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WO2018159846A1 - PROCÉDÉ DE PRODUCTION D'ESTER D'ACIDE α,β-INSATURÉ OU α-HALOESTER - Google Patents

PROCÉDÉ DE PRODUCTION D'ESTER D'ACIDE α,β-INSATURÉ OU α-HALOESTER Download PDF

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Publication number
WO2018159846A1
WO2018159846A1 PCT/JP2018/008169 JP2018008169W WO2018159846A1 WO 2018159846 A1 WO2018159846 A1 WO 2018159846A1 JP 2018008169 W JP2018008169 W JP 2018008169W WO 2018159846 A1 WO2018159846 A1 WO 2018159846A1
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formula
compound represented
group
organic base
compound
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PCT/JP2018/008169
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English (en)
Japanese (ja)
Inventor
岡添　隆
稔 公山
貴史 川上
京子 野崎
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Ａｇｃ株式会社
国立大学法人東京大学
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Publication of WO2018159846A1 publication Critical patent/WO2018159846A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic 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 an ⁇ , ⁇ -unsaturated acid ester or an ⁇ -haloester.
  • Non-Patent Document 1 1,1,1-trichloro-2-methyl-2-propanol (TCMP) is obtained from acetone and chloroform, and then 2-methoxy-2-methylpropanoic acid is obtained from TCMP.
  • TCMP 1,1,1-trichloro-2-methyl-2-propanol
  • 2-methoxy-2-methylpropanoic acid is obtained from TCMP.
  • a method for obtaining the methyl ester and further obtaining the methyl methacrylate (MMA) by dealcoholization is disclosed.
  • the manufacturing method of MMA described in Non-Patent Document 1 is as steps A to D below.
  • Step A CH 3 C (O) CH 3 + CHCl 3 ⁇ C (CH 3 ) 2 (OH) (CCl 3 )
  • Step B C (CH 3) 2 (OH) (CCl 3) + 4KOH + CH 3 OH ⁇ C (CH 3) 2 (OCH 3) (COOK) + 3KCl + 3H 2 O
  • Step C C (CH 3) 2 (OCH 3) (COOK) + CH 3 OH ⁇ C (CH 3) 2 (OCH 3) (COOCH 3) + KOH
  • Step D C (CH 3 ) 2 (OCH 3 ) (COOCH 3 ) ⁇ CH 2 ⁇ C (CH 3 ) C (O) OCH 3 + CH 3 OH
  • Patent Document 1 discloses a method of obtaining MMA by reacting TCMP and the like in the presence of zinc chloride to obtain a reaction crude liquid and then reacting the reaction crude liquid with methanol (Example 3).
  • Patent Document 2 discloses a method of obtaining MMA by reacting TCMP with methanol in the presence of zinc oxide (Example 1).
  • Non-Patent Document 1 Since the MMA production method described in Non-Patent Document 1 is performed in a multistage reaction, it is not economical from the viewpoints of process complexity and production cost.
  • the MMA manufacturing methods described in Patent Documents 1 and 2 use TCMP manufactured in advance. Therefore, when TCMP production is included in MMA production, it can be said that MMA is substantially produced by a multi-step reaction, and therefore there is room for improvement from an economical viewpoint.
  • ⁇ , ⁇ -unsaturated acid esters are conventionally produced by a reaction that requires a multi-step process, and it has been difficult to produce a short process, preferably in one pot.
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide a production method for obtaining an ⁇ , ⁇ -unsaturated acid ester or ⁇ -haloester in a short process (preferably 1 pot).
  • a compound represented by formula (1), formula (2) and formula (3) described below in the presence of an organic base containing a nitrogen atom.
  • a compound represented by formula (4) described later ⁇ , ⁇ -unsaturated ester
  • a compound represented by formula (5) described later ⁇ -haloester
  • the present invention has been found. That is, the present inventor has found that the above problem can be solved by the following configuration. [1] A compound represented by the following formula (1), a compound represented by the following formula (2), and a compound represented by the following formula (3) are reacted in the presence of an organic base containing a nitrogen atom.
  • Formula (1) CH 3 C (O) R Formula (2) CHX 3 Formula (3)
  • CH 3 CXRC (O) OQ The symbols in the formula represent the following meanings.
  • R represents an alkyl group or aryl group having 1 to 10 carbon atoms, an alkyl group or aryl group containing a hetero atom having 1 to 10 carbon atoms, or a hydrogen atom.
  • X represents a halogen atom.
  • Q represents a monovalent organic group having 1 to 20 carbon atoms.
  • Q represents a monovalent organic group having 1 to 20 carbon atoms.
  • pK BH in acetonitrile in an organic base containing a nitrogen atom is 20 or more, the production method according to any one of [1] to [3].
  • the organic base containing a nitrogen atom is an organic base having a phosphazene structure, an organic base having a guanidine structure, an organic base having an amidine structure, or an organic base having a proazaphosphatran structure.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • a compound represented by the formula (4) described below (hereinafter also referred to as “compound 4”) and a compound represented by the formula (5) described below (hereinafter also referred to as “compound 5”) are nitrogen.
  • a compound represented by the following formula (1) (hereinafter also referred to as “compound 1”) and a compound represented by the following formula (2) (hereinafter also referred to as “compound 2”).
  • a compound represented by the following formula (3) hereinafter also referred to as “compound 3”.
  • R represents an alkyl group or aryl group having 1 to 10 carbon atoms, an alkyl group or aryl group containing a hetero atom having 1 to 10 carbon atoms, or a hydrogen atom.
  • a compound represented by the formula (1-1) is preferable.
  • Formula (1-1) CH 3 C (O) R ′ R ′ represents an alkyl group having 1 to 10 carbon atoms, an alkyl group containing a hetero atom having 1 to 10 carbon atoms, or a hydrogen atom.
  • R is preferably a methyl group, an ethyl group, a trifluoromethyl group, or a hydrogen atom.
  • Examples of compound 1 include acetone, methyl ethyl ketone, 1,1,1-trifluoroacetone, acetaldehyde, and acetophenone.
  • X is a halogen atom.
  • Examples of the compound 2 include CHCl 3 , CHBr 3 , and CHI 3 , and CHCl 3 is preferable from the viewpoint of economy.
  • Q represents a monovalent organic group having 1 to 20 carbon atoms.
  • the monovalent organic group include a monovalent hydrocarbon group or a monovalent hydrocarbon group having a hetero atom.
  • the monovalent hydrocarbon group in the above formula (3) may be linear, branched or cyclic, and may be saturated or unsaturated.
  • Examples of the linear monovalent hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, and a vinyl group.
  • Examples of the branched monovalent hydrocarbon group include isopropyl group, isobutyl group, t-butyl group and the like.
  • the cyclic monovalent hydrocarbon group include an alicyclic hydrocarbon group and an aromatic hydrocarbon group.
  • Examples of the alicyclic hydrocarbon group include a monocyclic saturated hydrocarbon group such as a cyclohexyl group, a polycyclic alicyclic hydrocarbon group such as a decacyclonaphthyl group, a bridged cyclic saturated carbon such as a norbornyl group and an adamantyl group. Spiro hydrocarbon groups such as a hydrogen group and spiro [3.4] octyl group can be mentioned.
  • Examples of the aromatic hydrocarbon group include a phenyl group, a benzyl group, a naphthyl group, and a biphenyl group.
  • the “monovalent hydrocarbon group having a hetero atom” in the above formula (3) means that —O—, —S— or —NH— is inserted between the carbon atom-carbon atom bond of the monovalent hydrocarbon group. Or a group in which the hydrogen atom in the monovalent hydrocarbon group is substituted with a substituent such as a group having a halogen atom or an oxygen atom (for example, a hydroxyl group or a carbonyl group).
  • the cyclic monovalent hydrocarbon group may be either aromatic or non-aromatic.
  • the aromatic heterocyclic group examples include pyridyl group, thiophenyl group, quinolyl group, isoquinolyl group, thiazolyl group, and benzothiazolyl group.
  • the non-aromatic heterocyclic group examples include an epoxyethyl group, a glycidyl group, an epoxycyclohexyl group, a tetrahydrofuranyl group, and a dihydrofuranyl group.
  • the linear or branched monovalent hydrocarbon is a group in which the hydrogen atom in the linear or branched monovalent hydrocarbon group is substituted with a fluorine atom.
  • a group in which two hydrogen atoms in the linear or branched monovalent hydrocarbon group are substituted with oxygen atoms to form a carbonyl group.
  • Q in the above formula (3) include linear alkyl groups having 1 to 10 carbon atoms (methyl group, ethyl group, propyl group, butyl group, etc.), cyclic groups having 6 to 10 carbon atoms.
  • Alkyl groups cyclohexyl group, norbornyl group, adamantyl group, etc.
  • alkyl groups containing an etheric oxygen atom having 2-10 carbon atoms polyoxyalkylalkyl group, glycidyl group, dihydrofuranyl group, etc.
  • 10 aromatic hydrocarbon groups phenyl group, aralkyl group (benzyl group), etc.
  • C2-C10 fluoroalkyl groups R F CH 2 —, R F CH 2 CH 2 —, etc., where R F is the number of carbon atoms.
  • Specific examples of the fluoroalkyl group having 2 to 10 carbon atoms include CF 3 CH 2 —, (CF 3 ) 2 CH—, CF 3 CF 2 CF 2 CF 2 CH 2 CH 2 —, and CF 3 CF 2 CF 2 CF. 2 CF 2 CF 2 CH 2 CH 2 —.
  • fluoroalkyl group having 2 to 10 carbon atoms containing an etheric oxygen atom examples include CF 3 OCF 2 CF 2 OCF 2 CF 2 OCF 2 CH 2 —, CF 3 CF 2 OCF 2 CF 2 OCF 2 CF 2 OCF 2 CH 2 —.
  • the present invention is carried out in the presence of an organic base containing a nitrogen atom.
  • the “organic base” in the present invention is a general term for organic compounds used as a base.
  • Organic bases containing nitrogen atoms include primary amines, secondary amines, tertiary amines, organic bases having a phosphazene structure, organic bases having a guanidine structure, organic bases having an amidine structure, and proazaphospha Examples include organic bases having a tolan structure.
  • the primary amine, secondary amine, and tertiary amine include an organic base having a phosphazene structure, an organic base having a guanidine structure, an organic base having an amidine structure, and proazaphosphatran.
  • Organic bases having a structure are not included.
  • Examples of the primary amine include ethylamine, propylamine, octylamine, cyclohexylamine, 1,5-diaminopentane, N-methylbenzylamine, 4,4′-methylenedianiline and the like.
  • Examples of the secondary amine include dimethylamine and diethylamine.
  • the “phosphazene structure” in the present invention means a structure represented by the following formula (B1) (“*” in the formula represents a bonding position with another group or atom).
  • the “guanidine structure” in the present invention means a structure represented by the following formula (B2) (“*” in the formula represents a bonding position with another group or atom).
  • the “amidine structure” in the present invention means a structure represented by the following formula (B3) (“*” in the formula represents a bonding position with another group or atom).
  • the “organic base having a proazaphosphatran structure” in the present invention is a structure represented by the following formula (B4) (“*” in the formula represents a bonding position with another group or atom). means.
  • the organic base containing a nitrogen atom is preferably an organic base having no nitrogen atom bonded to a hydrogen atom from the viewpoint of further improving the yield of compound 4 or compound 5.
  • the organic base containing a nitrogen atom is an organic base having a phosphazene structure, an organic base having a guanidine structure, or an organic substance having an amidine structure because the yield of the compound 4 is further improved among the organic bases containing a nitrogen atom.
  • a base or an organic base having a proazaphosphatran structure is preferable, and it is more preferable that these organic bases do not have a nitrogen atom bonded to a hydrogen atom.
  • PK BH in acetonitrile organic bases including the nitrogen atom is preferably 20 or more, more preferably 22 or more, more preferably 24 or more. If pK BH of organic bases containing nitrogen atom is 20 or more, the yield of compound 4 or compound 5 is further improved. Incidentally, pK BH is usually 45 or less.
  • pK BH is an index representing the degree of basicity, and the basicity is higher as pK BH is larger.
  • the pK BH of the organic base B in the solvent S is expressed as follows using the acid dissociation constant K BH of the conjugate acid HB + of the base B defined by the following formula (X) and the following formula (Y): Calculated by the formula (Z).
  • pK BH of organic bases including the nitrogen atom is a value in acetonitrile.
  • “ ⁇ ” in the following formula (Y) represents an activity coefficient.
  • the pK BH of an organic base in acetonitrile containing the nitrogen atom Table 1 of "J.Org.Chem.2005,70,1019-1028". The value shown in pKa (AN) b may be adopted.
  • the organic base containing a nitrogen atom may be used alone or in combination of two or more.
  • the organic base containing a nitrogen atom may be present in the system all at once, or may be partially introduced into the system by split charging or the like.
  • compound 4 which is an ⁇ , ⁇ -unsaturated acid ester or compound 5 which is an ⁇ -haloester is obtained as a target product.
  • both compound 4 and compound 5 may be obtained, or only one of compound 4 or compound 5 may be obtained.
  • Compound 4 is used as a raw material for a monomer such as a chemical product or a coating agent. If dehydrochlorination of compound 5 is carried out, it can be used as compound 4.
  • Formula (4) CH 2 CRC (O) OQ
  • Formula (5) CH 3 CXRC (O) OQ
  • R, X and Q are as defined above.
  • the reaction of Compound 1, Compound 2, and Compound 3 is preferably performed in the presence of an aprotic polar solvent in addition to the organic base containing the nitrogen atom.
  • an aprotic polar solvent examples include dimethylformamide, dimethylacetamide, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, dimethyl sulfoxide, tetramethylene sulfoxide, 1-methyl-2-pyrrolidone, tetrahydrofuran, dimethylurea, 1, 1,3,3-tetramethylurea, acetonitrile, diglyme and the like can be mentioned.
  • the amount of compound 1 used is preferably 1 to 10-fold mol, more preferably 1 to 7-fold mol, and even more preferably 1 to 5-fold mol based on the amount of compound 2. If the usage-amount of the compound 1 is in the said range, the production amount of the by-product produced at the time of reaction will decrease.
  • the amount of compound 3 used is preferably 1 to 10 times the mole, more preferably 1 to 5 times the mole, and still more preferably 1 to 3 times the mole of compound 2. If the usage-amount of the compound 3 is the said upper limit, the production amount of a by-product will decrease.
  • the amount of the organic base containing a nitrogen atom is preferably 2 times mol or more, more preferably 3 times mol or more with respect to the amount of compound 2 used.
  • the amount of the organic base containing a nitrogen atom is usually 5 times or less the amount of compound 2 used. If the amount of the organic base containing a nitrogen atom is 2 times or more, it is a stoichiometrically appropriate amount when the target product in the production method of the present invention is the compound (4).
  • the amount of the aprotic polar solvent used is preferably 0.01 to 100 L, more preferably 0.1 to 1 L, relative to 1 mol of Compound 2.
  • compound 4 is obtained in one pot.
  • Base represents an organic base having a nitrogen atom
  • MMA represents methyl methacrylate which is one embodiment of Compound 4.
  • the compound obtained immediately before MMA is methyl 2-chloro-2-methylpropanoate which is one embodiment of compound 5.
  • the manufacturing cost can be reduced because the process can be simplified as compared with the conventional production method in which the raw material compound is reacted stepwise.
  • dehydrochlorination of compound 5 obtained by the production method of the present invention When dehydrochlorination of compound 5 obtained by the production method of the present invention is carried out, compound 4 is obtained.
  • the dehydrochlorination of Compound 5 can be easily carried out by the methods described in, for example, US Pat. No. 2013648, US Pat. No. 2,199,774, and International Publication No. 2014/038489. Specifically, it is preferably carried out based on Step B described in paragraphs 0043 to 0053 of International Publication No. 2014/038489, a method of reacting Compound 5 with a basic compound, The method of irradiating with an ultrasonic wave, a microwave, etc. is mentioned.
  • metal hydroxides, metal oxides, metal carbonates, metal alkoxides, metal amides, and amines are preferable because they are easily available.
  • Metal hydroxides, metal oxides, metal carbonates, metals Alkoxides and amines are more preferred. Examples of the metal in these compounds include lithium, sodium, potassium, calcium, and magnesium.
  • One of the by-products in the production method of the compound 4 of the present invention is a by-product based on an organic base having a nitrogen atom.
  • a by-product based on an organic base having a nitrogen atom is specifically a hydrohalide salt (for example, hydrochloride) of an organic base having a nitrogen atom.
  • a by-product based on an organic base having a nitrogen atom can be regenerated as an organic base having a nitrogen atom by dehydrohalogenation (for example, dehydrochlorination) as shown in the following reaction mechanism.
  • the recovered hydrogen halide (for example, hydrogen chloride) can be reused as a raw material for the compound 2 of the present invention, as exemplified in the following reaction mechanism.
  • “Base” in the following reaction mechanism means an organic base having a nitrogen atom.
  • the organic base having a nitrogen atom may be used while being supported on a carrier. That is, after carrying out the production method of the compound 4 using a carrier on which an organic base having a nitrogen atom is supported, this is recovered and dehydrohalogenated (for example, dehydrochlorinated) as described above, An organic base having a nitrogen atom supported on a carrier can be regenerated and reused.
  • the carrier include fine particles such as carbon black, silica (for example, colloidal silica, fumed silica, wet silica, silicate mineral), metal oxide, and metal nitride.
  • Japanese Patent Application Laid-Open No. 08-157570 can be referred to as a method for supporting an organic base having a nitrogen atom on a carrier.
  • Examples 27 to 29 are comparative examples.
  • surface mentioned later shows a mass reference
  • MMA methacrylate
  • 2-chloro Formation of methyl -2-methylpropanoate was confirmed.
  • the reaction yields of MMA and methyl 2-chloro-2-methylpropanoate were 61 mol% and 7.8 mol% based on chloroform, respectively.
  • Example 2 to Example 29 As shown in Table 1, Table 2 and Table 3, Examples 2 to 29 were carried out in the same manner as in Example 1 except that at least one of the type of base, the type of raw materials used, the reaction solvent and the reaction conditions was changed. Carried out. The reaction yield of the product in each example is summarized in Table 1.
  • compound 4 and compound 5 are methyl methacrylate and methyl 2-chloro-2-methylpropanoate in order when the used raw material combination is S1 to S13, and when the used raw material combination is S14.
  • ethyl methacrylate and ethyl 2-chloro-2-methylpropanoate in this order, and when the raw material combination is S15, tert-butyl methacrylate and tert-butyl 2-chloro-2-methylpropanoate are in order.
  • CH 2 C (CH 3 ) C (O) OCH 2 CF 3 and CH 3 CCl (CH 3 ) C (O) OCH 2 CF 3 are used in this order.
  • Each value in the combination of raw materials used in Table 2 is the molar ratio of each raw material to 1 mol of chloroform. Moreover, "Solv.” In the used raw material combination (S11) in Table 2 means that 8 mol times or more of raw material was used with respect to 1 mol of chloroform. Reaction condition C5 in Table 3 means that the reaction was carried out at 50 ° C. for 18 hours and then at 80 ° C. for 24 hours.
  • Example 30 Acetone (75 mg, 13 mmol), t-Bu-P 1 (2.0 g, 8.4 mmol), methanol (0.13 g, 4.0 mmol), internal standard 1,4-dibromobenzene (37 mg, 0.15 mmol) Then, chloroform (0.30 g, 2.5 mmol) was slowly added to a solution containing acetonitrile (6.9 g) with stirring at 0 ° C., followed by stirring at 50 ° C. for 20 hours. Further, DBU (0.76 g, 5.0 mmol) was slowly added, and the mixture was stirred at reflux (80 ° C.) for 26 hours, and then the reaction solution obtained at 25 ° C.
  • Example 31 To a solution of methyl 2-chloro-2-methylpropanoate (2.58 g, 19 mmol), 1,4-dibromobenzene (0.117 g, 0.50 mmol) as an internal standard in acetonitrile (8.0 mL) while stirring, 1 , 8-diazabicyclo [5.4.0] undec-7-ene (DBU, 3.21 g, 21 mmol) was added slowly. The reaction mixture was reacted under reflux for 13 hours. The formation of methyl methacrylate (MMA) was confirmed by 1 H-NMR analysis, and the reaction yield was 97 mol% based on methyl 2-chloro-2-methylpropanoate.
  • DBU 8-diazabicyclo [5.4.0] undec-7-ene
  • Examples 32 to 33 As shown in Tables 4 and 5, Examples 32 to 33 were carried out in the same manner as Example 1 except that at least one of the type of base, the type of raw material used, the reaction solvent and the reaction conditions was changed.
  • the reaction yield of the product in each example is summarized in Table 4.
  • Table 4 the reaction yields of compound 4 and compound 5 which are reaction products are based on chloroform (bromoform in Example 32), and the total value is the total reaction yield of compound 4 and compound 5.
  • Each value in the used raw material combinations in Table 5 is the molar ratio of each raw material to 1 mol of chloroform (1 mol of bromoform in Example 32).
  • Reaction condition C5 in Table 4 means that the reaction was carried out at 50 ° C. for 18 hours and then at 80 ° C. for 24 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'un ester d'acide α,β-insaturé ou d'un α-haloester, le procédé pouvant produire l'ester d'acide α,β-insaturé ou α-haloester par l'utilisation de quelques étapes. Le procédé de la présente invention, qui est destiné à produire un composé représenté par la formule CH2=CRC(O)OQ, qui consiste à faire réagir un composé représenté par CH3C(O)R, CHX3, et un composé représenté par la formule QOH en présence d'une base organique contenant un atome d'azote. Dans les formules, R représente un groupe alkyle ou aryle en C1-10, un groupe alkyle ou aryle contenant un hétéroatome en C1-10, ou un atome d'hydrogène, X représente un atome d'halogène, et Q représente un groupe organique monovalent en C1-20.
PCT/JP2018/008169 2017-03-02 2018-03-02 PROCÉDÉ DE PRODUCTION D'ESTER D'ACIDE α,β-INSATURÉ OU α-HALOESTER WO2018159846A1 (fr)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
JPS5566541A (en) * 1978-11-14 1980-05-20 Nitto Chem Ind Co Ltd Conversion of nitrile into corresponding ester
JPS55100336A (en) * 1979-01-26 1980-07-31 Nitto Chem Ind Co Ltd Preparation of ester from nitrile
JPS55100337A (en) * 1979-01-26 1980-07-31 Nitto Chem Ind Co Ltd Synthesis of ester from nitrile
JP2002511444A (ja) * 1998-04-15 2002-04-16 イーストマン ケミカル カンパニー ニオブ触媒を使用するα，β−不飽和カルボン酸及びエステルの製造方法
JP2003192632A (ja) * 2001-12-26 2003-07-09 Nippon Shokubai Co Ltd 不飽和カルボン酸エステルと不飽和カルボン酸の混合物の製造方法
JP2010138127A (ja) * 2008-12-12 2010-06-24 Sumitomo Chemical Co Ltd 含硫黄官能基を有するピリジルホスフィン化合物
JP2012197232A (ja) * 2010-03-09 2012-10-18 Sumitomo Chemical Co Ltd α，β−不飽和カルボン酸エステルの製造方法
WO2016069225A1 (fr) * 2014-10-31 2016-05-06 Rohm And Haas Company Procédé d'estérification oxydative pour la fabrication de méthacrylate de méthyle

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5566541A (en) * 1978-11-14 1980-05-20 Nitto Chem Ind Co Ltd Conversion of nitrile into corresponding ester
JPS55100336A (en) * 1979-01-26 1980-07-31 Nitto Chem Ind Co Ltd Preparation of ester from nitrile
JPS55100337A (en) * 1979-01-26 1980-07-31 Nitto Chem Ind Co Ltd Synthesis of ester from nitrile
JP2002511444A (ja) * 1998-04-15 2002-04-16 イーストマン ケミカル カンパニー ニオブ触媒を使用するα，β−不飽和カルボン酸及びエステルの製造方法
JP2003192632A (ja) * 2001-12-26 2003-07-09 Nippon Shokubai Co Ltd 不飽和カルボン酸エステルと不飽和カルボン酸の混合物の製造方法
JP2010138127A (ja) * 2008-12-12 2010-06-24 Sumitomo Chemical Co Ltd 含硫黄官能基を有するピリジルホスフィン化合物
JP2012197232A (ja) * 2010-03-09 2012-10-18 Sumitomo Chemical Co Ltd α，β−不飽和カルボン酸エステルの製造方法
WO2016069225A1 (fr) * 2014-10-31 2016-05-06 Rohm And Haas Company Procédé d'estérification oxydative pour la fabrication de méthacrylate de méthyle

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Title
NAGAI, KOICHI ET AL.: "Trends and Future of Monomer-MMA Technologies", SUMITOMO CHEMICAL CO, 30 November 2004 (2004-11-30), pages 1 - 12, XP055552263 *

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