CN105837447A - Synthetic method for neopentyl glycol diisocaprylate - Google Patents

Synthetic method for neopentyl glycol diisocaprylate Download PDF

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Publication number
CN105837447A
CN105837447A CN201610198289.1A CN201610198289A CN105837447A CN 105837447 A CN105837447 A CN 105837447A CN 201610198289 A CN201610198289 A CN 201610198289A CN 105837447 A CN105837447 A CN 105837447A
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China
Prior art keywords
neopentyl glycol
acid
synthetic method
catalyst
tricaprylate
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CN201610198289.1A
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Chinese (zh)
Inventor
肖林久
闵媛媛
张志刚
谢颖
李文泽
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Shenyang University of Chemical Technology
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Shenyang University of Chemical Technology
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Priority to CN201610198289.1A priority Critical patent/CN105837447A/en
Publication of CN105837447A publication Critical patent/CN105837447A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a synthetic method for neopentyl glycol diisocaprylate. The synthetic method comprises the following steps: step 1, adding neopentyl glycol and isocaprylic acid into a three-neck flask and carrying out heating by using a magnetic-stirring heating jacket; step 2, adding a catalyst after dissolving of reactants; step 3, heating to 100 to 170 DEG C for esterification; and step 4, carrying out pressure-reduced distillation and purifying the product; wherein the usage amount of the catalyst is 0.5 to 5% of the total mass of the reactants, a mol ratio of neopentyl glycol to isocaprylic acid is 0.5: 1-3, the vacuum degree of pressure-reduced distillation and purification is 100 Pa, and a faction in a temperature range of 142 to 145 DEG C is collected. According to method, synthesis conditions for neopentyl glycol diisocaprylate are free of a water-carrying agent; synthesized neopentyl glycol diisocaprylate is free of water-carrying agents like toluene, has low toxicity and accords with requirements of environmental protection; and through pressure-reduced distillation and purification of the product, the fraction has a small temperature range and the product is high in quality.

Description

A kind of synthetic method of neopentyl glycol two tricaprylate
Technical field
The present invention relates to the synthetic method of a kind of ester, particularly relate to the synthetic method of a kind of neopentyl glycol two tricaprylate.
Background technology
Neopentyl glycol two tricaprylate because of its good heat stability, non-oxidizability and readily degradable and become the most promising esters syntholube base oil.Esterification is typical reversible reaction, and this kind of reaction typically uses addition water entrainer to take the water produced in course of reaction or the amount of too much acid or alcohol that adds out of to make chemical equilibrium move to the direction generating ester.Such method there is also the problems such as solvent contamination equally, and the purification condition for product has had higher requirement.Therefore, find and more environment-friendly synthetic method is increasingly subject to people's attention.
Summary of the invention
It is an object of the invention to provide the synthetic method of a kind of neopentyl glycol two tricaprylate, the inventive method is a kind of synthesis condition without neopentyl glycol two tricaprylate under the conditions of water entrainer, the ester of synthesis is without water entrainer such as toluene, toxicity is low, meet environmental requirement, and through decompression distilation product, fraction interval is little, and product quality is high.
It is an object of the invention to be achieved through the following technical solutions:
A kind of synthetic method of neopentyl glycol two tricaprylate, described method includes procedure below:
The first step, adds neopentyl glycol and isooctyl acid in there-necked flask, uses magnetic agitation heating mantle heats；Second step, reactant adds catalyst after dissolving；It is continuously heating to 100-170 DEG C, carries out esterification；4th step, carries out decompression distillation, purifies product；Wherein the consumption of catalyst is at the 0.5-5% of reactant gross mass；The molar ratio of neopentyl glycol and isooctyl acid is at 0.5:1-3；The vacuum of decompression distilation is 100Pa , collecting temperature range is the fraction of 142-145 DEG C.
The synthetic method of described a kind of neopentyl glycol two tricaprylate, described catalyst is acidic catalyst, including liquid acid such as concentrated sulphuric acid, strong phosphoric acid, phosphorous acid.
The synthetic method of described a kind of neopentyl glycol two tricaprylate, described acidic catalyst also includes solid acid such as p-methyl benzenesulfonic acid, phosphotungstic acid
The synthetic method of described a kind of neopentyl glycol two tricaprylate, described acidic catalyst also includes solid super-strong acid such as TiO2/SO4 2-、ZrO2/SO4 2-And TiO2-ZrO2/SO4 2-。
Advantages of the present invention with effect is:
The ester of the inventive method synthesis is without water entrainer such as toluene, and toxicity is low, meets environmental requirement, and through decompression distilation product, fraction interval is little, and product quality is high.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in detail.
Neopentyl glycol two tricaprylate synthetic method provided by the present invention, is under conditions of without water entrainer, is 0.5-10KPa by neopentyl glycol and isooctyl acid at pressure, and temperature is 90-170 DEG C, obtains ester under conditions of acidic catalyst；1:0.5-1:3.5, the mass percent of catalyst is 0.5%-5%.Acidic catalyst has following a few class in the above-mentioned methods: 1) liquid acid such as concentrated sulphuric acid, strong phosphoric acid, phosphorous acid；2) solid acid such as p-methyl benzenesulfonic acid, phosphotungstic acid；3) solid super-strong acid such as TiO2/SO4 2-、ZrO2/SO4 2-And TiO2-ZrO2/SO4 2-。
Embodiment one
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.64mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 150 DEG C, after isothermal reaction 5h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, neopentyl glycol two tricaprylate ultimate yield is 81.2%.
Embodiment two
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 150 DEG C, treat isothermal reaction 5h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, neopentyl glycol two tricaprylate ultimate yield is 96.8%.
Embodiment three
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 2% addition catalyst of reactant gross mass.Control reaction temperature 150 DEG C, treat constant temperature 5h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, the ultimate yield of neopentyl glycol two tricaprylate is 80.6%.
Embodiment four
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 120 DEG C, after isothermal reaction 5h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, the ultimate yield of neopentyl glycol two tricaprylate is 92.6%.
Embodiment five
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 140 DEG C, after isothermal reaction 5h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, the ultimate yield of neopentyl glycol two tricaprylate is 96.8%.
Embodiment six
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 140 DEG C, after isothermal reaction 3h, naturally cool to room temperature.Being washed with deionized by crude product, the crude product after washing carries out decompression distillation, collects 142 ~ 145 under 100 Pa pressureoThe fraction of C, the ultimate yield of neopentyl glycol two tricaprylate is 88.9%.
Embodiment seven
In 250 mL there-necked flasks, add 0.32mol neopentyl glycol and 0.768mol isooctyl acid, water knockout drum and spherical reflux condensing tube are installed, heat with the temperature-controlled heating mantle of band magnetic agitation.After question response thing is completely dissolved, according to 4% addition catalyst of reactant gross mass.Control reaction temperature 140 DEG C, after isothermal reaction 4h, naturally cool to room temperature.Crude product is washed with deionized, the crude product after washing carry out decompression distillation, under 100 Pa pressure collect 142 ~ 145oThe fraction of C, the ultimate yield of neopentyl glycol two tricaprylate is 96.8%.

Claims (4)

1. the synthetic method of neopentyl glycol two tricaprylate, it is characterised in that described method includes procedure below:
The first step, adds neopentyl glycol and isooctyl acid in there-necked flask, uses magnetic agitation heating mantle heats；Second step, reactant adds catalyst after dissolving；It is continuously heating to 100-170 DEG C, carries out esterification；4th step, carries out decompression distillation, purifies product；Wherein the consumption of catalyst is at the 0.5-5% of reactant gross mass；The molar ratio of neopentyl glycol and isooctyl acid is at 0.5:1-3；The vacuum of decompression distilation is 100Pa , collecting temperature range is the fraction of 142-145 DEG C.
The synthetic method of a kind of neopentyl glycol two tricaprylate the most according to claim 1, it is characterised in that described catalyst is acidic catalyst, including liquid acid such as concentrated sulphuric acid, strong phosphoric acid, phosphorous acid.
The synthetic method of a kind of neopentyl glycol two tricaprylate the most according to claim 2, it is characterised in that described acidic catalyst also includes solid acid such as p-methyl benzenesulfonic acid, phosphotungstic acid.
The synthetic method of a kind of neopentyl glycol two tricaprylate the most according to claim 2, it is characterised in that described acidic catalyst also includes solid super-strong acid such as TiO2/SO4 2-、ZrO2/SO4 2-And TiO2-ZrO2/SO4 2-。
CN201610198289.1A 2016-04-01 2016-04-01 Synthetic method for neopentyl glycol diisocaprylate Pending CN105837447A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106496028A (en) * 2016-08-23 2017-03-15 盘锦洪鼎化工有限公司 A kind of method of synthesis two tricaprylate of neopentyl glycol

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008013546A (en) * 2006-06-07 2008-01-24 Kao Corp Method for producing ester
CN102030637A (en) * 2009-10-08 2011-04-27 奥克塞有限公司 Method for brightening the colour of polyol esters
CN102030634A (en) * 2009-10-08 2011-04-27 奥克塞有限公司 Method for manufacturing polyol esters

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008013546A (en) * 2006-06-07 2008-01-24 Kao Corp Method for producing ester
CN102030637A (en) * 2009-10-08 2011-04-27 奥克塞有限公司 Method for brightening the colour of polyol esters
CN102030634A (en) * 2009-10-08 2011-04-27 奥克塞有限公司 Method for manufacturing polyol esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
肖林久等: "新戊二醇二异辛酸酯的合成工艺研究", 《精细石油化工》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106496028A (en) * 2016-08-23 2017-03-15 盘锦洪鼎化工有限公司 A kind of method of synthesis two tricaprylate of neopentyl glycol
CN106496028B (en) * 2016-08-23 2018-11-30 盘锦洪鼎化工有限公司 A method of synthesis two tricaprylate of neopentyl glycol

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Application publication date: 20160810