CN106336354B - A kind of preparation method of low carbon fatty acid - Google Patents
A kind of preparation method of low carbon fatty acid Download PDFInfo
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- CN106336354B CN106336354B CN201610715638.2A CN201610715638A CN106336354B CN 106336354 B CN106336354 B CN 106336354B CN 201610715638 A CN201610715638 A CN 201610715638A CN 106336354 B CN106336354 B CN 106336354B
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- low carbon
- fatty acid
- hydrogen peroxide
- preparation
- carbon fatty
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- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 38
- -1 carbon fatty acid Chemical class 0.000 title claims abstract description 23
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 20
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 20
- 239000000194 fatty acid Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000004202 carbamide Substances 0.000 claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 19
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical class CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical class CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQVYMXCRDHDTTH-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)-2-[4-(diethoxyphosphorylmethyl)pyridin-2-yl]pyridine Chemical compound CCOP(=O)(OCC)CC1=CC=NC(C=2N=CC=C(CP(=O)(OCC)OCC)C=2)=C1 OQVYMXCRDHDTTH-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001760 fusel oil Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
Abstract
The invention discloses a kind of preparation method of low carbon fatty acid, belong to technical field of organic synthesis.The present invention is carried out according to following technical step：Low carbon fat alcohol, water and urea stirring mixing are weighed, hydrogen peroxide is then added dropwise and carries out oxidation reaction；Hydrogen peroxide concentration is 5 30%；0 50 DEG C of reaction temperature；The 20h of reaction time 5；Urea, hydrogen peroxide and low carbon fat alcohol mol ratio 0.1~1:2~5:1.The present invention prepare low carbon fatty acid method have simple to operate, environmental pollution it is small, to consersion unit not burn into efficiency high, the low advantage of processing cost, can be widely applied to prepare low carbon fatty acid field.
Description
Technical field
The present invention relates to technical field of organic synthesis, and in particular to a kind of nonmetal catalyzed hydrogen peroxide oxidation prepares low-carbon fat
The method of fat acid.
Background technology
Low carbon fat alcohol such as 1- propyl alcohol, n-butyl alcohol, isobutanol, 2- methyl butanols, 3- methyl butanols etc. are widely present in paddy
It is the important original for preparing biomass low-carbon aliphatic acid in the Main By product fusel oil of the fermented ethanol production of class crop and beer
Material.
It is one of important reaction in organic synthesis that fatty alcohol, which prepares aliphatic acid, while also challenging.It is prepared by tradition
Method includes alkali dehydriding and oxidizing process, and wherein alkali dehydriding needs high temperature, reaction under high pressure, and energy consumption is big, and reaction product is with sodium salt shape
Formula is present, it is necessary to neutralized with equimolar acid, pollutes larger, and fatty alcohol oxidizing process, then conducts extensive research both at home and abroad：1.
Nitric acid oxidation fatty alcohol method, the method major defect is：Strong acid medium, equipment corrosion are serious, a large amount of acid-bearing wastewaters are produced, nitrogen oxygen
Compound exhaust air is produced, and nitric acid oxidation, has the generation of accessory substance nitrile compounds, it is difficult to separate；2. use the height of stoichiometry
Potassium manganate, manganese dioxide, chromium trioxide, sodium hypochlorite etc. are oxidizing, produce a large amount of inorganic oxides or salt, and pollution is tight
Weight.In recent years, with the proposition of Green Chemistry, using eco-environmental evolvement to instruct, research does not have (or as small as possible to environment
) side effect, technically and financially feasible chemicals and chemical process, it is the direction of chemical future development.On
The document that fatty alcohol catalyzing oxidation prepares acid pours out, and such as air or oxygen catalysis oxidation fatty alcohol prepares aliphatic acid, exists
The shortcomings of catalyst preparation cost is high, disposable input cost is high, oxygenate impurities are more, separation rectifying device requires high；And
Using hydrogen peroxide oxidation method, oxidation of fat alcohol is mainly carried out as catalytic carrier using sodium tungstate, phase transfer catalyst and prepares aliphatic acid,
It is easily caused using the relatively inexpensive alkyl ammonium halide of price as carrier phase transfer catalyst in oxidizing process and forms alkyl halide, shadow
Sound product quality, and the disulfate phase transfer catalyst largely used at present, catalyst preparation is complicated, seriously polluted, cost
It is high.
The content of the invention
It is an object of the invention to provide a kind of preparation method of low carbon fatty acid, solve existing low carbon fatty acid and prepare cost
Height, the accessory substance of generation is more, the problems such as seriously polluted.
The technical solution adopted by the present invention is：A kind of preparation method of low carbon fatty acid, this method is using water as solvent, urea
For catalyst, hydrogen peroxide is the method that oxidizing low carbon fat alcohol prepares low carbon fatty acid.It is urea described in this method, low
The mol ratio of concentration hydrogen peroxide and low carbon fat alcohol is 0.1~1:2~5:1, and the oxidation time in the environment of 0~50 DEG C
5~20h is obtained.
Specifically, the low carbon fat alcohol is 1- propyl alcohol, n-butyl alcohol, isobutanol, 2- methyl butanols or 3- methyl butanols.
The low carbon fat alcohol makes solvent of water, and the weight ratio of water and low carbon fat alcohol is 0~5:1.
The concentration of the hydrogen peroxide is 5-30%.
The urea, hydrogen peroxide and low carbon fat alcohol optimum mole ratio 0.5:3:1.
The reaction specific operation process is as follows：Low carbon fat alcohol, water and urea stirring mixing are weighed, dioxygen is then added dropwise
Water carries out oxidation reaction and obtains low carbon fatty acid, and course of reaction is reacted after terminating by dividing by trace analysis in gas-chromatography
Liquid, rectifying obtain low carbon fatty acid.
The present invention has advantages below：Catalyst is non-metallic catalyst, and cheap and easy to get, efficient, byproduct of reaction is few；Institute
All it is water with what is generated after solvent and hydrogen peroxide oxidation, the pollution produced to environment is small；Low concentration hydrogen peroxide safe operation.
Embodiment
Below by specific embodiment, the present invention will be described, but the present invention implements to be not limited to these.
Embodiment 1：
A kind of preparation method of low carbon fatty acid, concrete operation method is as follows：Weigh 150g 1- propyl alcohol, 75g water and 75g
Urea is stirred at room temperature mixing, and the hydrogen peroxide of 1275g 20% is added dropwise, and maintains after 35 DEG C of reaction 12h, through gas chromatographic analysis, not instead
Raw material propyl alcohol 15%, product 81% are answered, through extraction, rectifying, propionic acid finished product is obtained.
Embodiment 2：
A kind of preparation method of low carbon fatty acid, concrete operation method is as follows：Weigh 220g 3- methyl butanols, 75g water and
Mixing is stirred at room temperature in 75g urea, and the hydrogen peroxide of 1700g 15% is added dropwise, and maintains after 45 DEG C of reaction 12h, through gas chromatographic analysis,
Unreacting material 3- methyl butanols 13%, product 82.5%, through point liquid, a rectifying, obtain 3 Methylbutanoic acid finished product.
Embodiment 3
A kind of preparation method of low carbon fatty acid, concrete operation method is as follows：Weigh 185g n-butyl alcohols, 75g water and 75g
Mixing is stirred at room temperature in urea, and the hydrogen peroxide of 2550g 10% is added dropwise, and maintains 35 DEG C of reaction 18h, and gas chromatographic analysis, unreacted is former
Expect butanol 14.8%, product 80.5%, through point liquid, a rectifying, obtain butyric acid finished product.
Embodiment 4：
A kind of preparation method of low carbon fatty acid, concrete operation method is as follows：Weigh 185g isobutanols, 75g water and 75g urine
Mixing is stirred at room temperature in element, and the hydrogen peroxide of 1275g 20% is added dropwise, and maintains 30 DEG C of reaction 16h, gas chromatographic analysis, unreacting material
Isobutanol 16%, product 75.3%, through point liquid, a rectifying, obtain isobutyric acid finished product.
Embodiment 5：
A kind of preparation method of low carbon fatty acid, concrete operation method is as follows：Weigh 220g 2- methyl butanols, 75g water and
Mixing is stirred at room temperature in 75g urea, and the hydrogen peroxide of 1500g 17% is added dropwise, and maintains after 45 DEG C of reaction 15h, through gas chromatographic analysis,
Unreacting material 2- methyl butanols 11%, product 83%, through point liquid, a rectifying, obtain 2-Methyl Butyric Acid finished product.
The present invention is described in detail above, principle and embodiment of the specific case used herein to the present invention
It is set forth, the explanation of above example is only intended to the method and its core concept for helping to understand the present invention, not to this
The scope of invention is defined, while on the premise of design spirit of the present invention is not departed from, those of ordinary skill in the art are to this
Equivalence changes or decoration that invention described construction, feature and principle are made, all should fall within the scope of protection of the present invention.
Claims (3)
1. a kind of preparation method of low carbon fatty acid, it is characterised in that follow the steps below：Weigh low carbon fat alcohol, water
Stir and mix with urea, low concentration hydrogen peroxide is then added dropwise and carries out oxidation reaction, low carbon fatty acid is obtained；
The mol ratio of the urea, low concentration hydrogen peroxide and low carbon fat alcohol is 0.1~1:2~5:1,
The low carbon fat alcohol be 1- propyl alcohol, n-butyl alcohol or isobutanol,
The concentration of the hydrogen peroxide is 5-30%,
The oxidation reaction 12~18h of reaction time in the environment of 30~35 DEG C.
2. the preparation method of low carbon fatty acid according to claim 1, it is characterised in that：The low carbon fat alcohol makes of water
The weight ratio of solvent, water and low carbon fat alcohol is 0~5:1.
3. the preparation method of low carbon fatty acid according to claim 1, it is characterised in that：The urea, low concentration dioxygen
The mol ratio of water and low carbon fat alcohol is 0.5:3:1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610715638.2A CN106336354B (en) | 2016-08-24 | 2016-08-24 | A kind of preparation method of low carbon fatty acid |
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|---|---|---|---|
| CN201610715638.2A CN106336354B (en) | 2016-08-24 | 2016-08-24 | A kind of preparation method of low carbon fatty acid |
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| Publication Number | Publication Date |
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| CN106336354A CN106336354A (en) | 2017-01-18 |
| CN106336354B true CN106336354B (en) | 2017-10-13 |
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| CN106905149B (en) * | 2017-02-10 | 2019-10-11 | 上海金兆节能科技有限公司 | Polyethylene glycol isomery alcohol ester and preparation method thereof and environmentally friendly micro lubricating agent is prepared with the ester |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1201026A (en) * | 1997-05-30 | 1998-12-09 | 滕州市香料厂 | Process for preparing 2-methyl butanol/butanoic acid with opticity |
| CN1762966A (en) * | 2005-09-08 | 2006-04-26 | 中国科学院山西煤炭化学研究所 | A kind of method of producing high purity punicic acid |
| EP1712609A1 (en) * | 2005-04-11 | 2006-10-18 | Dongbu Hannong Chemical Co., Ltd. | Method for preparing unsaturated fatty acids |
| CN101386563A (en) * | 2008-10-24 | 2009-03-18 | 江苏钟山化工有限公司 | Method for preparing plant oil-based polyol |
-
2016
- 2016-08-24 CN CN201610715638.2A patent/CN106336354B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1201026A (en) * | 1997-05-30 | 1998-12-09 | 滕州市香料厂 | Process for preparing 2-methyl butanol/butanoic acid with opticity |
| EP1712609A1 (en) * | 2005-04-11 | 2006-10-18 | Dongbu Hannong Chemical Co., Ltd. | Method for preparing unsaturated fatty acids |
| CN1762966A (en) * | 2005-09-08 | 2006-04-26 | 中国科学院山西煤炭化学研究所 | A kind of method of producing high purity punicic acid |
| CN101386563A (en) * | 2008-10-24 | 2009-03-18 | 江苏钟山化工有限公司 | Method for preparing plant oil-based polyol |
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| CN106336354A (en) | 2017-01-18 |
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Address after: No. 24, Weiyi Road, She County Circular Economy Park, Mount Huangshan City, Anhui Province 245000 Patentee after: Mount Huangshan Kehong Biotechnology Co.,Ltd. Country or region after: China Address before: No. 24, Weiyi Road, She County Circular Economy Park, Mount Huangshan City, Anhui Province 245000 Patentee before: HUANGSHAN KEHONG BIO-FLAVORS CO.,LTD. Country or region before: China |
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