CN113277928A - Method for recovering and degrading PETG (polyethylene terephthalate glycol) - Google Patents
Method for recovering and degrading PETG (polyethylene terephthalate glycol) Download PDFInfo
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- CN113277928A CN113277928A CN202110073240.4A CN202110073240A CN113277928A CN 113277928 A CN113277928 A CN 113277928A CN 202110073240 A CN202110073240 A CN 202110073240A CN 113277928 A CN113277928 A CN 113277928A
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- C07—ORGANIC CHEMISTRY
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
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- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/213—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by splitting of esters
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
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- C07F7/04—Esters of silicic acids
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention discloses a method for recovering and degrading PETG (polyethylene terephthalate glycol), which adopts the schemes of crushing, degrading, recycling and the like. Can convert the degraded PETG into new usable substances and does not generate any waste.
Description
Technical Field
The invention relates to the field of recycling, in particular to a method for recycling PETG (polyethylene terephthalate glycol).
Background
PETG is a very good material, which is the product of polycondensation of three monomers, terephthalic acid (PTA), Ethylene Glycol (EG) and 1, 4-Cyclohexanedimethanol (CHDM). The PETG sheet material has outstanding toughness and high impact strength, the impact strength of the PETG sheet material is 3-10 times that of modified polyacrylate, the PETG sheet material has a wide processing range, high mechanical strength and excellent flexibility, and compared with PVC, the PETG sheet material has the advantages of high transparency, good gloss, easiness in printing and environmental friendliness.
However, as PETG materials are used more and more, the problem that PETG cannot be naturally degraded is more and more regarded, so that many people begin to research how to recover and reuse PETG, and documents show that the mechanical capability of the PETG is obviously reduced compared with the original time, and the PETG is crushed and then passes through a twin-screw extruder again to be subjected to blow molding or injection molding to form a film.
Disclosure of Invention
In order to solve the problem of recycling the PETG material in the current market. The invention discloses a method for recovering and degrading PETG. Through the schemes of crushing, degrading, recycling and the like. Can convert the degraded PETG into new usable substances and does not generate any waste.
Which comprises the following steps:
(1) the PETG recovered material is subjected to primary crushing and low-temperature crushing.
(2) Hydrolyzing PETG after low-temperature crushing in a potassium hydroxide aqueous solution, and adding toluene for extraction. The upper and lower layers are separated into water phase and organic phase.
(3) And feeding the organic phase into a rectifying tower, and shunting to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol.
(4) And (3) filtering the water phase, evaporating the water to dryness, adding anhydrous DMF and trimethoxychlorosilane, and reacting to produce the bis (trimethoxy silane) terephthalate.
(5) Esterification of 1,4 cyclohexanedimethanol with acrylic acid gives the UV reactive diluent 1,4 cyclohexanedimethanol diacrylate.
As a further scheme of the invention, the primary crushing in the step (1) of the invention is normal-temperature crushing, and the diameter of the crushed particles is about 1cm-5 cm.
As a further aspect of the present invention, the low-temperature crushing in step (1) of the present invention has a crushing temperature of-10 to-40 ℃ and a particle diameter of about 0.1mm to 2mm after crushing.
The primary crushing of the first section can better improve the efficiency of low-temperature crushing. The PETG can be made more brittle by low-temperature crushing, so that the crushed particle size can be reduced, and the subsequent hydrolysis process can be carried out more thoroughly at the particle size.
As a further embodiment of the present invention, the concentration of the aqueous sodium hydroxide solution used in step (2) of the present invention is 30% to 40%.
As a further scheme of the invention, the hydrolysis temperature of the hydrolysis process in the step (2) of the invention is 80-100 ℃, the base number of the hydrolysis process needs to be continuously titrated, the titration method is carried out by using the GBT 4945-2002 scheme until the base number is lower than a set value, and the system is adjusted to be neutral by using a dilute hydrochloric acid aqueous solution.
In a further embodiment of the present invention, the amount of toluene added in step (2) of the present invention is 1 to 2 times the amount of the aqueous sodium hydroxide solution.
As a further aspect of the present invention, the distillation temperature of the distillation column used in step (3) of the present invention is 100-140 ℃.
As a further scheme of the invention, the product purity of the ethylene glycol finally obtained in the step (3) of the invention is more than 99.5%.
As a further scheme of the invention, the reaction process in the step (4) of the invention has the following principle:
as a further embodiment of the present invention, the reaction method in step (4) of the present invention is:
adding trimethoxysilylchlorosilane and potassium terephthalate into a reaction bottle containing DMF, adding a certain amount of benzyltriethylammonium chloride, and reacting at the temperature of 100-130 ℃. After the reaction is finished, filtering to remove the generated potassium chloride, and distilling DMF to obtain the product.
The bis (trimethoxy silane) terephthalate obtained by the reaction can be used as a silane coupling agent to be added into a coating or ink system to enhance the adhesion of the bis (trimethoxy silane) terephthalate to a substrate.
As a further scheme of the invention, the reaction process in the step (5) of the invention has the following principle:
as a further embodiment of the present invention, the reaction method in step (5) of the present invention is:
acrylic acid was added to a toluene solution containing 1,4 cyclohexanedimethanol and reacted at 100 ℃ under a p-toluenesulfonic acid catalyst. And after the reaction is finished, adding 10% of aqueous hydroxide solution for neutralization, separating to remove a water phase, and distilling at 70 ℃ to remove toluene to finally obtain the 1, 4-cyclohexanedimethanol diacrylate.
The 1,4 cyclohexane dimethanol diacrylate obtained by the reaction can be used as a UV active thinner to be added into a coating or an ink system, and has very good diluting capability to resin.
The PETG recovered by the method can be used as a further scheme of the invention, and the degraded PETG can be converted into new usable substances without any waste.
The technical scheme provided by the invention has the beneficial effects that:
the PETG is decomposed after being crushed at low temperature into fine particles, and the efficiency is higher than that of direct decomposition.
The PETG is decomposed by alkaline hydrolysis, and then the glycol with very good purity is obtained by means of rectification.
By further reacting potassium terephthalate and 1,4 cyclohexanedimethanol in the hydrolysis product, both can be reused.
The invention has low requirements on equipment, does not need high pressure or high temperature, and therefore, non-PETG manufacturers can recycle the PETG.
Drawings
FIG. 1 is a GC test chart of example 4.
Detailed description of the invention
The present invention will be further described below by way of specific examples.
In the following examples, those whose operations are not subject to the conditions indicated, are carried out according to the conventional conditions or conditions recommended by the manufacturer. The raw materials used in the scheme of the invention are purchased from Chinese medicines and alatin.
Example 1
PETG material (the mol ratio of the glycol to the 1,4 cyclohexane dimethanol is 1:1) is subjected to primary crushing and low-temperature crushing at-30 ℃ to obtain particles with the particle size of about 0.3 mm.
The crushed 100g of PETG material is added into a reactor containing potassium hydroxide aqueous solution with the concentration of 20 percent by mass, wherein the reactor contains 156g of the potassium hydroxide aqueous solution.
Stirring is started, the temperature is increased to 80 ℃, and the reaction is continued until the base number is lower than 30mg/g KOH. Dilute hydrochloric acid was added to adjust the system to neutral. Adding 300g of toluene, separating out an aqueous phase and an organic phase, and drying water in the aqueous phase for later use.
And rectifying the organic phase in a rectifying tower, and collecting the fraction at 120 ℃ to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol. Adding 50g of acrylic acid, 150g of toluene and 2% of p-toluenesulfonic acid by mass into 1,4 cyclohexanedimethanol, reacting at 100 ℃ until the acid value is lower than 25mg/g KOH, adding 10% of aqueous hydroxide solution into the system for neutralization, separating and removing a water layer, and distilling at 70 ℃ to remove toluene to finally obtain 1,4 cyclohexanedimethanol diacrylate.
24g of potassium terephthalate obtained by drying, 35g of trimethoxy chlorosilane and 0.5 percent of benzyltriethyl ammonium chloride by mass are added into a reactor of aviation fuel 100g of DMF and reacted at 130 ℃. After the reaction was completed, the formed potassium chloride was removed by filtration, and DMF was distilled to obtain bis (trimethoxysilane) terephthalate.
Example 2
PETG material (the mol ratio of the glycol to the 1,4 cyclohexane dimethanol is 1:1) is subjected to primary crushing and low-temperature crushing at the temperature of minus 20 ℃ to obtain particles with the particle size of about 0.5 mm.
And adding 124g of the crushed PETG material into a reactor containing a potassium hydroxide aqueous solution, wherein the concentration of the potassium hydroxide aqueous solution is 25% by mass.
Stirring was turned on and the temperature was raised to 80 ℃ and the reaction was continued until the base number was below 34mg/g KOH. Dilute hydrochloric acid was added to adjust the system to neutral. Adding 280g of toluene, separating an aqueous phase and an organic phase, and drying water in the aqueous phase for later use.
And (3) rectifying the organic phase in a rectifying tower, and collecting fractions at 130 ℃ to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol. Adding 50g of acrylic acid, 150g of toluene and 2% of p-toluenesulfonic acid by mass into 1,4 cyclohexanedimethanol, reacting at 100 ℃ until the acid value is lower than 25mg/g KOH, adding 10% of aqueous hydroxide solution into the system for neutralization, separating and removing a water layer, and distilling at 70 ℃ to remove toluene to finally obtain 1,4 cyclohexanedimethanol diacrylate.
24g of potassium terephthalate obtained by drying, 35g of trimethoxy chlorosilane and 0.3 percent of benzyltriethyl ammonium chloride by mass are added into a reactor of aviation fuel 100g of DMF and reacted at 120 ℃. After the reaction was completed, the formed potassium chloride was removed by filtration, and DMF was distilled to obtain bis (trimethoxysilane) terephthalate.
Example 3
PETG material (the mol ratio of the glycol to the 1,4 cyclohexane dimethanol is 1:1) is subjected to primary crushing and low-temperature crushing at-40 ℃ to obtain particles with the particle size of about 0.2 mm.
100g of the crushed PETG material is added into a reactor containing potassium hydroxide aqueous solution by 104g, wherein the concentration of the potassium hydroxide aqueous solution is 30 percent by mass.
Stirring was turned on and the temperature was raised to 90 ℃ and the reaction was continued until the base number was below 38mg/g KOH. Dilute hydrochloric acid was added to adjust the system to neutral. Adding 250g of toluene, separating out an aqueous phase and an organic phase, and drying water in the aqueous phase for later use.
And (3) rectifying the organic phase in a rectifying tower, and collecting fractions at 130 ℃ to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol. Adding 50g of acrylic acid, 150g of toluene and 2% of p-toluenesulfonic acid by mass into 1,4 cyclohexanedimethanol, reacting at 100 ℃ until the acid value is lower than 25mg/g KOH, adding 10% of aqueous hydroxide solution into the system for neutralization, separating and removing a water layer, and distilling at 70 ℃ to remove toluene to finally obtain 1,4 cyclohexanedimethanol diacrylate.
24g of potassium terephthalate obtained by drying, 35g of trimethoxy chlorosilane and 0.8 percent of benzyltriethyl ammonium chloride by mass are added into a reactor of aviation fuel 100g of DMF and reacted at 110 ℃. After the reaction was completed, the formed potassium chloride was removed by filtration, and DMF was distilled to obtain bis (trimethoxysilane) terephthalate.
Example 4
PETG material (the mol ratio of the glycol to the 1,4 cyclohexane dimethanol is 1:1) is subjected to primary crushing and low-temperature crushing at-40 ℃ to obtain particles with the particle size of about 0.1 mm.
The crushed 100g of PETG material is added into a reactor containing potassium hydroxide aqueous solution with the concentration of 20 percent by mass, wherein the reactor contains 156g of the potassium hydroxide aqueous solution.
Stirring is started, the temperature is raised to 90 ℃, and the reaction is continued until the base number is lower than 30mg/g KOH. Dilute hydrochloric acid was added to adjust the system to neutral. Adding 300g of toluene, separating out an aqueous phase and an organic phase, and drying water in the aqueous phase for later use.
And rectifying the organic phase in a rectifying tower, and collecting the distillate at 140 ℃ to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol. Adding 50g of acrylic acid, 150g of toluene and 2% of p-toluenesulfonic acid by mass into 1,4 cyclohexanedimethanol, reacting at 100 ℃ until the acid value is lower than 25mg/g KOH, adding 10% of aqueous hydroxide solution into the system for neutralization, separating and removing a water layer, and distilling at 70 ℃ to remove toluene to finally obtain 1,4 cyclohexanedimethanol diacrylate.
24g of potassium terephthalate obtained by drying, 35g of trimethoxy chlorosilane and 0.9 percent of benzyltriethyl ammonium chloride by mass are added into a reactor of aviation oil 100g of DMF and reacted at 140 ℃. After the reaction was completed, the formed potassium chloride was removed by filtration, and DMF was distilled to obtain bis (trimethoxysilane) terephthalate.
Example 5
PETG material (wherein the molar ratio of the glycol to the 1, 4-cyclohexanedimethanol is 1:1) is subjected to primary crushing and low-temperature crushing at-10 ℃ to obtain particles with the particle size of about 1 mm.
100g of the crushed PETG material is added into a reactor containing potassium hydroxide aqueous solution by 104g, wherein the concentration of the potassium hydroxide aqueous solution is 30 percent by mass.
Stirring was turned on and the temperature was raised to 100 ℃ and the reaction was continued until the base number was below 38mg/g KOH. Dilute hydrochloric acid was added to adjust the system to neutral. Adding 250g of toluene, separating out an aqueous phase and an organic phase, and drying water in the aqueous phase for later use.
And (3) rectifying the organic phase in a rectifying tower, and collecting fractions at 130 ℃ to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol. Adding 50g of acrylic acid, 150g of toluene and 2% of p-toluenesulfonic acid by mass into 1,4 cyclohexanedimethanol, reacting at 100 ℃ until the acid value is lower than 25mg/g KOH, adding 10% of aqueous hydroxide solution into the system for neutralization, separating and removing a water layer, and distilling at 70 ℃ to remove toluene to finally obtain 1,4 cyclohexanedimethanol diacrylate.
24g of potassium terephthalate obtained by drying, 35g of trimethoxy chlorosilane and 0.3 percent of benzyltriethyl ammonium chloride by mass are added into a reactor of aviation fuel 100g of DMF and reacted at 100 ℃. After the reaction was completed, the formed potassium chloride was removed by filtration, and DMF was distilled to obtain bis (trimethoxysilane) terephthalate. The above description is only exemplary of the present invention and should not be taken as limiting the scope of the present invention, as any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
The subject of the present invention is a method for recovering PETG, whereby the purity of the recovered glycol in examples 1-5 was tested. The adhesive force of the product of bis (trimethoxy silane) terephthalate and the diluting capability of the product of 1,4 cyclohexane dimethanol diacrylate in the ultraviolet curing coating.
The purity of the ethylene glycol is as follows:
the test was carried out using an Agilent GC6890N with an initial temperature of 100 ℃ and a ramp rate of 10 ℃ per minute to 280 ℃.
Adhesion of bis (trimethoxysilane) terephthalate:
0.5% of bis (trimethoxysilane) terephthalate was added to a formulation containing 100g of Yankee resin 6145H-80 and 0.5g of initiator 184, cured under UV light and tested for peel strength on glass substrates at a peel angle of 90.
Dilution ability of 1,4 cyclohexanedimethanol diacrylate in uv cured coatings:
yangxing resin 6145-100 was diluted with 1,4 cyclohexanedimethanol diacrylate, 1,6 hexanediol diacrylate, trimethylolpropane triacrylate, tripropylene glycol diacrylate at a dilution concentration of 10% and tested for viscosity at 25 ℃.
The purity of the ethylene glycol is as follows:
| example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Purity of | 99.59％ | 99.65％ | 99.77％ | 99.82％ | 99.75％ |
The FIGURE is a GC test chart for example 4.
Adhesion of bis (trimethoxysilane) terephthalate:
| 0.5％ | is not added | |
| Peeling force | 4.5KN/m | 3.1KN/m |
Dilution ability of 1,4 cyclohexanedimethanol diacrylate in uv cured coatings:
as can be seen from the above table, the final ethylene glycol obtained by the method for recycling the PETG material has very high purity, the other two products, namely 1, 4-cyclohexanedimethanol diacrylate, have very good diluting capability on resin, and are excellent active diluting monomers, and the di (trimethoxy silane) terephthalate has very good adhesion promotion on the formula.
Claims (11)
1. The invention relates to a method for recovering and degrading PETG, which comprises the following steps:
carrying out primary crushing and low-temperature crushing on the PETG recovered material;
hydrolyzing PETG after low-temperature crushing in a potassium hydroxide aqueous solution, adding toluene for extraction, and layering the PETG up and down to separate the PETG into a water phase and an organic phase;
the organic phase enters a rectifying tower and is shunted to obtain ethylene glycol, toluene and 1,4 cyclohexanedimethanol;
filtering the water phase, evaporating the water to dryness, adding anhydrous DMF and trimethoxychlorosilane, and reacting to produce bis (trimethoxy silane) terephthalate;
esterification of 1,4 cyclohexanedimethanol with acrylic acid gives the UV reactive diluent 1,4 cyclohexanedimethanol diacrylate.
2. The preliminary crushing in the step (1) according to claim 1, wherein the preliminary crushing is normal temperature crushing, and the particle diameter after crushing is about 1cm to 5 cm.
3. Cryogenic crushing in step (1) according to claim 1, characterised in that the crushing temperature of the cryogenic crushing is from-10 to-40 ℃ and the particle diameter after crushing is about 0.1mm to 2 mm.
4. The aqueous sodium hydroxide solution used in the step (2) according to claim 1, characterized in that the concentration of the aqueous sodium hydroxide solution is 20% to 30%.
5. Hydrolysis according to claim 1 in step (2), characterized in that the hydrolysis temperature is 80-100 ℃.
6. The toluene used in the step (2) according to claim 1, wherein the amount of the toluene added is 1 to 2 times by weight as much as the amount of the aqueous solution of sodium hydroxide.
7. The rectification column used in the step (3) according to claim 1, characterized in that the rectification temperature is 100-140 ℃.
8. The ethylene glycol obtained in step (3) according to claim 1, characterized in that the product purity is greater than 99.5%.
9. The use of the reaction process in step (4) according to claim 1, characterized by the principle of:
10. the use of the reaction process in step (5) according to claim 1, characterized by the principle of:
11. the method for recovering the degraded PETG according to claim 1, wherein the degraded PETG can be converted into new usable substances without any waste.
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