JPS6363638A - ４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法 - Google Patents
４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法Info
- Publication number
- JPS6363638A JPS6363638A JP61205770A JP20577086A JPS6363638A JP S6363638 A JPS6363638 A JP S6363638A JP 61205770 A JP61205770 A JP 61205770A JP 20577086 A JP20577086 A JP 20577086A JP S6363638 A JPS6363638 A JP S6363638A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- solvent
- methanol
- oxidation
- manganese
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 title claims description 4
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 title claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 150000002697 manganese compounds Chemical class 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000007789 gas Substances 0.000 claims abstract description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 150000002816 nickel compounds Chemical class 0.000 claims abstract description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000010408 film Substances 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 13
- LMYSNFBROWBKMB-UHFFFAOYSA-N 4-[2-(dipropylamino)ethyl]benzene-1,2-diol Chemical compound CCCN(CCC)CCC1=CC=C(O)C(O)=C1 LMYSNFBROWBKMB-UHFFFAOYSA-N 0.000 description 10
- -1 monomethyl ester Chemical class 0.000 description 7
- 230000007423 decrease Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 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
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 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
- 239000011261 inert gas Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006709 oxidative esterification reaction Methods 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61205770A JPS6363638A (ja) | 1986-09-03 | 1986-09-03 | ４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61205770A JPS6363638A (ja) | 1986-09-03 | 1986-09-03 | ４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6363638A true JPS6363638A (ja) | 1988-03-22 |
| JPH0571573B2 JPH0571573B2 (enrdf_load_stackoverflow) | 1993-10-07 |
Family
ID=16512378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61205770A Granted JPS6363638A (ja) | 1986-09-03 | 1986-09-03 | ４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6363638A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523473A (en) * | 1992-12-30 | 1996-06-04 | Nippon Shokubai Co., Ltd. | Method of producing naphthalenedicarboxylic acids and diaryldicarboxylic acids |
| WO2020067391A1 (ja) * | 2018-09-27 | 2020-04-02 | 富士フイルム株式会社 | ジカルボン酸モノエステルの製造方法 |
-
1986
- 1986-09-03 JP JP61205770A patent/JPS6363638A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523473A (en) * | 1992-12-30 | 1996-06-04 | Nippon Shokubai Co., Ltd. | Method of producing naphthalenedicarboxylic acids and diaryldicarboxylic acids |
| WO2020067391A1 (ja) * | 2018-09-27 | 2020-04-02 | 富士フイルム株式会社 | ジカルボン酸モノエステルの製造方法 |
| JPWO2020067391A1 (ja) * | 2018-09-27 | 2021-08-30 | 富士フイルム株式会社 | ジカルボン酸モノエステルの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0571573B2 (enrdf_load_stackoverflow) | 1993-10-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5321157A (en) | Process for the preparation of adipic acid and other aliphatic dibasic acids | |
| US3361806A (en) | Process for oxidizing cyclohexane to adipic acid | |
| US3234271A (en) | Adipic acid production by the two step oxidation of cyclohexane with oxygen | |
| US4950786A (en) | Method for making 2,6-naphthalene dicarboxylic acid | |
| US3431296A (en) | Process for preparation of high purity terephthalic acid | |
| JPS6363638A (ja) | ４，４’−ジフエニルジカルボン酸および／またはそのモノ，ジメチルエステルの製造方法 | |
| US4900865A (en) | Method for producing a di-(mono- or poly-)carboxyaryl ether | |
| US4346230A (en) | Process for the preparation of dimethyl terephthalate | |
| US5142097A (en) | Recovery and recycle of acetic acid in an oxidation process | |
| US6160159A (en) | Preparation of dimethyl terephthalate via the air oxidation of p-tolualdehyde | |
| US3064043A (en) | Oxidation of organic compounds | |
| JPS6168444A (ja) | ２，６−ナフタレンジカルボン酸の製造方法 | |
| JPH03130247A (ja) | 芳香族カルボン酸の製造方法 | |
| JP3027162B2 (ja) | ビフェニルカルボン酸の製造方法 | |
| US3923867A (en) | Method for producing monomethyl terephthalate | |
| JPH06172260A (ja) | ナフタレンカルボン酸の製造法 | |
| US4398037A (en) | Process for producing aromatic carboxylic acids and methyl esters thereof | |
| EP0018433B1 (en) | Process for producing aromatic carboxylic acids and methyl esters thereof | |
| KR0137665B1 (ko) | 2,6-나프탈렌 디카복실산을 제조하는 방법 | |
| GB1429471A (en) | Process for the production of phthalic acids | |
| US3649681A (en) | Method of preparing aromatic carboxylic acids | |
| JPS6284044A (ja) | パラトルイル酸および／またはテレフタル酸モノメチルの製造方法 | |
| US3036117A (en) | Preparation of esters of aromatic acids | |
| CN85103212A (zh) | 液相空气氧化制备3，3′，4，4′—二苯甲酮四羧酸 | |
| US3956362A (en) | Cooxidation process for the production of dimethyl terephthalate |