CN102329221B - Method for preparing isostearic acid - Google Patents
Method for preparing isostearic acid Download PDFInfo
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- CN102329221B CN102329221B CN 201110194088 CN201110194088A CN102329221B CN 102329221 B CN102329221 B CN 102329221B CN 201110194088 CN201110194088 CN 201110194088 CN 201110194088 A CN201110194088 A CN 201110194088A CN 102329221 B CN102329221 B CN 102329221B
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Abstract
The invention relates to a method for preparing isostearic acid. The technical scheme is that the method comprises the following steps of: (1) producing dimer acid by using vegetable oil acid by a carclazyte catalysis method to obtain a byproduct, namely monomer acid; (2) controlling the temperature to be 90 to 98 DEG C and performing atmospheric esterification on the monomer acid and lower alcohol to obtain monomer acid ester by taking toluenesulfonic acid as a catalyst; (3) performing catalytic hydrogenation on the monomer acid ester to obtain aliphatic ester with a low iodine value; (4) sequentially saponifying and acidifying the aliphatic ester to obtain a mixture of stearic acid and isostearic acid; and (5) dissolving the mixture of the stearic acid and the isostearic acid by using No.6 solvent oil, reducing the temperature to -2 to 2 DEG C and performing cold separation, filtering, distilling filtrate under reduced pressure, and collecting fractions of the isostearic acid to obtain a finished product. Compared with the prior art, the method has the advantages that: the process is simple, equipment investment is low, and the safe operation is also ensured; an obtained product has high purity; and an acid value of the finished product is 180 to 188 mgKOH/g, and an iodine value is less than 8g/100g.
Description
Technical field
The present invention relates to a kind of Chemicals manufacture method, particularly a kind of preparation method of Unimac 5680.
Background technology
At present, be mostly to synthesize the Unimac 5680 product with Fatty Alcohol(C12-C14 and C12-C18), but the Unimac 5680 side chain that this synthesis method generates is longer, with natural acid, very big-difference is arranged, its purity does not reach the quality of natural Unimac 5680.
also there is in addition another manufacture method in industry, namely take vegetable oil acid as raw material, separation and Extraction Unimac 5680 in the by product monomer acids of employing carclazyte catalysis method synthesis of dimmer acid, and the production of step carclazyte catalysis method wherein dimeracid obtains the by product monomer acids by extensively open and use, the technique comparative maturity, therefore there is document to disclose with the urea envelope method and directly extracts stearic method in monomer acids, such as Chinese patent 200610097344.4 discloses a kind of with stearic method in urea envelope method extraction monomer acids, its method is at the 30-80 temperature, with solvent, urea is dissolved, added the monomer acids backflow 0.5-5 hour, be chilled to after room temperature to-10-20 ℃ cold analysis 1-20 hour, obtain white adipose acid-urea inclusion and light yellow filtrate after suction filtration, then filtrate decompression is distilled desolventizing, get Unimac 5680 after hot wash, again in thermostat container with 30-100 ℃ of temperature under dry and obtain product.The shortcoming of this method is: the first, owing to there being the unsaturated fatty acids such as calculation again in monomer acids, and there is no the step of hydrogenation in technique, the iodine number of the product that therefore obtains is high, the antioxidant property of product is low, the color of product easily deepens, the second, Unimac 5680 and stearic acid iodine number difference are very little, and the effect that the urea envelope separates is undesirable.
Defective for aforesaid method, Chinese patent 200910042703.X discloses the separating and extracting method of Unimac 5680 in a kind of monomer acids, its method is the by product monomer acids when oleic acid, linolic acid carclazyte catalysis method are produced dimeracid, at first pass through the esterification of catalyst-free middle-pressure process, then press shortening in the monomer acid esters being adopted, separate through the urea envelope in solvent again and obtain the isostearate crude product, again crude product is obtained refining isostearate through molecular distillation, obtain Unimac 5680 through alkali and acid hydrolysis again, obtain the Unimac 5680 product after dehydrating.Because the study on mechanism such as the hydrogenation of the esterification of higher fatty acid and high-grade aliphatic ester, hydrolysis are more deep, technique is comparative maturity also, pass through hydrogenation reaction, make the saturated lipid acid such as unsaturated acid hydrogenation generation stearic acid such as oleic acid, reduced the iodine number of product, improved the oxidation-resistance of product, but still there is following shortcoming: the first, by product monomer acids, if use the middle-pressure process esterification, working pressure is high, need to use explosion-proof pressure reactor, fund input is larger, also is unfavorable for safety operation simultaneously; The second, the iodine number difference of the stearate of hydrogenation generation and isostearate is very little, and the effect that the urea envelope separates is undesirable.
Summary of the invention
Purpose of the present invention is exactly the defective that exists for prior art, step and control parameter to prior art are improved, processing step is by middle pressure esterification-hydrogenation-urea envelope-refining-hydrolysis, be improved to normal pressure esterification-hydrogenation-saponification-acidifying-crystallization and purification-distilation, simultaneously processing parameter is adjusted, provided that a kind of technique is simple, product purity is high, the Unimac 5680 method for manufacturing of operational safety.
The present invention is achieved by the following technical solutions: comprise the following steps
(1) vegetable oil acid carclazyte catalysis method is produced dimeracid and obtain the by product monomer acids;
(2) make catalyzer with tosic acid, 90～98 ℃ of temperature controls, monomer acids and lower alcohol carry out normal pressure esterification and generate the monomer acid esters;
(3) monomer acid esters shortening obtains the fatty acid ester of low iodine number;
(4) fatty acid ester successively through saponification, acidification, obtains low iodine number fatty acid mixt;
(5) after low iodine number fatty acid mixt dissolved with No. six solvent oils, Jiang Wen with the filtrate decompression distillation, collected the cut of Unimac 5680, thereby obtains finished product after filtration Dao 2 ℃～2 ℃ cold analysis of –.
In order to reach better reaction effect, the preferred version of such scheme is as follows:
(1) vegetable oil acid adopts acidic white earth as catalyzer, polyreaction under lower than 245 ℃ of conditions, and carclazyte is removed in press filtration, and the filtrate decompression distillation obtains the cut of monomer acids;
(2) make catalyzer with tosic acid, temperature control 90-98 ℃, monomer acids and lower alcohol carry out normal pressure esterification and generate the monomer acid esters, and reaction time of esterification is as the criterion lower than 5 g/100g with the acid number of resultant, the complete after washing of esterification, and the static layering disacidify is assorted;
(3) the monomer acid esters is under N120 type catalyst action, and pressure-controlling is between 1.5MPa～2.2 MPa, and 190～220 ℃ of temperature controls passed into hydrogen reaction 4～8 hours, then were cooled to 90 ℃ Celsius, filtered out catalyzer, namely gets the fatty acid ester of low iodine number;
(4) by low iodine number fatty acid ester weight 20～30% add wherein concentration 10～15% sodium hydroxide solutions, heat up and boiled 3～4 hours, and 95 ℃ of insulations 6～8 hours; Be cooled to 40 ℃ Celsius, emit alcohol-water mixture, after the Distillation recovery lower alcohol, adding concentration is 25～40% sulphuric acid solns, and consumption is transferred to 2～3 with pH value and is got final product, then boils 1～3 hour, and 95 ℃ of insulations 5～8 hours; Be cooled to again 45～55 ℃, standing 6 hours, put sour water, and leftover materials are washed to pH value equal 7, obtain low iodine number fatty acid mixt;
(5) low iodine number fatty acid mixt and No. six solvent oils, the ratio mixed freezing of 1:3 Zhi 2 ℃～2 ℃ of –, filters by weight; Filtrate is sent into stainless steel tubulation vacuum rising film evaporization process, under vacuum tightness 1500Pa and 100～130 ℃ of conditions, sloughs solvent, and reclaims solvent; Send into high vacuum tubulation falling-film distillation operation, the Unimac 5680 cut is collected in distillation under the condition of condition of high vacuum degree 15-25Pa and 220-280 ℃ again; Solvent-laden filter cake is sent into stainless steel falling film vacuum evaporization process, is cooled to 70 ℃ slough solvent under 130 ℃ and vacuum condition after, sends into the slicing machine section, namely gets stearic acid.
In order better to realize the present invention, the further preferred version of such scheme also comprises: described step (1) vegetable oil acid is under 220～224 ℃ of conditions, make catalyzer with carclazyte, synthesis under normal pressure adds phosphoric acid after 4 hours and removes metal complex, carclazyte is removed in press filtration, filtrate decompression distillation in vacuum tightness 8-12Pa and liquid phase 220-260 ℃, is collected the cut of monomer acids.
The cotton seed oleic acid of the preferred zero pour of vegetable oil acid in described step (1)≤8 ℃, catalyzer also comprises Quilonum Retard, improves speed of response; Lower alcohol in step (2) is methyl alcohol, and reaction time of esterification is 3-10 hour, and this reaction times is corresponding with the acid number detection, and esterification time is in 3-10 hour in normergic situation, and acid number all can be lower than 5 g/100g.
The present invention compared with prior art, technique is simple, by selecting suitable catalyzer, adopt the non-pressure process esterification, facility investment is few, also be conducive to simultaneously safety operation, after improving processing step simultaneously, the difference of stearic acid and Unimac 5680 solubleness in No. six solvent oils be can utilize, stearic acid and Unimac 5680 separated by the cooling cold analysis, and by the rectification and purification Unimac 5680, the product yield that this kind method obtains is high, purity is high, its acid number is 180～188mgKOH/g, and iodine number is less than 8 mgKOH/g, and zero pour is less than 8 ℃; Simultaneously can also obtain up-to-standard by product stearic acid, its acid number 190～203 mgKOH/g, iodine number are less than 4 mgKOH/g, zero pour 〉=55 ℃, remarkable in economical benefits.
Embodiment
Embodiment 1
The preparation method of Unimac 5680 comprises the following steps:
(1) vegetable oil acid adopts acidic white earth as catalyzer, polyreaction under 220 ℃ of conditions, and synthesis under normal pressure adds phosphoric acid after 4 hours and removes metal complex,, carclazyte is removed in press filtration, the filtrate decompression distillation, in 240 ℃ of vacuum tightness 10Pa and liquidus temperatures, collect the cut of monomer acids;
(2) make catalyzer with tosic acid, 90 ℃ of temperature controls, monomer acids and methyl alcohol carry out normal pressure esterification, react 10 hours, and iodine number is 4.8 g/100g, namely generates the monomer acid esters; The complete after washing of esterification, the static layering disacidify is assorted;
(3) the monomer acid esters is under N120 type catalyst action, and pressure-controlling is at 1.5 ~ 2.2MPa MPa, and 190 ℃ of temperature controls pass into hydrogen reaction after 8 hours, then are cooled to 90 ℃, filter out catalyzer, namely gets the fatty acid methyl ester of low iodine number;
(4) add wherein concentration 15% hydroxide molten by 20% of the weight of hanging down the iodine number fatty acid methyl ester, heat up and boiled 4 hours, 95 ℃ are incubated 6 hours; Be cooled to 40 ℃, emit alcohol-water mixture, after Distillation recovery methyl alcohol, adding concentration is 25～40% sulphuric acid solns, transfers pH value to 2 to get final product, then boils 1 hour, and 95 ℃ are incubated 8 hours; Be cooled to again 45～55 ℃, standing 6 hours, put sour water, and material water is washed till pH value equals 7, obtain low iodine number fatty acid mixt;
(5) low iodine number fatty acid mixt and No. six solvent oils, after the ratio mixed dissolution of 1:3, be refrigerated to 2 ℃～2 ℃ of She Shi –, vacuum filtration.
Filtrate is sent into stainless steel tubulation vacuum rising film evaporization process, under 100～130 ℃ and vacuum 1500Pa condition, sloughs and recovered solvent oil; Send into again high vacuum tubulation falling-film distillation operation, be collected in the Unimac 5680 cut under high vacuum 20Pa and 250 ℃ of conditions, thereby obtain the finished product of acid number 188KOH/g, iodine number 7.50 g/100g.
Solvent-laden filter cake is sent into stainless steel falling film vacuum evaporization process, is cooled to 70 ℃ slough solvent under 130 ℃ and vacuum condition after, sends into the slicing machine section, namely gets stearic acid, its index; Acid number 190mgKOH/g, iodine number 3.8 g/100g, 60 ℃, zero pour.
Embodiment 2
The preparation method of Unimac 5680 comprises the following steps:
(1) vegetable oil acid adopts acidic white earth as catalyzer, polyreaction under 224 ℃ of conditions, and the polymerization under atmospheric pressure reaction adds phosphoric acid after 4 hours and removes metal complex,, carclazyte is removed in press filtration, the filtrate decompression distillation, when being collected in 240 ℃ of vacuum 10Pa and liquidus temperatures, collect the cut of monomer acids;
(2) make catalyzer with tosic acid, 98 ℃ of temperature controls, monomer acids and methyl alcohol carry out normal pressure esterification, react 3 hours, and iodine number is 4.5 g/100g, namely generates the monomer acid esters; The complete after washing of esterification, the precipitation disacidify is assorted;
(3) the monomer acid esters is under effect under N120 type catalyst action, and pressure-controlling is at 1.5 ~ 2.2MPa MPa, and 220 ℃ of temperature controls passed into hydrogen reaction 4 hours, then are cooled to 90 ℃, filtered out catalyzer, namely gets the fatty acid methyl ester of low iodine number;
(4) add wherein concentration 10% hydroxide molten by 30% of low iodine number fatty acid methyl ester weight, heat up and boiled 3 hours, and 95 ℃ of insulations 8 hours; Be cooled to 40 ℃, emit alcohol-water mixture, after Distillation recovery methyl alcohol, adding concentration is 25～40% sulphuric acid solns, transfers pH value to 3 to get final product, then boils 3 hours, and 95 ℃ are incubated 5 hours; Be cooled to again 45～55 ℃, standing 6 hours, put sour water, and material water is washed till pH value equals 7, obtain low iodine number fatty acid mixt;
(5) low iodine number fatty acid mixt and No. six solvent oils, after the ratio mixed dissolution of 1:3, be refrigerated to 2 ℃～2 ℃ of She Shi –, vacuum filtration.
Filtrate is sent into stainless steel tubulation vacuum rising film evaporization process, under 100～130 ℃ and vacuum 1500Pa condition, sloughs and recovered solvent oil; Send into again high vacuum tubulation falling-film distillation operation, be collected in the Unimac 5680 cut under high vacuum 20Pa and 250 ℃ of conditions, thereby obtain acid number 180mgKOH/g, iodine number 7.56 g/100g finished products.
Solvent-laden filter cake is sent into stainless steel falling film vacuum evaporization process, is cooled to 70 ℃ slough solvent under 130 ℃ and vacuum condition after, sends into the slicing machine section, namely gets stearic acid, its index; Acid number 203mgKOH/g, iodine number 3.5g/100g, 55 ℃, zero pour.
Embodiment 3
The preparation method of Unimac 5680 comprises the following steps:
(1) vegetable oil acid adopts acidic white earth as catalyzer, polyreaction under preparation method's ℃ condition of Unimac 5680, and synthesis under normal pressure adds phosphoric acid after 4 hours and removes metal complex, carclazyte is removed in press filtration, and filtrate is collected the cut of monomer acids in 240 ℃ of vacuum 10Pa and liquidus temperatures;
(2) make catalyzer with tosic acid, 90 ℃ of temperature controls, monomer acids and methyl alcohol carry out normal pressure esterification, react 10 hours, and iodine number is 4.3 g/100g, namely generates the monomer acid esters; The complete after washing of esterification, the static layering disacidify is assorted;
(3) the monomer acid esters is under effect under N120 type catalyst action, and pressure-controlling is at 1.5 ~ 2.2MPa MPa, and 190 ℃ of temperature controls pass into hydrogen reaction after 6 hours, then are cooled to 90 ℃, filter out catalyzer, namely gets the fatty acid methyl ester of low iodine number;
(4) add wherein concentration 15% hydroxide molten by 25% of low iodine number fatty acid methyl ester weight, heat up and boiled 3.5 hours, and 95 ℃ of insulations 7 hours; Be cooled to 40 ℃, emit alcohol-water mixture, after Distillation recovery methyl alcohol, adding concentration is 25～40% sulphuric acid solns, transfers pH value to 2.5 to get final product, then boils 2 hours, and 95 ℃ are incubated 6.5 hours; Be cooled to again 45～55 ℃, standing 6 hours, put sour water, and material water is washed till pH value equals 7, obtain low iodine number fatty acid mixt;
(5) low iodine number fatty acid mixt and No. six solvent oils, after the ratio mixed dissolution of 1:3, be refrigerated to 2 ℃～2 ℃ of She Shi –, vacuum filtration;
Filtrate is sent into stainless steel tubulation vacuum rising film evaporization process, under 100～130 ℃ and vacuum 1500Pa condition, sloughs and recovered solvent oil; Send into again high vacuum tubulation falling-film distillation operation, be collected in the Unimac 5680 cut under high vacuum 20Pa and 250 ℃ of conditions, thereby obtain the Unimac 5680 finished product of acid number 184 mgKOH/g, iodine number 7.52 g/100g.
Solvent-laden filter cake is sent into stainless steel falling film vacuum evaporization process, is cooled to 70 ℃ slough solvent under 130 ℃ and vacuum condition after, sends into the slicing machine section, namely gets stearic acid, its index; Acid number 196 mgKOH/g, iodine number 3.7 g/100g, 65 ℃, zero pour.
Embodiment 4
The preparation method of Unimac 5680, increase the Quilonum Retard catalyzer in embodiment 1 step (1), improve speed of response, other steps remain unchanged, finally obtain the Unimac 5680 finished product of acid number 187KOH/g, iodine number 7.44 g/100g, its index of by product stearic acid: acid number 195 mgKOH/g, iodine number 3.6g/100g, 62 ℃, zero pour.
Embodiment 5
The preparation method of Unimac 5680, increase the Quilonum Retard catalyzer in embodiment 2 steps (1), improve speed of response, other steps remain unchanged, finally obtain the Unimac 5680 finished product of acid number 186mgKOH/g, iodine number 7.46 g/100g, its index of by product stearic acid: acid number 196 mgKOH/g, iodine number 3.9g/100g, 61 ℃, zero pour.
Embodiment 6
The preparation method of Unimac 5680, increase the Quilonum Retard catalyzer in embodiment 3 steps (1), improve speed of response, other steps remain unchanged, finally obtain the Unimac 5680 finished product of acid number 186KOH/g, iodine number 7.45 g/100g, its index of by product stearic acid: acid number 193 mgKOH/g, iodine number 3.7g/100g, 58 ℃, zero pour.
Embodiment 7
The preparation method of Unimac 5680, vegetable oil acid in embodiment 1 step (1) is preferably zero pour less than the cotton seed oleic acid of 8 ℃, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 188KOH/g, iodine number 7.20g/100g, its index of by product stearic acid: acid number 194mgKOH/g, iodine number 3.59g/100g, 59 ℃, zero pour.
Embodiment 8
The preparation method of Unimac 5680, vegetable oil acid in embodiment 2 steps (1) is preferably zero pour less than the cotton seed oleic acid of 8 ℃, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 187KOH/g, iodine number 7.10g/100g, its index of by product stearic acid: acid number 201 mgKOH/g, iodine number 3.5g/100g, 64 ℃, zero pour.
Embodiment 9
The preparation method of Unimac 5680, vegetable oil acid in embodiment 3 steps (1) is preferably zero pour less than the cotton seed oleic acid of 8 ℃, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 186KOH/g, iodine number 7.21g/100g, its index of by product stearic acid: acid number 202 mgKOH/g, iodine number 3.5g/100g, 65 ℃, zero pour.
Embodiment 10
The preparation method of Unimac 5680, methyl alcohol in embodiment 1 step (2) is changed to butanols, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 182KOH/g, iodine number 7.74 g/100g, its index of by product stearic acid: acid number 196 mgKOH/g, iodine number 3.9g/100g, 56 ℃, zero pour.
Embodiment 11
The preparation method of Unimac 5680, methyl alcohol in embodiment 2 steps (2) is changed to Virahol, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 183KOH/g, iodine number 7.60 g/100g, its index of by product stearic acid: acid number 195 mgKOH/g, iodine number 3.7g/100g, 58 ℃, zero pour.
Embodiment 12
The preparation method of Unimac 5680, methyl alcohol in embodiment 2 steps (2) is changed to ethanol, other steps are constant, finally obtain the Unimac 5680 finished product of acid number 184KOH/g, iodine number 7.56 g/100g, its index of by product stearic acid: acid number 196 mgKOH/g, iodine number 3.6g/100g, 57 ℃, zero pour.
Above embodiment is only the preferred embodiments of the present invention, can realize best-of-breed technology effect of the present invention.Within protection scope of the present invention; those skilled in the art can adopt other technical parameter to realize fully; such as hydrogenation according to the catalyzer of selecting other; such as rhodium, platinum etc.; and select corresponding temperature of reaction, pressure; the appropriateness adjustment of the processing parameter of the saponification of monomer acid esters and acidifying for another example, carclazyte catalytic production dimeracid etc., all identical with technical scheme substance of the present invention, therefore do not enumerate in the present embodiment.
Claims (3)
1. the preparation method of a Unimac 5680, is characterized in that, comprises the following steps:
(1) vegetable oil acid adopts acidic white earth as catalyzer, polyreaction under condition under 220～224 ℃ of conditions, synthesis under normal pressure adds phosphoric acid after 4 hours and removes metal complex, carclazyte is removed in press filtration, the filtrate decompression distillation, in vacuum tightness 8-12Pa and liquidus temperature 220-260 ℃, collect the cut of monomer acids;
(2) make catalyzer with tosic acid, temperature control 90-98 ℃, monomer acids and lower alcohol carry out normal pressure esterification and generate the monomer acid esters, and reaction time of esterification is as the criterion lower than 5 g/100g with the acid number of resultant, the complete after washing of esterification, and the static layering disacidify is assorted; Described reaction time of esterification is 3-10 hour; Lower alcohol is methyl alcohol;
(3) the monomer acid esters is under N120 type catalyst action, and pressure-controlling is between 1.5MPa～2.2 MPa, and 190～220 ℃ of temperature controls passed into hydrogen reaction 4～8 hours, then were cooled to 90 ℃ Celsius, filtered out catalyzer, namely gets the fatty acid ester of low iodine number;
(4) by low iodine number fatty acid ester weight 20～30% add wherein concentration 10～15% sodium hydroxide solutions, heat up and boiled 3～4 hours, and 95 ℃ of insulations 6～8 hours; Be cooled to 40 ℃ Celsius, emit alcohol-water mixture, after the Distillation recovery lower alcohol, adding concentration is 25～40% sulphuric acid solns, and consumption is transferred to 2～3 with pH value and is got final product, then boils 1～3 hour, and 95 ℃ of insulations 5～8 hours; Be cooled to again 45～55 ℃, standing 6 hours, put sour water, and leftover materials are washed to pH value equal 7, obtain low iodine number fatty acid mixt;
(5) low iodine number fatty acid mixt and No. six solvent oils by weight the ratio mixed freezing of 1:3 Zhi 2 ℃～2 ℃ of –, filter, filtrate is sent into stainless steel tubulation vacuum rising film evaporization process, under vacuum tightness 1500Pa and 100～130 ℃ of conditions, sloughs and recovered solvent oil; Send into high vacuum tubulation falling-film distillation operation, the Unimac 5680 cut is collected in distillation under the condition of condition of high vacuum degree 15-25Pa and 220-280 ℃ again.
2. the preparation method of Unimac 5680 according to claim 1, it is characterized in that: the catalyzer in described step (1) also comprises Quilonum Retard.
3. the preparation method of Unimac 5680 according to claim 1 is characterized in that: the vegetable oil acid in described step (1) is the cotton seed oleic acid of zero pour≤8 ℃.
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| CN108342926A (en) * | 2017-12-30 | 2018-07-31 | 苏州丰倍生物科技有限公司 | A kind of environment-friendly type impact paper solvent and preparation method thereof |
| CN108299188A (en) * | 2018-03-12 | 2018-07-20 | 徐州市腾顺工贸有限公司 | A kind of freezing and crystallizing point puies forward the stearic preparation method of isomery |
| CN110252098A (en) * | 2018-03-12 | 2019-09-20 | 山东奥古生物科技有限公司 | A kind of air cleaning cream and preparation method thereof |
| CN114573451B (en) * | 2022-02-16 | 2023-03-24 | 华南理工大学 | Method for separating 12-hydroxystearic acid, gamma-oleic acid lactone and delta-oleic acid lactone |
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| US20060111502A1 (en) * | 2004-10-18 | 2006-05-25 | Groeneveld Daan Y | Teak deck caulking |
| CN1944375A (en) * | 2006-10-31 | 2007-04-11 | 南京工业大学 | Method for extracting isostearic acid from mono acid |
| CN101492358A (en) * | 2009-03-07 | 2009-07-29 | 江西省宜春远大化工有限公司 | Method for producing low-phosphor dimer acid |
| CN101544559A (en) * | 2009-02-18 | 2009-09-30 | 江西省宜春远大化工有限公司 | Method for separating and extracting isostearic acid from monomer acid |
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| US20060111502A1 (en) * | 2004-10-18 | 2006-05-25 | Groeneveld Daan Y | Teak deck caulking |
| CN1944375A (en) * | 2006-10-31 | 2007-04-11 | 南京工业大学 | Method for extracting isostearic acid from mono acid |
| CN101544559A (en) * | 2009-02-18 | 2009-09-30 | 江西省宜春远大化工有限公司 | Method for separating and extracting isostearic acid from monomer acid |
| CN101492358A (en) * | 2009-03-07 | 2009-07-29 | 江西省宜春远大化工有限公司 | Method for producing low-phosphor dimer acid |
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