CN101979371A - Method for producing 2-butenoic acid - Google Patents
Method for producing 2-butenoic acid Download PDFInfo
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- CN101979371A CN101979371A CN2010102877359A CN201010287735A CN101979371A CN 101979371 A CN101979371 A CN 101979371A CN 2010102877359 A CN2010102877359 A CN 2010102877359A CN 201010287735 A CN201010287735 A CN 201010287735A CN 101979371 A CN101979371 A CN 101979371A
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- Prior art keywords
- butylene acid
- oxidizing reactor
- production method
- oxidizing
- reaction
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 239000000047 product Substances 0.000 claims abstract description 32
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 42
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 42
- 230000003647 oxidation Effects 0.000 claims description 24
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 18
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 5
- 230000000153 supplemental effect Effects 0.000 claims description 5
- 238000013329 compounding Methods 0.000 claims description 2
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 241000486679 Antitype Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RLYNGYDVXRKEOO-SQQVDAMQSA-N but-2-enoic acid;(e)-but-2-enoic acid Chemical group CC=CC(O)=O.C\C=C\C(O)=O RLYNGYDVXRKEOO-SQQVDAMQSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for producing 2-butenoic acid, which comprises the following steps: preparing mixed feed liquid from 2-butenoic aldehyde, normal hexane and water in a weight ratio of 1:1:0.05-0.08; mounting an ejector pump on an oxidation reaction kettle for spraying the mixed feed liquid into the oxidation reaction kettle; introducing oxygen into the oxidation reaction kettle to perform a reaction under a condition that the reaction pressure in the oxidation reaction kettle is 0.1 to 0.6MPa and a condition that the temperature is 25 to 35 DEG C to obtain oxidation reaction solution; distilling the oxidation reaction, distilling the remaining 2-butenoic aldehyde under a reduced pressure, recovering the 2-butenoic aldehyde, distilling the remaining normal hexane at normal pressure and obtaining filtrate; and cooling the filtrate to -5 DEG C to 5 DEG C, precipitating, crystallizing and filtering and drying the crystals to obtain the 2-butenoic acid product. The production method has the advantages that: the reaction speed is high; the product yield is high; the energy consumption is small; and the quality of the product obtained is high.
Description
Technical field
The present invention relates to a kind of production method of 2-butylene acid, belong to chemical production technical field.
Background technology
The trade name of 2-butylene acid is a Ba Dousuan, and its English name is Crotonic acid Butenoic acid, and its chemical structural formula is CH
3CH=CHCOOH, molecular formula is C
4H
6O
2, molecular weight is 86.09, its physico-chemical property: white crystals has rank smell; 2-butylene acid has along anti-two kinds of isomerss, wherein the fusing point of anti-type isomerism body is 71.6 ℃, boiling point is 185 ℃, water-soluble, pure, acetone, toluene, ether equal solvent, it has pungency to skin, eyes, and it can be used for synthetic resins, sterilant, topcoating, softening agent, Rubber Softener, thermally melting sizing agent.
It is reported that the industrial preparation of 2-butylene acid is raw material with the crotonic aldehyde all, makes through oxidation, crotonic aldehyde is oxidized to peroxide 2-butylene acid intermediate in reaction process, generates 2-butylene acid then.
On the oxidizing process of crotonaldehyde, can be divided into catalyzed oxidation and non-catalytic oxidation; In recent years, along with updating of production technique, people constantly attempt using the catalytic oxidation of catalyzer, and for example shawinigan chemical company is with Cobaltous diacetate-neutralized verdigris catalyzed oxidation, and early stage lenpold.E.O. is with Ba Dousuan cobalt-Ba Dousuan copper catalyzed oxidation; Compound multicomponent catalysts such as silver catalyst agent and thallous chloride, Cobaltous diacetate, neutralized verdigris, oxidization-hydrogenation ratio about 43.1% to 62.7% were also once studied by China; Xiamen University's research in 1993 reports that the western Buddhist alkali complex compound with activated manganese dioxide neutralized verdigris, Cobaltous diacetate and cobalt carries out selective oxidation, and the highest yield can reach 60%.More than studies show that, by adding catalyzer such as noble metal, metal acetate salt, Silver Nitrate, can fast reaction speed, shorten the reaction times, improve the yield in the unit time, but product all contains a certain amount of metallic impurity, and quality can not reach the requirement in American-European market, so be not suitable for carrying out Industry Promotion.
On the other hand, do not use any catalyzer, crotonic aldehyde is direct oxidation into 2-butylene acid, but the catalyzed reaction time is long, product quality is not high; For example hochst is with pure oxygen oxidation crotonic aldehyde, and temperature of reaction 30-35 ℃, oxidation obtained the 2-butylene acid of yield 55% in three days; Afterwards, the oxidation in the air under 3～5 normal atmosphere once of German huils factory obtained the 2-butylene acid of burgundy, yield 75%, and this method long reaction time, colourity is not good, and energy consumption is bigger, and yield is lower, and being difficult to carry out industrialization must promote; U.S. Eastman Kodak Company utilizes certain density oxygen-containing gas, and pressure is that 0.34～0.68Mpa adds the thinner oxidation down, can make the 2-butylene acid of white, and content is more than 98%, and yield can reach 85%～91%.
Sum up above method, use catalyzer to carry out the oxidizing reaction of crotonaldehyde, need to consume metal oxide containing precious metals, or use very unsafe superoxide, exist drawbacks such as production cost height, severe reaction conditions, aftertreatment technology complexity, yield be low, the former capital is unsuitable for industrialization production; And the reaction of the non-catalytic oxidation of crotonaldehyde, though cost is low, its reaction time is longer, and yield is lower, and energy consumption is big, and product quality is lower, also is difficult to carry out the popularization of industrialization.
For this reason, people are seeking a kind of ideal technical solution always.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, the production method of the 2-butylene acid that a kind of speed of response is fast, product yield is high, energy consumption is little, the products obtained therefrom quality is high is provided.
The technical solution adopted in the present invention is as follows: a kind of production method of 2-butylene acid, and this production method may further comprise the steps:
Step 1, according to crotonic aldehyde: normal hexane: feed liquid is closed in the part by weight compounding of water=1: 1: 0.05～0.08, squirt pump is installed on oxidizing reactor, in oxidizing reactor, spray into mixed liquor with squirt pump, aerating oxygen again, reaction pressure in keeping oxidizing reactor is that 0.1～0.6MPa, temperature are to carry out oxidizing reaction under 25 ℃～35 ℃ the condition, obtains oxidation liquid;
Step 2, described oxidation liquid is distilled, unreacted crotonic aldehyde underpressure distillation is reclaimed, with unreacted normal hexane normal pressure down distillation reclaim, obtain filtrate at last;
Step 3, described filtrate is cooled to-5 ℃～5 ℃, separates out crystallization,, can obtain the 2-butylene acid product gained crystallization filtration, drying.
Based on above-mentioned, in step 3, in described 2-butylene acid product, add entry, to add water weight be 2～2.5 times of described 2-butylene acid product weight, then, be heated to 55 ℃～65 ℃ and kept 12～18 minutes, be cooled to-5 ℃～5 ℃ again, carry out recrystallize, again the gained crystallization is filtered, dried, promptly get 2-butylene acid finished product.
Based on above-mentioned, in step 1, when the reaction pressure in the oxidizing reactor descended and be progressively constant, supplemental oxygen in oxidizing reactor remained under 18%～24% the state oxygen content gas in the oxidizing reactor and carries out oxidizing reaction.
Based on above-mentioned, interchanger and external heat exchanger on oxidizing reactor, installing.
The relative prior art of the present invention has outstanding substantive distinguishing features and marked improvement, and specifically, the present invention has the following advantages:
1, this method is utilized squirt pump high-velocity jet feed liquid to form vacuum and is sucked air rapidly, make the air that is inhaled into and react feed liquid and mix fully, has promoted mixing and increasing reaction pressure of gas and liquid, has improved transformation efficiency;
2, carry out owing to being reflected in the enclosed system, discharging has not realized cleaner production, has solved environmental pollution problems, and the cost of product also significantly reduces;
3, in oxidizing reactor, increase in interchanger and external heat exchanger, increase heat interchanging area, make the heat of reaction process generation in time be transferred out of reaction system; Because the heat that reaction process produces in time is transferred, make reaction pressure descend, oxygen can continually feed, guaranteed the abundance of amount of oxygen, reached and shortened the purpose in reaction times, and can reach the ideal yield, obviously reduced the generation of polymkeric substance, the 2-butylene acid content is improved, and quality is guaranteed;
4, this method adopts underpressure distillation to reclaim crotonic aldehyde, has shortened distillation time, has reduced steam and electric quantity consumption;
5, this method shortens oxidation time greatly, has saved the energy, and industrial scale improves greatly, and cost reduces greatly, and production technology and safety technique have all reached industrialized requirement;
6, the quality product of this method production obviously improves, and product quality reaches American-European customer requirement, has increased the international competitiveness of enterprise;
7, this method production process does not pollute environment, has embodied the environmental protection concept of Green Chemistry.
Embodiment
Below by embodiment, technical scheme of the present invention is described in further detail.
Embodiment 1
A kind of production method of 2-butylene acid, this production method may further comprise the steps:
Step 1, crotonic aldehyde 150kg, normal hexane 150kg, water 10kg are made into mixed liquor, squirt pump, interior interchanger and external heat exchanger are installed on the 1000L oxidizing reactor, in oxidizing reactor, spray into mixed liquor with squirt pump, aerating oxygen again, reaction pressure in keeping oxidizing reactor is that 0.1MPa, temperature are to carry out oxidizing reaction under 29 ℃～32 ℃ the condition, obtains oxidation liquid;
Step 2, described oxidation liquid is distilled, unreacted crotonic aldehyde underpressure distillation is reclaimed, with unreacted normal hexane normal pressure down distillation reclaim, obtain filtrate at last;
Step 3, described filtrate is cooled to-5 ℃～5 ℃, separates out crystallization,, can obtain the 2-butylene acid product gained crystallization filtration, drying;
Step 4, in described 2-butylene acid product, add entry, to add water weight be 2 times of described 2-butylene acid product weight, then, be heated to 58 ℃～62 ℃ and kept 15 minutes, be cooled to-5 ℃～5 ℃ again, carry out recrystallize, again the gained crystallization is filtered, dried, promptly get 2-butylene acid finished product.
Based on above-mentioned, in step 1, when the reaction pressure in the oxidizing reactor descended and be progressively constant, supplemental oxygen in oxidizing reactor remained under 20%～21% the state oxygen content gas in the oxidizing reactor and carries out oxidizing reaction.
Embodiment 2
A kind of production method of 2-butylene acid, this production method may further comprise the steps:
Step 1, crotonic aldehyde 75kg, normal hexane 75kg, water 4.5kg are made into mixed liquor, squirt pump, interior interchanger and external heat exchanger are installed on the 500L oxidizing reactor, in oxidizing reactor, spray into mixed liquor rapidly with squirt pump, aerating oxygen again, reaction pressure in keeping oxidizing reactor is that 0.12MPa, temperature are to carry out oxidizing reaction under 28 ℃～30 ℃ the condition, obtains oxidation liquid;
Step 2, described oxidation liquid is distilled, unreacted crotonic aldehyde underpressure distillation is reclaimed, with unreacted normal hexane normal pressure down distillation reclaim, obtain filtrate at last;
Step 3, described filtrate is cooled to-5 ℃～5 ℃, separates out crystallization,, can obtain the 2-butylene acid product gained crystallization filtration, drying;
Step 4, in described 2-butylene acid product, add entry, to add water weight be 2 times of described 2-butylene acid product weight, then, be heated to 60 ℃～62 ℃ and kept 16 minutes, be cooled to-5 ℃～5 ℃ again, carry out recrystallize, again the gained crystallization is filtered, dried, promptly get 2-butylene acid finished product.
Based on above-mentioned, in step 1, when the reaction pressure in the oxidizing reactor descended and be progressively constant, supplemental oxygen in oxidizing reactor remained under 18%～21% the state oxygen content gas in the oxidizing reactor and carries out oxidizing reaction.
Embodiment 3
A kind of production method of 2-butylene acid, this production method may further comprise the steps:
Step 1, crotonic aldehyde 15kg, normal hexane 15kg, water 1.1kg are made into mixed liquor, squirt pump, interior interchanger and external heat exchanger are installed on the 100L oxidizing reactor, in oxidizing reactor, spray into mixed liquor with squirt pump, aerating oxygen again, reaction pressure in keeping oxidizing reactor is that 0.15MPa, temperature are to carry out oxidizing reaction under 30 ℃～33 ℃ the condition, obtains oxidation liquid;
Step 2, described oxidation liquid is distilled, unreacted crotonic aldehyde underpressure distillation is reclaimed, with unreacted normal hexane normal pressure down distillation reclaim, obtain filtrate at last;
Step 3, described filtrate is cooled to-5 ℃～5 ℃, separates out crystallization,, can obtain the 2-butylene acid product gained crystallization filtration, drying;
Step 4, in described 2-butylene acid product, add entry, to add water weight be 2 times of described 2-butylene acid product weight, then, be heated to 56 ℃～60 ℃ and kept 14 minutes, be cooled to-5 ℃～5 ℃ again, carry out recrystallize, again the gained crystallization is filtered, dried, promptly get 2-butylene acid finished product.
Based on above-mentioned, in step 1, when the reaction pressure in the oxidizing reactor descended and be progressively constant, supplemental oxygen in oxidizing reactor remained under 22%～24% the state oxygen content gas in the oxidizing reactor and carries out oxidizing reaction.
The quality of above embodiment gained finished product has all reached standard:
Outward appearance: white granular;
Moisture :≤0.6%;
Content: 〉=99%;
Content of isomer :≤0.3%;
Fusing point: 70～73 ℃;
Colourity :≤No. 10 standard color solutions.
Should be noted that at last: above embodiment is only in order to illustrate that technical scheme of the present invention is not intended to limit; Although with reference to preferred embodiment the present invention is had been described in detail, those of ordinary skill in the field are to be understood that: still can make amendment or the part technical characterictic is equal to replacement the specific embodiment of the present invention; And not breaking away from the spirit of technical solution of the present invention, it all should be encompassed in the middle of the technical scheme scope that the present invention asks for protection.
Claims (5)
1. the production method of a 2-butylene acid, it is characterized in that: this production method may further comprise the steps:
Step 1, according to crotonic aldehyde: normal hexane: feed liquid is closed in the part by weight compounding of water=1: 1: 0.05～0.08, squirt pump is installed on oxidizing reactor, in oxidizing reactor, spray into mixed liquor with squirt pump, aerating oxygen again, reaction pressure in keeping oxidizing reactor is that 0.1～0.6MPa, temperature are to carry out oxidizing reaction under 25 ℃～35 ℃ the condition, obtains oxidation liquid;
Step 2, described oxidation liquid is distilled, unreacted crotonic aldehyde underpressure distillation is reclaimed, with unreacted normal hexane normal pressure down distillation reclaim, obtain filtrate at last;
Step 3, described filtrate is cooled to-5 ℃～5 ℃, separates out crystallization,, can obtain the 2-butylene acid product gained crystallization filtration, drying.
2. the production method of 2-butylene acid according to claim 1, it is characterized in that: in step 3, in described 2-butylene acid product, add entry, to add water weight be 2～2.5 times of described 2-butylene acid product weight, then, be heated to 55 ℃～65 ℃ and kept 12～18 minutes, be cooled to-5 ℃～5 ℃ again, carry out recrystallize, again the gained crystallization is filtered, dried, promptly get 2-butylene acid finished product.
3. the production method of 2-butylene acid according to claim 1 and 2, it is characterized in that: in step 1, when the reaction pressure in the oxidizing reactor descends and is progressively constant, supplemental oxygen in oxidizing reactor remains under 18%～24% the state oxygen content gas in the oxidizing reactor and carries out oxidizing reaction.
4. the production method of 2-butylene acid according to claim 1 and 2 is characterized in that: interchanger and external heat exchanger in installing on oxidizing reactor.
5. the production method of 2-butylene acid according to claim 3 is characterized in that: interchanger and external heat exchanger in installing on oxidizing reactor.
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|---|---|---|---|
| CN 201010287735 CN101979371B (en) | 2010-09-20 | 2010-09-20 | Method for producing 2-butenoic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111116348A (en) * | 2019-12-27 | 2020-05-08 | 浙江工业大学 | Preparation method for synthesizing carboxylic acid by oxidizing aldehyde with bimetallic catalyst |
| CN114315557A (en) * | 2022-02-11 | 2022-04-12 | 北京弗莱明科技有限公司 | Production method of trans-butene-2-acid with high yield |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396148A (en) * | 2002-08-30 | 2003-02-12 | 天津市捷鑫化学工业有限公司 | Process for preparing 2-butenoic acid industrially by oxygen oxidizing method |
-
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- 2010-09-20 CN CN 201010287735 patent/CN101979371B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396148A (en) * | 2002-08-30 | 2003-02-12 | 天津市捷鑫化学工业有限公司 | Process for preparing 2-butenoic acid industrially by oxygen oxidizing method |
Non-Patent Citations (1)
| Title |
|---|
| 谢雪珍等: "巴豆醛氧化合成巴豆酸的研究进展", 《化工技术与开发》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111116348A (en) * | 2019-12-27 | 2020-05-08 | 浙江工业大学 | Preparation method for synthesizing carboxylic acid by oxidizing aldehyde with bimetallic catalyst |
| CN111116348B (en) * | 2019-12-27 | 2023-02-03 | 浙江工业大学 | Preparation method for synthesizing carboxylic acid by oxidizing aldehyde with bimetallic catalyst |
| CN114315557A (en) * | 2022-02-11 | 2022-04-12 | 北京弗莱明科技有限公司 | Production method of trans-butene-2-acid with high yield |
| CN114315557B (en) * | 2022-02-11 | 2022-06-10 | 北京弗莱明科技有限公司 | Production method of trans-2-butenoic acid with high yield |
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| CN101979371B (en) | 2013-10-23 |
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