CN102060707A - Preparation method of polymerization type environment-friendly plasticizer diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate - Google Patents
Preparation method of polymerization type environment-friendly plasticizer diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate Download PDFInfo
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- CN102060707A CN102060707A CN2010105204187A CN201010520418A CN102060707A CN 102060707 A CN102060707 A CN 102060707A CN 2010105204187 A CN2010105204187 A CN 2010105204187A CN 201010520418 A CN201010520418 A CN 201010520418A CN 102060707 A CN102060707 A CN 102060707A
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Abstract
The invention discloses a preparation method of polymerization type environment-friendly plasticizer diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate. The preparation method comprises the following steps of: putting 1 molar of diethylene glycol, 4.25 molar of cyclohexane-1,3-dicardoxylic acid anhydride and a catalyst into a reactor, and then stirring and heating the obtained mixture to 150 DEG C for cross-linking reaction; adding 1.7-2.1 molar of 2-ethylhexanol and a catalyst in the reaction system, and then stirring and heating the mixture to 220 DEG C for esterification reaction; removing the excessive alcohol to obtain the crude diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate; cooling the crude diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate to 85 DEG C, then adding 1% Na2CO3 aqueous solution for neutralization; washing the neutralized product with non-ion water at the temperature of 90 DEG C; and steaming stripping and refining for 3-4 hours under the condition of reduced pressure, adding activated carbon for absorption and decoloration, filterng and then obtaining the purified product. The heat-resisting environment-friendly plasticizer prepared by the method can be used for heat-resisting and perdurable articles, such as heat-resisting electric wire and cable materials, plank stuffs, sheets, sealing gaskets and the like.
Description
Technical field
The present invention relates to technical field of chemical engineering, relate in particular to a kind of aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method of 3-2-dicarboxylic acid diethylhexyl ester.
Background technology
Polyvinyl chloride (PVC) industrial expansion be unable to do without softening agent, and 90% of all output of softening agent are applied to PVC industry, and wherein special plasticiser accounts for 1/5 of the market share.PVC is because its excellent cost performance, thereby is widely used in wire cable insulating layer and sheath.105 ℃ of level CABLE MATERIALS are the highest kinds of temperature resistant grade in the electric wire, distribution, hot machine fixture wire and the distribution of required high temperature resistant machinery equipment when being mainly used in to raising electric wire current capacity, distribution as Steel Plant, fuel-burning power plant steam-boiler, stove, and aviation, resistant to elevated temperatures occasion such as peculiar to vessel, development prospect is very wide.Softening agent is mainly selected trioctyl trimellitate (TOTM) for use in present 105 ℃ of level CABLE MATERIALS, but the raw alcohol consumption big (TOTM per ton needs more than the 2-Ethylhexyl Alcohol 715kg) that domestic synthetic TOTM is used, for many years should the domestic long run supply anxiety of alcohol, hold at high price, it is the secular importer of last resort in the world, thereby directly cause domestic plasticizer production cost up, therefore, how to fully utilize domestic existing available stock, reducing the plasticizer production cost, is that pendulum is in vast plasticizer production enterprise key subjects in front.The present invention utilizes part glycol ether instead of part 2-Ethylhexyl Alcohol to synthesize glycol ether bis cyclohexane-1,3-dicarboxyl di-isooctyl is a kind of higher molecular weight aggretion type environment-friendly plasticizer that has, owing in molecule, add the 3rd component glycol ether, not only reduced cost, but also make synthetic product resistance toheat obtain raising, good with the PVC consistency, product is in volatility, resistance to migration, aspect such as lower temperature resistance and electrical property is good, the goods transparency is good, better mechanical property such as tensile strength and elongation at break, have the advantage of monomeric plasticizer and polymeric plasticiser concurrently, can substitute trioctyl trimellitate (TOTM) fully and be used for heatproof wire CABLE MATERIALS (105 ℃ of levels) sheet material, sheet material, gaskets etc. require heat-resisting and competent goods.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, provide a kind of aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method of 3-2-dicarboxylic acid diethylhexyl ester.
Aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method's of 3-2-dicarboxylic acid diethylhexyl ester step is as follows:
1) with 1 mole glycol ether, 4.25 moles hexanaphthene-1,3-dicarboxylic anhydride and catalyst mix stirring heating crosslinking reaction, control reaction temperature is at 150 ℃, and behind 150 ℃ of following insulation reaction 2-3h, in reaction system, add the 2-Ethylhexyl Alcohol and the catalyzer of 1.7-2.1 mole again, continue stirring and be warmed up to 220 ℃, reaction 3-4h, remove excessive 2-Ethylhexyl Alcohol, get glycol ether bis cyclohexane-1, the thick product of 3-2-dicarboxylic acid diethylhexyl ester;
2) with glycol ether bis cyclohexane-1,3-2-dicarboxylic acid diethylhexyl ester crude product is cooled to the Na of 85 ℃ of addings 1%
2CO
3Catalyzer in the micro-single acid esters, hydrolyzation system in the aqueous solution and in the material system, under 90 ℃, remove the alkali lye of carrying secretly in the thick ester with the deionized water washing, catalyzer after the hydrolysis and other impurity soluble in water, the refining 3-4h of stripping under reduced pressure, the charcoal absorption decolouring that adds material total amount 0.1%, get glycol ether bis cyclohexane-1 through press filtration, 3-2-dicarboxylic acid diethylhexyl ester purified product.
Acid number is controlled at 200mgNaOH/g after the described crosslinking reaction.Described catalyzer is zinc acetate and titanium isopropylate, and the two adds total amount is hexanaphthene-1,0.8% of 3-dicarboxylic anhydride quality.
The glycol ether bis cyclohexane-1 that the present invention makes, 3-2-dicarboxylic acid diethylhexyl ester softening agent can be used for heatproof wire CABLE MATERIALS (105 ℃ of levels), sheet material, sheet material, gasket etc. and requires heat-resisting and competent goods.The purity of the softening agent product that the present invention makes can be tested by gas chromatograph, and product purity is more than or equal to 99.5%.
Embodiment
Aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method's of 3-2-dicarboxylic acid diethylhexyl ester step is as follows:
1) with 1 mole glycol ether, 4.25 moles hexanaphthene-1,3-dicarboxylic anhydride and catalyst mix stirring heating crosslinking reaction, control reaction temperature is at 150 ℃, and behind 150 ℃ of following insulation reaction 2-3h, in reaction system, add the 2-Ethylhexyl Alcohol and the catalyzer of 1.7-2.1 mole again, continue stirring and be warmed up to 220 ℃, reaction 3-4h, remove excessive 2-Ethylhexyl Alcohol, get glycol ether bis cyclohexane-1, the thick product of 3-2-dicarboxylic acid diethylhexyl ester;
2) with glycol ether bis cyclohexane-1,3-2-dicarboxylic acid diethylhexyl ester crude product is cooled to the Na of 85 ℃ of addings 1%
2CO
3Catalyzer in the micro-single acid esters, hydrolyzation system in the aqueous solution and in the material system, under 90 ℃, remove the alkali lye of carrying secretly in the thick ester with the deionized water washing, catalyzer after the hydrolysis and other impurity soluble in water, the refining 3-4h of stripping under reduced pressure, the charcoal absorption decolouring that adds material total amount 0.1%, get glycol ether bis cyclohexane-1 through press filtration, 3-2-dicarboxylic acid diethylhexyl ester purified product.
Acid number is controlled at 200mgNaOH/g after the described crosslinking reaction.
Described catalyzer is zinc acetate and titanium isopropylate, and the two adds total amount is hexanaphthene-1,0.8% of 3-dicarboxylic anhydride quality.
Embodiment 1
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 1.7 moles of total masses again after 2 hours be 1490kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 3h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 98.27%, and purity is 99.05%, No. 55, colourity (Pt-Co is), acid number is 0.09mgKOH/g, and relative density (20 ℃) is 0.995g/cm
3, flash-point (open cup) is 267 ℃, volume specific resistance is 5.1 * 10
11Ω m.
Embodiment 2
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 1.8 moles of total masses again after 2.5 hours be 1580kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 3h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.13%, and purity is 99.21%, and colourity (Pt-Co) is No. 55, acid number is 0.08mgKOH/g, and relative density (20 ℃) is 0.996g/cm
3, flash-point (open cup) is 266 ℃, volume specific resistance is 5.3 * 10
11Ω m.
Embodiment 3
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 1.8 moles of total masses again after 3 hours be 1580kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3.5h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 4h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.24%, and purity is 99.37%, and colourity (Pt-Co) is No. 50, acid number is 0.07mgKOH/g, and relative density (20 ℃) is 0.996g/cm
3, flash-point (open cup) is 265 ℃, volume specific resistance is 5.3 * 10
11Ω m.
Embodiment 4
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 1.9 moles of total masses again after 2.5 hours be 1670kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 3.5h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.61%, and purity is 99.50%, and colourity (Pt-Co) is No. 50, acid number is 0.05mgKOH/g, and relative density (20 ℃) is 0.997g/cm
3, flash-point (open cup) is 269 ℃, volume specific resistance is 5.2 * 10
11Ω m.
Embodiment 5
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 1.9 moles of total masses again after 3 hours be 1670kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 4h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 4h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.65%, and purity is 99.53%, and colourity (Pt-Co) is No. 50, acid number is 0.07mgKOH/g, and relative density (20 ℃) is 0.995g/cm
3, flash-point (open cup) is 268 ℃, volume specific resistance is 5.5 * 10
11Ω m.
Embodiment 6
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 2.0 moles of total masses again after 2.5 hours be 1760kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3.5h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 3h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.72%, and purity is 99.61%, and colourity (Pt-Co) is No. 55, acid number is 0.05mgKOH/g, and relative density (20 ℃) is 0.997g/cm
3, flash-point (open cup) is 268 ℃, volume specific resistance is 5.3 * 10
11Ω m.
Embodiment 7
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 2.0 moles of total masses again after 3 hours be 17600kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 4h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 4h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.86%, and purity is 99.63%, and colourity (Pt-Co) is No. 50, acid number is 0.05mgKOH/g, and relative density (20 ℃) is 0.996g/cm
3, flash-point (open cup) is 267 ℃, volume specific resistance is 5.4 * 10
11Ω m.
Embodiment 8
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 2.1 moles of total masses again after 2 hours be 1840kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 3h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 3h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.30%, and purity is 99.43%, and colourity (Pt-Co) is No. 55, acid number is 0.06mgKOH/g, and relative density (20 ℃) is 0.997g/cm
3, flash-point (open cup) is 265 ℃, volume specific resistance is 5.2 * 10
11Ω m.
Embodiment 9
With glycol ether and hexanaphthene-1,3-dicarboxylic anhydride mol ratio is 1/4.25, total mass is glycol ether and the hexanaphthene-1 of 1180kg, the 3-dicarboxylic anhydride adds in the reactor, add relative hexanaphthene-1 again, the zinc acetate catalyst of 3-dicarboxylic anhydride quality 0.5%, be heated with stirring to 150 ℃, and at 150 ℃ of following insulation reaction 2-Ethylhexyl Alcohol and relative hexanaphthene-1 that to add 2.1 moles of total masses again after 3 hours be 1840kg, the titanium isopropylate catalyzer of 3-dicarboxylic anhydride quality 0.3%, continue to stir and to be warming up to dealcoholysis behind 220 ℃ of reaction 4h, be cooled to 85 ℃ of Na that add 100kg1.0wt%
2CO
3Aqueous solution neutralization, wash with deionized water for 90 ℃, decompression adds the charcoal absorption decolouring 30min of still material total amount 0.1% down with the refining 4h of open steam stripping, gets glycol ether bis cyclohexane-1 through press filtration, the 3-2-dicarboxylic acid diethylhexyl ester, its yield is 99.41%, and purity is 99.48%, and colourity (Pt-Co) is No. 60, acid number is 0.07mgKOH/g, and relative density (20 ℃) is 0.995g/cm
3, flash-point (open cup) is 266 ℃, volume specific resistance is 5.1 * 10
11Ω m.
Claims (3)
1. aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method of 3-2-dicarboxylic acid diethylhexyl ester is characterized in that its step is as follows:
1) with 1 mole glycol ether, 4.25 moles hexanaphthene-1,3-dicarboxylic anhydride and catalyst mix stirring heating are carried out crosslinking reaction, control reaction temperature is at 150 ℃, and behind 150 ℃ of following insulation reaction 2-3h, in reaction system, add the 2-Ethylhexyl Alcohol and the catalyzer of 1.7-2.1 mole again, continue stirring and be warmed up to 220 ℃, reaction 3-4h, remove excessive 2-Ethylhexyl Alcohol, get glycol ether bis cyclohexane-1, the thick product of 3-2-dicarboxylic acid diethylhexyl ester;
2) with glycol ether bis cyclohexane-1,3-2-dicarboxylic acid diethylhexyl ester crude product is cooled to the Na of 85 ℃ of addings 1%
2CO
3Catalyzer in the micro-single acid esters, hydrolyzation system in the aqueous solution and in the material system, under 90 ℃, remove the alkali lye of carrying secretly in the thick ester with the deionized water washing, catalyzer after the hydrolysis and other impurity soluble in water, the refining 3-4h of stripping under reduced pressure, the charcoal absorption decolouring that adds material total amount 0.1%, get glycol ether bis cyclohexane-1 through press filtration, 3-2-dicarboxylic acid diethylhexyl ester purified product.
2. according to right characteristic 1 desired a kind of aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method of 3-2-dicarboxylic acid diethylhexyl ester, it is characterized in that described crosslinking reaction after, the control acid number is 200mgNaOH/g.
3. according to right characteristic 1 desired a kind of aggretion type environment-friendly plasticizer glycol ether bis cyclohexane-1, the preparation method of 3-2-dicarboxylic acid diethylhexyl ester, it is characterized in that described catalyzer is zinc acetate and titanium isopropylate, the two adds total amount is hexanaphthene-1,0.8% of 3-dicarboxylic anhydride quality.
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| CN2010105204187A CN102060707A (en) | 2010-10-26 | 2010-10-26 | Preparation method of polymerization type environment-friendly plasticizer diethylene glycol dicyclohexyl-1,3-diisobutyl dicarboxylate |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107108447A (en) * | 2014-12-18 | 2017-08-29 | 韩华化学株式会社 | Vaporizing extract process |
| CN112661635A (en) * | 2020-12-22 | 2021-04-16 | 浙江弘博新材料科技有限公司 | Environment-friendly synthesis method of plasticizer dibutyl phthalate |
-
2010
- 2010-10-26 CN CN2010105204187A patent/CN102060707A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107108447A (en) * | 2014-12-18 | 2017-08-29 | 韩华化学株式会社 | Vaporizing extract process |
| EP3235802A4 (en) * | 2014-12-18 | 2018-08-08 | Hanwha Chemical Corporation | Stripping method |
| US10081583B2 (en) | 2014-12-18 | 2018-09-25 | Hanwha Chemical Corporation | Stripping method |
| CN107108447B (en) * | 2014-12-18 | 2020-10-16 | 韩华化学株式会社 | Steam stripping process |
| CN112661635A (en) * | 2020-12-22 | 2021-04-16 | 浙江弘博新材料科技有限公司 | Environment-friendly synthesis method of plasticizer dibutyl phthalate |
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Application publication date: 20110518 |