CN104672085A - Synthesis of trimethylolpropane organic acid ester and application in special oil - Google Patents
Synthesis of trimethylolpropane organic acid ester and application in special oil Download PDFInfo
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- -1 trimethylolpropane organic acid ester Chemical class 0.000 title claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002608 ionic liquid Substances 0.000 claims abstract description 19
- 150000007524 organic acids Chemical class 0.000 claims abstract description 19
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 18
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 14
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 14
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 10
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000008117 stearic acid Substances 0.000 claims abstract description 10
- 239000005639 Lauric acid Substances 0.000 claims abstract description 7
- 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000012467 final product Substances 0.000 claims description 14
- 229960002446 octanoic acid Drugs 0.000 claims description 6
- 238000010189 synthetic method Methods 0.000 claims description 5
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 4
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 21
- 238000005886 esterification reaction Methods 0.000 abstract description 9
- 230000032050 esterification Effects 0.000 abstract description 8
- CAAULPUQFIIOTL-UHFFFAOYSA-L methyl phosphate(2-) Chemical compound COP([O-])([O-])=O CAAULPUQFIIOTL-UHFFFAOYSA-L 0.000 abstract description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 33
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 6
- 239000002173 cutting fluid Substances 0.000 description 4
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- BTGGRPUPMPLZNT-PGEUSFDPSA-N 2,2-bis[[(z)-octadec-9-enoyl]oxymethyl]butyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC BTGGRPUPMPLZNT-PGEUSFDPSA-N 0.000 description 2
- 229910001018 Cast iron Inorganic materials 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001593 sorbitan monooleate Substances 0.000 description 2
- 229940035049 sorbitan monooleate Drugs 0.000 description 2
- 235000011069 sorbitan monooleate Nutrition 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- Lubricants (AREA)
Abstract
本发明公开了一种三羟甲基丙烷有机酸酯的合成方法，其特征在于，以有机酸和有机醇为原料，并加入适量催化剂，在110℃-130℃条件下常压反应3-5小时，即得三羟甲基丙烷有机酸酯；所述有机酸选自油酸，月桂酸，辛酸，硬脂酸，棕榈酸中的任意一种，所述有机醇为三羟甲基丙烷，所述有机酸和有机醇的摩尔比为1:3；所述催化剂为N-烷基吡咯烷酮基团甲基磷酸离子液体催化剂。本发明通过选择N-烷基吡咯烷酮基团甲基磷酸离子液体催化剂合成三羟甲基丙烷有机酸酯，具有反应温度低，催化剂添加量少，反应时间短，酯化率高等特点，生产的产品酸值小。The invention discloses a synthesis method of trimethylolpropane organic acid ester, which is characterized in that organic acid and organic alcohol are used as raw materials, and an appropriate amount of catalyst is added, and the reaction is carried out under normal pressure at 110°C-130°C for 3-5 hours, to obtain trimethylolpropane organic acid ester; described organic acid is selected from oleic acid, lauric acid, octanoic acid, stearic acid, any one in palmitic acid, and described organic alcohol is trimethylolpropane, The molar ratio of the organic acid to the organic alcohol is 1:3; the catalyst is an N-alkylpyrrolidone group methylphosphoric acid ionic liquid catalyst. The present invention synthesizes trimethylolpropane organic acid ester by selecting N-alkylpyrrolidone group methyl phosphoric acid ionic liquid catalyst, has the characteristics of low reaction temperature, less catalyst addition, short reaction time, high esterification rate, etc., and the produced product The acid value is small.
Description
技术领域 technical field
本发明涉及化工领域，具体地说是一种三羟甲基丙烷有机酸酯的合成及在特种油中的应用。 The invention relates to the field of chemical industry, in particular to the synthesis of trimethylolpropane organic acid ester and its application in special oil.
背景技术 Background technique
三羟甲基丙烷有机酸酯(Trimethylolpropane trioleate)简称为TMPTO,它具有合成酯类的优良抗磨性能.具有优良的粘温特性，良好的低温特性，高温稳定性，低挥发性，因而能满足较高的润滑要求，尤其适合在特种油行业中的应用。 Trimethylolpropane trioleate (TMPTO) has excellent anti-wear performance of synthetic esters. It has excellent viscosity-temperature characteristics, good low-temperature characteristics, high-temperature stability, and low volatility, so it can meet Higher lubrication requirements, especially suitable for applications in the special oil industry.
三羟甲基丙烷有机酸酯具有润滑性能优、粘度指数高、抗燃性好，生物降解率高、毒性低等特性，是一种绿色润滑油，其作为油性剂在冷轧薄板轧制油、钢管拉拔油、切削油及其它金属加工液中广泛使用，三羟甲基丙烷有机酸酯也可作为纺织皮革助剂的中间体和纺织油剂。 Trimethylolpropane organic acid ester has the characteristics of excellent lubricating performance, high viscosity index, good flame resistance, high biodegradation rate and low toxicity. It is a kind of green lubricating oil. It is widely used in steel pipe drawing oil, cutting oil and other metal processing fluids. Trimethylolpropane organic acid ester can also be used as an intermediate of textile leather auxiliaries and textile oil agent.
现有三羟甲基丙烷有机酸酯的合成方法主要有直接酯化法与酯交换法，这些方法多使用质子酸、金属氧化物、无机盐催化剂等，合成法不是反应温度高，就是反应时间长，且转化率低，产品质量差、设备腐蚀严重、反应后处理困难、废酸污染严重等。 The synthetic method of existing trimethylolpropane organic acid ester mainly contains direct esterification method and transesterification method, and these methods use protonic acid, metal oxide, inorganic salt catalyst etc. more, and synthetic method is either that reaction temperature is high, or reaction time is long , and the conversion rate is low, the product quality is poor, the equipment is severely corroded, the post-reaction treatment is difficult, and the waste acid pollution is serious.
发明内容 Contents of the invention
本发明为了避免现有技术存在的不足之处，提供一种羟甲基丙烷油酸酯的合成及在特种油中的应用。 In order to avoid the disadvantages of the prior art, the present invention provides a synthesis of methylolpropane oleate and its application in special oils.
本发明解决技术问题采用如下技术方案： The present invention solves technical problem and adopts following technical scheme:
三羟甲基丙烷有机酸酯的合成方法，其特点在于，以有机酸和有机醇为原料，并加入适量催化剂，在110℃-130℃条件下常压反应3-5小时，即得三羟甲基丙烷有机酸酯；所述有机酸选自油酸，月桂酸，辛酸，硬脂酸，棕榈酸中的任意一种，所述有机醇为三羟甲基丙烷，所述有机酸和有机醇的摩尔比为1:3；所述催化剂为N-烷基吡咯烷酮基团甲基磷酸离子液体催化剂。 The synthesis method of trimethylolpropane organic acid ester is characterized in that organic acid and organic alcohol are used as raw materials, and an appropriate amount of catalyst is added, and the reaction is carried out under normal pressure at 110°C-130°C for 3-5 hours to obtain trihydroxy Methylpropane organic acid ester; the organic acid is selected from any one of oleic acid, lauric acid, caprylic acid, stearic acid, and palmitic acid, and the organic alcohol is trimethylol propane, and the organic acid and organic acid The molar ratio of alcohol is 1:3; the catalyst is an N-alkylpyrrolidone group methylphosphoric acid ionic liquid catalyst.
作为优选，所述化剂的添加量为原料质量的0.25％-0.75％。 As a preference, the added amount of the chemical agent is 0.25%-0.75% of the raw material mass.
作为优选，所述有机酸为油酸或硬脂酸，所述催化剂添加量为0.5％，反应温度为130℃，反应时间为4小时。 Preferably, the organic acid is oleic acid or stearic acid, the added amount of the catalyst is 0.5%, the reaction temperature is 130° C., and the reaction time is 4 hours.
本发明的另一目的是提供一种三羟甲基丙烷有机酸酯在特种油中的应用。 Another object of the present invention is to provide an application of trimethylolpropane organic acid ester in special oil.
与已有技术相比，本发明有益效果体现在： Compared with the prior art, the beneficial effects of the present invention are reflected in:
1、本发明通过选择N-烷基吡咯烷酮基团甲基磷酸离子液体催化剂合成三羟甲基丙烷有机酸酯，具有反应温度低，催化剂添加量少，反应时间短，酯化率高等特点，生产的产品酸值小。 1. The present invention synthesizes trimethylolpropane organic acid ester by selecting N-alkylpyrrolidone group methylphosphoric acid ionic liquid catalyst, which has the characteristics of low reaction temperature, less catalyst addition, short reaction time and high esterification rate. The acid value of the product is small.
2、本发明所合成的三羟甲基丙烷有机酸酯具有生物降解性，同时具有毒性低和润滑功能。 2. The trimethylolpropane organic acid ester synthesized by the present invention has biodegradability, low toxicity and lubricating function.
3、本发明在特种油中用三羟甲基丙烷有机酸酯代替部分润滑剂，可以提高特种油的使用寿命。 3. The present invention uses trimethylolpropane organic acid ester to replace part of the lubricant in special oil, which can improve the service life of special oil.
具体实施方式 Detailed ways
本发明有机酸选择油酸，月桂酸，辛酸，硬脂酸，棕榈酸等，有机醇选择三羟甲基丙烷，催化剂选择N-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，通过正交化试验研究有机醇与有机酸的不同反应摩尔比，催化剂添加量、反应时间、反应温度对酯化程度的影响，如下表(酸值越低，酯化度越高)： The organic acid of the present invention is selected from oleic acid, lauric acid, caprylic acid, stearic acid, palmitic acid, etc., the organic alcohol is selected from trimethylolpropane, and the catalyst is selected from N-alkylpyrrolidone group methyl phosphoric acid ionic liquid catalyst. Experimental study of the different reaction molar ratios of organic alcohols and organic acids, the effect of catalyst addition, reaction time, and reaction temperature on the degree of esterification, as shown in the following table (the lower the acid value, the higher the degree of esterification):
表1、油酸和三羟甲基丙烷的正交化试验 Table 1. Orthogonalization test of oleic acid and trimethylolpropane
由表1可知，当有机醇和有机酸的反应摩尔比为1:3，催化剂添加量为0.75％，反应温度130℃，在常压下反应3个小时，酸值为0.8mgKOH/g，酯化度最高；当有机醇和有机酸的反应摩尔比为1：3，催化剂添加量为0.50％，反应温度为130℃，在常压下反应4个小时，酸值为1.2mgKOH/g,酯化度次之；当有机醇和有机酸的反应摩尔比为1:3，催化剂添加量为0.750％，反应温度为110℃，在常压下反应5个小时，酸值为2.6mgKOH/g；通过综合经济效 益考虑，最终我们选择有机醇和有机酸的反应摩尔比为1:3，催化剂添加量为0.50％--0.75％，反应温度为130℃，常压下反应3-4个小时。 It can be seen from Table 1 that when the reaction molar ratio of organic alcohol and organic acid is 1:3, the amount of catalyst added is 0.75%, the reaction temperature is 130°C, and the reaction is carried out under normal pressure for 3 hours, the acid value is 0.8 mgKOH/g, and the esterification highest degree; when the reaction molar ratio of organic alcohol and organic acid is 1:3, the amount of catalyst added is 0.50%, the reaction temperature is 130°C, and the reaction is under normal pressure for 4 hours, the acid value is 1.2mgKOH/g, and the degree of esterification Secondly; when the reaction molar ratio of organic alcohol and organic acid is 1:3, the amount of catalyst added is 0.750%, the reaction temperature is 110°C, and the acid value is 2.6mgKOH/g under normal pressure for 5 hours; through comprehensive economic Considering the benefit, we finally choose the reaction molar ratio of organic alcohol and organic acid as 1:3, the amount of catalyst added is 0.50%-0.75%, the reaction temperature is 130°C, and the reaction is under normal pressure for 3-4 hours.
根据油酸和三羟甲基丙烷的正交试验结果，我们又利用辛酸、硬脂酸、月桂酸和棕榈酸进行了反应，结果如下表： According to the orthogonal test results of oleic acid and trimethylolpropane, we have carried out the reaction with caprylic acid, stearic acid, lauric acid and palmitic acid, and the results are as follows:
表2、辛酸和三羟甲基丙烷的反应 Table 2, the reaction of octanoic acid and trimethylolpropane
表3、月桂酸和三羟甲基丙烷的反应 Table 3, the reaction of lauric acid and trimethylolpropane
表4、硬脂酸和三羟甲基丙烷的反应 Table 4, the reaction of stearic acid and trimethylolpropane
表5、棕榈酸和三羟甲基丙烷的反应 Table 5, reaction of palmitic acid and trimethylolpropane
通过表1-5，可以看出：在同等条件下，硬脂酸和三羟甲基丙烷酯化度最高，但五种有机酸都可以和三羟甲基丙烷进行酯化反应。 From Table 1-5, it can be seen that under the same conditions, stearic acid and trimethylolpropane have the highest degree of esterification, but all five organic acids can undergo esterification reaction with trimethylolpropane.
实施例1 Example 1
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入2.45gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为110℃，反应3小时，即得最终产品，酸值为11.2mgKOH/g。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 2.45g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 110°C, and react for 3 hours. The final product was obtained with an acid value of 11.2 mgKOH/g.
实施例2 Example 2
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入2.45gN-烷基吡 咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为120℃，反应4小时，即得最终产品，酸值为10.9mgKOH/g。 Take by weighing 134g trimethylolpropane and 846g oleic acid and add in the flat-bottomed flask, after stirring evenly, add 2.45gN-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control temperature is 120 ℃, react After 4 hours, the final product was obtained with an acid value of 10.9 mgKOH/g.
实施例3 Example 3
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入2.45gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应5小时，即得最终产品，酸值为6.0mgKOH/g。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 2.45g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 5 hours. The final product was obtained with an acid value of 6.0 mgKOH/g.
实施例4 Example 4
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入4.9gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为120℃，反应3小时，即得最终产品，酸值为9.2mgKOH/g。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 4.9g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 120°C, and react for 3 hours. The final product was obtained with an acid value of 9.2 mgKOH/g.
实施例5 Example 5
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入4.9gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应4小时，即得最终产品，酸值为1.2mgKOH/g。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 4.9g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 4 hours. The final product was obtained with an acid value of 1.2 mgKOH/g.
实施例6 Example 6
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入4.9gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为110℃，反应5小时，即得最终产品，酸值为6.2mgKOH/g。。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 4.9g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 110°C, and react for 5 hours. The final product was obtained with an acid value of 6.2 mgKOH/g. .
实施例7 Example 7
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入7.35gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应3小时，即得最终产品，酸值为0.8mgKOH/g。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 7.35g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 3 hours. The final product was obtained with an acid value of 0.8 mgKOH/g.
实施例8 Example 8
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入7.35gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为120℃，反应4小时，即得最终产品，酸值为3.1mgKOH/g。。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 7.35g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 120°C, and react for 4 hours. The final product was obtained with an acid value of 3.1 mgKOH/g. .
实施例9 Example 9
称取134g三羟甲基丙烷和846g油酸加入平底烧瓶中，搅拌均匀后加入7.35gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为110℃，反应5小时，即得 最终产品，酸值为2.6mgKOH/g。。 Weigh 134g of trimethylolpropane and 846g of oleic acid into a flat-bottomed flask, stir evenly, add 7.35g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 110°C, and react for 5 hours. Promptly get final product, acid number 2.6mgKOH/g. .
实施例10 Example 10
称取134g三羟甲基丙烷和432g辛酸加入平底烧瓶中，搅拌均匀后加入2.83gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应4小时，即得最终产品，酸值为2.2mgKOH/g。 Weigh 134g of trimethylolpropane and 432g of octanoic acid into a flat-bottomed flask, stir evenly, add 2.83g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 4 hours, namely The final product was obtained with an acid value of 2.2 mgKOH/g.
实施例11 Example 11
称取134g三羟甲基丙烷和600g月桂酸加入平底烧瓶中，搅拌均匀后加入3.67gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应4小时，即得最终产品，酸值为2.3mgKOH/g。 Weigh 134g of trimethylolpropane and 600g of lauric acid into a flat-bottomed flask, stir evenly, add 3.67g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 4 hours. The final product was obtained with an acid value of 2.3 mgKOH/g.
实施例12 Example 12
称取134g三羟甲基丙烷和582g硬脂酸加入平底烧瓶中，搅拌均匀后加入4.93gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应4小时，即得最终产品，酸值为1.3mgKOH/g。 Weigh 134g of trimethylolpropane and 582g of stearic acid into a flat-bottomed flask, stir evenly, add 4.93g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature at 130°C, and react for 4 hours , to obtain the final product with an acid value of 1.3 mgKOH/g.
实施例13 Example 13
称取134g三羟甲基丙烷和768g棕榈酸加入平底烧瓶中，搅拌均匀后加入4.51gN-烷基吡咯烷酮基团甲基磷酸离子液体催化剂，搅拌，加热，控制温度为130℃，反应4小时，即得最终产品，酸值为2.3mgKOH/g。 Weigh 134g of trimethylolpropane and 768g of palmitic acid into a flat-bottomed flask, stir evenly, add 4.51g of N-alkylpyrrolidone group methyl phosphate ionic liquid catalyst, stir, heat, control the temperature to 130°C, and react for 4 hours. The final product was obtained with an acid value of 2.3 mgKOH/g.
实施例14 Example 14
称取3g妥尔油加入烧杯中，再加入6g的二乙醇胺、3g的超酰胺和5g三羟甲基丙烷有机酸酯，边加热边搅拌,升温至50度，搅拌均匀后加入15g石油磺酸钠、5g硼酸酯、1g山梨醇酐单油酸酯S-80、40g 22#锭子油，搅拌均匀，最后边搅拌边加入22g水，最后得到黄色透明的切削液，所得切削液PB值为650N，5％铸铁屑/滤纸法防锈性0级，5％pH值9.2。 Weigh 3g of tall oil and put it into a beaker, then add 6g of diethanolamine, 3g of superamide and 5g of trimethylolpropane organic acid ester, stir while heating, raise the temperature to 50 degrees, stir well and add 15g of petroleum sulfonic acid Sodium, 5g boric acid ester, 1g sorbitan monooleate S-80, 40g 22# spindle oil, stir well, and finally add 22g water while stirring, finally get yellow transparent cutting fluid, the obtained cutting fluid PB value is 650N, 5% cast iron shavings/filter paper method rust resistance level 0, 5% pH value 9.2.
实施例15 Example 15
称取2g妥尔油加入烧杯中，再加入6g的二乙醇胺、8g的超酰胺和4g三羟甲基丙烷有机酸酯，边加热边搅拌,升温至50度，搅拌均匀后加入12g重苯基石油磺酸钠、2g乙二醇单丁醚、2g硼酸酯、1g山梨醇酐单油酸酯S-80、20g 22#锭子油，搅拌均匀，最后边搅拌边加入43g水，最后得到黄色透明的切削液，所得切削液PB值为646N，5％铸铁屑/滤纸法防锈性0级，5％pH值9.5。 Weigh 2g of tall oil and put it into a beaker, then add 6g of diethanolamine, 8g of superamide and 4g of trimethylolpropane organic acid ester, stir while heating, raise the temperature to 50 degrees, add 12g of heavy phenyl Sodium petroleum sulfonate, 2g ethylene glycol monobutyl ether, 2g boric acid ester, 1g sorbitan monooleate S-80, 20g 22# spindle oil, stir evenly, add 43g water while stirring, and finally get yellow Transparent cutting fluid, the obtained cutting fluid has a PB value of 646N, 5% cast iron chips/filter paper method rust resistance level 0, and 5% pH value of 9.5.
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| CN105037146A (en) * | 2015-06-30 | 2015-11-11 | 百川化工(如皋)有限公司 | Ditrimethylolpropane laurate and preparation method thereof |
| CN105218364A (en) * | 2015-10-27 | 2016-01-06 | 诺泰生物科技(合肥)有限公司 | A kind of synthetic method of isopropyl fatty acid ester and the application in extraordinary oil thereof |
| CN105481692A (en) * | 2015-11-30 | 2016-04-13 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
| CN105481692B (en) * | 2015-11-30 | 2017-05-10 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
| CN105669449A (en) * | 2016-02-29 | 2016-06-15 | 诺泰生物科技(合肥)有限公司 | Chlorine hydroxyl ester synthesis method and application of chlorine hydroxyl ester in special oil |
| CN105669449B (en) * | 2016-02-29 | 2018-04-06 | 诺泰生物科技(合肥)有限公司 | A kind of synthetic method of chlorine hydroxyl ester and its application in extraordinary oil |
| CN106106485A (en) * | 2016-06-22 | 2016-11-16 | 赵思璐 | A kind of compositions preventing and treating spider and preparation method thereof |
| CN109401814A (en) * | 2018-12-26 | 2019-03-01 | 诺泰生物科技(合肥)有限公司 | P t butylbenzoic acid alkanolamide class corrosion inhibitor and its synthetic method and the application in extraordinary oil |
| CN109652213A (en) * | 2019-01-18 | 2019-04-19 | 重庆大学 | A kind of esters insulating oil and preparation method thereof |
| CN115403472A (en) * | 2022-08-31 | 2022-11-29 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
| CN115403472B (en) * | 2022-08-31 | 2024-04-05 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
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