CN105837447A - Synthetic method for neopentyl glycol diisocaprylate - Google Patents
Synthetic method for neopentyl glycol diisocaprylate Download PDFInfo
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000010189 synthetic method Methods 0.000 title claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000000376 reactant Substances 0.000 claims abstract description 20
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000003760 magnetic stirring Methods 0.000 claims abstract description 10
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000011973 solid acid Substances 0.000 claims description 3
- 239000003930 superacid Substances 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 9
- 150000002148 esters Chemical class 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 14
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
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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
一种新戊二醇二异辛酸酯的合成方法，涉及一种新戊二醇二异辛酸酯的合成方法，包括以下过程：第一步，在三口烧瓶中加入新戊二醇和异辛酸，用磁力搅拌加热套加热；第二步，反应物溶解后加入催化剂；继续升温至100‑170℃，进行酯化反应；第四步，进行减压蒸馏，对产物进行提纯；其中催化剂的用量在反应物总质量的0.5‑5%；新戊二醇和异辛酸的摩尔比例在0.5：1‑3；减压蒸馏提纯的真空度为100Pa，收集温度区间为142‑145℃的馏分。本发明方法是一种无带水剂条件下的新戊二醇二异辛酸酯的合成条件，合成的酯无甲苯等带水剂，毒性低，符合环保要求，并且经过减压蒸馏提纯产物，馏分区间小，产品质量高。A kind of synthetic method of neopentyl glycol diisocaprylate, relate to a kind of synthetic method of neopentyl glycol diisocaprylic acid ester, comprise the following process: the first step, add neopentyl glycol and isooctanoic acid in the there-necked flask , heating with a magnetic stirring heating mantle; the second step, add the catalyst after the reactants are dissolved; continue to heat up to 100-170 ° C, and carry out the esterification reaction; the fourth step, carry out vacuum distillation to purify the product; the amount of the catalyst 0.5-5% of the total mass of reactants; the molar ratio of neopentyl glycol and isooctanoic acid is 0.5:1-3; the vacuum degree of vacuum distillation and purification is 100Pa, and the fraction collected at a temperature range of 142-145°C. The method of the present invention is a synthesis condition of neopentyl glycol diisocaprylate under the condition of no water-carrying agent, the synthesized ester has no water-carrying agent such as toluene, has low toxicity, meets environmental protection requirements, and the product is purified through vacuum distillation , the fraction interval is small, and the product quality is high.
Description
技术领域 technical field
本发明涉及一种酯的合成方法，特别是涉及一种新戊二醇二异辛酸酯的合成方法。 The present invention relates to a kind of synthetic method of ester, particularly relate to a kind of synthetic method of neopentyl glycol diisocaprylate.
背景技术 Background technique
新戊二醇二异辛酸酯因其良好的热稳定性，抗氧化性和易降解性而成为非常有前景的酯类合成润滑油基础油。酯化反应是典型的可逆反应，这类反应一般采用加入带水剂带出反应过程中产生的水或者加入过多的酸或醇的量来使化学平衡向生成酯的方向移动。这样的方法同样也存在溶剂污染等问题，并且为产物的提纯条件有了更高的要求。因此，寻找对环境更加友好的合成方法日益受到人们重视。 Neopentyl glycol diisocaprylate is a very promising ester synthetic lubricating base oil because of its good thermal stability, oxidation resistance and ease of degradation. The esterification reaction is a typical reversible reaction. This type of reaction generally adopts adding a water-carrying agent to take out the water generated during the reaction or adding too much acid or alcohol to move the chemical balance to the direction of ester formation. Such a method also has problems such as solvent pollution, and has higher requirements for the purification conditions of the product. Therefore, people pay more and more attention to finding more environmentally friendly synthetic methods.
发明内容 Contents of the invention
本发明的目的在于提供一种新戊二醇二异辛酸酯的合成方法，本发明方法是一种无带水剂条件下的新戊二醇二异辛酸酯的合成条件，合成的酯无甲苯等带水剂，毒性低，符合环保要求，并且经过减压蒸馏提纯产物，馏分区间小，产品质量高。 The object of the present invention is to provide a kind of synthetic method of neopentyl glycol diisocaprylate, and the inventive method is a kind of synthetic condition of neopentyl glycol diisocaprylate under the condition of no water agent, the synthetic ester No toluene and other water-carrying agents, low toxicity, in line with environmental protection requirements, and the product is purified by vacuum distillation, the fraction interval is small, and the product quality is high.
本发明的目的是通过以下技术方案实现的： The purpose of the present invention is achieved through the following technical solutions:
一种新戊二醇二异辛酸酯的合成方法，所述方法包括以下过程： A kind of synthetic method of neopentyl glycol diisocaprylate, described method comprises the following process:
第一步，在三口烧瓶中加入新戊二醇和异辛酸，用磁力搅拌加热套加热；第二步，反应物溶解后加入催化剂；继续升温至100-170℃，进行酯化反应；第四步，进行减压蒸馏，对产物进行提纯；其中催化剂的用量在反应物总质量的0.5-5%；新戊二醇和异辛酸的摩尔比例在0.5：1-3；减压蒸馏提纯的真空度为100Pa ，收集温度区间为142-145℃的馏分。 The first step is to add neopentyl glycol and isooctanoic acid into the three-necked flask, and heat it with a magnetic stirring heating mantle; the second step is to add the catalyst after the reactants are dissolved; continue to heat up to 100-170°C to carry out the esterification reaction; the fourth step , carry out vacuum distillation, and the product is purified; wherein the amount of catalyst is 0.5-5% of the total mass of reactants; the molar ratio of neopentyl glycol and isooctanoic acid is 0.5:1-3; the vacuum degree of vacuum distillation purification is 100Pa , collecting fractions in the temperature interval 142-145°C.
所述的一种新戊二醇二异辛酸酯的合成方法，所述催化剂为酸性催化剂，包括液体酸如浓硫酸、 浓磷酸、亚磷酸。 The synthetic method of described a kind of neopentyl glycol diisocaprylate, described catalyst is acidic catalyst, comprises liquid acid such as concentrated sulfuric acid, concentrated phosphoric acid, phosphorous acid.
所述的一种新戊二醇二异辛酸酯的合成方法，所述酸性催化剂还包括固体酸如对甲苯磺酸、 磷钨酸 The synthetic method of described a kind of neopentyl glycol diisocaprylate, described acidic catalyst also comprises solid acid such as p-toluenesulfonic acid, phosphotungstic acid
所述的一种新戊二醇二异辛酸酯的合成方法，所述酸性催化剂还包括固体超强酸如TiO2/SO4 2-、ZrO2/SO4 2-以及TiO2-ZrO2/SO4 2-。 In the synthetic method of neopentyl glycol diisocaprylate, the acidic catalyst also includes solid superacids such as TiO 2 /SO 4 2- , ZrO 2 /SO 4 2- and TiO 2 -ZrO 2 / SO 4 2- .
本发明的优点与效果是： Advantage and effect of the present invention are:
本发明方法合成的酯无甲苯等带水剂，毒性低，符合环保要求，并且经过减压蒸馏提纯产物，馏分区间小，产品质量高。 The ester synthesized by the method of the invention has no water-carrying agent such as toluene, has low toxicity, meets the requirement of environmental protection, and the product is purified through vacuum distillation, has small distillate intervals and high product quality.
具体实施方式 detailed description
下面结合实施例对本发明进行详细说明。 The present invention will be described in detail below in conjunction with examples.
本发明所提供的新戊二醇二异辛酸酯合成方法，是在无带水剂的条件下，将新戊二醇与异辛酸在压力为0.5-10KPa，温度为90-170℃，酸性催化剂的条件下得到酯；1：0.5-1：3.5，催化剂的质量百分比为0.5%-5%。在上述方法中酸性催化剂有以下几类：1）液体酸如浓硫酸、 浓磷酸、亚磷酸；2）固体酸如对甲苯磺酸、 磷钨酸；3）固体超强酸如TiO2/SO4 2-、ZrO2/SO4 2-以及TiO2-ZrO2/SO4 2-。 The synthesis method of neopentyl glycol diisocaprylate provided by the present invention is to prepare neopentyl glycol and isooctanoic acid at a pressure of 0.5-10KPa and a temperature of 90-170°C under the condition of no water-carrying agent. The ester is obtained under the condition of the catalyst; 1:0.5-1:3.5, the mass percentage of the catalyst is 0.5%-5%. The acidic catalysts in the above methods are as follows: 1) liquid acids such as concentrated sulfuric acid, concentrated phosphoric acid, phosphorous acid; 2) solid acids such as p-toluenesulfonic acid, phosphotungstic acid; 3) solid superacids such as TiO 2 /SO 4 2- , ZrO 2 /SO 4 2- and TiO 2 -ZrO 2 /SO 4 2- .
实施例一 Embodiment one
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.64mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度150℃，待恒温反应5h后，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯最终产率为81.2%。 Add 0.32 mol of neopentyl glycol and 0.64 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. The reaction temperature was controlled at 150° C., and after a constant temperature reaction for 5 hours, it was naturally cooled to room temperature. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 81.2%.
实施例二 Embodiment two
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度150℃，待恒温反应5h，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯最终产率为96.8%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. Control the reaction temperature at 150°C, wait for constant temperature reaction for 5 hours, and cool to room temperature naturally. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 96.8%.
实施例三 Embodiment three
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的2%加入催化剂。控制反应温度150℃，待恒温5h，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯的最终产率为80.6%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactants are completely dissolved, the catalyst is added according to 2% of the total mass of the reactants. Control the reaction temperature at 150°C, wait for 5 hours at constant temperature, and cool to room temperature naturally. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 80.6%.
实施例四 Embodiment Four
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度120℃，待恒温反应5h后，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯的最终产率为92.6%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. The reaction temperature was controlled at 120° C., and after a constant temperature reaction for 5 hours, it was naturally cooled to room temperature. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 92.6%.
实施例五 Embodiment five
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度140℃，待恒温反应5h后，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯的最终产率为96.8%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. The reaction temperature was controlled at 140° C., and after a constant temperature reaction for 5 hours, it was naturally cooled to room temperature. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 96.8%.
实施例六 Embodiment six
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度140℃，待恒温反应3h后，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯的最终产率为88.9%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. The reaction temperature was controlled at 140° C., and after a constant temperature reaction for 3 hours, it was naturally cooled to room temperature. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 88.9%.
实施例七 Embodiment seven
在250 mL三口烧瓶中加入0.32mol新戊二醇和0.768mol异辛酸，安装分水器与球形回流冷凝管，用带磁力搅拌的控温加热套加热。待反应物完全溶解后，按照反应物总质量的4%加入催化剂。控制反应温度140℃，待恒温反应4h后，自然冷却至室温。将粗产物用去离子水洗涤，洗涤后的粗产物进行减压蒸馏，在100 Pa压力下收集142 ~ 145oC的馏分，新戊二醇二异辛酸酯的最终产率为96.8%。 Add 0.32 mol of neopentyl glycol and 0.768 mol of isooctanoic acid into a 250 mL three-neck flask, install a water separator and a spherical reflux condenser, and heat with a temperature-controlled heating mantle with magnetic stirring. After the reactant is completely dissolved, add the catalyst according to 4% of the total mass of the reactant. The reaction temperature was controlled at 140° C., and after 4 hours of constant temperature reaction, it was naturally cooled to room temperature. The crude product was washed with deionized water, and the washed crude product was distilled under reduced pressure, and the fraction at 142 ~ 145 o C was collected under a pressure of 100 Pa. The final yield of neopentyl glycol diisocaprylate was 96.8%.
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| CN201610198289.1A Pending CN105837447A (en) | 2016-04-01 | 2016-04-01 | Synthetic method for neopentyl glycol diisocaprylate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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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