JPS6214537B2 - - Google Patents

Info

Publication number: JPS6214537B2
Authority: JP; Japan
Prior art keywords: oxidation; toluate; methyl; xylene; mpt
Prior art date: 1979-01-26
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.): Expired

Application number

JP701979A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55100341A (en

Inventor

Shinichi Takeda

Takao Fujii

Yoshifumi Takeda

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.)

Teijin Hercules Chemical Co Ltd

Original Assignee

Teijin Hercules Chemical Co Ltd

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.)

1979-01-26

Filing date

1979-01-26

Publication date

1987-04-02

1979-01-26 Application filed by Teijin Hercules Chemical Co Ltd filed Critical Teijin Hercules Chemical Co Ltd

1979-01-26 Priority to JP701979A priority Critical patent/JPS55100341A/ja

1980-07-31 Publication of JPS55100341A publication Critical patent/JPS55100341A/ja

1987-04-02 Publication of JPS6214537B2 publication Critical patent/JPS6214537B2/ja

Status Granted legal-status Critical Current

Links

238000007254 oxidation reaction Methods 0.000 claims description 55
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 49
230000003647 oxidation Effects 0.000 claims description 46
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
239000003054 catalyst Substances 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 12
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
238000005886 esterification reaction Methods 0.000 claims description 11
229910001385 heavy metal Inorganic materials 0.000 claims description 11
QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 10
229910001882 dioxygen Inorganic materials 0.000 claims description 9
229910017052 cobalt Inorganic materials 0.000 claims description 8
239000010941 cobalt Substances 0.000 claims description 8
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
239000007789 gas Substances 0.000 claims description 7
239000007791 liquid phase Substances 0.000 claims description 4
WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 description 15
238000004821 distillation Methods 0.000 description 11
239000002994 raw material Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000008569 process Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
-1 toluic acid Aromatic carboxylic acids Chemical class 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000011572 manganese Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000000047 product Substances 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
101150020570 fbpC gene Proteins 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
ZAUUZASCMSWKGX-UHFFFAOYSA-N manganese nickel Chemical compound [Mn].[Ni] ZAUUZASCMSWKGX-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP701979A 1979-01-26 1979-01-26 Preparation of dimethyl terephthalate Granted JPS55100341A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP701979A JPS55100341A (en)	1979-01-26	1979-01-26	Preparation of dimethyl terephthalate

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP701979A JPS55100341A (en)	1979-01-26	1979-01-26	Preparation of dimethyl terephthalate

Publications (2)

Publication Number	Publication Date
JPS55100341A JPS55100341A (en)	1980-07-31
JPS6214537B2 true JPS6214537B2 (de)	1987-04-02

Family

ID=11654318

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP701979A Granted JPS55100341A (en)	1979-01-26	1979-01-26	Preparation of dimethyl terephthalate

Country Status (1)

Country	Link
JP (1)	JPS55100341A (de)

1979
- 1979-01-26 JP JP701979A patent/JPS55100341A/ja active Granted

Also Published As

Publication number	Publication date
JPS55100341A (en)	1980-07-31

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US7485746B2 (en)	2009-02-03	Staged countercurrent oxidation
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DE69924523T3 (de)	2008-09-18	Verfahren zur herstellung aromatischer carbonsäuren
JP2004529197A (ja)	2004-09-24	芳香族ジカルボン酸の製造のための２段階酸化方法
DE69925316T2 (de)	2006-03-16	Ein verfahren zur herstellung von aromatischen carbonsäuren
EP1856019B1 (de)	2013-04-24	Verfahren zur herstellung aromatischer dicarbonsäuren
EP1860092B1 (de)	2012-01-11	Verfahren zur Herstellung von Naphthalindicarbonsäure
US4354037A (en)	1982-10-12	Process for preparing benzenecarboxylic acids
JPS6214537B2 (de)	1987-04-02
US6160159A (en)	2000-12-12	Preparation of dimethyl terephthalate via the air oxidation of p-tolualdehyde
US5028737A (en)	1991-07-02	Preparation of isopropylidene bis(phthalic acid)
US4131741A (en)	1978-12-26	Cobalt-catalyzed oxidation of C3 to C7 saturated aliphatic hydrocarbons to oxygenated products
US4086267A (en)	1978-04-25	Cobalt-catalyzed oxidation of C3 to C7 saturated aliphatic hydrocarbons to oxygenated products including acetic acid
JPS6050775B2 (ja)	1985-11-11	テレフタル酸の連続製法
US4398037A (en)	1983-08-09	Process for producing aromatic carboxylic acids and methyl esters thereof
EP0018433B1 (de)	1983-07-06	Verfahren zur Herstellung aromatischer Carbonsäuren und deren Methylester
CA1067095A (en)	1979-11-27	Process for producing terephthalic acid
US4754062A (en)	1988-06-28	Iron-enhanced selectivity of heavy metal-bromine catalysis in the oxidation of polyalkylaromatics
EP1501778B1 (de)	2006-03-08	Verfahren zur herstellung von carboxylsäuren
KR19980032729A (ko)	1998-07-25	디메틸 테레프탈레이트를 제조하는 위튼-헤르쿨레스 방법에서의개선된 산화 방법
WO2006096313A1 (en)	2006-09-14	Processes for producing aromatic dicarboxylic acids
WO1999018059A1 (en)	1999-04-15	Preparation of 2,6-naphthalenedicarboxylic acid
EP0443856B1 (de)	1995-04-26	Herstellung von Isopropylidenbisphthalsäure und von Isopropylidenbisphthalsäureanhydrid
JPH10182548A (ja)	1998-07-07	安息香酸の製造方法