JP5441914B2 - テレフタル酸組成物及びその製造方法 - Google Patents
テレフタル酸組成物及びその製造方法 Download PDFInfo
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- JP5441914B2 JP5441914B2 JP2010534068A JP2010534068A JP5441914B2 JP 5441914 B2 JP5441914 B2 JP 5441914B2 JP 2010534068 A JP2010534068 A JP 2010534068A JP 2010534068 A JP2010534068 A JP 2010534068A JP 5441914 B2 JP5441914 B2 JP 5441914B2
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- Prior art keywords
- furandicarboxylate
- fdca
- solvent
- bicyclic ether
- process according
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
Description
本発明方法によって、パラキシレンのような従来のアルキル芳香族供給材料を用いることなくTAが有効に製造される。本発明者らは驚くべきことに、溶媒の存在下で2,5−フランジカルボキシレートをエチレンと反応させて二環式エーテルを製造し、次に二環式エーテルを脱水することによって、高純度のTA組成物が製造されることを発見した。実際、TAの純度は、パラキシレンの酸化からの粗生成物の水素化によって精製した従来のPTAのものと同等であり、少なくとも1種類のグリコールとの反応によって更なる精製の必要なしに繊維及びフィルムを製造するために好適なポリエステルに直接転化させるために十分なものである。
5gのFDCA(Atlantic Chemical Companyから入手できる)及び100gの蒸留脱イオン(D&D)水をオートクレーブ内で配合し、次にエチレンで加圧し、120℃に加熱した。反応時間が経過した後、ユニットを冷却及び減圧し、反応混合物(則ち、「母液」として知られている反応溶媒によって覆われている固体の混合物)を回収した。次に、この混合物を濾過によって分離して、濾過ケーキ(則ち固形分)及び母液を得た。濾過ケーキ及び母液の両方を、高圧液体クロマトグラフィー(HPLC)によって分析した。
ガス入口及び出口を取り付けた高圧反応器中に、100gのFDCA、800gのメタノール、9.41gのリン酸(85%)、及び1.26gの水を充填した。反応器を密閉し、窒素を9回充填及びフラッシュした。次に、入口及び出口を閉止し、反応混合物を撹拌し、200℃に9時間加熱した。反応器を冷却し、排気し、878.95gの全反応器内容物を回収した。固体についてガスクロマトグラフィー分析を行って、以下のガスクロマトグラフィーピーク面積割合が明らかになった:63%−DM−FDCA;21%−モノメチルFDCA;及び14.9%−未反応FDCA。存在していると見積もられる1.1%の未知物質があった。
Claims (18)
- a.溶媒の存在下で2,5−フランジカルボキシレートをエチレンと反応させて二環式エーテルを製造し;そして
b.二環式エーテルを脱水する;
ことを含むテレフタル酸の製造方法。 - 2,5−フランジカルボキシレートをバイオマスから誘導する、請求項1に記載の方法。
- 2,5−フランジカルボキシレートを、
a.バイオマスを、フルクトース、スクロース、及びこれらの混合物を含む糖類に転化し;
b.糖類を5−ヒドロキシメチルフルフラールに転化し;そして
c.5−ヒドロキシメチルフルフラールを2,5−フランジカルボキシレートに酸化する;
ことを含む工程によってバイオマスから誘導する、請求項2に記載の方法。 - 2,5−フランジカルボキシレートが2,5−フランジカルボン酸である、請求項1に記載の方法。
- 溶媒が、水、ジメチルスルホキシド、N−メチル−2−ピロリジノン、N,N−ジメチルホルムアミド、C1〜C10アルコール、C2〜C6ケトン、及びC2〜C10エステルからなる群から選択される、請求項4に記載の方法。
- 溶媒が水である、請求項5に記載の方法。
- 二環式エーテルが7−オキサビシクロ[2.2.1]ヘプト−2−エン−1,4−ジカルボン酸である、請求項4に記載の方法。
- 2,5−フランジカルボキシレートがジメチル−2,5−フランジカルボキシレートである、請求項1に記載の方法。
- 溶媒が、芳香族炭化水素、ジメチルスルホキシド、N−メチル−2−ピロリジノン、N,N−ジメチルホルムアミド、C1〜C10アルコール、C2〜C6ケトン、及びC2〜C10エステルからなる群から選択される、請求項8に記載の方法。
- 溶媒がトルエンである、請求項9に記載の方法。
- 二環式エーテルがジメチル−7−オキサビシクロ[2.2.1]ヘプト−2−エン−1,4−ジカルボキシレートである、請求項8に記載の方法。
- 2,5−フランジカルボキシレートが2,5−フランジカルボン酸とジメチル−2,5−フランジカルボキシレートとの混合物である、請求項1に記載の方法。
- 溶媒が、水、芳香族炭化水素、ジメチルスルホキシド、N−メチル−2−ピロリジノン、N,N−ジメチルホルムアミド、C1〜C10アルコール、C2〜C6ケトン、C2〜C10エステル、及びこれらの混合物からなる群から選択される、請求項12に記載の方法。
- 二環式エーテルが製造される時に二環式エーテルを脱水する、請求項1に記載の方法。
- 二環式エーテルを脱水する前に二環式エーテルを単離する、請求項1に記載の方法。
- 2,5−フランジカルボキシレートをエチレンと反応させ、二環式エーテルを100℃〜250℃の範囲の温度で脱水する、請求項1に記載の方法。
- 2,5−フランジカルボキシレートを10psig〜2000psig(68.9kPaG〜13.8MPaG)の圧力でエチレンと反応させる、請求項1に記載の方法。
- 2,5−フランジカルボキシレートを60分間〜480分間反応させる、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/940,097 | 2007-11-14 | ||
US11/940,097 US7385081B1 (en) | 2007-11-14 | 2007-11-14 | Terephthalic acid composition and process for the production thereof |
PCT/US2008/063703 WO2009064515A1 (en) | 2007-11-14 | 2008-05-15 | Terephthalic acid composition and process for the production thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011503187A JP2011503187A (ja) | 2011-01-27 |
JP5441914B2 true JP5441914B2 (ja) | 2014-03-12 |
Family
ID=39484342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010534068A Expired - Fee Related JP5441914B2 (ja) | 2007-11-14 | 2008-05-15 | テレフタル酸組成物及びその製造方法 |
Country Status (19)
Country | Link |
---|---|
US (2) | US7385081B1 (ja) |
EP (2) | EP2220021B1 (ja) |
JP (1) | JP5441914B2 (ja) |
KR (1) | KR101624362B1 (ja) |
CN (1) | CN101868441B (ja) |
AR (1) | AR071044A1 (ja) |
BR (1) | BRPI0820238A2 (ja) |
CA (1) | CA2705425C (ja) |
DK (1) | DK2220021T3 (ja) |
ES (1) | ES2393075T3 (ja) |
MX (2) | MX2010005230A (ja) |
MY (1) | MY152954A (ja) |
PH (1) | PH12010501044A1 (ja) |
PT (1) | PT2220021E (ja) |
RU (1) | RU2519254C2 (ja) |
SA (1) | SA08290341B1 (ja) |
TW (1) | TWI415834B (ja) |
WO (1) | WO2009064515A1 (ja) |
ZA (1) | ZA201003332B (ja) |
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US3265762A (en) * | 1962-10-24 | 1966-08-09 | Du Pont | Segmented linear copolyesters of 2, 5-disubstituted terephthalic acids |
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CA2705425A1 (en) | 2009-05-22 |
JP2011503187A (ja) | 2011-01-27 |
ZA201003332B (ja) | 2011-04-28 |
CN101868441A (zh) | 2010-10-20 |
KR20100096152A (ko) | 2010-09-01 |
EP2527316A1 (en) | 2012-11-28 |
CA2705425C (en) | 2015-02-03 |
BRPI0820238A2 (pt) | 2015-06-16 |
RU2010123826A (ru) | 2011-12-20 |
US7385081B1 (en) | 2008-06-10 |
RU2519254C2 (ru) | 2014-06-10 |
MX322437B (ja) | 2014-07-31 |
PH12010501044A1 (ja) | 2009-05-22 |
CN101868441B (zh) | 2015-01-07 |
KR101624362B1 (ko) | 2016-05-25 |
MX306900B (ja) | 2013-01-21 |
WO2009064515A1 (en) | 2009-05-22 |
EP2220021A1 (en) | 2010-08-25 |
ES2393075T3 (es) | 2012-12-18 |
TWI415834B (zh) | 2013-11-21 |
AR071044A1 (es) | 2010-05-26 |
US8299278B2 (en) | 2012-10-30 |
US20090124829A1 (en) | 2009-05-14 |
MX2010005230A (es) | 2010-05-27 |
EP2220021B1 (en) | 2012-08-15 |
DK2220021T3 (da) | 2012-09-10 |
SA08290341B1 (ar) | 2010-11-22 |
MY152954A (en) | 2014-12-15 |
PT2220021E (pt) | 2012-08-31 |
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