CN106317117A - Method for synthesizing 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane through oxidation safely and efficiently by utilizing micro-channel continuous flow reactor - Google Patents
Method for synthesizing 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane through oxidation safely and efficiently by utilizing micro-channel continuous flow reactor Download PDFInfo
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- CN106317117A CN106317117A CN201610689396.4A CN201610689396A CN106317117A CN 106317117 A CN106317117 A CN 106317117A CN 201610689396 A CN201610689396 A CN 201610689396A CN 106317117 A CN106317117 A CN 106317117A
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- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000007254 oxidation reaction Methods 0.000 title abstract description 17
- 230000003647 oxidation Effects 0.000 title abstract description 14
- 230000002194 synthesizing effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 239000001301 oxygen Substances 0.000 claims abstract description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000001590 oxidative effect Effects 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 238000003786 synthesis reaction Methods 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 6
- 230000010354 integration Effects 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethyl hydrogen phosphate Chemical class C[N+](C)(C)CCOP(O)([O-])=O YHHSONZFOIEMCP-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000011981 development test Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an efficient oxidation method for oxidizing 2-chlorine-1,3,2-dioxaphospholane (CDP) into 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane (COP) by utilizing a micro-channel continuous flow reactor. The CDP and an oxygen source are subjected to mixing enhancement by the micro-channel continuous flow reactor, and continuous flow reaction is realized through modularized series connection of the micro-channel reaction unit, so that the speed, the productivity, the purity and the safety of the oxidation reaction are improved.
Description
Technical field
The present invention relates to the safe and efficient oxidative synthesis 2-chloro-2-oxygen from chloro-1,3, the 2-dioxaphospholane (CDP) of 2-
The method closing-1,3,2-dioxaphospholane (COP).
Technical background
COP (COP) is synthesis anticoagulant material, blood compatibility material, life
Thing compatible material, controlled drug delivery system, phosphocholine class medicine, high-end cosmetics, biological friendly surface activating agent and antibiosis
Thing stains the important intermediate of the biological conformation friendly interface materials such as material.Approach the simplest and the most direct for synthesis COP is from 2-chloro-1,3,
The oxidation of 2-dioxaphospholane (CDP).The useful chlorosulfonic acid of approach preparing COP from CDP oxidation carries out aoxidizing (Gross, U.S.
State's patent 4371509), carry out aoxidizing (JACS, 80,5441,1958) with dinitrogen tetroxide；With oxygen be oxidant benzene be molten
Agent, carries out aoxidizing (Lerourneur, et al., United States Patent (USP) 4,950,712 under the reflux temperature of benzene；Straford,et
Al., United States Patent (USP) 5,591,882；Leong, et al., United States Patent (USP) 6,805,876；Driver,Michael John,et
al.,WO/1992/007885；Bowers, et al., United States Patent (USP) 5,648,442；5,705,583；6,225,431 and
Edmundson et al., ChemInd, London, 1828,1962) and be oxidant solvent-free green oxidation method with oxygen
(Chinese patent ZL 201110102217.X).
Chinese patent ZL 201110102217.X discloses a kind of solvent-free green oxidation method, by solvent benzol from technique
Remove, greatly reduce manufacturing process toxicity, simplify product purifying technique step, but, in place of this patent still has some deficits, just
Being that oxidation rate is fast not, efficiency is not high enough, and tradition autoclave oxidation technology is high-risk technique, at the shape that response magnitude is huge
Having potential safety hazard under condition, we, in order to develop its advantage, overcome its weak point, and we are through a lot of development tests, the completeest
Become the art of this patent, i.e. utilize microchannel continuous flow reactor safe and efficient oxidative synthesis 2-chloro-2-oxygenate-1,3,2-dioxies
The method of phospholane.
Summary of the invention
It is an object of the invention to: provide one to utilize microchannel continuous flow reactor from chloro-1,3, the 2-dioxy phosphorus heterocycles of 2-
The method of pentane (CDP) safe and efficient oxidative synthesis COP (COP).
Described microchannel continuous flow reactor include piezometer and thermometer, effusion meter, material transferring pump and control system,
Valve, relief valve, heat exchange control system, microchannel reaction member integration module, high/low temperature all-in-one and various connected pipeline；
As shown in Figure 1.The continuous stream in described microchannel refers to, by microchannel reaction member integrated modular, and by multiple block coupled in series, real
Flow reaction the most continuously.
Described synthetic method comprises the following steps:
In CDP stock bottle, add CDP raw material, open high/low temperature all-in-one and set oxidizing reaction temperature as 1～200 DEG C,
Regulation residence time of material is 0.05～600 second, opens oxygen source valve and oxygen source imports microchannel continuous flow reactor, then open
Transmission pump squeezes into microchannel continuous flow reactor CDP, and reaction starts, and reaction temperature maintains preliminary set time, and pressure is
0.05～1.8MPa, the response time is 0.5～120 minute, and reaction obtains COP product after terminating.
Preferably, high/low temperature all-in-one sets oxidizing reaction temperature as 60～150 DEG C；
Preferably, described pressure is 0.10～0.6MPa；
Preferably, described oxygen source includes pure oxygen and oxygen-enriched air；
Preferably, described residence time of material is 5～60 seconds；
Preferably, the oxygen content of described oxygen-enriched air is 30%～98%, and oxidizing reaction temperature is 30～200 DEG C, pressure
It is 0.15～1.8MPa.
Beneficial effect:
Owing to this patent is improving the aspect innovations such as CDP oxidation rate, reaction yield, product purity and process safety,
Therefore, compared with existing dioxygen oxidation CDP synthesis COP technology, it is higher that technical solution of the present invention makes CDP oxidation technology have
Oxidation rate, oxidation productivity and safety.Including:
1. the strengthening that technical solution of the present invention utilizes CDP and oxygen to enter microchannel reaction member mix and improves oxidation instead
The speed answered and productivity, make the time of CDP oxidation reaction be greatly shortened；
2. the yield of reaction significantly improves；
3. reduce owing to the response time shortens side reaction, substantially increase product purity；
4. microchannel is reacted unit-modularized series connection, it is achieved flow reaction, the more traditional autoclave of reaction member liquid holdup continuously
Reaction reduces by more than 1000 times, and in the instant microchannel of device of annual output kiloton, the inventory of participation oxidation reaction is less than 3 liters, thus
Avoid enlarge-effect, improve production security.
Accompanying drawing explanation
Fig. 1 is to utilize microchannel continuous flow reactor that COP is oxidized to the technique diagram of COP.
1, oxygen source, 2, CDP raw material, 3, COP product, 4, effusion meter, 5, material transferring pump and control system, 6, high/low temperature one
Body machine, 7, microchannel reaction member, 8, microchannel reaction member integration module, 9, heat exchange control system.
CDP of the present invention is chloro-1,3, the 2-dioxaphospholane of 2-, and COP is 2-chloro-2-oxygenate-1,3,2-dioxies
Phospholane.
Detailed description of the invention
Below by concrete implementation, the invention will be further described.
Embodiment one:
Microchannel continuous flow reactor includes piezometer and thermometer, effusion meter 4, material transferring pump and control system 5, valve
Door, relief valve, heat exchange control system 9, microchannel reaction member integration module 8, high/low temperature all-in-one 6 and various connected pipe
Road, as shown in Figure 1.Described microchannel reaction member integration module 8 is that microchannel reaction member 7 is integrated.
126.48 grams of CDP raw materials 2 it are weighed in CDP stock bottle.Open high/low temperature all-in-one set oxidizing reaction temperature as
150 DEG C, regulation residence time of material is 15 seconds, opens oxygen source valve and oxygen source 1 is imported microchannel continuous flow reactor, then open
Transmission pump squeezes into microchannel continuous flow reactor CDP, and reaction starts, and reaction temperature maintains preliminary set time 150 DEG C, pressure
Power is 0.25MPa, terminates, obtain COP product 3 after reacting 5 minutes.Sample analysis, passes through31P-NMR measures the conversion ratio of CDP.?
Under conditions of isolation dampness, pour out retained material from CDP stock bottle and claim to obtain 2.75 grams, COP is weighed to obtain product 136 grams.
Atlas analysis: FTIR composes the characteristic peak 1310cm of existing P=O-1；31P-NMR composes the characteristic peak of existing COP
23.05ppm；The characteristic peak of CDP diminishes, purity 92%, yield 90%.
Embodiment two:
Apparatus is with example one.126.31 grams of CDP raw materials it are weighed in CDP stock bottle.Open high/low temperature all-in-one to set
Determining oxidizing reaction temperature is 90 DEG C, and regulation residence time of material is 30 seconds, opens oxygen source valve and oxygen source is imported microchannel flows continuously
Reactor, then opens transmission pump and CDP is squeezed into microchannel continuous flow reactor, and reaction starts, and reaction temperature maintains initially
Design temperature 90 DEG C, pressure is 0.21MPa, terminates, obtain COP product after reacting 10 minutes.Sample analysis, passes through31P-NMR measures
The conversion ratio of CDP.Under conditions of isolation dampness, pour out retained material from CDP stock bottle and claim to obtain 2.1 grams, weigh COP to produce
Thing 137 grams.
Atlas analysis: FTIR composes the characteristic peak 1310cm of existing P=O-1；31P-NMR composes the characteristic peak of existing COP
23.05ppm；The characteristic peak of CDP diminishes, purity 95%, yield 93%.
Embodiment three:
Apparatus is with example one.126.52 grams of CDP raw materials it are weighed in CDP stock bottle.Open high/low temperature all-in-one to set
Determining oxidizing reaction temperature is 60 DEG C, and regulation residence time of material is 50 seconds, opens oxygen source valve and oxygen source is imported microchannel flows continuously
Reactor, then opens transmission pump and CDP is squeezed into microchannel continuous flow reactor, and reaction starts, and reaction temperature maintains initially
Design temperature 60 DEG C, pressure is 0.18MPa, terminates, obtain COP product after reacting 15 minutes.Sample analysis, passes through31P-NMR measures
The conversion ratio of CDP.Under conditions of isolation dampness, pour out retained material from CDP stock bottle and claim to obtain 2.7 grams, weigh COP to produce
Thing 136.5 grams.
Atlas analysis: FTIR composes the characteristic peak 1310cm of existing P=O-1；31P-NMR composes the characteristic peak of existing COP
23.05ppm；The characteristic peak of CDP diminishes, purity 91%, yield 89%.
Embodiment four:
Apparatus is with example one.126.40 grams of CDP raw materials it are weighed in CDP stock bottle.Open high/low temperature all-in-one to set
Determining oxidizing reaction temperature is 80 DEG C, and regulation residence time of material is 30 seconds, opens oxygen-enriched air valve and is imported by 90% oxygen-enriched air
Microchannel continuous flow reactor, then opens transmission pump and CDP is squeezed into microchannel continuous flow reactor, and reaction starts, reaction temperature
Degree maintains preliminary set time 80 DEG C, and pressure is 0.2MPa, terminates, obtain COP product after reacting 10 minutes.Sample analysis is logical
Cross31P-NMR measures the conversion ratio of CDP.Under conditions of isolation dampness, pour out retained material from CDP stock bottle and claim to obtain 2.3 grams,
COP is weighed to obtain product 130 grams.
Atlas analysis: FTIR composes the characteristic peak 1310cm of existing P=O-1；31P-NMR composes the characteristic peak of existing COP
23.05ppm；The characteristic peak of CDP diminishes, purity 83%, yield 77%.
It is only the preferred implementation of the application described on, makes to skilled artisans appreciate that or realize the application's
Invention.Multiple amendment and combination for these embodiments will be apparent from for a person skilled in the art, this
General Principle defined in literary composition can be real in other embodiments in the case of without departing from spirit herein or scope
Existing.Therefore, the application will not be limited in the embodiments shown herein, and is to fit to and principles disclosed herein
The widest scope consistent with features of novelty.
Claims (6)
1. the method utilizing microchannel continuous flow reactor synthesis COP, described microchannel continuous flow reactor includes pressure
Meter and thermometer, effusion meter, material transferring pump react single with control system, valve, relief valve, heat exchange control system, microchannel
Unit's integration module, high/low temperature all-in-one and various connected pipeline；The step of synthesis COP is as follows: add in CDP stock bottle
CDP raw material, opens high/low temperature all-in-one and sets oxidizing reaction temperature as 1～200 DEG C, regulation residence time of material be 0.05～
600 seconds, open oxygen source valve and oxygen source is imported microchannel continuous flow reactor, then open transmission pump and CDP is squeezed into microchannel even
Afterflow reactor, reaction starts, and reaction temperature maintains preliminary set time, and pressure is 0.05～1.8MPa, and the response time is
0.5～120 minute, reaction obtained COP product after terminating.
The method utilizing microchannel continuous flow reactor synthesis COP the most according to claim 1, it is characterised in that described
High/low temperature all-in-one sets oxidizing reaction temperature as 60～150 DEG C.
The method utilizing microchannel continuous flow reactor synthesis COP the most according to claim 1, it is characterised in that described
Pressure is 0.10～0.6MPa.
The method utilizing microchannel continuous flow reactor synthesis COP the most according to claim 1, it is characterised in that described
Residence time of material is 5～60 seconds.
The method utilizing microchannel continuous flow reactor synthesis COP the most according to claim 1, it is characterised in that described
Oxygen source includes pure oxygen and oxygen-enriched air.
The method utilizing microchannel continuous flow reactor synthesis COP the most according to claim 5, it is characterised in that described
The oxygen content of oxygen-enriched air is 30%～98%, and oxidizing reaction temperature is 30～200 DEG C, and pressure is 0.15～1.8MPa.
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| CN201610689396.4A CN106317117A (en) | 2016-08-16 | 2016-08-16 | Method for synthesizing 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane through oxidation safely and efficiently by utilizing micro-channel continuous flow reactor |
| CN201710137158.7A CN106946936B (en) | 2016-08-16 | 2017-03-09 | A method of 2-chloro-2-oxo-1,3,2-dioxaphospholane is synthesized using microchannel continuous flow reactor |
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| CN201610689396.4A CN106317117A (en) | 2016-08-16 | 2016-08-16 | Method for synthesizing 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane through oxidation safely and efficiently by utilizing micro-channel continuous flow reactor |
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| CN201710137158.7A Active CN106946936B (en) | 2016-08-16 | 2017-03-09 | A method of 2-chloro-2-oxo-1,3,2-dioxaphospholane is synthesized using microchannel continuous flow reactor |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106946936A (en) * | 2016-08-16 | 2017-07-14 | 南京构友生物材料有限公司 | The method that a kind of continuous flow reactor safe and efficient oxygen of 2 chlorine of oxidative synthesis 2 in utilization microchannel closes 1,3,2 dioxaphospholane |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2933412B2 (en) * | 1991-03-08 | 1999-08-16 | 日清製油株式会社 | Method for producing phosphatidylcholine |
| JP2001206892A (en) * | 2000-01-27 | 2001-07-31 | Nissan Chem Ind Ltd | Method for producing 2-alkoxyethoxy-1,3,2- dioxaphospholan-2-one |
| CN102746339B (en) * | 2011-04-22 | 2016-01-13 | 林晖 | The method of COP or its homologue is prepared in a kind of oxidation |
| CN102432448A (en) * | 2011-11-07 | 2012-05-02 | 常州大学 | Method for preparing acetophenone by oxidizing ethylbenzene in continuous flow micro-channel reactor |
| CN102424692B (en) * | 2011-12-16 | 2012-11-07 | 常熟富士莱医药化工有限公司 | Preparation method for 2-chloro-2-oxo-1,3,2-dioxaphospholane |
| CN102775446A (en) * | 2012-07-01 | 2012-11-14 | 周珮 | Method for preparing 2-chloro-1,3,2-dioxaphospholane-2-oxide |
| CN104557644B (en) * | 2013-10-09 | 2017-09-22 | 中国石油化工股份有限公司 | The method that dialkyl dithio amino formate is prepared using continuous flow tubular reactor |
| CN104478701B (en) * | 2014-11-24 | 2016-08-24 | 常州大学 | The method of alcohol ketone oil nitric acid oxidation synthesizing adipic acid in stream micro passage reaction continuously |
| CN105213348B (en) * | 2015-10-29 | 2018-08-28 | 合肥工业大学 | A kind of drug-loading nanoparticles and its preparation method and application of reduction response |
| CN106317117A (en) * | 2016-08-16 | 2017-01-11 | 林晖 | Method for synthesizing 2-chlorine-2-oxygenation-1,3,2-dioxaphospholane through oxidation safely and efficiently by utilizing micro-channel continuous flow reactor |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106946936A (en) * | 2016-08-16 | 2017-07-14 | 南京构友生物材料有限公司 | The method that a kind of continuous flow reactor safe and efficient oxygen of 2 chlorine of oxidative synthesis 2 in utilization microchannel closes 1,3,2 dioxaphospholane |
| CN106946936B (en) * | 2016-08-16 | 2019-01-25 | 南京构友生物材料有限公司 | A method of 2-chloro-2-oxo-1,3,2-dioxaphospholane is synthesized using microchannel continuous flow reactor |
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