CN101381304A - Synthetic method of tricaprylin-carboxyl-<13>C3 - Google Patents

Synthetic method of tricaprylin-carboxyl-<13>C3 Download PDF

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CN101381304A
CN101381304A CNA2008102015665A CN200810201566A CN101381304A CN 101381304 A CN101381304 A CN 101381304A CN A2008102015665 A CNA2008102015665 A CN A2008102015665A CN 200810201566 A CN200810201566 A CN 200810201566A CN 101381304 A CN101381304 A CN 101381304A
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acid
nitrobenzene
sulfonic acid
tricaprylin
ether
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卢伟京
李帅
卢浩
李美华
李卫霞
潘洁
侯秀红
杨维成
徐仲杰
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Shanghai Research Institute of Chemical Industry SRICI
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Shanghai Research Institute of Chemical Industry SRICI
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Abstract

The invention relates to a synthesis method for glycerol triallyl caprylic acid ester carboxy-13C3. The synthesis method is as follows: caprylic acid-1-13C and glycerine at a mole ratio of 3-10:1 are used as raw materials and are subjected to a catalytic esterification reaction with a catalyst and a solvent added to the raw materials for 0.1 to 100 hours at a temperature of between 0 and 260 DEG C and then are dehydrated to obtain the glycerol triallyl caprylic acid ester carboxy-13C3, wherein a ratio of the mass of the catalyst to the mass of the caprylic acid-1-13C is 0.01-100:1, and a ratio of the volume of the solvent to the mass of the caprylic acid-1-13C is 1-400ml:1g. Compared with the prior art, yield of the glycerol triallyl caprylic acid ester carboxy-13C3 of the invention can reach 80.1 percent which is calculated by consumption of the caprylic acid-1-13C , the abundance of 13C is more than 99 percent (atom), and the purity of 13C is above 98 percent.

Description

A kind of tricaprylin-carboxyl- 13C 3Synthetic method
Technical field
The present invention relates to a kind of tricaprylin-carboxyl- 13C 3Synthetic method.
Background technology
Purified tricaprylin-carboxyl- 13C 3Be colourless oil liquid, 9～10 ℃ at zero pour, 233 ℃/1mmHg of boiling point, 2～8 ℃ of storing temps are dissolved in ethanol, ether and sherwood oil.Aspect medical science, tricaprylin-carboxyl- 13C 3Be that diagnosis effect is good 13The C mark is breathed reagent, is applied to the test of pancreas lipase, comprises Nutrition and Metabolism and fat absorbing, the especially test of the greasy absorption of medium chain fatty acid, and wherein the test of the fat absorbing of paediatrics, particularly baby is an important use; Can also detect gallbladder cystic fibrosis, steatorrhea, diarrhoea, metabolism of fat test behind pancreas, duodenum and the stomach operation, research pancreas enzyme is to fat absorption and effect etc.
Do not find at present synthetic glycerine three octanoates-carboxyl- 13C 3The bibliographical information of (three esters).Glycerine is glycerol, and 3 hydroxyls are arranged on the glycerol molecule, and all complete esterification of the glycerine of input (3 hydroxyls) has bigger difficulty.Have 1 or 2 hydroxyls not have esterification as partial glycerol, have in the reaction product by-product glycerin dicaprylate-carboxyl- 13C 2(diester) and glycerine one octanoate-carboxyl- 13C (ester).In the short run synthetic product, three esters are difficult with separating of a diester and an ester, also do not have suitable method.
Summary of the invention
Purpose of the present invention be exactly tricaprylin-carboxyl that a kind of high purity, high yield are provided in order to overcome the defective that above-mentioned prior art exists- 13C 3Synthetic method.
Purpose of the present invention can be achieved through the following technical solutions: a kind of tricaprylin-carboxyl- 13C 3Synthetic method, it is characterized in that this method is to be sad-1-of 3～10:1 with mol ratio 13C and glycerine are raw material, add catalyzer and solvent, in 0～260 ℃ of following catalytic esterification 0.1～100 hour, dehydration, make the tricaprylin carboxyl- 13C 3, described catalyst consumption is catalyzer and sad-1- 13The C mass ratio is 0.01～100:1, and the consumption of described solvent is 1～400ml solvent/sad-1-of 1 gram 13C.
Described catalyzer is selected from Phenylsulfonic acid, tosic acid, naphthene sulfonic acid, Witco 1298 Soft Acid, p-nitrophenyl sulfonic acid, m-nitrobenzene sulfonic acid, neighbour-nitrobenzene-sulfonic acid, 3-fluoro-4-nitrobenzene-sulfonic acid, 2-fluoro-4-nitrobenzene-sulfonic acid, 4-fluoro-3-nitrobenzene-sulfonic acid, 4-fluoro-2-nitrobenzene-sulfonic acid, 3-chloro-4-nitrobenzene-sulfonic acid, 2-chloro-4-nitrobenzene-sulfonic acid, 4-chloro-3-nitrobenzene-sulfonic acid, 4-chloro-2-nitrobenzene-sulfonic acid, 3-bromo-4-nitrobenzene-sulfonic acid, 2-bromo-4-nitrobenzene-sulfonic acid, 4-bromo-3-nitrobenzene-sulfonic acid, 4-bromo-2-nitrobenzene-sulfonic acid, phospho-wolframic acid, phospho-molybdic acid, silicotungstic acid, silicomolybdic acid, molybdenum vanadium phosphate, phosphorus molybdenum chromic acid, phosphorus bismuth molybdic acid, the acid of tungsten zinc-aluminium, phosphorus antimony molybdic acid, sulfuric acid, phosphoric acid, in the hydrochloric acid one or more.
Described solvent is selected from hexane, heptane, nonane, certain herbaceous plants with big flowers alkane, dodecane, hexanaphthene, methylcyclohexane, ethylcyclohexane, the 2-methylpentane, 2, the 2-dimethylbutane, 2, the 3-dimethylbutane, heptane, perhydronaphthalene, benzene, toluene, ethylbenzene, propyl benzene, isopropyl benzene, butylbenzene, sec-butylbenzene, tert-butylbenzene, amylbenzene, penta benzene, hexyl benzene, heptyl benzene, diethylbenzene, right-dimethylbenzene, m-xylene, o-Xylol, ether, propyl ether, isopropyl ether, butyl ether, amyl ether, isoamyl oxide, hexyl ether, metopryl, methyl-n-butyl ether, b-butyl ether, tetrahydrofuran (THF), tetrahydropyrans diox, methyl-phenoxide, phenyl ethyl ether, 1,2-dimethoxy benzene, the propyl group phenyl ether, butyl phenylate, the amyl group phenyl ether, the benzene hexyl ether, O-methoxy toluene, meta-methoxy toluene, to methoxy toluene, glycol dimethyl ether, adjacent two diethylene glycol diethyl ethers, ethylene glycol dibutyl ether, diglyme, diethyl carbitol, in the Terpane one or more.
Described dehydration uses the combination of dewatering agent, water trap and dewatering agent and water trap to carry out.
Described dewatering agent is selected from one or more in molecular sieve, anhydrous magnesium sulfate, anhydrous sodium sulphate, anhydrous calciumsulphate, anhydrous calcium oxide, Calcium Chloride Powder Anhydrous, the anhydrous cupric sulfate.
Described sad-1- 13The mol ratio of C and glycerine is 3～6:1.
Described catalyst consumption is catalyzer and sad-1- 13The C mass ratio is 0.1～10:1.
The consumption of described solvent is 4～100ml solvent/sad-1-of 1 gram 13C.
The temperature of described reaction is a reflux temperature.
The time of described reaction is 0.2～50 hour.
Compared with prior art, the present invention propose a kind of new tricaprylin-carboxyl- 13C 3Synthetic method is promptly with sad-1- 13C and glycerine are raw material, adopt the catalytic esterification mode prepare the tricaprylin carboxyl- 13C 3, reaction formula is:
Figure A200810201566D00061
Synthetic method of the present invention, constantly the water that reaction process is produced is removed, and makes three hydroxyl reactions on the glycerine complete, acquisition tricaprylin-carboxyl- 13C 3Tricaprylin-carboxyl- 13It is 80.1% (sad to consume-1-that the C yield can reach 13C calculates), 13The C abundance is greater than 99% (atom), and purity is greater than 98%.
Embodiment
The present invention relates to a kind of new synthetic glycerine three octanoates-carboxyl- 13C 3Method, concrete steps are as follows:
Tricaprylin-carboxyl- 13C 3Synthetic
Press the method for document and synthesize sad-1- 13C (S.Weihouse, G.Medes and N.F.Floyd, Fattyacid metabolism, J.Biol.Chem.1944,155:143-151).
Sad-1- 13C and glycerine reaction obtain tricaprylin-carboxyl- 13C 3Catalyzer is at Phenylsulfonic acid, tosic acid, naphthene sulfonic acid, Witco 1298 Soft Acid, p-nitrophenyl sulfonic acid, m-nitrobenzene sulfonic acid, neighbour-nitrobenzene-sulfonic acid, 3-fluoro-4-nitrobenzene-sulfonic acid, 2-fluoro-4-nitrobenzene-sulfonic acid, 4-fluoro-3-nitrobenzene-sulfonic acid, 4-fluoro-2-nitrobenzene-sulfonic acid, 3-chloro-4-nitrobenzene-sulfonic acid, 2-chloro-4-nitrobenzene-sulfonic acid, 4-chloro-3-nitrobenzene-sulfonic acid, 4-chloro-2-nitrobenzene-sulfonic acid, 3-bromo-4-nitrobenzene-sulfonic acid, 2-bromo-4-nitrobenzene-sulfonic acid, 4-bromo-3-nitrobenzene-sulfonic acid, 4-bromo-2-nitrobenzene-sulfonic acid, phospho-wolframic acid, phospho-molybdic acid, silicotungstic acid, silicomolybdic acid, molybdenum vanadium phosphate, phosphorus molybdenum chromic acid, phosphorus bismuth molybdic acid, the acid of tungsten zinc-aluminium, phosphorus antimony molybdic acid, sulfuric acid, phosphoric acid, select catalyzer and sad-1-in the hydrochloric acid for use 13The mass ratio of C is 0.01～100:1, preferred 0.1～10:1;
Solvent is at hexane, heptane, nonane, certain herbaceous plants with big flowers alkane, dodecane, hexanaphthene, methylcyclohexane, ethylcyclohexane, the 2-methylpentane, 2, the 2-dimethylbutane, 2, the 3-dimethylbutane, heptane, perhydronaphthalene, benzene, toluene, ethylbenzene, propyl benzene, isopropyl benzene, butylbenzene, sec-butylbenzene, tert-butylbenzene, amylbenzene, penta benzene, hexyl benzene, heptyl benzene, diethylbenzene, right-dimethylbenzene, m-xylene, o-Xylol, ether, propyl ether, isopropyl ether, butyl ether, amyl ether, isoamyl oxide, hexyl ether, metopryl, methyl-n-butyl ether, b-butyl ether, tetrahydrofuran (THF), tetrahydropyrans diox (dioxane), methyl-phenoxide, phenyl ethyl ether, 1,2-dimethoxy benzene, the propyl group phenyl ether, butyl phenylate, the amyl group phenyl ether, the benzene hexyl ether, O-methoxy toluene, meta-methoxy toluene, to methoxy toluene, glycol dimethyl ether, adjacent two diethylene glycol diethyl ethers, ethylene glycol dibutyl ether, diglyme, diethyl carbitol, Terpane, and composition thereof in select for use;
Dewatering agent is selected for use in molecular sieve, anhydrous magnesium sulfate, anhydrous sodium sulphate, anhydrous calciumsulphate, anhydrous calcium oxide, Calcium Chloride Powder Anhydrous, anhydrous cupric sulfate;
Temperature of reaction is 0～260 ℃, preferred reflux temperature;
Sad-1- 13C and glycerine mol ratio are 3～10:1, preferred 3～6:1;
Solvent load is 1～400ml solvent/sad-1-of 1 gram 13C, the preferred 4～100ml solvent/sad-1-of 1 gram 13In the C scope.
Tricaprylin-carboxyl- 13C 3Analysis
Product 13The C abundance detects and adopts TSQ QUANTUN ACCESS liquid chromatograph-mass spectrometer (Thermo Fisher company) to analyze.
Product purity is measured and is used FULI9790 gas chromatograph (Chinese good fortune is upright) to analyze SPB-50 capillary column, hydrogen flame detector.
Raw material is sad-1- 13C uses gas chromatograph analysis, NUOKL post; The monitoring of reaction process adopts thin-layer chromatography and LC-20AT type high performance liquid chromatograph (day island proper Tianjin company) to carry out, the C-18 reversed-phase column, and methyl alcohol moving phase, UV-detector, the detection wavelength is 220nm.
Now further narrate the present invention according to embodiment, just represent a kind of typical example, claim is not limited by the represented scope of embodiment should.
Embodiment 1
250mL there-necked flask difference is water trap, feed hopper and the stopper of prolong in succession, 300ml dimethylbenzene, the sad-1-of 34.85 grams 13C (0.24mol, 13C abundance 99%), 2.8 gram 1-naphthalene sulfonic aicds and 4.60 gram glycerine (0.05mol) add this there-necked flask successively, reflux is 16 hours under nitrogen atmosphere, constantly will react the water layering in water trap that produces and emit, and finishes to reacting.Product is cooled to room temperature, is transferred to separating funnel, and with saturated nacl aqueous solution washing, organic phase is steamed with rotatory evaporator and removed dimethylbenzene, obtain tricaprylin-carboxyl- 13C 320.04 gram, water reclaims sad-1- 13The C11.79 gram, yield ( 13The C utilization ratio) is 80.04% (by the sad-1-that consumes 13The C meter), 13C abundance 99%atom, chemical purity 98.6%.
Embodiment 2
Replace 2.8 gram 1-naphthalene sulfonic aicds with 2.2 gram phosphorus molybdenum chromic acid in embodiment 1, the 280ml methyl-phenoxide replaces 300ml dimethylbenzene, tricaprylin-carboxyl- 13C 320.56 gram reclaims sad-1- 13The C11.23 gram, yield ( 13The C utilization ratio) is 80.17% (by the sad-1-that consumes 13The C meter), 13C abundance 99%atom, chemical purity 98.4%.
Embodiment 3
In embodiment 3, replace 1-naphthalene sulfonic aicd, replace dimethylbenzene with propyl ether with silicomolybdic acid (1.6 gram), tricaprylin-carboxyl- 13C 319.81 gram reclaims sad-1- 13The C11.62 gram, yield 78.54% is (by the sad-1-that consumes 13The C meter), 13C abundance 99%atom, chemical purity 98.7%.
Embodiment 4
In embodiment 1, p-nitrophenyl sulfonic acid replaces 1-naphthalene sulfonic aicd, butyl ether to replace dimethylbenzene, the water trap 20 mol sieve of packing into, and feeding intake changes sad-1-into 13C30.49 restrains (0.21mol), glycerine 4.60 gram (0.05mol), tricaprylin-carboxyl- 13C 320.34 gram reclaims sad-1- 13The C5.63 gram, yield 75.34% is (by the sad-1-that consumes 13The C meter), 13C abundance 99%atom, chemical purity 98.5%.
Embodiment 5
A kind of tricaprylin-carboxyl- 13C 3Synthetic method, this method is to be sad-1-of 3:1 with the mol ratio 13C and glycerine are raw material, add phospho-wolframic acid and ethylene glycol dibutyl ether, in 10 ℃ of following catalytic esterifications 0.1 hour, dehydration, make the tricaprylin carboxyl- 13C 3, the consumption of described phospho-wolframic acid is phospho-wolframic acid and sad-1- 13The C mass ratio is 0.01:1, and the consumption of described ethylene glycol dibutyl ether is 1ml ethylene glycol dibutyl ether/sad-1-of 1 gram 13C.
Embodiment 6
A kind of tricaprylin-carboxyl- 13C 3Synthetic method, this method is to be sad-1-of 10:1 with the mol ratio 13C and glycerine are raw material, add Witco 1298 Soft Acid and diethylbenzene, in 260 ℃ of following catalytic esterifications 100 hours, dehydration, make the tricaprylin carboxyl- 13C 3, the consumption of described Witco 1298 Soft Acid is Witco 1298 Soft Acid and sad-1- 13The C mass ratio is 100:1, and the consumption of described diethylbenzene is 400ml diethylbenzene/sad-1-of 1 gram 13C.

Claims (10)

  1. A tricaprylin-carboxyl- 13C 3Synthetic method, it is characterized in that this method is to be sad-1-of 3～10:1 with mol ratio 13C and glycerine are raw material, add catalyzer and solvent, in 0～260 ℃ of following catalytic esterification 0.1～100 hour, dehydration, make the tricaprylin carboxyl- 13C 3, described catalyst consumption is catalyzer and sad-1- 13The C mass ratio is 0.01～100:1, and the consumption of described solvent is 1～400ml solvent/sad-1-of 1 gram 13C.
  2. 2. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that described catalyzer is selected from Phenylsulfonic acid, tosic acid, naphthene sulfonic acid, Witco 1298 Soft Acid, p-nitrophenyl sulfonic acid, m-nitrobenzene sulfonic acid, neighbour-nitrobenzene-sulfonic acid, 3-fluoro-4-nitrobenzene-sulfonic acid, 2-fluoro-4-nitrobenzene-sulfonic acid, 4-fluoro-3-nitrobenzene-sulfonic acid, 4-fluoro-2-nitrobenzene-sulfonic acid, 3-chloro-4-nitrobenzene-sulfonic acid, 2-chloro-4-nitrobenzene-sulfonic acid, 4-chloro-3-nitrobenzene-sulfonic acid, 4-chloro-2-nitrobenzene-sulfonic acid, 3-bromo-4-nitrobenzene-sulfonic acid, 2-bromo-4-nitrobenzene-sulfonic acid, 4-bromo-3-nitrobenzene-sulfonic acid, 4-bromo-2-nitrobenzene-sulfonic acid, phospho-wolframic acid, phospho-molybdic acid, silicotungstic acid, silicomolybdic acid, molybdenum vanadium phosphate, phosphorus molybdenum chromic acid, phosphorus bismuth molybdic acid, the acid of tungsten zinc-aluminium, phosphorus antimony molybdic acid, sulfuric acid, phosphoric acid, in the hydrochloric acid one or more.
  3. 3. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that, described solvent is selected from hexane, heptane, nonane, certain herbaceous plants with big flowers alkane, dodecane, hexanaphthene, methylcyclohexane, ethylcyclohexane, the 2-methylpentane, 2, the 2-dimethylbutane, 2, the 3-dimethylbutane, heptane, perhydronaphthalene, benzene, toluene, ethylbenzene, propyl benzene, isopropyl benzene, butylbenzene, sec-butylbenzene, tert-butylbenzene, amylbenzene, penta benzene, hexyl benzene, heptyl benzene, diethylbenzene, right-dimethylbenzene, m-xylene, o-Xylol, ether, propyl ether, isopropyl ether, butyl ether, amyl ether, isoamyl oxide, hexyl ether, metopryl, methyl-n-butyl ether, b-butyl ether, tetrahydrofuran (THF), tetrahydropyrans diox, methyl-phenoxide, phenyl ethyl ether, 1,2-dimethoxy benzene, the propyl group phenyl ether, butyl phenylate, the amyl group phenyl ether, the benzene hexyl ether, O-methoxy toluene, meta-methoxy toluene, to methoxy toluene, glycol dimethyl ether, adjacent two diethylene glycol diethyl ethers, ethylene glycol dibutyl ether, diglyme, diethyl carbitol, in the Terpane one or more.
  4. 4. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that described dehydration uses the combination of dewatering agent, water trap and dewatering agent and water trap to carry out.
  5. 5. a kind of tricaprylin-carboxyl according to claim 4- 13C 3Synthetic method, it is characterized in that described dewatering agent is selected from one or more in molecular sieve, anhydrous magnesium sulfate, anhydrous sodium sulphate, anhydrous calciumsulphate, anhydrous calcium oxide, Calcium Chloride Powder Anhydrous, the anhydrous cupric sulfate.
  6. 6. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that, described sad-1- 13The mol ratio of C and glycerine is 3～6:1.
  7. 7. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that described catalyst consumption is catalyzer and sad-1- 13The C mass ratio is 0.1～10:1.
  8. 8. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that the consumption of described solvent is the sad-1-of 4～100ml solvent/1 gram 13C.
  9. 9. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that the temperature of described reaction is a reflux temperature.
  10. 10. a kind of tricaprylin-carboxyl according to claim 1- 13C 3Synthetic method, it is characterized in that the time of described reaction is 0.2～50 hour.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102336663A (en) * 2011-07-08 2012-02-01 广东轻工职业技术学院 Preparation and application of tri(2-ethylhexoic acid)glyceride
CN104203896A (en) * 2012-03-01 2014-12-10 普罗米蒂克生物科学公司 Method for the preparation of triglycerides of medium-chain length fatty acids
CN106365987A (en) * 2016-08-25 2017-02-01 上海化工研究院 Synthesis method of paraben compounds marked by stable isotope 13C or D
CN113797968A (en) * 2021-08-19 2021-12-17 万华化学集团股份有限公司 Preparation of 2-chloroisonicotinic acid-phosphomolybdic acid catalyst and preparation method of polyglycerol fatty acid ester
CN114805122A (en) * 2021-01-22 2022-07-29 江苏和成新材料有限公司 Esterification reaction method

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102336663A (en) * 2011-07-08 2012-02-01 广东轻工职业技术学院 Preparation and application of tri(2-ethylhexoic acid)glyceride
CN102336663B (en) * 2011-07-08 2013-04-03 澳宝化妆品（惠州）有限公司 Preparation and application of tri(2-ethylhexoic acid)glyceride
CN104203896A (en) * 2012-03-01 2014-12-10 普罗米蒂克生物科学公司 Method for the preparation of triglycerides of medium-chain length fatty acids
EP2819989A4 (en) * 2012-03-01 2016-03-09 Prometic Biosciences Inc Method for the preparation of triglycerides of medium-chain length fatty acids
AU2013225572B2 (en) * 2012-03-01 2017-02-23 Liminal Biosciences Limited Method for the preparation of triglycerides of medium-chain length fatty acids
CN104203896B (en) * 2012-03-01 2018-05-15 普罗米蒂克医药Smt有限公司 It is used to prepare the method for the triglyceride of medium chain length aliphatic acid
CN106365987A (en) * 2016-08-25 2017-02-01 上海化工研究院 Synthesis method of paraben compounds marked by stable isotope 13C or D
CN114805122A (en) * 2021-01-22 2022-07-29 江苏和成新材料有限公司 Esterification reaction method
CN114805122B (en) * 2021-01-22 2024-03-01 江苏和成新材料有限公司 Esterification reaction method
CN113797968A (en) * 2021-08-19 2021-12-17 万华化学集团股份有限公司 Preparation of 2-chloroisonicotinic acid-phosphomolybdic acid catalyst and preparation method of polyglycerol fatty acid ester
CN113797968B (en) * 2021-08-19 2022-08-05 万华化学集团股份有限公司 Preparation of 2-chloroisonicotinic acid-phosphomolybdic acid catalyst and preparation method of polyglycerol fatty acid ester

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