NL2029670B1 - Chemical synthesis method of diphenyl chlorophosphate - Google Patents
Chemical synthesis method of diphenyl chlorophosphate Download PDFInfo
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- NL2029670B1 NL2029670B1 NL2029670A NL2029670A NL2029670B1 NL 2029670 B1 NL2029670 B1 NL 2029670B1 NL 2029670 A NL2029670 A NL 2029670A NL 2029670 A NL2029670 A NL 2029670A NL 2029670 B1 NL2029670 B1 NL 2029670B1
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- Prior art keywords
- diphenyl
- synthesis method
- diphenyl phosphate
- salt
- diphenyl chlorophosphate
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- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title abstract description 19
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000001308 synthesis method Methods 0.000 claims abstract description 14
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 5
- FVOMJWZIGNBHOA-UHFFFAOYSA-M sodium;diphenyl phosphate Chemical compound [Na+].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 FVOMJWZIGNBHOA-UHFFFAOYSA-M 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- AJZFEJQZIOIQSR-UHFFFAOYSA-M potassium;diphenyl phosphate Chemical compound [K+].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 AJZFEJQZIOIQSR-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- -1 diphenyl phosphate salt Chemical class 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 9
- 238000004821 distillation Methods 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 5
- 239000011574 phosphorus Substances 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000002910 solid waste Substances 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 1
- 229960002260 meropenem Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1406—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-aryl
Landscapes
- 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)
Abstract
The present disclosure relates to a synthesis method of diphenyl chlorophosphate, comprising the following steps: taking a certain amount of organic amine as a catalyst, 5 mixing one or two of a certain amount of diphenyl phosphate or diphenyl phosphate salt in any proportion, and then reacting with a certain amount of bis (trichloromethyl) carbonate in an organic solvent for l-lO h, wherein the reaction temperature is 0-6OOC, and the diphenyl phosphate salt is any one of diphenyl phosphate sodium salt or diphenyl phosphate potassium salt, after the reaction in the step l) is finished, cooling 10 the product, washing with water, drying, recovering the solvent at normal pressure or reduced pressure, cooling, and filtering to remove insoluble substances, thereby obtaining the diphenyl chlorophosphate. The present disclosure has the beneficial effects of simple process route, mild reaction conditions, low post-treatment energy consumption, no need of high-vacuum and high-temperature distillation, low 15 production cost and relatively high product yield and quality, meanwhile, the problem of generation of a large amount of phosphorus-containing wastewater and solid waste is avoided.
Description
[01] The present disclosure relates to the technical field of chemical engineering, more particularly to a chemical synthesis method of diphenyl chlorophosphate.
[02] The diphenyl chlorophosphate is an important intermediate for synthesizing penem medicines, phosphorus-containing flame retardants and liquid crystal materials, and can be used to produce medicines such as meropenem and 4-diphenoxy diphenyl phosphate.
[03] Before this present invention, chemical synthesis methods of the diphenyl chlorophosphate in the prior art adopt phosphorus oxychloride and phenol as raw materials, and synthesis is carried out under the catalysis of Lewis acid.
[04] The synthesis route is as follows: oH PHO, Gomme EEX mo “a PHO a — —
[05] (Main product (By-product)
[06] For example: chemical research 2012, 23 (6) proposes that 0.8 g of anhydrous aluminum trichloride and 15.3 g of phosphorus oxychloride are heated to 60°C, a mixed solution of 10 ml of dichloroethane and 18.8 g of phenol is dropwise added to the reaction system, the temperature is controlled to be below 70°C during dropwise adding, the temperature is increased to 70°C after dropwise adding, the temperature is maintained and the reaction is carried out for 15 h, a proper amount of water is dropwise added, the reaction product is filtered, the obtained filtrate is subjected to normal pressure distillation to remove low boiling point substances and then is subjected to reduced pressure distillation, and 140-160°C/3mmHg fraction is collected.
[07] The phosphorus oxychloride used in the method causes severe corrosion to devices, a large amount of high phosphorus wastewater is difficultly treated, and severe pollution is caused; many byproducts are produced; and the product needs high vacuum high temperature distillation which leads to high energy consumption, and the distillation residues cause a large amount of solid wastes. The method has problems such as high corrosion, high energy consumption, high pollution, low yield, high production cost and other problems that need to be solved urgently.
[08] Meanwhile, the diphenyl chlorophosphate and the diphenylphosphoryl azide are important raw materials in the chemical synthesis industry, especially the chemical pharmacy industry, and are converted into diphenyl phosphate after being used, which is a difficult problem in the environmental protection work of related industries due to slow release of phenol and high phosphorus content in sewage treatment, it is a problem in sewage treatment; and because of the flame retardancy of the diphenyl phosphate, incineration is also difficult. The diphenyl phosphate can be conveniently separated from water, and a method can be found for utilizing the diphenyl phosphate so as to solve the environmental protection problem. The present disclosure is a method for reconverting the diphenyl chlorophosphate into the diphenyl chlorophosphate.
[09] In view of the shortcomings of the prior art, the present disclosure provides a chemical synthesis method of diphenyl chlorophosphate. The method has the characteristics of simple process, mild production conditions, high yield, low cost and less three wastes.
[10] In order to achieve the above object, the present disclosure provides the following technical solution:
[11] A synthesis method of diphenyl chlorophosphate, comprising the following steps:
[12] 1) taking a certain amount of organic amine as a catalyst, mixing one or two of a certain amount of diphenyl phosphate or diphenyl phosphate salt in any proportion, and then reacting with a certain amount of bis (trichloromethyl) carbonate in an organic solvent for 1-10 h, wherein the reaction temperature is 0-60°C, and the diphenyl phosphate salt is any one of diphenyl phosphate sodium salt or diphenyl phosphate potassium salt; and
[13] 2) after the reaction in the step 1) is finished, cooling the product, washing with water, drying, recovering the solvent at normal pressure or reduced pressure, cooling, and filtering to remove insoluble substances, thereby obtaining the diphenyl chlorophosphate.
[14] The reaction equation is as follows: CL Ï jg oe I NM “a Sk OLO 15] dpa trp pleat Ingheny! shinplemse
[16] Or QUST Ak = j Ig em Seve
[17] Tighe] chlamophin phate
[18] Wherein, M is sodium or potassium.
[19] In the step 1), one or two of a certain amount of diphenyl phosphate or diphenyl phosphate salt is/are mixed in any proportion and then reacts with a certain amount of bis (trichloromethyl) carbonate in the organic solvent for 3-6 h.
[20] In the step 2), the product is cooled to 10°C or below, washed with water, dried, and subjected to solvent recovery under normal pressure or reduced pressure, and the insoluble substances are removed by cooling and filtering, to obtain the diphenyl chlorophosphate.
[21] The mass ratio of the diphenyl phosphate (or diphenyl phosphate salt) to the bis (trichloromethyl) carbonate to the organic amine catalyst is 1: (0.35-1.0): (0.01-1.5).
[22] The mass ratio of the diphenyl phosphate (or diphenyl phosphate salt) to the bis (trichloromethyl) carbonate to the organic amine catalyst is 1: (0.35-0.5): (0.1-0.5).
[23] The organic amine catalyst is one of or a mixture of more than one of triethylamine, diisopropylethylamine, pyridine, morpholine, imidazole, 2-methylimidazole, tetramethylguanidine, tetramethylurea, N-dimethylformamide, N-dimethylacetamide, N-dibutyl formamide, N-methylpyrrole and N-methyltetrahydropyrrole in any proportion.
[24] The organic amine catalyst is N, N-dimethylformamide.
[25] The organic solvent is one of or a mixture of more than one of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, N-hexane, cyclohexane, diisopropyl ether, dibutyl ether, tetrahydrofuran, ethyl acetate, dichloromethane, trichloromethane or dichloroethane in any proportion.
[26] The organic solvent is dichloromethane.
[27] The dosage of the organic solvent is 3-8 times the mass of the diphenyl phosphate or the diphenyl phosphate salt, materials with the dosage lower than this dosage are not fully reacted, and materials with the dosage higher than this dosage cause cost increase and reaction efficiency reduction.
[28] Compared with the prior art, the present disclosure has the following beneficial effects: diphenyl chlorophosphate (or diphenyl phosphate salt) and di (trichloromethyl) carbonate are used as the raw materials, and diphenyl chlorophosphate is synthesized under the catalysis of organic amine; this solution replaces the existing synthesis method using phenol and phosphorus oxychloride as the raw materials, compared with the existing solution, the technical solution used in this application has the advantages of simple process route, mild reaction conditions, low post-treatment energy consumption, no need of high-vacuum and high-temperature distillation, low production cost and relatively high product yield and quality; meanwhile, the problem of generation of a large amount of phosphorus-containing wastewater and solid waste is avoided; and the synthesis method of diphenyl chlorophosphate has relatively high economic value and environmental protection value.
[29] The technical solutions in the embodiments of the present disclosure are described clearly and completely. Obviously, embodiments described are only a part of embodiments of the present disclosure, and are not all of embodiments thereof. All other embodiments obtained by persons of ordinary skill in the art based on the embodiments of the present disclosure without creative efforts shall fall within the protection scope of the present disclosure.
[30] Example 1
[31] To a 500 ml four-neck reaction bottle provided with a thermometer, a reflux condensing tube and a mechanical stirrer, 120 g of dichloromethane and 7.3 g of N, N-dimethylformamide are added; the added materials are stirred, and the temperature is controlled to be below 10°C; 28 g of bis (trichloromethyl) carbonate is added; a solution of 50 g of diphenyl phosphate and 120 g of dichloromethane is added in a flowing manner, the reaction is carried out for 3 h after adding; the temperature is controlled to be below 10°C after the reaction is detected to be finished; 20 g of water is slowly added; the materials are stirred and liquid is separated; an organic phase is dried by using anhydrous sodium sulfate; a drying agent is removed by filtering; the filtrate is evaporated at normal pressure to remove dichloromethane, the temperature is decreased to 0°C, and the insoluble substances are removed by filtering, thereby obtaining 48.9 g of diphenyl chlorophosphate. The purity detected by GC is 99.2%, and the yield 1s 90.3%.
[32] Example 2
[33] To a 500 ml four-neck reaction bottle provided with a thermometer, a reflux condensing tube and a mechanical stirrer, 120 g of dichloromethane and 3.6 g of N, N-dimethylformamide are added; the added materials are stirred, and the temperature is controlled to be below 10°C; 28 g of bis (trichloromethyl) carbonate is added, a solution of 50 g of diphenyl phosphate and 120 g of dichloromethane is added in a flowing manner; the reaction is carried out for 3 h after adding; the temperature is controlled to be below 10°C after the reaction is detected to be finished; 20 g of water is slowly added; the materials are stirred and liquid is separated; an organic phase is dried by using anhydrous sodium sulfate; a drying agent is removed by filtering; the filtrate 1s evaporated at normal pressure to remove dichloromethane, the temperature is decreased to 0°C, and the insoluble substances are removed by filtering, thereby obtaining 47.2 g of diphenyl chlorophosphate. The purity detected by GC is 98.1%, and the yield is 86.2%.
[34] Example 3
[35] To a 500 ml four-neck reaction bottle provided with a thermometer, a reflux condensing tube and a mechanical stirrer, 330 g of dichloromethane and 7.3 g of N, N-dimethylformamide are added; the added materials are stirred, and the temperature is controlled to be below 10°C; 28 g of bis (trichloromethyl) carbonate is added, and 55 g of diphenyl phosphate sodium salt is added in batches; the reaction is carried out for 5 h after adding; the temperature is controlled to be below 10°C after the reaction is detected to be finished; 20 g of water is slowly added; the materials are stirred and liquid is separated; an organic phase is dried by using anhydrous sodium sulfate; a drying agent is removed by filtering; the filtrate is evaporated at normal pressure to remove dichloromethane, the temperature is decreased to 0°C, and the insoluble substances are removed by filtering, thereby obtaining 47.5 g of diphenyl chlorophosphate. The purity detected by GC is 99.3%, and the yield is 87.8%.
[36] It should be noted that, the terms "include", "comprise" or any other variants thereof mean non-exclusive inclusions, so that a process, a method, an item or a device including a series of elements not only include those elements, but also include other elements that are not explicitly listed, or also include elements inherent to this process, method, item or device. In the case of no more restrictions, the inclusion of an element defined by the sentence "including a..." does not exclude the existence of other identical elements in the process, method, item or device that includes the element.
[37] Although the present disclosure has been described in detail with reference to the foregoing embodiments, for those skilled in the art, it is still possible for those skilled in the art to modify the technical solutions described in the foregoing embodiments, or make equivalent substitutions to some of the technical features.
Any modification, equivalent replacement, improvement, etc. made within the essence and principle of the present disclosure shall fall within the scope of protection of the present invention.
Claims (10)
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