US20160115114A1 - Device and process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material - Google Patents

Device and process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material Download PDF

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Publication number
US20160115114A1
US20160115114A1 US14/922,775 US201514922775A US2016115114A1 US 20160115114 A1 US20160115114 A1 US 20160115114A1 US 201514922775 A US201514922775 A US 201514922775A US 2016115114 A1 US2016115114 A1 US 2016115114A1
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microwave
catalytic reactor
methyl
raw material
ricinoleate
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Inventor
Yong Nie
Ying Duan
Ruchao GONG
Shangzhi YU
Meizhen LU
Jianbing Ji
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Zhejiang University of Technology ZJUT
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Zhejiang University of Technology ZJUT
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Assigned to ZHEJIANG UNIVERSITY OF TECHNOLOGY reassignment ZHEJIANG UNIVERSITY OF TECHNOLOGY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DUAN, Ying, GONG, RUCHAO, JI, JIANBING, LU, MEIZHEN, NIE, Yong, YU, SHANGZHI
Publication of US20160115114A1 publication Critical patent/US20160115114A1/en
Priority to US15/687,470 priority Critical patent/US10081590B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122—Incoherent waves
    • B01J19/126—Microwaves
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • B01J8/0285—Heating or cooling the reactor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
    • B01J2208/00176—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles outside the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00433—Controlling the temperature using electromagnetic heating
    • B01J2208/00442—Microwaves
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/0053—Controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/0801—Controlling the process
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/0869—Feeding or evacuating the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/0871—Heating or cooling of the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/0873—Materials to be treated
    • B01J2219/0892—Materials to be treated involving catalytically active material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/12—Processes employing electromagnetic waves
    • B01J2219/1203—Incoherent waves
    • B01J2219/1206—Microwaves
    • B01J2219/1209—Features relating to the reactor or vessel
    • B01J2219/1212—Arrangements of the reactor or the reactors
    • B01J2219/1215—Single reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/12—Processes employing electromagnetic waves
    • B01J2219/1203—Incoherent waves
    • B01J2219/1206—Microwaves
    • B01J2219/1209—Features relating to the reactor or vessel
    • B01J2219/1221—Features relating to the reactor or vessel the reactor per se
    • B01J2219/1242—Materials of construction
    • B01J2219/1245—Parts of the reactor being microwave absorbing, dielectric
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency

Definitions

  • the present invention relates to the field of lipid chemical production technology, and particularly, to a device and a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material.
  • undecylenic acid methyl ester can be obtained from undecylenic acid.
  • Undecylenic acid has extensive applications. Particularly, after bromide and ammonolysis undecylenic acid can become aminoundecanoic acid, which can be polymerized to form tonylon-11 (PA11).
  • PA11 has several advantages: it has a low water absorption rate, is good in oil resistance, can well withstand low temperature, and is easy processing, etc. PA11 has been widely used in automotive industry, military industry, electrical and electronic devices, sports equipment, food industry, medical devices, and so on. Undecylenic acid is used in large quantities in manufacturing flavors and fragrances.
  • Musk T which is made of undecylenic acid and has strong musk fragrance, is the raw material for the remixing of the three main synthetic flavors including the daily-use flavor.
  • undecylenic acid also has a wide range of applications in medicine and surfactant.
  • the production methods of undecylenic acid mainly include direct pyrolysis of castor oil and pyrolysis of methyl ricinoleate.
  • the method of direct pyrolysis of castor oil has some shortcomings such as high boiling point, high viscosity of castor oil and high pyrolysis temperature.
  • the direct pyrolysis of castor oil in lead bath was once used in China to produce undecylenic acid, with the reaction temperature of higher than 600 degrees centigrade. Further issues with this process include serious coking and pollution, as well as low product yield. Since the 1980s, the direct catalytic cracking method has been studied; however, it still requires a temperature higher than 550 degrees centigrade and also has the issues of high cost of catalyst and low reusing rate.
  • the method for producing undecylenic acid used by the French company ATO is to crack methyl esterified castor oil under high temperature, and method has already been industrialized.
  • the technology of producing nylon-11 from undecylenic acid is monopolized by ATO.
  • it also has the issues of high cracking temperature and easy coking, and the yield is only about 30%.
  • an electric heater tower's cracking furnace was provided to directly crack castor oil at the cracking temperature of 500 ⁇ 600 degrees centigrade. It needs superheated steam of 500 ⁇ 600 degrees centigrade, and the method has issues of high energy consumption, low productivity, low yield, and high equipment requirement.
  • Microwave heating is widely used in drying because of its unique advantages: the process of microwave heating does not need direct contact to heat supply, or other intermediate conversion processes. A microwave absorbing material can be directly and quickly heated through absorption of microwave. Microwave heating can save electricity by up to 30 ⁇ 50% compared to conventional heating methods. The process of producing undecylenic acid methyl ester by pyrolysis of methyl ricinoleate under microwave heating has not been reported before.
  • This invention intends to overcome the deficiencies of the known techniques and provides a device and a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material.
  • the device and the process have advantages of low energy consumption, high product yield, and less coking.
  • castor oil can be converted into methyl ricinoleate of good fluidity and high purity.
  • methyl ricinoleate can be quickly cracked to undecylenic acid methyl ester; then, isolation and purification processes are used to obtain high-purity undecylenic acid methyl ester.
  • the device for producing undecylenic acid methyl ester using methyl ricinoleate as raw material comprises: a feed pump, a raw material pre-heater, a microwave catalytic reactor, a microwave generator, a temperature controller and an infrared sensor, a condenser, a product tank and a discharge pump.
  • the feed pump is connected with the raw material pre-heater, which is connected with the inlet of the microwave catalytic reactor.
  • the outlet of the microwave catalytic reactor is connected with the condenser, which is connected with the product tank and the discharge pump.
  • the microwave catalytic reactor mentioned above is located in the microwave generator, which is connected with the temperature controller and the infrared sensor.
  • the microwave catalytic reactor is designed with an inlet and an outlet.
  • the inlet and the outlet are arranged in the upper or side portion of the reactor.
  • the microwave catalytic reactor can be made of glass, ceramics or any other wave-transparent material that can stand high temperature.
  • a layer of microwave absorbing material is arranged inside the microwave catalytic reactor.
  • the microwave absorbing material may be silicon carbide, activated carbon, Fe/Co/Ni loaded alumina or zeolites, etc.
  • the microwave catalytic reactor is arranged inside the microwave generator, and the microwave generator is connected with a feed inlet, a product outlet and a temperature measurement port.
  • the feed inlet, product outlet and temperature measurement port are arranged on the top or the side of the microwave generator.
  • the microwave generator is connected with the temperature controller, the infrared sensor and a paperless recorder.
  • the present invention also provides a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material, with specific steps as follows:
  • the temperature of the cracking reaction is between 400 and 600 degrees centigrade.
  • the pyrolysis system is under atmospheric pressure or negative pressure. This may be achieved by venting the product tank or connecting it to a vacuum.
  • the beneficial effects of the present invention are as follows: 1.
  • the process of microwave heating does not need direct contact to heat supply and other intermediate conversion process; microwave absorbing material can be directly and quickly heated through absorption of microwave; microwave heating can save electricity by up to 30 ⁇ 50% compared to conventional heating methods.
  • the present invention uses microwave generating device and microwave absorbing catalytic material, leading to a uniform heating process which can reduce energy consumption and carbon deposition. 2.
  • the present invention eliminates lead pollution, shortens reaction time, improves reaction efficiency, and increases product yield.
  • FIG. 1 shows a diagram showing a device and a process according to the present invention.
  • FIG. 2 presents a gas chromatography-mass spectrometer (GC-MS) total ion chromatogram of raw material and products in microwave-assisted cracking of methyl ricinoleate at high temperature.
  • GC-MS gas chromatography-mass spectrometer
  • the device for producing undecylenic acid methyl ester using methyl ricinoleate as raw material comprises, among other parts, a feed pump ( 1 - 1 ), a raw material pre-heater ( 2 ), a microwave catalysis reactor ( 3 ), a microwave generator ( 6 - 1 ), a temperature controller ( 6 - 2 ) and an infrared sensor ( 6 - 3 ), a condenser ( 4 ), a product tank ( 5 ) and a discharge pump ( 1 - 2 ).
  • the feed pump ( 1 - 1 ) is connected with the material pre-heater ( 2 ), which is connected to the inlet of the microwave catalytic reactor ( 3 ).
  • the outlet of the microwave catalytic reactor ( 3 ) is connected with the condenser ( 4 ), which is connected to the upper port of the product tank ( 5 ).
  • the lower port of the product tank ( 5 ) is then connected to the discharge pump ( 1 - 2 ).
  • the microwave catalytic reactor ( 3 ) is placed in the microwave generator ( 6 - 1 ), which is connected with the temperature controller ( 6 - 2 ) and infrared sensor ( 6 - 3 ), and also a paperless recorder if necessary.
  • the microwave catalytic reactor ( 3 ) mentioned above has an inlet and an outlet, which are located on the top or the side of the microwave catalytic reactor ( 3 ).
  • the microwave catalytic reactor ( 3 ) can be made of glass, ceramics or other wave-transparent material that can withstand high temperature.
  • Inside the microwave catalytic reactor ( 3 ) is a layer of microwave absorbing material, which can be silicon carbide, activated carbon, Fe/Co/Ni loaded alumina or zeolites.
  • the microwave catalytic reactor ( 3 ) is arranged inside the microwave generator ( 6 - 1 ), and the microwave generator ( 6 - 1 ) is connected with a feed inlet, a product outlet and a temperature measurement port. The feed inlet, the product outlet and the temperature measurement port are arranged on the top or the side of the microwave generator ( 6 - 1 ).
  • a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material comprises the specific steps as follows:
  • the crude methyl ester is then distilled at the reduced pressure of 100 PaA and reflux ratio of 5, during which temperature at the bottom of the distillation device is controlled at 190 ⁇ 210 degrees centigrade and the temperature at the top of the distillation device is controlled at about 170 degrees centigrade.
  • the purity of the methylricinoleate obtained is higher than 99%, and the methylricinoleate obtained is used as the feedstock, or the raw material, for the subsequent microwave pyrolysis.
  • Silicon carbide is input to the microwave catalytic reactor ( 3 ), and the temperature of the microwave generator ( 6 - 1 ) is set at 500 degrees centigrade.
  • the feed tube N is connected to the import port E of the microwave catalytic reactor ( 3 ) and the outlet tube O is connected to the export port F of the microwave catalytic reactor ( 3 ).
  • the export F is then connected with the condenser ( 4 ), on which the ports J and I are the import and export of freezing water, respectively.
  • the microwave generator ( 6 - 1 ) is turned on to make the microwave absorbing material in the microwave catalytic reactor ( 3 ) reach the set temperature and stabilize for a period of time.
  • the methyl undecene and heptaldehyde gases are condensed in the condense to form a liquid, which flows out of the condenser through port H and enters the product tank through port K.
  • Port L of the product tank can be vented or vacuumed or connected to a vacuum to provide a negative pressure for the pyrolysis system.
  • the pyrolysis system may be under atmospheric pressure or negative pressure. This may be achieved by venting the product tank or connecting it to a vacuum.
  • the liquid is pumped into a downstream distillation unit by the feed pump ( 1 - 2 ), and isolation and purification processes can be carried out on the liquid to obtain high-purity methyl undecene, and saponification and acidification processes may follow to finally obtain the undecylenic acid.
  • results of the embodiment are as follows: the liquid yield is 90.5%; the yield of the undecylenic acid is 70.2%; and selectivity of the undecylenic acid is 80.5%.
  • the yield is only 34 ⁇ 38% in the electrical heating process as reported by Chinese patent CN101289383A, and the yield in the melting lead process is only 30 ⁇ 32%.
  • the yield of undecylenic acid in the present invention can be at least doubled.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US14/922,775 2014-10-27 2015-10-26 Device and process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material Abandoned US20160115114A1 (en)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN107759627A (zh) * 2017-11-27 2018-03-06 黑龙江省科学院石油化学研究院 高纯度3‑异氰酸酯基丙基三乙氧基硅烷的合成装置及其合成方法
RU2740975C1 (ru) * 2020-05-29 2021-01-22 Андрей Андреевич Тюхтий Автоклавная микроволновая установка
CN113578247A (zh) * 2021-09-02 2021-11-02 东营益盛化工有限公司 醋酸丁酯生产用酯化反应釜

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CN106057267B (zh) * 2015-05-28 2018-11-30 官爱平 能量叠加物质改性平台及其改性方法
CN106008188B (zh) * 2016-05-30 2018-05-29 浙江工业大学 一种甘油催化脱水制备丙烯醛的新方法
CN108246210B (zh) * 2018-01-30 2023-08-08 浙江工业大学 一种高温裂解反应装置
CN111135780B (zh) * 2020-01-02 2021-09-07 中国科学院广州能源研究所 利用微波连续反应装置解聚木质素的方法
CN115477582A (zh) * 2022-09-19 2022-12-16 中国五环工程有限公司 蓖麻油酸甲酯裂解制备十一烯酸甲酯的工艺系统及方法

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US5879643A (en) * 1995-07-24 1999-03-09 Helmut Katschnig Microwave apparatus for heating, disinfecting and sterilizing materials
US20050095168A1 (en) * 2002-06-12 2005-05-05 Steris Inc. Method for vaporizing a fluid using an electromagnetically responsive heating apparatus
US20110049134A1 (en) * 2009-09-03 2011-03-03 Duncan Linden L Enhanced flash chamber

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CN101289383B (zh) * 2008-06-12 2011-06-15 山西宏远科技股份有限公司 蓖麻油裂解制十一烯酸的方法
CN103113224A (zh) * 2013-01-05 2013-05-22 六安市晖润粉末新材料有限公司 一种十一烯酸甲酯裂解制备反应装置及裂解工艺
US20150191409A1 (en) * 2014-01-07 2015-07-09 Naturally Scientific Technologies Limited Process
CN204211672U (zh) * 2014-10-27 2015-03-18 浙江工业大学 一种以蓖麻油酸甲酯为原料裂解制备十一碳烯酸甲酯的装置

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5539673A (en) * 1993-06-18 1996-07-23 Charm Sciences, Inc. Non-invasive infrared temperature sensor, system and method
US5879643A (en) * 1995-07-24 1999-03-09 Helmut Katschnig Microwave apparatus for heating, disinfecting and sterilizing materials
US20050095168A1 (en) * 2002-06-12 2005-05-05 Steris Inc. Method for vaporizing a fluid using an electromagnetically responsive heating apparatus
US20110049134A1 (en) * 2009-09-03 2011-03-03 Duncan Linden L Enhanced flash chamber

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107759627A (zh) * 2017-11-27 2018-03-06 黑龙江省科学院石油化学研究院 高纯度3‑异氰酸酯基丙基三乙氧基硅烷的合成装置及其合成方法
RU2740975C1 (ru) * 2020-05-29 2021-01-22 Андрей Андреевич Тюхтий Автоклавная микроволновая установка
CN113578247A (zh) * 2021-09-02 2021-11-02 东营益盛化工有限公司 醋酸丁酯生产用酯化反应釜

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CN104341298A (zh) 2015-02-11
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US20170355657A1 (en) 2017-12-14

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