CN108190837A - A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material - Google Patents

A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material Download PDF

Info

Publication number
CN108190837A
CN108190837A CN201711474002.4A CN201711474002A CN108190837A CN 108190837 A CN108190837 A CN 108190837A CN 201711474002 A CN201711474002 A CN 201711474002A CN 108190837 A CN108190837 A CN 108190837A
Authority
CN
China
Prior art keywords
hydrogen
hydroiodic acid
elemental iodine
catalyst
raw material
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201711474002.4A
Other languages
Chinese (zh)
Inventor
杨维冉
金平
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanchang University
Original Assignee
Nanchang University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanchang University filed Critical Nanchang University
Priority to CN201711474002.4A priority Critical patent/CN108190837A/en
Publication of CN108190837A publication Critical patent/CN108190837A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00Halogens; Halogen acids
    • C01B7/13Iodine; Hydrogen iodide
    • C01B7/135Hydrogen iodide
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/584Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)

Abstract

A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material.The present invention under mild reaction conditions, using elemental iodine as raw material, in aqueous solvent, makes elemental iodine be reduced to hydrogen iodide by excess hydrogen, hydrogen iodide is dissolved in water and obtains high concentration of hydrogen acid iodide under the catalytic action of loaded noble metal catalyst.Catalyst used in the present invention is cheap and easy to get;Reaction time is short, energy-efficient;Target product hydriodic acid concentration can reach more than 76%, and yield is more than 95wt%, and byproduct of reaction amount is seldom;Heterogeneous catalytic system, product and catalyst can be easily separated, and post processing is simple, is easy to industrialize;Catalyst is easy to reuse, and waste discharge is few, environmentally protective, has highly important application value.

Description

A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material
Technical field
The invention belongs to the field of chemical synthesis, are related to the production method of hydroiodic acid.
Background technology
Hydroiodic acid is the aqueous solution of hydrogen iodide, is a kind of strong acid with strong corrosive and strong reducing property.Hydroiodic acid is nothing Color is to the liquid of light yellow irritant stink, in air strong smoke.Hydroiodic acid, which is shown in light or is long placed in, becomes brown, energy and water With alcohol it is miscible, have reproducibility.It is mainly used for the synthesis of the fine chemicals such as methyl iodide, ammonium iodide, and organic reaction helps Agent and production medicine and disinfectant etc..Hydrogen iodide and water can form azeotropic mixture, generate the hydroiodic acid of 55-58wt%.
《Chemical reagent chemicals handbook》The preparation method of the hydroiodic acid of middle record mainly has iodine and red phosphorus hydrolysis, sulphur Change hydrogen reduction iodine, iodine is reacted with hydrogen, iodine is reacted with CO and iodine and hydrazine reaction method.
(1)Iodine and red phosphorus Hydrolyze method.Its reaction equation is:2P+3I2+6H2O=6HI+2H3PO3.Red phosphorus is in this reaction Elemental iodine, is reduced to hydrogen iodide by reducing agent, itself is oxidized to phosphorous acid.It reacts acquired solution after filtering, is distilled, Then Fractional Collections hydroiodic acid fraction.This method is in the lab using more;But this method is scarce there are some Point, such as reaction is easily exploded dangerous, and low production efficiency, it is difficult to be industrialized.
(2)Vulcanize hydrogen reduction iodine method.Displacement occurs with iodine with hydrogen sulfide to react, H2S+I2=2HI+S ↓, this method The shortcomings that be that the preparation speed of hydrogen sulfide gas is slow, technique line length, if moreover, hydrogen sulfide gas controls improper easy generation Leakage, so as to which worker be made to be poisoned, is not easy large-scale production.
(3)Hydrogen and Iod R method.Directly synthesized through platinum black or platinized asbestos catalysis with hydrogen and iodine:H2+I2=2HI, This reaction is reversible, and this method is reacted under conditions of 500 DEG C or more, severe reaction conditions, high to equipment requirement, equipment Disposable input is big, moreover, the catalyst Pt needed for it is expensive so that the cost of entire synthesis technology is higher.
(4)Iodine and CO reaction methods.Reaction equation is CO+I2+H2O=2HI+CO2↑.Simple substance is added in autoclave Iodine, rhodium carbonyl catalyst and aqueous solvent in CO atmosphere, react at 140 DEG C.The shortcomings that the method is to use carbon monoxide conduct Reducing gas.
(5)Iodine and hydrazine reaction method.Using thick iodine as raw material, hydrazine hydrate is reducing agent, and hydrogen is prepared using dynamic ion-exchange method Acid iodide.The method is complicated for operation, and cost is higher.
These prepare the method for hydroiodic acid all using water dissolution hydrogen iodide and then the post-processing approach of rectifying concentration.Due to iodine Change hydrogen azeotrope with water, so the hydroiodic acid maximum concentration obtained by rectifying is about 57wt%.
Following Chinese patent also reports some methods for efficiently preparing hydroiodic acid.
Chinese patent CN102674253A discloses one kind using sodium iodide and pure water as raw material, in the presence of solid phosphorous acid It is reacted, the method that target product hydroiodic acid is collected from organic phase.Phosphorous acid and pure water, temperature control 85 are first added in a reservoir ~95 DEG C, lower addition sodium iodide by several times is stirred, 3~4h of sustained response is filtered, and target product is obtained after rectifying.The invention obtains The hydroiodic acid purity arrived is more than 99%, more than 90% yield.But the raw materials used sodium iodide of this method is expensive, in distillation process It easily decomposed in the ortho phosphorous acid of addition, distillation process, have security risk.
Chinese patent CN103523753A discloses another method for preparing high-purity hydrogen acid iodide.The method utilizes iodine The aqueous solution of simple substance be raw material, by reduction, desulfurization, defluorinate, concentrate and etc. after prepare high-purity hydrogen acid iodide.Its product purity Up to more than 98%.The shortcomings that the method is to prepare hydroiodic acid with sodium sulfite reduction, can release sulfur dioxide and be unfavorable for environmental protection.
Chinese patent CN104085857B discloses a kind of new side that hydroiodic acid is prepared with ortho phosphorous acid sodium reduction elemental iodine Method.Elemental iodine of the method in sodium hypophosphite reductive water, obtains hydroiodic acid;Then, with sulfide precipitation excess elemental iodine; Then, refined filtration, rectifying obtain more than 99.7% purity of hydroiodic acid, and yield is more than 95%.But the method sodium hypophosphite It is of high cost as reducing agent, it is difficult to recycle.
Invention content
The purpose of the present invention is to propose to a kind of methods that hydroiodic acid is produced using elemental iodine and hydrogen as raw material.
The present invention is achieved by the following technical solutions.
A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material of the present invention, as follows:
Elemental iodine and noble metal catalyst are pressed into I2:Metallic catalyst(M)=10 ~ 6000 molar ratios are added to high temperature high pressure reverse It answers in kettle, then by I2 :The mass ratio of water=0 ~ 4 adds in water, seals reaction kettle, and charged pressure is the hydrogen of 100 ~ 600 psi or contains The gaseous mixture of hydrogen rises to 40 ~ 200 DEG C of temperature under stirring, be chilled to room temperature after reacting 1 ~ 25 h, collected under the conditions of ice-water bath anti- Liquid and refined filtration are answered, hydroiodic acid is obtained, is washed with water and washs, 140oC is dried, and recycles catalyst.
To obtain high concentration(More than 76wt%)Hydroiodic acid, the present invention can be as follows:
Elemental iodine and noble metal catalyst are pressed into I2:Metallic catalyst(M)=10 ~ 6000 molar ratios are added to high temperature high pressure reverse It answers in kettle, then by I2 :The mass ratio of hydroiodic acid=0 ~ 1.15 adds in hydroiodic acid(57wt%), seal reaction kettle, charged pressure 100 The hydrogen of ~ 600 psi or the gaseous mixture of hydrogen rise to 40 ~ 200 DEG C of temperature under stirring, room temperature is chilled to after reacting 1 ~ 25 h, Reaction solution and refined filtration are collected under the conditions of ice-water bath, the hydroiodic acid of a concentration of more than 76wt% can be obtained, be washed with water and wash, 140oUnder C It is dry, recycle catalyst.
The metallic catalyst can be to be supported on activated carbon, zirconium dioxide, titanium dioxide, silica or molecular sieve etc. The rhodium of different loads amount on carrier(Rh), platinum(Pt), palladium(Pd), ruthenium(Ru)Or iridium(Ir)Wait noble metal catalysts.
The elemental iodine and the dosage of metal are preferably I2:M=100 ~ 600 (molar ratio).
The reaction temperature is preferably 90 ~ 110 DEG C.
The present invention provides a kind of methods that hydroiodic acid is produced using elemental iodine and hydrogen as raw material very efficiently, green. This method reaction condition is mild, and activity is high, and catalyst recovery yield is high;Amount of by-products is seldom, and target product concentration can reach 76wt%, yield can reach 95%;Heterogeneous catalytic system, product and catalyst can be easily separated, and post processing is simple, is easy to industrialize; Catalyst stability is good, is easy to reuse, and waste discharge is few, environmentally protective, has highly important application value.
Specific embodiment
Below by specific embodiment, the present invention will be described, but the present invention is not limited thereto.
Experimental method described in following embodiments is conventional method unless otherwise specified;The reagent and material, such as Without specified otherwise, commercially obtain.
Embodiment 1.
3 g elemental iodines, 0.03 g Rh/C are sequentially added in 10 mL high-temperature high-pressure reaction kettles(5%), 2mL water, sealing Reaction kettle is filled with excess hydrogen(400 psi), it stirs and quickly heats up to 100 DEG C, 10 h of holding.Reaction kettle ice-water bath is cold But it to room temperature, collects and with filter membrane refined filtration reaction solution, obtains the hydroiodic acid of a concentration of 56.5wt%, yield 95.0%, elemental iodine Content 0.07wt%, conversion ratio 99.9%.
Elemental iodine content, the detection of hydriodic acid concentration and hydrogen iodide yield and calculation basis following methods carry out.
The content of elemental iodine is titrated with sodium thiosulfate, and by the use of starch solution as indicator.Concentration of hydrogen iodide silver consuming amount Method titrates.
The calculation of yield of hydrogen iodide:
The output mole of yield=HI of HI/(2×I2The mole of input)
Embodiment 2.
3 g elemental iodines, 2 mL, 57% hydroiodic acids, 0.03 g 5% are sequentially added in 10 mL high-temperature high-pressure reaction kettles Rh/C seals reaction kettle, is filled with excess hydrogen(400 psi), it stirs and quickly heats up to 100 DEG C, 20 h of holding.By reaction kettle Ice-water bath is cooled to room temperature, and is collected and with filter membrane refined filtration reaction solution under low temperature, is obtained the hydroiodic acid of a concentration of 73.3wt%, yield It is 95.0%, elemental iodine content 0.05wt%, conversion ratio 99.9%.
Embodiment 3.
4 g elemental iodines, 2 mL, 57% hydroiodic acids, 0.05 g Rh/C are sequentially added in 10 mL high-temperature high-pressure reaction kettles (5%), reaction kettle is sealed, is filled with excess hydrogen(400 psi), it stirs and quickly heats up to 140 DEG C, 5 h of holding.By reaction kettle Ice-water bath is cooled to room temperature, and is collected and with filter membrane refined filtration reaction solution under low temperature, is obtained the hydroiodic acid of a concentration of 76.3wt%, yield It is 95.1%, elemental iodine content 0.03wt%, conversion ratio 99.9%.
Embodiment 4.
4 g elemental iodines, 2 mL, 57% hydroiodic acids, 0.03 g Pt/ are sequentially added in 10 mL high-temperature high-pressure reaction kettles SiO2(5%), reaction kettle is sealed, is filled with excess hydrogen(400 psi), it stirs and quickly heats up to 100 DEG C, 20 h of holding.It will be anti- Kettle ice-water bath is answered to be cooled to room temperature, is collected and with filter membrane refined filtration reaction solution under low temperature, obtains the hydroiodic acid of a concentration of 76.0wt%, Yield is 94.5.0%, elemental iodine content 0.05wt%, conversion ratio 99.9%.
Embodiment 5.
4 g elemental iodines, 2 mL, 57% hydroiodic acids, 0.05 g Pd/C are sequentially added in 10 mL high-temperature high-pressure reaction kettles (10%), reaction kettle is sealed, is filled with excess hydrogen(400 psi), it stirs and quickly heats up to 100 DEG C, 24 h of holding.It will reaction Kettle ice-water bath is cooled to room temperature, under low temperature collect and use filter membrane refined filtration reaction solution, obtain the hydroiodic acid of a concentration of 76.4wt%, production Rate is 95.3%, elemental iodine content 0.06wt%, conversion ratio 99.9%.
Embodiment 6.
4 g elemental iodines, 2 mL, 57% hydroiodic acids, 0.03 g Rh/C are sequentially added in 10 mL high-temperature high-pressure reaction kettles (5%), reaction kettle is sealed, is filled with excess hydrogen(100 psi), it stirs and quickly heats up to 100 DEG C, 24 h of holding.By reaction kettle Ice-water bath is cooled to room temperature, and is collected and with filter membrane refined filtration reaction solution under low temperature, is obtained the hydroiodic acid of a concentration of 76.5wt%, yield It is 95.4%, elemental iodine content 0.06wt%, conversion ratio 99.9%.

Claims (4)

1. a kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material, it is characterized in that as follows:
Elemental iodine and noble metal catalyst are pressed into I2:The molar ratio of metallic catalyst=10 ~ 6000 is added to high-temperature high-pressure reaction kettle In, then by I2 :The mass ratio of water=0 ~ 4 adds in water, seals reaction kettle, and charged pressure is the hydrogen or hydrogen of 100 ~ 600 psi Gaseous mixture, rise to 40 ~ 200 DEG C of temperature under stirring, be chilled to room temperature after reacting 1 ~ 25 h, reaction solution is collected under the conditions of ice-water bath And refined filtration, hydroiodic acid is obtained, is washed with water and washs, metallic catalyst is recycled in 140 DEG C of dryings;
The metallic catalyst is to be supported on activated carbon, zirconium dioxide, titanium dioxide, silica or molecular sieve carrier Rhodium, platinum, palladium, ruthenium or the iraurite metal catalyst of different loads amount.
2. a kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material, it is characterized in that as follows:
Elemental iodine and noble metal catalyst are pressed into I2:The molar ratio of metallic catalyst=10 ~ 6000 is added to high-temperature high-pressure reaction kettle In, then by I2 :The mass ratio of hydroiodic acid=0 ~ 1.15 adds in hydroiodic acid, seals reaction kettle, and charged pressure is 100 ~ 600 psi's The gaseous mixture of hydrogen or hydrogen rises to 40 ~ 200 DEG C of temperature under stirring, room temperature, ice-water bath condition are chilled to after reacting 1 ~ 25 h Lower collection reaction solution and refined filtration, obtain the hydroiodic acid of a concentration of more than 76wt%, are washed with water and wash, dry at 140 DEG C, recycling gold Metal catalyst;
The metallic catalyst is to be supported on activated carbon, zirconium dioxide, titanium dioxide, silica or molecular sieve carrier Rhodium, platinum, palladium, ruthenium or the iraurite metal catalyst of different loads amount.
3. a kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material according to claim 1 or 2, it is characterized in that The elemental iodine and the dosage of metal are I2:M=100 ~ 600 (molar ratio).
4. a kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material according to claim 1 or 2, it is characterized in that The reaction temperature is 90 ~ 110 DEG C.
CN201711474002.4A 2017-12-29 2017-12-29 A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material Pending CN108190837A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201711474002.4A CN108190837A (en) 2017-12-29 2017-12-29 A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711474002.4A CN108190837A (en) 2017-12-29 2017-12-29 A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material

Publications (1)

Publication Number Publication Date
CN108190837A true CN108190837A (en) 2018-06-22

Family

ID=62585948

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711474002.4A Pending CN108190837A (en) 2017-12-29 2017-12-29 A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material

Country Status (1)

Country Link
CN (1) CN108190837A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109824015A (en) * 2019-01-10 2019-05-31 南昌大学 A method of catalysis reduction elemental iodine prepares hydroiodic acid
CN110901083A (en) * 2019-12-23 2020-03-24 苏州和福汽车饰件有限公司 Rapid-cooling composite leather flame laminating machine and working method
WO2020247346A1 (en) * 2019-06-03 2020-12-10 Honeywell International Inc. Hydrogen iodide (hi) production by reaction of hydrogen (h2)with iodine (i2) dissolved in a solvent
CN115571858A (en) * 2022-10-19 2023-01-06 江苏东鼎化学科技有限公司 Synthetic method of hydrogen iodide

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3848065A (en) * 1972-09-29 1974-11-12 Monsanto Co Method for producing hydrogen iodide
EP0064504A1 (en) * 1980-11-21 1982-11-17 Eastman Kodak Co Preparation of substantially anhydrous iodine compounds.
CN101935021A (en) * 2010-09-17 2011-01-05 自贡市金典化工有限公司 Production method of hydrogen iodide
CN102674253A (en) * 2012-05-22 2012-09-19 太仓沪试试剂有限公司 Preparation method of hydroiodic acid
CN104085857A (en) * 2014-06-26 2014-10-08 周海军 New method for preparing high-purity hydroiodic acid

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3848065A (en) * 1972-09-29 1974-11-12 Monsanto Co Method for producing hydrogen iodide
EP0064504A1 (en) * 1980-11-21 1982-11-17 Eastman Kodak Co Preparation of substantially anhydrous iodine compounds.
CN101935021A (en) * 2010-09-17 2011-01-05 自贡市金典化工有限公司 Production method of hydrogen iodide
CN102674253A (en) * 2012-05-22 2012-09-19 太仓沪试试剂有限公司 Preparation method of hydroiodic acid
CN104085857A (en) * 2014-06-26 2014-10-08 周海军 New method for preparing high-purity hydroiodic acid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
陈群文 等: ""单质碘制备碘化氢的机理初探"", 《天然气化工》 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109824015A (en) * 2019-01-10 2019-05-31 南昌大学 A method of catalysis reduction elemental iodine prepares hydroiodic acid
CN109824015B (en) * 2019-01-10 2022-03-22 南昌大学 Method for preparing hydroiodic acid by catalytic reduction of iodine elementary substance
WO2020247346A1 (en) * 2019-06-03 2020-12-10 Honeywell International Inc. Hydrogen iodide (hi) production by reaction of hydrogen (h2)with iodine (i2) dissolved in a solvent
CN114051486A (en) * 2019-06-03 2022-02-15 霍尼韦尔国际公司 By hydrogen (H)2) With iodine (I) dissolved in a solvent2) Production of Hydrogen Iodide (HI) by the reaction of (1)
EP3976530A4 (en) * 2019-06-03 2023-07-12 Honeywell International Inc. Hydrogen iodide (hi) production by reaction of hydrogen (h2)with iodine (i2) dissolved in a solvent
CN110901083A (en) * 2019-12-23 2020-03-24 苏州和福汽车饰件有限公司 Rapid-cooling composite leather flame laminating machine and working method
CN110901083B (en) * 2019-12-23 2024-05-07 苏州和福汽车饰件有限公司 Rapid cooling composite leather flame compounding machine and working method
CN115571858A (en) * 2022-10-19 2023-01-06 江苏东鼎化学科技有限公司 Synthetic method of hydrogen iodide
CN115571858B (en) * 2022-10-19 2024-02-13 江苏东鼎化学科技有限公司 Method for synthesizing hydrogen iodide

Similar Documents

Publication Publication Date Title
CN108190837A (en) A kind of method that hydroiodic acid is produced using elemental iodine and hydrogen as raw material
CA1195314A (en) Method and catalyst for making chlorine dioxide
CN108659213A (en) A method of polyether carboxylation is prepared using micro flow field reaction technology
CN104788271A (en) Synthetic method for preparing alpha, beta-unsaturated ketone
Zheng et al. CO2 capturing and in situ conversion at mild condition: Efficient synthesis of methyl phenyl carbonate
CN109970544B (en) Device and method for preparing benzoic acid from toluene
CN106748763B (en) The method of two kettles joint phase-transfer Wittig reaction methyl benzoate
CN1149047A (en) Diethyl oxalate by gas phase CO link-coupled regeneration catalyzing circulation
CN102476984A (en) Method for preparing 1,1,1-trifluoroacetone
CN106008183A (en) Preparation methods for ephedrine or pseudoephedrine and for ephedrine or pseudoephedrine intermediate
EP3323801B1 (en) Methods of preparing cyclohexanone and derivatives
CN101591248A (en) A kind of synthetic method of methyl benzoate
CN101348236B (en) Method for recovering iodine from alkyl iodides catalyst
CN108329202B (en) Method for preparing 3-iodopropionic acid from glyceric acid
CN1133501C (en) Catalyst for catalytic carboxylation to synthesize phenylacetic acid
JP4026350B2 (en) Method for producing alkyl nitrite
CN105884602B (en) A kind of synthetic method of 4 dihydroxy benaophenonel
CN105198840A (en) Method for preparing 2,5-dihydro-2,5-dimethoxyfuran by using fixed bed method
CN104628559A (en) Ozone oxidation method used for preparing halogenated acetic acid and esters of halogenated acetic acid
CN101307016A (en) Method for synthesizing 2,6-diisopropyl-4-phenoxy phenylthiourea
RU2470005C1 (en) Method of producing hexafluoropropanol
CN104671219A (en) Sulfuric chloride separation and purification technique
CN102633619A (en) Preparation method of 6-halo-caproic acid
JP3876682B2 (en) Nitric oxide production method
CN114057565B (en) Preparation method of 3, 3-trifluoro propionic acid

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20180622