WO2018037998A1 - メタクリル酸製造用触媒の製造方法、メタクリル酸の製造方法およびメタクリル酸エステルの製造方法 - Google Patents

メタクリル酸製造用触媒の製造方法、メタクリル酸の製造方法およびメタクリル酸エステルの製造方法 Download PDF

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Publication number
WO2018037998A1
WO2018037998A1 PCT/JP2017/029556 JP2017029556W WO2018037998A1 WO 2018037998 A1 WO2018037998 A1 WO 2018037998A1 JP 2017029556 W JP2017029556 W JP 2017029556W WO 2018037998 A1 WO2018037998 A1 WO 2018037998A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
raw material
methacrylic acid
liquid
material liquid
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.)
Ceased
Application number
PCT/JP2017/029556
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English (en)
French (fr)
Japanese (ja)
Inventor
加藤　裕樹
雄一 田川
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.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
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 Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to CN202210741113.1A priority Critical patent/CN115155630A/zh
Priority to KR1020197007450A priority patent/KR102228713B1/ko
Priority to CN201780050136.5A priority patent/CN109641202A/zh
Priority to MYPI2019000088A priority patent/MY190344A/en
Priority to JP2017545978A priority patent/JPWO2018037998A1/ja
Priority to SG11201900018RA priority patent/SG11201900018RA/en
Publication of WO2018037998A1 publication Critical patent/WO2018037998A1/ja
Priority to SA519400951A priority patent/SA519400951B1/ar
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/04—Mixing
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
    • 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
    • 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
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters

Definitions

  • the present invention relates to a method for producing a catalyst for producing methacrylic acid, a method for producing methacrylic acid, and a method for producing a methacrylic ester.
  • the present invention includes the following [1] to [18].
  • the catalyst raw material liquid A is preferably prepared by adding a raw material compound of a catalyst component to a solvent using a preparation vessel and stirring while heating.
  • the heating temperature is preferably 80 to 130 ° C, and the lower limit is more preferably 90 ° C or higher.
  • the pH of the catalyst raw material liquid A is preferably 3.0 or less, and more preferably 2.5 or less. Examples of the method of setting the pH of the catalyst raw material liquid A to 3.0 or less include a method of using molybdenum trioxide as a molybdenum raw material, or selecting a raw material compound of the catalyst component so as to contain a large amount of nitrate ions. .
  • the concentration of the raw material compound of the catalyst component in the catalyst raw material liquid A is not particularly limited, but can be, for example, 5 to 90% by mass.
  • the volume flow rate u1 of the additive liquid affects the contact speed of the two liquids when the catalyst raw material liquid A and the catalyst raw material liquid B are mixed. Therefore, it is presumed that by adding the other liquid to either one of the catalyst raw material liquid A and the catalyst raw material liquid B so as to satisfy the formula (ii), catalyst particles effective for improving the methacrylic acid yield are likely to be generated.
  • the value of u1 satisfies 0.01 ⁇ u1 ⁇ 1.0, and the lower limit is preferably 0.05 or more, and more preferably 0.1 or more.
  • the upper limit is preferably 0.5 or less, more preferably 0.4 or less, and even more preferably 0.3 or less.
  • S is not particularly limited, but is preferably 0.01m 2 ⁇ S ⁇ 3m 2, the lower limit is 0.05 m 2 or more, the upper limit is 2m 2 or less being more preferred.
  • W is not particularly limited, but 0.1 m 3 ⁇ W ⁇ 4.5 m 3 is preferable, the lower limit is 0.5 m 3 or more, and the upper limit is more preferably 3.0 m 3 or less.
  • catalyst raw material liquid B1 was 0.22 mol / min
  • catalyst raw material liquid B2 was 0.49 mol / min. Except for these, a slurry was obtained in the same manner as in Example 1.
  • the resulting slurry contained a heteropolyacid having a Keggin structure or a salt thereof.
  • a catalyst for producing methacrylic acid was prepared in the same manner as in Example 1.
  • the resulting catalyst for methacrylic acid production had a Keggin type structure.
  • elemental compositions other than oxygen of the obtained catalyst for methacrylic acid production were Mo 12 P 1.7 V 1.1 Cu 0.5 Cs 1.4 .
  • methacrylic acid was produced in the same manner as in Example 1 except that the methacrylic acid production catalyst was used. The results are shown in Table 1.
  • a catalyst for producing methacrylic acid was prepared in the same manner as in Example 1.
  • the resulting catalyst for methacrylic acid production had a Dawson type structure.
  • elemental compositions other than oxygen of the obtained catalyst for methacrylic acid production were Mo 12 P 1.7 V 1.1 Cu 0.5 Cs 1.4 .
  • methacrylic acid was produced in the same manner as in Example 1 except that the methacrylic acid production catalyst was used. The results are shown in Table 1.
  • a methacrylic acid ester can be obtained by esterifying the methacrylic acid obtained in the present Example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/JP2017/029556 2016-08-22 2017-08-17 メタクリル酸製造用触媒の製造方法、メタクリル酸の製造方法およびメタクリル酸エステルの製造方法 Ceased WO2018037998A1 (ja)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CN202210741113.1A CN115155630A (zh) 2016-08-22 2017-08-17 甲基丙烯酸制造用催化剂的制造方法、甲基丙烯酸的制造方法和甲基丙烯酸酯的制造方法
KR1020197007450A KR102228713B1 (ko) 2016-08-22 2017-08-17 메타크릴산 제조용 촉매의 제조 방법, 메타크릴산의 제조 방법 및 메타크릴산 에스터의 제조 방법
CN201780050136.5A CN109641202A (zh) 2016-08-22 2017-08-17 甲基丙烯酸制造用催化剂的制造方法、甲基丙烯酸的制造方法和甲基丙烯酸酯的制造方法
MYPI2019000088A MY190344A (en) 2016-08-22 2017-08-17 Method for producing catalyst for methacrylic acid production, method for producing methacrylic acid, and method for producing methacrylic acid ester
JP2017545978A JPWO2018037998A1 (ja) 2016-08-22 2017-08-17 メタクリル酸製造用触媒の製造方法、メタクリル酸の製造方法およびメタクリル酸エステルの製造方法
SG11201900018RA SG11201900018RA (en) 2016-08-22 2017-08-17 Method for producing catalyst for methacrylic acid production, method for producing methacrylic acid, and method for producing methacrylic acid ester
SA519400951A SA519400951B1 (ar) 2016-08-22 2019-01-23 طريقة لإنتاج محفز لإنتاج حمض ميثاكريليك

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-161888 2016-08-22
JP2016161888 2016-08-22

Publications (1)

Publication Number Publication Date
WO2018037998A1 true WO2018037998A1 (ja) 2018-03-01

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PCT/JP2017/029556 Ceased WO2018037998A1 (ja) 2016-08-22 2017-08-17 メタクリル酸製造用触媒の製造方法、メタクリル酸の製造方法およびメタクリル酸エステルの製造方法

Country Status (7)

Country Link
JP (2) JPWO2018037998A1 (enExample)
KR (1) KR102228713B1 (enExample)
CN (2) CN109641202A (enExample)
MY (1) MY190344A (enExample)
SA (1) SA519400951B1 (enExample)
SG (1) SG11201900018RA (enExample)
WO (1) WO2018037998A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220098013A (ko) 2020-01-08 2022-07-08 미쯔비시 케미컬 주식회사 메타크릴산 제조용 촉매의 제조 방법, 메타크릴산의 제조 방법 및 메타크릴산 에스터의 제조 방법, 및 메타크릴산 제조용 촉매의 제조 장치

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JP7512048B2 (ja) * 2019-10-29 2024-07-08 Ｇｏ株式会社 管理装置、車両提示方法、プログラム及び配車管理システム

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JP2007098345A (ja) * 2005-10-07 2007-04-19 Mitsubishi Rayon Co Ltd メタクリル酸製造用触媒及びその製造方法、並びにその触媒を用いたメタクリル酸の製造方法
JP2010162460A (ja) * 2009-01-14 2010-07-29 Mitsubishi Rayon Co Ltd メタクリル酸合成用触媒の製造方法
JP2014226614A (ja) * 2013-05-23 2014-12-08 住友化学株式会社 メタクリル酸製造用触媒の製造方法及びメタクリル酸の製造方法
WO2015037611A1 (ja) * 2013-09-11 2015-03-19 三菱レイヨン株式会社 メタクリル酸製造用触媒の製造方法

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JP3763245B2 (ja) * 2000-04-06 2006-04-05 住友化学株式会社 ヘテロポリ酸系触媒の再生方法およびメタクリル酸の製造方法
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WO2005039760A1 (ja) * 2003-10-27 2005-05-06 Mitsubishi Rayon Co., Ltd. メタクリル酸製造用触媒の製造方法、メタクリル酸製造用触媒、メタクリル酸の製造方法
JP2007098345A (ja) * 2005-10-07 2007-04-19 Mitsubishi Rayon Co Ltd メタクリル酸製造用触媒及びその製造方法、並びにその触媒を用いたメタクリル酸の製造方法
JP2010162460A (ja) * 2009-01-14 2010-07-29 Mitsubishi Rayon Co Ltd メタクリル酸合成用触媒の製造方法
JP2014226614A (ja) * 2013-05-23 2014-12-08 住友化学株式会社 メタクリル酸製造用触媒の製造方法及びメタクリル酸の製造方法
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220098013A (ko) 2020-01-08 2022-07-08 미쯔비시 케미컬 주식회사 메타크릴산 제조용 촉매의 제조 방법, 메타크릴산의 제조 방법 및 메타크릴산 에스터의 제조 방법, 및 메타크릴산 제조용 촉매의 제조 장치

Also Published As

Publication number Publication date
SA519400951B1 (ar) 2024-01-23
KR102228713B1 (ko) 2021-03-16
CN109641202A (zh) 2019-04-16
MY190344A (en) 2022-04-15
SG11201900018RA (en) 2019-02-27
JPWO2018037998A1 (ja) 2018-08-23
JP7003974B2 (ja) 2022-02-04
KR20190039262A (ko) 2019-04-10
JP2019195807A (ja) 2019-11-14
CN115155630A (zh) 2022-10-11

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