepare three
Phenyl methanol fine work；Solvent for use is the mixed solution of first alcohol and water, and the mass ratio of first alcohol and water is 1:2～5；Triphenylcarbinol
Crude product is 1:3～6 with the mass ratio of solvent.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 1, it is characterised in that:
In step (1), bleaching temperature is 50～80 DEG C, and bleaching time is 20～40min.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 1, it is characterised in that:
In step (1), filter pressing temperature is 50～80 DEG C, and filter pressing pressure is 0.1～0.3MPa；Vacuum >=-0.06Mpa during decompression,
Temperature is 50～60 DEG C.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 1, it is characterised in that:
In step (1), crystallization temperature is 10～25 DEG C, and crystallization time is 30～60min.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 1, it is characterised in that:
In step (2), recrystallization process is dissolving, filter pressing and crystallization.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 5, it is characterised in that:
In step (2), solution temperature is 50～70 DEG C, and dissolution time is 20～40min；Filter pressing temperature is 50～70 DEG C, and pressure is
0.1～0.3Mpa；Crystallization temperature is 5～15 DEG C, and crystallization time is 30～60min.
The method reclaiming triphenylcarbinol from olmesartan medoxomil production waste liquid the most according to claim 1, it is characterised in that:
In step (2), last handling process is centrifugal and vacuum drying；Vacuum >=-0.08MPa, baking temperature is 50～80 DEG C, dry
The dry time 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 |
|---|
| 奥美沙坦酯及其关键中间体的合成方法;韩薇薇等;《化学试剂》;20131231;第35卷(第8期);第711-716页 * |
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