CN103408415A - Synthesis method of capacitance grade 2-sebacate - Google Patents
Synthesis method of capacitance grade 2-sebacate Download PDFInfo
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- CN103408415A CN103408415A CN2013103056362A CN201310305636A CN103408415A CN 103408415 A CN103408415 A CN 103408415A CN 2013103056362 A CN2013103056362 A CN 2013103056362A CN 201310305636 A CN201310305636 A CN 201310305636A CN 103408415 A CN103408415 A CN 103408415A
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Abstract
The invention discloses a synthesis method of capacitance grade 2-sebacate. The method includes: taking n-butylammonic acid diethyl ester and ethyl 8-bromooctanoate as raw materials, conducting a nucleophilic substitution reaction in a strong alkaline environment to obtain 9, 9-bis(methoxycarbonyl)-undecarbon carboxylic acid ethyl ester, performing hydrolysis and acid precipitation reaction to obtain 9, 9-dicarboxyl-undecarbon carboxylic acid, then using a copper catalyst to carry out catalytic decarboxylation to obtain a 2-sebacate crude product, and finally using high purity water to wash it several times and performing drying, thus obtaining the capacitance grade 2-sebacate. The synthesis method provided in the invention has a simple process and high yield, the obtained product has a low ion content, and meets the quality requirements of capacitance grade.
Description
Technical field
The invention belongs to the field of chemical synthesis, particularly a kind of synthetic method of capacitor stage 2-butyl sebacic acid.
Background technology
Along with the popularization without boron system high-pressure aluminum electrolytic capacitor, the electrolytic solution of side chain diprotic acid series becomes the market new lover gradually.Popular high-pressure electrolysis liquid system mainly contains following several in the market: I) 2-methyl nonane diacid (Noritaka Miyoshi; Kazuhisa Takii; Masashi Uehata. Composition comprising long chain dibasic acids and electrolytic solution using thereof[P]. US:6258288B1,2001,7,10.); II) 8-vinyl-10-18 carbon diacid (wooden field, lucky heavy Taki well, and field etc. too for a long time. many salt of Long Lock base acid of many orders and び そ Lure Guide body development と industrialization [J]. oiling is learned, 1991,40 (3): 180-187.); III) 1,6-DDA (Zhou Yihai, Yuan Xueju, all strong equality. the new manufacturing method of dicarboxylic acid for electrolyte and salt thereof [P]. CN:101805255 A, 2010,8,18.) etc.Wherein in the electrolytic solution of I and II system, the purity of branched acids is not high, and specific conductivity is on the low side; In the electrolytic solution of III system, have high conductivity and oxidation efficiency, but flash over voltage is on the low side, there is no clear superiority.
Summary of the invention
The object of the invention is to solve the above-mentioned specific conductivity that causes because purity is low low, carbochain is short and cause the problem that flash over voltage is not high, a kind of synthetic method of capacitor stage 2-butyl sebacic acid is provided, this product has than 1, the carbochain that 6-DDA is longer, and purity is higher, has excellent over-all properties.
Purpose of the present invention is achieved through the following technical solutions:
A kind of synthetic method of capacitor stage 2-butyl sebacic acid, comprise the steps:
Step 1: first get diethyl butylmalonate and 8-bromine ethyl octylate in there-necked flask, with anhydrous organic solvent, dilute, add highly basic, wherein the mol ratio of diethyl butylmalonate, highly basic and 8-bromine ethyl octylate is (1.0 ~ 1.5): (1.0 ~ 1.5): 1, under reflux state, stir after 2～10 hours and be cooled to room temperature, filter;
Step 2: above-mentioned filtrate is carried out to rectifying, collect the cut of 185 ~ 210 ℃ (3mmHg), obtain 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester;
Step 3: get that step 2 obtains 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester is in there-necked flask, add strong alkaline aqueous solution, under pH=10 ~ 13 conditions, be cooled to room temperature after return stirring 4 ~ 8h, add strong acid aqueous solution, regulate pH=1 ~ 3, filter and obtain white powder 9,9-dicarboxyl-11 carbon carboxylic acid;
Step 4: get that step 3 obtains 9,9-dicarboxyl-11 carbon carboxylic acid is in there-necked flask, add and 9, the organic solvent of the quality such as 9-dicarboxyl-11 carbon carboxylic acid, with 9, the deionized water of the quality such as 9-dicarboxyl-11 carbon carboxylic acid and a small amount of catalyzer, under reflux state, stir after 2 ~ 8 hours and be cooled to room temperature, reaction solution is regulated pH value to 1 ~ 2 with strong acid aqueous solution, filters and obtains 2-butyl sebacic acid crude product; Described catalyzer is one or both in copper powder and cupric oxide, and addition is 0.5 ~ 1% of total reaction liquid total mass;
Step 5: by above-mentioned crude product with the high purity water washing for several times, obtain the capacitor stage 2-butyl sebacic acid of low ion content, ion content wherein is: K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, the anhydrous organic solvent described in step 1 is at least a in methyl alcohol, ethanol, methylene dichloride and toluene.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, the highly basic described in step 1 is at least a in alcohol sodium alcohol solution, potassium hydroxide, sodium hydroxide and salt of wormwood.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, the strong alkaline aqueous solution described in step 3 is a kind of in sodium hydroxide and potassium hydroxide aqueous solution, mass concentration is 10 ~ 50%.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, the strong acid aqueous solution described in step 3 is a kind of in hydrochloric acid, sulfuric acid and phosphoric acid, mass concentration is 10 ~ 40%.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, the organic solvent described in step 4 is at least a in acetonitrile, ethanol, acetone, DMF, N-Methyl pyrrolidone and dioxane.
Further, the synthetic method of aforesaid capacitor stage 2-butyl sebacic acid, wherein, and a kind of for in hydrochloric acid, sulfuric acid and phosphoric acid of the strong acid aqueous solution described in step 4, mass concentration is 10 ~ 40%.
Beneficial effect of the present invention: synthetic method craft is simple, route is short, yield is high, and products obtained therefrom has the carbochain longer than 1,6-DDA, and purity is higher, has excellent over-all properties, is applicable to suitability for industrialized production; And specific conductivity and the flash over voltage of electrolytic solution that comprises products obtained therefrom of the present invention is all higher.
Embodiment
Below in conjunction with embodiment to technical solutions according to the invention elaborate (the Structural Identification data of compound are shown in appendix 1).
Embodiment 1.
Step 1: add diethyl butylmalonate (A) 1297.6g(6.00 mol in the 10L there-necked flask), 8-bromine ethyl octylate (B) 1255.8g(5 .00mol), the dropping mass concentration is 20% alcohol sodium alcohol solution 2040.6g(6.00 mol), dropwise under rear reflux state and stirred 8 hours, be cooled to room temperature, after filtration, obtain 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) ethanolic soln 4060.5g;
Step 2: above-mentioned solution is carried out to rectifying, collect 185 ~ 210 ℃ of (3mmHg) cuts 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester 1567.2g, yield is 87.4%, purity is 99.1%;
Step 3: add 9 in the 5L there-necked flask, 9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) 1000g(2.79 mol), the dropping mass concentration is 32% NaOH aqueous solution 1087.5g(8.7 mol), temperature is controlled at 60 ℃ of left and right, after dropwising by reaction solution stirred for several hour under reflux state, by gas-chromatography, control reaction end, after C reacts completely, be cooled to room temperature, dripping mass concentration is 30% phosphate aqueous solution 4263.0g(13.05mol), the adularescent powder is separated out, after filtration drying, obtain 9, 9-dicarboxyl-11 carbon carboxylic acid (D) 819.9g, yield is 97.2%.；
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), CH
3CN 250.0g, H
2O 250.0g, CuO 10g(0.12mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 20% the HCl aqueous solution, regulates pH=1, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 402.0g, yield is 94.1%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 290.7g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 96.9%.
Embodiment 2.
Step 1: add diethyl butylmalonate (A) 1297.6g(6.00 mol in the 10L there-necked flask), 8-bromine ethyl octylate (B) 1255.8g(5 .00mol), add dehydrated alcohol 2000g, potassium hydroxide 336g(6mol), under reflux state, stirred 8 hours, be cooled to room temperature, after filtration, obtain 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) ethanolic soln 4460.5g;
Step 2: above-mentioned solution is carried out to rectifying, collect 185 ~ 210 ℃ of (3mmHg) cuts 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester 1569.7g, yield is 87.6%, purity is 99.0%;
Step 3: add 9 in the 5L there-necked flask, 9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) 1000g(2.79 mol), the dropping mass concentration is 32% KOH aqueous solution 1522.5g(8.7 mol), temperature is controlled at 60 ℃ of left and right, after dropwising by reaction solution stirred for several hour under reflux state, by gas-chromatography, control reaction end, after C reacts completely, be cooled to room temperature, the dropping mass concentration is 30% phosphate aqueous solution 4263.0g(13.05mol), the adularescent powder is separated out, after filtration drying, obtain 9, 9-dicarboxyl-11 carbon carboxylic acid (D) 813.1g, yield is 96.4%,
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), CH
3CN 250.0g, H
2O 250.0g, CuO 5.0g(0.06mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 30% the HCl aqueous solution, regulates pH=1, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 399.0g, yield is 93.4%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 291.2g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 97.1%.
Embodiment 3.
Step 1: add diethyl butylmalonate (A) 1297.6g(6.00 mol in the 10L there-necked flask), 8-bromine ethyl octylate (B) 1255.8g(5 .00mol), add anhydrous methylene chloride 2000g, sodium hydroxide 240g(6mol), under reflux state, stirred 10 hours, be cooled to room temperature, after filtration, obtain 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) dichloromethane solution 4452.4g;
Step 2: above-mentioned solution is carried out to rectifying, collect 185 ~ 210 ℃ of (3mmHg) cuts 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester 1557.3g, yield is 86.9%, purity is 99.3%;
Step 3: add 9 in the 5L there-necked flask, 9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester (C) 1000g(2.79 mol), the dropping mass concentration is 32% KOH aqueous solution 1522.5g(8.7 mol), temperature is controlled at 60 ℃ of left and right, after dropwising by reaction solution stirred for several hour under reflux state, by gas-chromatography, control reaction end, after C reacts completely, be cooled to room temperature, the dropping mass concentration is 36.5% aqueous hydrochloric acid 1305.0g(13.05mol), the adularescent powder is separated out, after filtration drying, obtain 9, 9-dicarboxyl-11 carbon carboxylic acid (D) 803.8g, yield is 95.3%,
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), CH
3CN 250.0g, H
2O 250.0g, CuO 5.0g(0.06mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 30% the HCl aqueous solution, regulates pH=1, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 411.8g, yield is 96.4%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 285.0g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 95.0%.
Embodiment 4.
Step 1～step 3 is with embodiment 1;
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), ethanol 250.0g, H
2O 250.0g, Cu powder 5.0g(0.078mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 20% the HCl aqueous solution, regulates pH=2, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 387.5g, yield is 90.7%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 287.4g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 95.8%.
Embodiment 5.
Step 1～step 3 is with embodiment 1;
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), acetone 250.0g, H
2O 250.0g, CuO 5.0g(0.06mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 20% the HCl aqueous solution, regulates pH=1, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 377.6g, yield is 88.4%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 287.8g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 95.9%.
Embodiment 6.
Step 1～step 3 is with embodiment 1;
Step 4: add 9,9-dicarboxyl-11 carbon carboxylic acid (D) 500.0g(1.65mol in the 2L there-necked flask), N-Methyl pyrrolidone 250.0g, H
2O 250.0g, Cu powder 2.5g(0.039 mol), CuO 2.5 g(0.031mol), stirred for several hour under reflux state, control reaction end by gas-chromatography, after D reacts completely, be cooled to room temperature, the dropping mass concentration is 20% the HCl aqueous solution, regulates pH=1, and the adularescent powder is separated out, after filtration, obtain 2-butyl sebacic acid (E) crude product 411.0g, yield is 96.2%;
Step 5: above-mentioned white powder E 300g is joined in the 2L there-necked flask, with dry after the washing for several times of 300g high purity water, obtain capacitor stage 2-butyl sebacic acid 289.6g(K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm), yield 96.5%.
The present invention still has multiple concrete embodiment, and all employings are equal to replacement or equivalent transformation and all technical schemes of forming, all within the scope of protection of present invention.
Appendix 1Compound C ~ E's
1H NMR, IR and results of elemental analyses.
Compound C:
1H NMR(CDCl
3, 400MHz), 0.901(t, 3H), 1.289(m, 15H) and, 1.642(m, 2H), 1.990(m, 4H) and, 2.312(m, 2H), 3.681(s, 6H) and, 4.123(m, 2H); I R(KBr): ν/cm
-1: 2969,2930,2873,2857,1730,1376,1231,1157,726; Anal. calcd for C
19H
34O
6: C 63.66, and H 9.56, found C 64.35, and H 9.39.
Compound D:
1H NMR(CDCl
3, 400MHz), 0.891(t, 3H), 1.292(m, 12H) and, 1.522(m, 2H), 1.754(m, 4H) and, 2.310(m, 2H), 11.011(s, 3H); I R(KBr): ν/cm
-1: 3401,2989,2849,1711,1368,938,729; Anal. calcd for C
15H
26O
6: C 59.58, and H 8.67, found C 60.12, and H 8.49.
Compd E:
1H NMR(CDCl
3, 400MHz), 0.903(t, 3H), 1.251(m, 12H) and, 1.532(m, 6H), 2.301(m, 2H) and, 2.345(m, 1H), 11.023(s, 2H); I R(KBr): ν/cm
-1: 3994,2987,1717,1376,1342,931,727; Anal. calcd for C
14H
26O
4: C 65.09, and H 10.14, found C 65.32, and H 9.97.
Claims (7)
1. the synthetic method of a capacitor stage 2-butyl sebacic acid comprises the following steps:
Step 1: first get diethyl butylmalonate and 8-bromine ethyl octylate in there-necked flask, with anhydrous organic solvent, dilute, add highly basic, wherein the mol ratio of diethyl butylmalonate, highly basic and 8-bromine ethyl octylate is (1.0 ~ 1.5): (1.0 ~ 1.5): 1, under reflux state, stir after 2～10 hours and be cooled to room temperature, filter;
Step 2: above-mentioned filtrate is carried out to rectifying, collect the cut of 185 ~ 210 ℃ (3mmHg), obtain 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester;
Step 3: get that step 2 obtains 9,9-bis-(methoxycarbonyl)-11 carbon carboxylic acid, ethyl ester is in there-necked flask, add strong alkaline aqueous solution, under pH=10 ~ 13 conditions, be cooled to room temperature after return stirring 4 ~ 8h, add strong acid aqueous solution, regulate pH=1 ~ 3, filter and obtain white powder 9,9-dicarboxyl-11 carbon carboxylic acid;
Step 4: get that step 3 obtains 9,9-dicarboxyl-11 carbon carboxylic acid is in there-necked flask, add and 9, the organic solvent of the quality such as 9-dicarboxyl-11 carbon carboxylic acid, with 9, the deionized water of the quality such as 9-dicarboxyl-11 carbon carboxylic acid and a small amount of catalyzer, under reflux state, stir after 2 ~ 8 hours and be cooled to room temperature, reaction solution is regulated pH value to 1 ~ 2 with strong acid aqueous solution, filters and obtains 2-butyl sebacic acid crude product; Described catalyzer is one or both in copper powder and cupric oxide, and addition is 0.5 ~ 1% of total reaction liquid total mass;
Step 5: by above-mentioned crude product with the high purity water washing for several times, obtain the capacitor stage 2-butyl sebacic acid of low ion content, ion content wherein is: K
+≤ 1ppm, Na
+≤ 1ppm, Fe
3+≤ 2ppm, Pb
2+≤ 2ppm, Cl
-≤ 1ppm, SO
4 2-≤ 2ppm.
2. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: the anhydrous organic solvent described in step 1 is at least a in methyl alcohol, ethanol, methylene dichloride and toluene.
3. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: the highly basic described in step 1 is at least a in alcohol sodium alcohol solution, potassium hydroxide, sodium hydroxide and salt of wormwood.
4. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: the strong alkaline aqueous solution described in step 3 is a kind of in sodium hydroxide and potassium hydroxide aqueous solution, and mass concentration is 10 ~ 50%.
5. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: the strong acid aqueous solution described in step 3 is a kind of in hydrochloric acid, sulfuric acid and phosphoric acid, and mass concentration is 10 ~ 40%.
6. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: the organic solvent described in step 4 is at least a in acetonitrile, ethanol, acetone, DMF, N-Methyl pyrrolidone and dioxane.
7. the synthetic method of capacitor stage 2-butyl sebacic acid as claimed in claim 1 is characterized in that: a kind of for in hydrochloric acid, sulfuric acid and phosphoric acid of the strong acid aqueous solution described in step 4, mass concentration is 10 ~ 40%.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447277A (en) * | 2014-10-29 | 2015-03-25 | 江苏国泰超威新材料有限公司 | Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid |
| CN106024390A (en) * | 2016-05-31 | 2016-10-12 | 常州工程职业技术学院 | Preparation method of 2-butyl ammonium sebate glycol electrolyte solution |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374266A (en) * | 1963-03-06 | 1968-03-19 | Lonza Ag | Preparation of acrylic acid esters |
| CN1602532A (en) * | 2001-12-11 | 2005-03-30 | 冈村制油株式会社 | Composition for electrolytic solution and process for producing the same |
| CN1759119A (en) * | 2002-12-16 | 2006-04-12 | 兰爱克谢斯德国有限责任公司 | Method for the decarboxylation of dicarboxylic acids |
| CN1970694A (en) * | 2006-12-07 | 2007-05-30 | 张以光 | Production process of biological diesel oil |
| CN101805255A (en) * | 2010-04-14 | 2010-08-18 | 武汉海斯普林科技发展有限公司 | New manufacturing method of dicarboxylic acid for electrolyte and salts thereof |
-
2013
- 2013-07-22 CN CN2013103056362A patent/CN103408415A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374266A (en) * | 1963-03-06 | 1968-03-19 | Lonza Ag | Preparation of acrylic acid esters |
| CN1602532A (en) * | 2001-12-11 | 2005-03-30 | 冈村制油株式会社 | Composition for electrolytic solution and process for producing the same |
| CN1759119A (en) * | 2002-12-16 | 2006-04-12 | 兰爱克谢斯德国有限责任公司 | Method for the decarboxylation of dicarboxylic acids |
| CN1970694A (en) * | 2006-12-07 | 2007-05-30 | 张以光 | Production process of biological diesel oil |
| CN101805255A (en) * | 2010-04-14 | 2010-08-18 | 武汉海斯普林科技发展有限公司 | New manufacturing method of dicarboxylic acid for electrolyte and salts thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447277A (en) * | 2014-10-29 | 2015-03-25 | 江苏国泰超威新材料有限公司 | Co-production method for capacitance-grade 2-butylsebacic acid and 2, 9-butylsebacic acid |
| CN106024390A (en) * | 2016-05-31 | 2016-10-12 | 常州工程职业技术学院 | Preparation method of 2-butyl ammonium sebate glycol electrolyte solution |
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Application publication date: 20131127 |