US20060089505A1 - Cyclobutanetetracarboxylate compound and preparation method thereof - Google Patents

Cyclobutanetetracarboxylate compound and preparation method thereof Download PDF

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Publication number
US20060089505A1
US20060089505A1 US11/253,798 US25379805A US2006089505A1 US 20060089505 A1 US20060089505 A1 US 20060089505A1 US 25379805 A US25379805 A US 25379805A US 2006089505 A1 US2006089505 A1 US 2006089505A1
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Prior art keywords
compound
cyclobutanetetracarboxylate
general formula
reaction
conducted
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Abandoned
Application number
US11/253,798
Inventor
Ming-Chih Lai
Chia-Wen Chang
Chi-Wi Ong
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Eternal Materials Co Ltd
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Eternal Chemical Co Ltd
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Assigned to ETERNAL CHEMICAL CO., LTD. reassignment ETERNAL CHEMICAL CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ONG, CHI-WI, CHANG, CHIA-WEN, LAI, MING-CHIH
Publication of US20060089505A1 publication Critical patent/US20060089505A1/en
Priority to US11/888,703 priority Critical patent/US7402693B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07C67/343—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 by increase in the number of carbon atoms
    • C07C67/347—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 by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Definitions

  • the present invention relates to a cyclobutanetetracarboxylate compound and a preparation method thereof.
  • Cyclobutanetetracarboxylic dianhydrides are important monomer materials for the preparation of an alignment film useful for flat panel displays.
  • Japanese Laid-open Hei 2003-192685 discloses a process for producing cyclobutanetetracarboxylic dianhydride comprising irradiating maleic anhydride to synthesize the cyclobutanetetracarboxylic dianhydride. This process, however, suffers from the shortcomings of a low yield in the production of the butane structure.
  • the inventors of the subject application developed a new synthesis route comprising synthesizing a cyclobutanetetracarboxylate, hydrolyzing the cyclobutanetetracarboxylate, and dehydrating the hydrolyzed product to obtain the corresponding cyclobutanetetracarboxylic dianhydride.
  • the new route according to the present invention achieves an improved yield of the desired compounds.
  • One of the objects of the invention is to provide a cyclobutanetetracarboxylate compound.
  • Another object of the invention is to provide a process for preparing the cyclobutanetetracarboxylate compound.
  • the invention provides a cyclobutanetetracarboxylate compound of the general formula (I): in which:
  • the monovalent organic radical is a C1-C4 alkyl, which can be straight-chained, branched, or cyclic; and more preferably, is methyl, ethyl, propyl, isopropyl, butyl, or isobutyl.
  • the invention further provides a process for preparing the cyclobutanetetracarboxylate compound of formula (I).
  • the inventive process comprises the steps of:
  • the acidic solvent used in the inventive process can also be used as a catalyst to enhance the reaction rate.
  • Suitable acidic solvent can be a mono-protonic inorganic acid, a multi-protonic inorganic acid, or an organic acid, which preferably is hydrochloric acid or sulfuric acid.
  • the esterification reaction in step (a) of the inventive process is obvious to persons skilled in the art.
  • the suitable species of the alcohol will vary with the desired product to be obtained and may include, for example, methanol, ethanol, propanol, or isopropanol.
  • the diacid compound used in the present invention is a fumaric acid.
  • the esterification reaction is conducted at a temperature ranging from 60 to 110° C. for 2 to 20 hours.
  • the energy ray used in step (b) of the inventive process refers to a light source with a wavelength of from 200 to 600 nm, preferably an ultraviolet light.
  • the irradiation time will vary with the wavelength of the energy ray and is normally in the range of from about 30 minutes to 30 hours.
  • the reaction of step (b) can be conducted in the presence of a solvent that is beneficial to the progress of the reaction. Examples of such solvent include ethyl acetate, acetone, water, or a mixture thereof.
  • the compound of formula (I) according to the present invention can be catalytically hydrolyzed in the presence of an acid or a base in a conventional manner known to persons skilled in the art to form the corresponding cyclobutanetetracarboxylic acid, which can be further dehydrated to form the corresponding cyclobutanetetracarboxylic dianhydride.
  • the dimethyl fumarate (1224 g, 8.5 mol) and water (4000 ml) were added to a 6-liter flask and irradiated by 365 nm ultraviolet lights for 7 hours.
  • the resultant solid in the flask was vacuum filtered to obtain tetramethyl cyclobutane-1,2,3,4-tetracarboxylate (1224 g, 4.25 mol).
  • cyclobutane-1,2,3,4-tetracarboxylic acid (501 g, 2.16 mol) and acetic anhydride (3000 ml) were added to a 5-liter flask and reacted at a controlled temperature of 150° C. for 24 hours. The reaction was cooled to room temperature; concentrated; and dried to obtain 1,2,3,4-cyclobutanetetracarboxylic dianhydride (573 g, 2.93 mol).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention provides a cyclobutanetetracarboxylate compound of general formula (I) and a preparation method thereof:
Figure US20060089505A1-20060427-C00001
in which R and R1 are as defined in the specification.

Description

    BACKGROUND OF THE INVENTION
  • 1. Field of the Invention
  • The present invention relates to a cyclobutanetetracarboxylate compound and a preparation method thereof.
  • 2. Description of the Prior Art
  • Cyclobutanetetracarboxylic dianhydrides are important monomer materials for the preparation of an alignment film useful for flat panel displays. Japanese Laid-open Hei 2003-192685 discloses a process for producing cyclobutanetetracarboxylic dianhydride comprising irradiating maleic anhydride to synthesize the cyclobutanetetracarboxylic dianhydride. This process, however, suffers from the shortcomings of a low yield in the production of the butane structure.
  • To overcome the above shortcomings, the inventors of the subject application developed a new synthesis route comprising synthesizing a cyclobutanetetracarboxylate, hydrolyzing the cyclobutanetetracarboxylate, and dehydrating the hydrolyzed product to obtain the corresponding cyclobutanetetracarboxylic dianhydride. The new route according to the present invention achieves an improved yield of the desired compounds.
    • SUMMARY OF THE INVENTION
  • One of the objects of the invention is to provide a cyclobutanetetracarboxylate compound.
  • Another object of the invention is to provide a process for preparing the cyclobutanetetracarboxylate compound.
    • DETAILED DESCRIPTION OF THE INVENTION
  • The invention provides a cyclobutanetetracarboxylate compound of the general formula (I):
    Figure US20060089505A1-20060427-C00002
    in which:
    • R can be the same or R is different from each other and independently represents hydrogen or a halogen or a monovalent organic radical; and R1 is a C1-C4 alkyl.
  • There are no special requirements for the species of the monovalent organic radical suitable for the present invention. Preferably, the monovalent organic radical is a C1-C4 alkyl, which can be straight-chained, branched, or cyclic; and more preferably, is methyl, ethyl, propyl, isopropyl, butyl, or isobutyl.
  • The invention further provides a process for preparing the cyclobutanetetracarboxylate compound of formula (I). The inventive process comprises the steps of:
  • (a) conducting an esterification reaction of a diacid compound of general formula (II)
    Figure US20060089505A1-20060427-C00003
    (in which R is as defined hereinbefore) with an alcohol of general formula (III)
    R1—OH  Formula (III)
    in the presence of an acidic solvent to obtain a precursor compound of general formula (IV)
    Figure US20060089505A1-20060427-C00004
  • (b) conducting a cyclization reaction by irradiating the precursor compound of general formula (IV) with an energy ray to obtain the cyclobutanetetracarboxylate compound of general formula (I).
  • The acidic solvent used in the inventive process can also be used as a catalyst to enhance the reaction rate. Suitable acidic solvent can be a mono-protonic inorganic acid, a multi-protonic inorganic acid, or an organic acid, which preferably is hydrochloric acid or sulfuric acid.
  • The esterification reaction in step (a) of the inventive process is obvious to persons skilled in the art. The suitable species of the alcohol will vary with the desired product to be obtained and may include, for example, methanol, ethanol, propanol, or isopropanol. The diacid compound used in the present invention is a fumaric acid. The esterification reaction is conducted at a temperature ranging from 60 to 110° C. for 2 to 20 hours.
  • The energy ray used in step (b) of the inventive process refers to a light source with a wavelength of from 200 to 600 nm, preferably an ultraviolet light. In general, the irradiation time will vary with the wavelength of the energy ray and is normally in the range of from about 30 minutes to 30 hours. In addition, if desired, the reaction of step (b) can be conducted in the presence of a solvent that is beneficial to the progress of the reaction. Examples of such solvent include ethyl acetate, acetone, water, or a mixture thereof.
  • The compound of formula (I) according to the present invention can be catalytically hydrolyzed in the presence of an acid or a base in a conventional manner known to persons skilled in the art to form the corresponding cyclobutanetetracarboxylic acid, which can be further dehydrated to form the corresponding cyclobutanetetracarboxylic dianhydride.
  • The present invention will be further described in the following example. However, the example will not make any limitations to the scope of the invention. Any modifications or alterations on the invention that can be easily accomplished by persons skilled in the art are encompassed in the disclosure of the specification and the accompanying claims.
    • EXAMPLE
  • Synthesis of a cyclobutanetetracarboxylic dianhydride
  • In a 5-liter flask, methanol (3000 ml, 75 mol) and then fumaric acid (1160 g, 10 mol) and concentrated sulfuric acid (10 ml, 0.2 mol) were added. The reaction was conducted at a controlled temperature of 75° C. for 10 hours and then cooled to room temperature. The resultant solid was collected by vacuum filtration and washed with methanol to obtain dimethyl fumarate (1224 g, 8.5 mol).
  • The dimethyl fumarate (1224 g, 8.5 mol) and water (4000 ml) were added to a 6-liter flask and irradiated by 365 nm ultraviolet lights for 7 hours. The resultant solid in the flask was vacuum filtered to obtain tetramethyl cyclobutane-1,2,3,4-tetracarboxylate (1224 g, 4.25 mol).
  • The resultant tetramethyl cyclobutane-1,2,3,4-tetracarboxylate (1224 g, 4.25 mol) and aqueous hydrochloric acid (3000 ml) were added to a 5-liter flask; reacted at a controlled temperature of 85° C. for 24 hours; cooled to room temperature; concentrated; and dried to obtain cyclobutane-1,2,3,4-tetracarboxylic acid (870 g, 3.75 mol).
  • The cyclobutane-1,2,3,4-tetracarboxylic acid (501 g, 2.16 mol) and acetic anhydride (3000 ml) were added to a 5-liter flask and reacted at a controlled temperature of 150° C. for 24 hours. The reaction was cooled to room temperature; concentrated; and dried to obtain 1,2,3,4-cyclobutanetetracarboxylic dianhydride (573 g, 2.93 mol).

Claims (12)

1. A cyclobutanetetracarboxylate compound of general formula (I):
Figure US20060089505A1-20060427-C00005
in which:
R can be the same or R is different from each other and independently represents hydrogen or a halogen or a monovalent organic radical;
and R1 is a C1-C4 alkyl.
2. The cyclobutanetetracarboxylate compound of claim 1, wherein said monovalent organic radical is a straight-chained, branched, or cyclic C1-C4 alkyl.
3. The cyclobutanetetracarboxylate compound of claim 1, wherein said monovalent organic radical is methyl, ethyl, propyl, isopropyl, butyl, or isobutyl.
4. A process for the preparation of the cyclobutanetetracarboxylate compound as defined in claim 1, comprising:
(a) conducting an esterification reaction of a diacid compound of general formula (II)
Figure US20060089505A1-20060427-C00006
(in which R is as defined hereinbefore) with an alcohol of general formula (III)

R1—OH  Formula (III)
in the presence of an acidic solvent to obtain a precursor compound of general formula (IV)
Figure US20060089505A1-20060427-C00007
(b) conducting a cyclization reaction by irradiating the precursor compound of general formula (IV) with an energy ray to obtain the cyclobutanetetracarboxylate compound of general formula (I).
5. The process of claim 4 wherein the alcohol of general formula (III) is methanol, ethanol, propanol, or isopropanol.
6. The process of claim 4 wherein the reaction of step (a) is conducted at a temperature from 60 to 110° C.
7. The process of claim 4 wherein the reaction of step (a) is conducted for 2 to 20 hours.
8. The process of claim 4 wherein the energy ray used in step (b) is a light source having a wavelength of from 200 to 600 nm.
9. The process of claim 4 wherein the energy ray used in step (b) is an ultraviolet light.
10. The process of claim 4 wherein the reaction of step (b) is conducted for 30 minutes to 30 hours.
11. The process of claim 4 wherein the reaction of step (b) is conducted in the presence of a solvent.
12. The process of claim 11 wherein the solvent is ethyl acetate, acetone, water, or methanol, or a mixture thereof.
US11/253,798 2004-10-20 2005-10-19 Cyclobutanetetracarboxylate compound and preparation method thereof Abandoned US20060089505A1 (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102432464A (en) * 2011-12-14 2012-05-02 费近峰 Continuous production process for dimethyl fumarate
CN104151165A (en) * 2014-08-11 2014-11-19 广东东阳光药业有限公司 Preparation method of dimethyl fumarate
EP2718257A4 (en) * 2011-06-08 2015-08-12 Biogen Ma Inc Process for preparing high purity and crystalline dimethyl fumarate
CN110590798A (en) * 2014-01-17 2019-12-20 日产化学工业株式会社 Process for producing cyclobutanetetracarboxylic acid derivative

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JP5639764B2 (en) * 2007-03-08 2014-12-10 シンク−アールエックス，リミティド Imaging and tools for use with moving organs
JP4973304B2 (en) * 2007-04-27 2012-07-11 日油株式会社 Process for producing 1,2,3,4-cyclobutanetetracarboxylic acid
DK2334378T3 (en) 2008-08-19 2014-07-07 Xenoport Inc Methyl hydrogen fumarate prodrugs, pharmaceutical compositions thereof and methods of use
US10945984B2 (en) 2012-08-22 2021-03-16 Arbor Pharmaceuticals, Llc Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects
AU2013305684B2 (en) 2012-08-22 2016-11-24 Xenoport, Inc. Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof
WO2014160633A1 (en) 2013-03-24 2014-10-02 Xenoport, Inc. Pharmaceutical compositions of dimethyl fumarate
US9302977B2 (en) 2013-06-07 2016-04-05 Xenoport, Inc. Method of making monomethyl fumarate
WO2014205392A1 (en) 2013-06-21 2014-12-24 Xenoport, Inc. Cocrystals of dimethyl fumarate
TW201516020A (en) 2013-09-06 2015-05-01 Xenoport Inc Crystalline forms of (N,N-diethylcarbamoyl)methyl methyl (2E)but-2-ene-1,4-dioate, methods of synthesis and use
JP6697178B2 (en) * 2014-01-17 2020-05-20 日産化学株式会社 Process for producing cyclobutane tetracarboxylic acid and its anhydride
US9999672B2 (en) 2014-03-24 2018-06-19 Xenoport, Inc. Pharmaceutical compositions of fumaric acid esters
WO2015170713A1 (en) * 2014-05-09 2015-11-12 日産化学工業株式会社 Novel method for producing 1,3-di-substituted-cyclobutane-1,2,3,4-tetracarboxylic acid and dianhydride of said acid
CN114516882A (en) * 2020-11-19 2022-05-20 烟台弘邦医药科技有限公司 Preparation method of cycloalkane tetracarboxylic dianhydride

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US3236801A (en) * 1963-01-30 1966-02-22 Exxon Research Engineering Co Esters of 1, 2, 3, 4-cyclobutanetetracarboxylic acid and plastic compositions comprising same
CN1103398A (en) * 1993-11-30 1995-06-07 张治明 Process for producing dimethyl fumarate with cis-butanedioic anhydride

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US3139395A (en) * 1961-01-09 1964-06-30 American Cyanamid Co Photodimerization of fumaric acid derivatives

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2718257A4 (en) * 2011-06-08 2015-08-12 Biogen Ma Inc Process for preparing high purity and crystalline dimethyl fumarate
US9422226B2 (en) 2011-06-08 2016-08-23 Biogen Ma Inc. Process for preparing high purity and crystalline dimethyl fumarate
CN102432464A (en) * 2011-12-14 2012-05-02 费近峰 Continuous production process for dimethyl fumarate
CN110590798A (en) * 2014-01-17 2019-12-20 日产化学工业株式会社 Process for producing cyclobutanetetracarboxylic acid derivative
CN104151165A (en) * 2014-08-11 2014-11-19 广东东阳光药业有限公司 Preparation method of dimethyl fumarate

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JP2006117673A (en) 2006-05-11
JP4977353B2 (en) 2012-07-18
TWI279403B (en) 2007-04-21
US7402693B2 (en) 2008-07-22
TW200613308A (en) 2006-05-01
US20080033199A1 (en) 2008-02-07

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