CA1042918A - Hydrogenation of molten aldehydic dimethyl terephthalate - Google Patents
Hydrogenation of molten aldehydic dimethyl terephthalateInfo
- Publication number
- CA1042918A CA1042918A CA216,081A CA216081A CA1042918A CA 1042918 A CA1042918 A CA 1042918A CA 216081 A CA216081 A CA 216081A CA 1042918 A CA1042918 A CA 1042918A
- Authority
- CA
- Canada
- Prior art keywords
- aldehydic
- hydrogenation
- molten
- dmt
- catalyst
- 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.)
- Expired
Links
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims abstract description 171
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- -1 aldehyde ester Chemical class 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000013529 heat transfer fluid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 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
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43031774A | 1974-01-02 | 1974-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042918A true CA1042918A (en) | 1978-11-21 |
Family
ID=23707005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,081A Expired CA1042918A (en) | 1974-01-02 | 1974-12-16 | Hydrogenation of molten aldehydic dimethyl terephthalate |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5432412A (en) * | 1977-08-16 | 1979-03-09 | Mitsui Petrochem Ind Ltd | Purification of ketone |
| US7390869B2 (en) | 2005-06-13 | 2008-06-24 | Eastman Chemical Company | Process for removing metal species in the presence of hydrogen and a porous material and polyester polymer containing reduced amounts of metal species |
-
1974
- 1974-12-03 GB GB5217174A patent/GB1454690A/en not_active Expired
- 1974-12-16 CA CA216,081A patent/CA1042918A/en not_active Expired
- 1974-12-19 FR FR7441952A patent/FR2272071A1/fr not_active Withdrawn
- 1974-12-21 DE DE19742460887 patent/DE2460887A1/de not_active Withdrawn
- 1974-12-24 IN IN2849/CAL/74A patent/IN142692B/en unknown
- 1974-12-25 JP JP50004153A patent/JPS5096538A/ja active Pending
- 1974-12-30 BR BR10952/74A patent/BR7410952D0/pt unknown
- 1974-12-30 RO RO7481013A patent/RO65265A/ro unknown
- 1974-12-30 BE BE152051A patent/BE823995A/xx unknown
- 1974-12-31 SU SU2093116A patent/SU550974A3/ru active
- 1974-12-31 NL NL7417057A patent/NL7417057A/xx not_active Application Discontinuation
- 1974-12-31 BG BG028636A patent/BG26365A3/xx unknown
- 1974-12-31 IT IT31151/74A patent/IT1028152B/it active
-
1975
- 1975-01-02 TR TR18982A patent/TR18982A/xx unknown
- 1975-01-02 DD DD183471A patent/DD118274A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2460887A1 (de) | 1975-07-10 |
| BE823995A (fr) | 1975-04-16 |
| NL7417057A (nl) | 1975-07-04 |
| DD118274A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-20 |
| IT1028152B (it) | 1979-01-30 |
| GB1454690A (en) | 1976-11-03 |
| BG26365A3 (bg) | 1979-03-15 |
| JPS5096538A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-31 |
| FR2272071A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-19 |
| RO65265A (ro) | 1980-01-15 |
| BR7410952D0 (pt) | 1975-08-26 |
| IN142692B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-13 |
| TR18982A (tr) | 1978-02-06 |
| SU550974A3 (ru) | 1977-03-15 |
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