CN112707935A - Preparation method of environment-friendly aromatic phosphate nucleating agent - Google Patents
Preparation method of environment-friendly aromatic phosphate nucleating agent Download PDFInfo
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- CN112707935A CN112707935A CN202011569450.4A CN202011569450A CN112707935A CN 112707935 A CN112707935 A CN 112707935A CN 202011569450 A CN202011569450 A CN 202011569450A CN 112707935 A CN112707935 A CN 112707935A
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- nucleating agent
- aromatic phosphate
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- phosphate nucleating
- friendly aromatic
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- 239000002667 nucleating agent Substances 0.000 title claims abstract description 37
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 33
- 239000010452 phosphate Substances 0.000 title claims abstract description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 4, 6-di-tert-butyl phenoxy Chemical group 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000011968 lewis acid catalyst Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 239000002351 wastewater Substances 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002841 Lewis acid Substances 0.000 abstract description 3
- 150000007517 lewis acids Chemical class 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 150000001348 alkyl chlorides Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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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
- C07F9/547—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
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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)
Abstract
The invention relates to a preparation method of an environment-friendly aromatic phosphate nucleating agent, belonging to the technical field of polymer nucleating agents, and the preparation method of the environment-friendly aromatic phosphate nucleating agent comprises the following steps: the method adopts the inorganic Lewis acid to replace the traditional triethylamine or pyridine, subsequently avoids the residue of the triethylamine or pyridine and the treatment problem of metal salt wastewater, simplifies the production process, reduces the production cost, improves the operation safety coefficient and reduces the environmental protection pressure.
Description
Technical Field
The invention relates to a preparation method of an environment-friendly aromatic phosphate nucleating agent, belonging to the technical field of polymer nucleating agents.
Background
As a typical alpha crystal form nucleating agent, the phosphate ester metal salt with aromatic groups has good compatibility and easy dispersibility with resin, can accelerate the crystallization speed of polypropylene resin (PP) at relatively low concentration, shorten the molding period of products, endow the resin with good rigidity, transparency and thermal stability, and is widely used for modified products such as high-rigidity PP special materials, transparent injection molding products, PP accessories for vehicles and the like. In addition, it has good nucleation effect on engineering plastics such as PET, PBT, PA and the like. Chinese patents CN201010267862.2 and CN200910236251.9 disclose the preparation process of aromatic phosphate nucleating agent.
In the prior art, raw material substituted aryl phenol is dissolved in an organic solvent and then reacts with a phosphorylation reagent, an organic acid-binding agent triethylamine or pyridine is added for further catalytic reaction, then substituted aryl organic phosphate is obtained by hydrolysis, and then inorganic base is used for neutralization to prepare the substituted aryl organic phosphate nucleating agent. The use of organic acid-binding agents in the method brings a series of problems for the subsequent process: the operation process has large smell, high danger coefficient and poor process operation stability; the product can achieve the satisfactory effect by repeatedly washing for many times, and has the advantages of high environmental protection pressure and high production cost.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a preparation method of an environment-friendly aromatic phosphate nucleating agent, which overcomes the defects of an organic acid-binding agent in the prior art and adopts inorganic Lewis acid to catalyze the reaction.
In order to achieve the purpose, the technical scheme adopted by the invention is a preparation method of an environment-friendly aromatic phosphate nucleating agent, which comprises the following steps of adding an organic solvent, 2-methylene-bis (4, 6-di-tert-butylphenol) and an inorganic Lewis acid catalyst into a reaction bottle, stirring at room temperature until the organic solvent, the 2, 2-methylene-bis (4, 6-di-tert-butylphenol) and the inorganic Lewis acid catalyst are completely dissolved, then starting to dropwise add phosphorus oxychloride/xylene mixed solution for 1.5h, slowly heating to about 100 ℃ after the dropwise addition is finished, and reacting for 5-6 h; then cooling to about 80 ℃, adding water to remove salt, and reserving an organic layer for use; and finally, adding a sodium hydroxide solution, heating to reflux, reacting for two hours, distilling to recover the solvent, cooling, filtering, and drying to obtain the aromatic phosphate nucleating agent.
Preferably, the raw materials are fed according to the following mass ratio, wherein the 2, 2-methylene-bis (4, 6-di-tert-butylphenol): 40g of the total weight of the mixture; anhydrous aluminum chloride: 0.6-1.0 g; phosphorus oxychloride: 10-30 g; 10% sodium hydroxide: 30-50 ml; and (2) toluene: 100 ml.
Preferably, the aromatic phosphate nucleating agent is [ bis [2, 2' -methylenebis (4, 6-di-tert-butylphenoxy) phosphate ] hydroxy sodium salt ].
Preferably, the inorganic lewis acid catalyst is at least one alkaline earth metal halide, such as aluminum chloride, magnesium chloride, zinc chloride, or the like.
Preferably, for 2, 2-methylene-bis (4, 6-di-tert-butylphenol), the catalyst is used in an amount of 1% to 3%.
Preferably, the organic solvent is chloroalkane such as alkane, cycloalkane, benzene, toluene, xylene, dichloromethane, chloroform, etc.
Preferably, the structure of the phosphate salt nucleating agent is determined by infrared.
Preferably, the purity of the phosphate salt nucleating agent is determined by liquid phase.
Compared with the prior art, the invention has the following technical effects: the preparation method has no peculiar smell in the operation process, stable production process and high operational safety coefficient; the product treatment can achieve satisfactory effect without repeated washing, and the salt-containing wastewater can be used for other process production or repeated use, so that the production cost is reduced, and the environmental pressure is reduced.
Drawings
FIG. 1 is a diagram of a liquid phase analysis of the present invention.
FIG. 2 is an infrared analysis chart of the present invention.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more clearly apparent, the present invention is further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example one
A preparation method of an environment-friendly aromatic phosphate nucleating agent comprises the following steps of adding 120ml of dimethylbenzene, 42.4g of 2, 2-methylene-bis (4, 6-di-tert-butylphenol) and 0.8g of anhydrous aluminum chloride into a reaction bottle, heating to about 115 ℃ under stirring, starting dropwise adding a phosphorus oxychloride/toluene mixed solution after complete dissolution, wherein the dropwise adding time is 1.5h, slowly heating to about 150 ℃ after the dropwise adding is finished, and reacting for 5-6 h; then cooling to about 80 ℃, sequentially adding 100ml of distilled water into a reaction bottle for liquid separation twice, and reserving an organic layer for use; and finally, adding 80ml of 10% sodium hydroxide solution, heating to reflux, reacting for two hours, distilling to recover the solvent, cooling, filtering, and drying to obtain the aromatic phosphate nucleating agent.
Example two
100ml of dimethylbenzene, 40g of 2, 2-methylene-bis (4, 6-di-tert-butylphenol) and 50g of triethylamine are added into a reaction bottle, the mixture is stirred at room temperature until the mixture is completely dissolved, phosphorus oxychloride/dimethylbenzene mixed solution is dropwise added for 1.5h, the temperature is slowly raised to about 100 ℃ after the dropwise addition, and the reaction is carried out for 5-6 h; then cooling to about 80 ℃, adding 120ml of distilled water into the reaction bottle for three times for liquid separation treatment, and reserving an organic layer for use; and finally, adding 40ml of 10% sodium hydroxide solution, heating to reflux, reacting for two hours, distilling to recover the solvent, cooling, filtering, and drying to obtain the aromatic phosphate nucleating agent.
EXAMPLE III
100ml of dimethylbenzene, 40g of 2, 2-methylene-bis (4, 6-di-tert-butylphenol) and 39g of pyridine are added into a reaction bottle, the mixture is stirred at room temperature until the mixture is completely dissolved, phosphorus oxychloride/dimethylbenzene mixed solution is dropwise added for 1.5h, and after the dropwise addition, the temperature is slowly raised to about 100 ℃ for reaction for 5-6 h; then cooling to about 80 ℃, adding 120ml of distilled water into the reaction bottle for three times for liquid separation treatment, and reserving an organic layer for use; and finally, adding 40ml of 10% sodium hydroxide solution, heating to reflux, reacting for two hours, distilling to recover the solvent, cooling, filtering, and drying to obtain the aromatic phosphate nucleating agent.
When the aromatic phosphate nucleating agent obtained by the preparation method is detected, the liquid phase analysis diagram of the aromatic phosphate nucleating agent is shown in figure 1. From a liquid phase spectrum, the main peak position of the aromatic phosphate nucleating agent is basically kept consistent. As shown in FIG. 2, the infrared analysis of the nucleating agent of aromatic phosphate salts. From the infrared spectrum, it is found that the use of anhydrous aluminum chloride does not have a great influence on the main structure of the aromatic phosphate salt nucleating agent.
In conclusion, the use of inorganic Lewis acid instead of organic base catalyzed reaction has little effect on the final reaction product, and the scheme is feasible. The method avoids the problems that intermediate materials are washed for many times, the generated waste water is heavy in odor, triethylamine salt or pyridine salt waste water is difficult to treat, the final product is large in odor, the operation is unsafe and the like. Not only makes the subsequent treatment easy and simple to handle, has reduced the discharge of waste water moreover, has reduced the environmental protection pressure to a certain extent, and the production cost reduces, and the operation is safe, and the environmental protection coefficient is high.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, as any variations, equivalents, or improvements made within the spirit and principles of the present invention are intended to be covered thereby.
Claims (8)
1. The preparation method of the environment-friendly aromatic phosphate nucleating agent is characterized by comprising the following steps: adding an organic solvent, 2-methylene-bis (4, 6-di-tert-butylphenol) and an inorganic Lewis acid catalyst into a reaction bottle, stirring at room temperature until the mixture is completely dissolved, starting to dropwise add phosphorus oxychloride/xylene mixed solution for 1.5h, slowly heating to about 100 ℃ after the dropwise addition is finished, and reacting for 5-6 h; then cooling to about 80 ℃, adding water to remove salt, and reserving an organic layer for use; and finally, adding a sodium hydroxide solution, heating to reflux, reacting for two hours, distilling to recover the solvent, cooling, filtering, and drying to obtain the aromatic phosphate nucleating agent.
2. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the raw materials are fed according to the following mass, and the 2, 2-methylene-bis (4, 6-di-tert-butylphenol): 40g of the total weight of the mixture; anhydrous aluminum chloride: 0.6-1.0 g; phosphorus oxychloride: 10-30 g; 10% sodium hydroxide: 30-50 ml; xylene: 100 ml.
3. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the aromatic phosphate nucleating agent is [ di [2, 2' -methylene bis (4, 6-di-tert-butyl phenoxy) phosphate ] hydroxy sodium salt ].
4. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the inorganic Lewis acid catalyst is at least one alkaline earth metal halide.
5. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the dosage of the catalyst is 1-3%.
6. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the organic solvent is alkane, cyclane, benzene, toluene, xylene, dichloromethane or chloroform.
7. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the structure of the phosphate nucleating agent is determined by infrared.
8. The method for preparing the environment-friendly aromatic phosphate nucleating agent according to claim 1, characterized in that: the purity of the phosphate salt nucleating agent is determined by liquid phase.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3940765A1 (en) * | 1989-12-09 | 1991-06-13 | Hoechst Ag | METHOD FOR PRODUCING PURE CYCLIC PHOSPHORSAEUREDIARYLESTER |
| JP2001151787A (en) * | 1999-11-26 | 2001-06-05 | Asahi Denka Kogyo Kk | Method for producing phosphoric ester compound |
| CN1358728A (en) * | 2001-10-30 | 2002-07-17 | 上海晟霖新材料科技有限公司 | Process for one-stage synthesizing substituted diaryl organic metal phosphate |
| CN101253184A (en) * | 2005-09-14 | 2008-08-27 | 大八化学工业株式会社 | Phosphorus compound, use thereof and flame-retardant polyester fiber |
| CN101302234A (en) * | 2008-06-27 | 2008-11-12 | 洛阳市中达化工有限公司 | Synthetic method of 2,2'-methano-bis (4,6-ditertbutyl phenol) phosphate |
-
2020
- 2020-12-26 CN CN202011569450.4A patent/CN112707935A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3940765A1 (en) * | 1989-12-09 | 1991-06-13 | Hoechst Ag | METHOD FOR PRODUCING PURE CYCLIC PHOSPHORSAEUREDIARYLESTER |
| JP2001151787A (en) * | 1999-11-26 | 2001-06-05 | Asahi Denka Kogyo Kk | Method for producing phosphoric ester compound |
| CN1358728A (en) * | 2001-10-30 | 2002-07-17 | 上海晟霖新材料科技有限公司 | Process for one-stage synthesizing substituted diaryl organic metal phosphate |
| CN101253184A (en) * | 2005-09-14 | 2008-08-27 | 大八化学工业株式会社 | Phosphorus compound, use thereof and flame-retardant polyester fiber |
| CN101302234A (en) * | 2008-06-27 | 2008-11-12 | 洛阳市中达化工有限公司 | Synthetic method of 2,2'-methano-bis (4,6-ditertbutyl phenol) phosphate |
Non-Patent Citations (1)
| Title |
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| 吴淑玲，等: "2-联苯基二苯基磷酸酯的合成", 《信息记录材料》 * |
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Application publication date: 20210427 |