CN101225064A - New method for preparing neta-thia-alpha-alkyl fatty acid - Google Patents
New method for preparing neta-thia-alpha-alkyl fatty acid Download PDFInfo
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- CN101225064A CN101225064A CNA2007100366484A CN200710036648A CN101225064A CN 101225064 A CN101225064 A CN 101225064A CN A2007100366484 A CNA2007100366484 A CN A2007100366484A CN 200710036648 A CN200710036648 A CN 200710036648A CN 101225064 A CN101225064 A CN 101225064A
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Abstract
The invention relates to a new preparation method of Beta-thia- Alpha -alkyl fatty acid, using alkyl halides and 2- mercapto carboxylic acid as materials. The alkyl halides and the 2- mercapto carboxylic acid are condensed, and then the Beta-thia- Alpha -alkyl fatty acid is obtained by one-step method. Beta-thia- Alpha -alkyl fatty acid with high purity is obtained by salting out, pumping filtration and recrystallization. The new preparation method of Beta-thia- Alpha -alkyl fatty acid has the advantages of little environmental pollution, high efficiency and stabilization, simple and easy operation, high purity of products, low production cost and adaptation of mass production.
Description
Technical field
The present invention relates to the synthetic field of compound, more specifically, relate to a kind of novel method for preparing neta-thia-alpha-alkyl fatty acid.
Background technology
Long-chain thia lipid acid claims 3-thia-2-alkyl fatty acid again, and its chemical property is similar to common fats acid, but its metabolic mechanism and effect are very different.Recently find neta-thia-alpha-alkyl fatty acid, claim 3-thia-2-alkyl fatty acid again, the lipid acid that can change phosphatide in heart and the liver cell is formed, activate the oxidation of fatty acids effect and blood fat reducing, and the lipid acid and the cholesterol that can suppress in the liver cell are synthetic, thereby the application in medicine and field of health care products more and more widely.
The molecular formula of neta-thia-alpha-alkyl fatty acid is shown below:
Wherein R1 is C
10-C
30Saturated or unsaturated alkyl or aryl can be to have or do not have hydroxyl, carbonyl, carboxyl, cyano group or the like substituting group on the carbon atom of alkyl or aryl; R2 is C
1-C
10Saturated or do not embrace and alkyl or aryl, can be to have or do not have hydroxyl, carbonyl, carboxyl, cyano group or the like substituting group on the carbon atom of alkyl or aryl.
The synthetic of neta-thia-alpha-alkyl fatty acid all was to react with long-chain mercaptan and alpha-position halogenated acid to produce (J.Am.Chem.Soc.Vol65,2301 in the past; J.Org.Chem.Vol24,849; Arch.Biochem.Biophys.Vol357 (1), 76), owing to having industrial goods, the long-chain mercaptan as raw material can not get, and it gets and makes (Org.Synth.Vol21,36) by the long-chain haloalkane earlier.
Its conventional synthetic method is as follows:
But the long-chain thiol smell is very smelly, environment is caused great pollution, and oxidation easily takes place, cause reaction yield lower, problems such as product purification difficult, make product purity low, and because long-chain mercaptan does not have industrial goods and can supply, need to increase the processing step of thiol synthesis, make that the entire reaction course step is many, complicated, waste time and energy.The production cost height.
Summary of the invention
Main purpose of the present invention is exactly the problems and shortcomings at above existence, and a kind of novel method for preparing neta-thia-alpha-alkyl fatty acid is provided, and this preparation method is simple, efficient, stable, environmental protection, cost are low.
To achieve these goals, the technical scheme of employing of the present invention is: a kind of novel method for preparing neta-thia-alpha-alkyl fatty acid, be characterized in: with haloalkane and 2-mercaptan carboxylic acid is raw material, and single step reaction prepares described neta-thia-alpha-alkyl fatty acid in alkali alcosol.
The molecular formula of described haloalkane is R1-X, and wherein R1 is C
10-C
30Saturated or unsaturated alkyl or aryl, wherein X is a chlorine, bromine or iodine, described 2-mercaptan carboxylic acid is:
Wherein R2 is C
1-C
10Saturated or do not embrace and alkyl or aryl.
Can have substituting group on the carbon atom of described alkyl or aryl, described substituting group can be hydroxyl, carbonyl, carboxyl or cyano group.
Described R1 can be CH
3(CH
2)
9-29, described R2 can be CH
3(CH
2)
0-9
Described haloalkane splashes in the described alkali alcosol that contains described 2-mercaptan carboxylic acid, or described 2-mercaptan carboxylic acid splashes in the described alkali alcosol that contains described haloalkane.
Described reaction can be carried out at normal temperatures.
Described haloalkane and described 2-mercaptan carboxylic acid's mol ratio can be 1: 1 to 1: 3.Described haloalkane and described 2-mercaptan carboxylic acid's mol ratio is less than 1: 1 or greater than 1: 3, though reaction can be carried out the still waste of the raw material that can cause.
The time of described reaction was generally 0.5 hour-24 hours.
Time time optimal of described reaction is 1.5 hours-5 hours, to shorten the production cycle, raises the efficiency.
Also comprise follow-up saltout, suction filtration, recrystallization, with further raising product purity.
Beneficial effect of the present invention is as follows:
1. single stage method of the present invention prepares neta-thia-alpha-alkyl fatty acid, the production technique simple and stable, and environmental pollution is little,
Production cost is low.
2. because the raw material that the present invention adopts is haloalkane and 2-mercaptan carboxylic acid, and starting material are easy to get, be convenient to gather materials on the spot,
Convenient, and further reduce cost.
3. through simple subsequent step: saltout, suction filtration, recrystallization, can obtain highly purified product, be fit to big
Scale production.
By following about detailed description of the present invention, with make of the present invention other and further purpose become obvious.
Embodiment
In order more to be expressly understood technology contents of the present invention, now further specify as follows in conjunction with preferred embodiment of the present invention:
Utilization of the present invention be the total character of halogen, but comparatively speaking, chlorine active low, iodine is too expensive.Have only bromine practical.Therefore, in concrete the enforcement, be raw material generally with bromoalkane and 2-mercaptan carboxylic acid, condensation under alkaline condition makes neta-thia-alpha-alkyl fatty acid, and building-up reactions is shown below:
Wherein R1 is C
10-C
30Saturated or unsaturated alkyl or aryl can be to have or do not have hydroxyl, carbonyl, carboxyl, cyano group or the like substituting group on the carbon atom of alkyl or aryl; R2 is C
1-C
10Saturated or do not embrace and alkyl or aryl, can be to have or do not have hydroxyl, carbonyl, carboxyl, cyano group or the like substituting group on the carbon atom of alkyl or aryl.
In order further to simplify reaction formula, R1 is CH in the bromoalkane molecular formula
3(CH
2)
9-29, R2 is CH among the 2-mercaptan carboxylic acid
3(CH
2)
0-9, the alkaline condition of employing is the alkali alcosol of preparation, is about to alkali and is dissolved in the solution that forms in the alcohol.
The preparation of embodiment 1.3-thia-2-methyl tridecanoic acid
Under the normal temperature, 15.94g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, (21.88g, 0.206mol) 2 mercaptopropionic acid are added dropwise to 22.1g (0.1mol) 1-bromo-decane again to drip 18.3ml, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hcl acidifying then, abundant stirring and evenly mixing, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 17.2g crystallization, productive rate is 75%, and mp.38.1-38.3 ℃, the GC purity assay is 97.0%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.38.1-38.3 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1。
1H?NMR(300MHz，CDCl
3)：δ10.13(bs，OH)，3.43(q，1H，J＝7.2Hz，-SC
HCOOH)，2.61-2.67(m，2H，-C
H 2-S-)，1.65-1.50(m，2H，-C
H 2-CH
2S-)，1.42(d，3H，J＝7.2Hz，C
H 3CHCOOH)，1.41-1.30(m，2H，CH3-
CH 2-)1.10-1.40(m，12H，-(C
H 2)
6-)，0.87(t，3H，J＝7.0Hz，C
H 3-CH
2-)；
MS(EI)：246(M
+)，201[CH
3(CH
2)
9SC
+HCH
3]，173[CH
3(CH
2)
9S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-methyl tridecanoic acid.
The preparation of embodiment 2.3-thia-2-methyl pentadecylic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, drips 18.3ml (21.88g, 0.206mol) 2 mercaptopropionic acid, add 24.9g (0.1mol) bromododecane again, reacted 1.5-2 hour, and separated out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, filter, obtain the 20.6g crystallization, productive rate is 75.4%, mp.51-52 ℃, the GC purity assay is 97.0%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.51-52 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.13(bs，OH)，3.43(q，1H，J＝6.6Hz，-SC
HCOOH)，2.59-2.69(m，2H，-C
H 2-S-)，1.50-1.54(m，2H，-C
H 2-CH
2S-)，1.51(d，3H，J＝6.6Hz，C
H 3CHCOOH)，1.15-1.32(m，18H，-(CH
H 2)
9-)，0.88(t，3H，J＝7.0Hz，C
H 3-CH
2-)；
MS(EI)：274(M
+)，229[CH
3(CH
2)
11SC
+HCH
3]，201[CH
3(CH
2)
11S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-methyl pentadecylic acid.
The preparation of embodiment 3.3-thia-2-methylheptadecanoic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, drips 18.3ml (21.88g, 0.206mol) 2 mercaptopropionic acid, add 25ml (27.7g again, 0.1mol) bromotetradecane, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir the precipitation that suction filtration is separated out, wash with water, recrystallization from ethanol obtains the 24.1g crystallization, and productive rate is 79.8%, mp.51.8-52.2 ℃, the GC purity assay is 97.5%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.51.8-52.2 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.13(bs，OH)，3.41(q，1H，J＝7.2Hz，-SC
HCOOH)，2.75-2.60(m，2H，-C
H 2-S-)，1.65-1.50(m，2H，-C
H 2-CH
2S-)，1.45(d，3H，J＝7.2Hz，C
H 3CHCOOH)，1.10-1.40(m，22H，-(C
H 2)
11)，0.87(t，3H，J＝6.9Hz，C
H 3-CH
2-)；
MS(EI)：302(M
+)，257[CH
3(CH
2)
13SC
+HCH
3]，229[CH
3(CH
2)
13S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-methylheptadecanoic acid.
The preparation of embodiment 4.3-thia-2-methyl nondecylic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, (21.88g, 0.206mol) 2 mercaptopropionic acid add 30.5g (0.1mol) bromohexadecane again to drip 18.3ml, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 27.1g crystallization, productive rate is 75.8%, and mp.57.9-58.7 ℃, the GC purity assay is 97.6%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.57.9-58.7 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.13(bs，OH)，3.43(q，1H，J＝7.0Hz，-SC
HCOOH)，2.61-2.67(m，2H，-C
H 2-S-)，1.64-1.53(m，2H，-C
H 2-CH
2S-)，1.42(d，3H，J＝7.2Hz，C
H 3CHCOOH)，1.32-1.38(m，2H，CH3-C
H 2-)，1.18-1.41(m，26H，-(C
H 2)
13-)，0.87(t，3H，J＝7.0Hz，C
H 3-CH
2-)；
MS(EI)：330(M
+)，285[CH
3(CH
2)
15SC
+HCH
3]，257[CH
3(CH
2)
15S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-methyl nondecylic acid.
The preparation of embodiment 5.3-thia-2-ethyl margaric acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stir and make its dissolving, drip 24.7g (0.206mol) 2-sulfydryl butyric acid.(27.7g, 0.1mol) bromotetradecane reacted 1.5-2 hour to add 25ml again, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 22.2g crystallization, productive rate is 70%, and mp.38-39 ℃, the GC purity assay is 97.0%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.38-39 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.94(bs，OH)，2.91(dd，1H，J
1＝J
2＝6.8Hz，-SC
H(CH2CH3)CO
2H)，2.60-2.70(m，2H，-C
H 2S-)，1.76-2.01(m，2H，CH
3-C
H 2-CHCOOH)，1.20-1.39(m，24H，-(C
H 2)
12-CH
2S-)，0.873(t，3H，J＝7.0Hz，C
H 3-(CH
2)
13-)，0.871(t，3H，J＝7.39Hz，C
H 3-CH
2-CHCOOH)；
MS(EI)：316(M
+)，271[CH
3(CH
2)
13SC
+HC
2H
5]，229[CH
3(CH
2)
13S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-ethyl margaric acid.
The preparation of embodiment 6.3-thia-2-propyl group margaric acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stir and make its dissolving.Drip 29.7g (0.206mol) 2-sulfydryl valeric acid.(27.7g, 0.1mol) bromotetradecane reacted 1.5-2 hour to add 25ml again.Separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, and recrystallization from ethanol obtains the 24.3g crystallization, productive rate is 68%, and mp.47.5-49 ℃, the GC purity assay is 97.0%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.47.5-49 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.23(bs，OH)，2.91(dd，1H，J
1＝J
2＝6.8Hz，-SC
H(CH
2CH
2CH
3)CO
2H)，2.60-2.70(m，2H，-C
H 2S-)，1.92-2.22(m，2H，CH
3CH
2-C
H 2-CHCOOH)，1.39-1.49(m，2H，CH
3-C
H 2-CH
2CHCOOH)，1.20-1.39(m，24H，-(C
H 2)
12-CH
2S-)，0.873(t，3H，J＝7.0Hz，C
H 3-(CH
2)
13-)，0.871(t，3H，J＝7.39Hz，C
H 3-CH
2-CHCOOH)；
MS(EI)：358(M
+)，313[CH
3(CH
2)
15SC
+HC
2H
5]，257[CH
3(CH
2)
15S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-propyl group margaric acid.
The preparation of embodiment 7.3-thia-2-butyl margaric acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stir and make its dissolving.Drip 32.55g (0.206mol) 2-mercaptohexanoic acid.(27.7g, 0.1mol) bromotetradecane reacted 1.5-2 hour to add 25ml again, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 24.8g crystallization, productive rate is 66.5%, and mp.48.5-49.5 ℃, the GC purity assay is 97.5%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.48.5-49.5 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.84(bS，OH)，2.96(dd，1H，J
1＝J
2＝8.3Hz，-SC
H(CH
2CH
2CH
2CH
3)CO
2H)，2.56-2.66(m，2H，-C
H 2S-)，1.95-2.15(m，2H，CH
3CH
2CH
2-C
H 2-CHCOOH)，1.39-1.49(m，4H，CH
3C
H 2-C
H 2-CH
2CHCOOH)，1.20-1.39(m，24H，-(C
H 2)
12-CH
2S-)，0.901(t，3H，J＝7.0Hz，C
H 3-(CH
2)
13-)，0.904(t，3H，J＝7.0Hz，C
H 3CH
2-CH
2-CHCOOH)；
MS(EI)：372(M
+)，327[CH
3(CH
2)
15SC
+HC
3H
7]，257[CH
3(CH
2)
15S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-butyl margaric acid.
The preparation of embodiment 8.3-thia-2-decyl margaric acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, drip 45.32g (0.206mol) 2-sulfydryl undeeanoic acid, add 25ml (27.7g, 0.1mol) bromotetradecane again, reacted 2-3 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stirring is spent the night, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 27.5g crystallization, productive rate is 66.2%, and mp.46-48 ℃, the GC purity assay is 97.6%.
The product that obtains is analyzed as follows:
The white flake-like crystal;
Mp.46-48 ℃ (recrystallization from EtOH);
IR(KBr)ν
max：2960，2920，2870，1700，1470，1250cm
-1；
1H?NMR(300MHz，CDCl
3)：δ10.1(OH)，3.0(dd，1H，J
1＝J
2＝6.8Hz，-SC
HCOOH)，2.58-2.68(m，2H，J＝7.1Hz，-C
H 2S-)，1.99-2.19(m，2H，CH
3-(CH
2)
8C
H 2-CHCOOH)，1.49-1.53(m，2H，-C
H 2CH
2SCHCOOH)，1.29-1.31(m，24H，-(C
H 2)
12-CH
2S-)，1.29-1.31(m，14H，-(C
H 2)
7-CH
2CH
2SCHCOOH)，0.91(t，3H，J＝7.4Hz，C
H 3-(CH
2)
15-)，0.865(t，3H，J＝7.0Hz，C
H 3-(CH
2)
8CHCOOH)；
MS：456(M
+)，411[CH
3(CH
2)
15SC
+HC
10H
21]，257[CH
3(CH
2)
15S
+](B)。
Determine that according to above analysis the structure of this product is 3-thia-2-decyl margaric acid.
The preparation of embodiment 9.3-thia-2-methylheptadecanoic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml ethanol, stirring makes its dissolving, drips 18.3ml (21.88g, 0.206mol) 2 mercaptopropionic acid, add 25ml (27.7g again, 0.1mol) bromotetradecane, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir the precipitation that suction filtration is separated out, wash with water, recrystallization from ethanol obtains the 23.5g crystallization, and productive rate is 77.8%, mp.51.8-52.2 ℃, the GC purity assay is 97.4%.
The preparation of embodiment 10.3-thia-2-methylheptadecanoic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stir and make its dissolving, drip 25ml (27.7g, 0.1mol) bromotetradecane, stir down, drip 18.3ml (21.88g, 0.206mol) 2 mercaptopropionic acid, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir, the precipitation that suction filtration is separated out washes with water, recrystallization from ethanol, obtain the 23.3g crystallization, productive rate is 77.15%, and mp.51.8-52.2 ℃, the GC purity assay is 97.5%.
The preparation of embodiment 11.3-thia-2-methylheptadecanoic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, drips 9.15ml (10.94g, 0.103mol) 2 mercaptopropionic acid, add 25ml (27.7g again, 0.1mol) bromotetradecane, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir the precipitation that suction filtration is separated out, wash with water, recrystallization from ethanol obtains the 20.4g crystallization, and productive rate is 67.5%, mp.51.4-52.1 ℃, the GC purity assay is 97.0%.
The preparation of embodiment 12.3-thia-2-methylheptadecanoic acid
Under the normal temperature, 17.4g sodium hydroxide (excessive) is added in the 200ml methyl alcohol, stirring makes its dissolving, drips 27.5ml (32.8g, 0.309mol) 2 mercaptopropionic acid, add 25ml (27.7g again, 0.1mol) bromotetradecane, reacted 1.5-2 hour, separate out a large amount of white solids, continue to be stirred to and react completely, in system, add entry and hydrochloric acid then, stir the precipitation that suction filtration is separated out, wash with water, recrystallization from ethanol obtains the 23.9g crystallization, and productive rate is 79.1%, mp.51.7-52.2 ℃, the GC purity assay is 97.4%.
In sum, the present invention is a raw material with haloalkane and 2-mercaptan carboxylic acid, condensation under alkaline condition, and single stage method makes neta-thia-alpha-alkyl fatty acid, have that environmental pollution is little, efficient stable, simple, product purity is high, production cost is low characteristics, be fit to scale operation.
Need to prove, all quote in this application as a reference, just quoted as a reference separately as each piece document at all documents that the present invention mentions.Should understand in addition, above-described is specific embodiments of the invention and the know-why used, after having read above-mentioned teachings of the present invention, those skilled in the art can make various changes or modifications and not deviate from spirit of the present invention and scope the present invention, and these equivalent form of values fall within the scope of the invention equally.
Claims (10)
1. a novel method for preparing neta-thia-alpha-alkyl fatty acid is characterized in that, is raw material with haloalkane and 2-mercaptan carboxylic acid, and single step reaction prepares described neta-thia-alpha-alkyl fatty acid in alkali alcosol.
2. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, the molecular formula of described haloalkane is R1-X, and wherein R1 is C
10-C
30Saturated or unsaturated alkyl or aryl, wherein X is a chlorine, bromine or iodine, described 2-mercaptan carboxylic acid is:
Wherein R2 is C
1-C
10Saturated or do not embrace and alkyl or aryl.
3. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 2 is characterized in that, has substituting group on the carbon atom of described alkyl or aryl, and described substituting group is hydroxyl, carbonyl, carboxyl or cyano group.
4. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 2 is characterized in that, described R1 is CH
3(CH
2)
9-29, described R2 is CH
3(CH
2)
0-9.
5. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, described haloalkane splashes in the described alkali alcosol that contains described 2-mercaptan carboxylic acid.
6. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, described reaction is carried out at normal temperatures.
7. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, described haloalkane and described 2-mercaptan carboxylic acid's mol ratio is 1: 1 to 1: 3.
8. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, the time of described reaction is 0.5 hour-24 hours.
9. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, the time of described reaction is 1.5 hours-5 hours.
10. the novel method of preparation neta-thia-alpha-alkyl fatty acid as claimed in claim 1 is characterized in that, also comprise follow-up saltout, suction filtration, recrystallization.
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| CNA2007100366484A CN101225064A (en) | 2007-01-19 | 2007-01-19 | New method for preparing neta-thia-alpha-alkyl fatty acid |
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| CNA2007100366484A CN101225064A (en) | 2007-01-19 | 2007-01-19 | New method for preparing neta-thia-alpha-alkyl fatty acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010008299A1 (en) * | 2008-07-15 | 2010-01-21 | Pronova Biopharma Norge As | Novel sulphur containing lipids for use as food supplement or as medicament |
| US8735436B2 (en) | 2009-05-08 | 2014-05-27 | Pronova Biopharma Norge As | Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas |
| US8741966B2 (en) | 2007-11-09 | 2014-06-03 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| US9394228B2 (en) | 2010-11-05 | 2016-07-19 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
| US10722481B2 (en) | 2015-04-28 | 2020-07-28 | Basf As | Substituted fatty acids for treating non-alcoholic steatohepatitis |
| US11351139B2 (en) | 2013-02-28 | 2022-06-07 | Basf As | Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| US11925614B2 (en) | 2017-12-06 | 2024-03-12 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
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2007
- 2007-01-19 CN CNA2007100366484A patent/CN101225064A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8741966B2 (en) | 2007-11-09 | 2014-06-03 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| WO2010008299A1 (en) * | 2008-07-15 | 2010-01-21 | Pronova Biopharma Norge As | Novel sulphur containing lipids for use as food supplement or as medicament |
| US8759558B2 (en) | 2008-07-15 | 2014-06-24 | Pronova Biopharma Norge As | Sulphur containing lipids for use as food supplement or as medicament |
| EA022593B1 (en) * | 2008-07-15 | 2016-01-29 | Пронова Биофарма Норге Ас | Sulphur containing lipids for use as food supplement or as medicament |
| US8735436B2 (en) | 2009-05-08 | 2014-05-27 | Pronova Biopharma Norge As | Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas |
| US9394228B2 (en) | 2010-11-05 | 2016-07-19 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
| US11351139B2 (en) | 2013-02-28 | 2022-06-07 | Basf As | Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| US10722481B2 (en) | 2015-04-28 | 2020-07-28 | Basf As | Substituted fatty acids for treating non-alcoholic steatohepatitis |
| US11234948B2 (en) | 2015-04-28 | 2022-02-01 | Basf As | Substituted fatty acids for treating non-alcoholic steatohepatitis |
| US11911354B2 (en) | 2015-04-28 | 2024-02-27 | Basf | Substituted fatty acids for treating non-alcoholic steatohepatitis |
| US11925614B2 (en) | 2017-12-06 | 2024-03-12 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
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