DE1072620B - Verfahren zur Herstellung von Hexahydroterephthalsäure - Google Patents
Verfahren zur Herstellung von HexahydroterephthalsäureInfo
- Publication number
- DE1072620B DE1072620B DENDAT1072620D DE1072620DA DE1072620B DE 1072620 B DE1072620 B DE 1072620B DE NDAT1072620 D DENDAT1072620 D DE NDAT1072620D DE 1072620D A DE1072620D A DE 1072620DA DE 1072620 B DE1072620 B DE 1072620B
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- acid
- reaction
- palladium
- 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.)
- Pending
Links
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 24
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 85
- 238000006243 chemical reaction Methods 0.000 claims description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
- 229910052763 palladium Inorganic materials 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 description 27
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-IZLXSQMJSA-N OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 Chemical class OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 PXGZQGDTEZPERC-IZLXSQMJSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- -1 terephthalic acid ester Chemical class 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US682632A US2888484A (en) | 1957-09-09 | 1957-09-09 | Production of hexahydroterephthalic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1072620B true DE1072620B (de) | 1960-01-07 |
Family
ID=24740507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1072620D Pending DE1072620B (de) | 1957-09-09 | Verfahren zur Herstellung von Hexahydroterephthalsäure |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2888484A (enrdf_load_html_response) |
| BE (1) | BE571022A (enrdf_load_html_response) |
| DE (1) | DE1072620B (enrdf_load_html_response) |
| NL (1) | NL103362C (enrdf_load_html_response) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1202269B (de) * | 1960-07-18 | 1965-10-07 | Eastman Kodak Co | Verfahren zur Herstellung von 1, 4-Dimethylolcyclohexan |
| DE1271709B (de) * | 1964-04-02 | 1968-07-04 | Allied Chem | Verfahren zur Herstellung von Cyclohexancarbonsaeure |
| DE1280245B (de) * | 1962-12-17 | 1968-10-17 | Engelhard Ind Inc | Verfahren zur Herstellung von Hexahydrobenzoesaeure |
| DE1282647B (de) * | 1963-12-26 | 1968-11-14 | Engelhard Ind Inc | Verfahren zur Herstellung von Hexahydrobenzoesaeure |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3027398A (en) * | 1960-02-01 | 1962-03-27 | Du Pont | Process for preparing dimethyl 1, 4-cyclohexanedicarboxylate |
| US3210411A (en) * | 1960-10-04 | 1965-10-05 | Stamicarbon | Hydrogenation of benzoic acid to cyclohexane-carboxylic acid |
| US3141036A (en) * | 1961-07-27 | 1964-07-14 | Allied Chem | Cyclohexane carboxylic acid produced by hydrogenation of molten benzoic acid |
| US3238251A (en) * | 1961-12-20 | 1966-03-01 | Du Pont | Production of substituted naphthalene derivatives by rearrangement of substituted dicyclopentadiene derivatives with a friedel-crafts catalyst |
| NL293104A (enrdf_load_html_response) * | 1962-05-26 | |||
| US3162679A (en) * | 1962-12-28 | 1964-12-22 | Engelhard Ind Inc | Production of a tetrahydrophthalic acid and salts thereof |
| US3520921A (en) * | 1967-04-05 | 1970-07-21 | Koppers Co Inc | Preparation of cis-hexahydrophthalic acid from phthalic acid |
| US4754064A (en) * | 1983-10-24 | 1988-06-28 | Amoco Corporation | Preparation of cyclohexane dicarboxylic acids |
| US5486562A (en) * | 1990-07-12 | 1996-01-23 | General Electric Company | Modifications of poly(alkylene cyclohexanedicarboxylate) blends |
| US5306785A (en) * | 1990-07-12 | 1994-04-26 | General Electric Company | Poly(alkylene cyclohexane-dicarboxylate) binary blends |
| US5399661A (en) * | 1990-07-12 | 1995-03-21 | General Electric Company | Poly(alkylene cyclohexanedicarboxylate)-(alkylene terephthalate) copolyesters |
| US5202475A (en) * | 1990-09-27 | 1993-04-13 | Eastman Kodak Company | Process for preparation of cyclohexanedicarboxylic acid |
| JP3106411B2 (ja) * | 1992-12-21 | 2000-11-06 | 東和化成工業株式会社 | １，４−シクロヘキサンジカルボン酸の製造方法 |
| US6136441A (en) * | 1998-03-24 | 2000-10-24 | General Electric Company | Multilayer plastic articles |
| US6221556B1 (en) | 1999-03-05 | 2001-04-24 | General Electric Company | Article for optical data storage device |
| US6989190B2 (en) * | 2000-10-17 | 2006-01-24 | General Electric Company | Transparent polycarbonate polyester composition and process |
| US6448334B1 (en) | 2000-12-19 | 2002-09-10 | General Electric Company | Translucent polycarbonate composition, method for preparation thereof, and articles derived therefrom |
| US6635698B2 (en) | 2000-12-22 | 2003-10-21 | General Electric Company | Flame retardant polycarbonate polyester composition |
| EP1219586B1 (en) * | 2000-12-26 | 2006-04-05 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a hydrogenation product of an aromatic carboxylic acid |
| US6586527B2 (en) | 2001-03-20 | 2003-07-01 | General Electric Company | Polyester resin molding compositions |
| US6465102B1 (en) | 2001-03-22 | 2002-10-15 | General Electric Company | Formed decorative article |
| US6458913B1 (en) | 2001-03-22 | 2002-10-01 | General Electric Company | Insert molded article |
| DE60230050D1 (de) | 2001-09-25 | 2009-01-08 | Exxonmobil Chem Patents Inc | Weich-polyvinylchlorid |
| US7297409B2 (en) * | 2001-10-12 | 2007-11-20 | Sabic Innovative Plastics Ip Bv | Multilayer, weatherable compositions and method of manufacture thereof |
| US6630527B2 (en) | 2001-10-19 | 2003-10-07 | General Electric Company | UV stabilized, impact modified polyester/polycarbonate blends, articles, and methods of manufacture thereof |
| CN1310868C (zh) * | 2001-10-26 | 2007-04-18 | 三菱化学株式会社 | 反式－1,4－环己烷二羧酸的生产方法 |
| US7090926B2 (en) * | 2001-11-09 | 2006-08-15 | General Electric Company | Multi-layer, weatherable compositions and method of manufacture thereof |
| EP1323700B1 (en) * | 2001-12-28 | 2007-08-22 | Mitsubishi Gas Chemical Company, Inc. | process for producing hydrogenated aromatic polycarboxylic acid and process for producing hydrogenated aromatic polycarboxylic anhydride |
| EP1483308A1 (en) * | 2002-03-01 | 2004-12-08 | General Electric Company | Aliphatic polyester-acrylic blend molding composition having good ductility and weatherability |
| US6887573B2 (en) * | 2002-07-30 | 2005-05-03 | General Electric Company | Polycarbonate polyester articles with enhanced adhesion between outer layer and base substrate |
| US20070049703A1 (en) * | 2002-12-18 | 2007-03-01 | Murray Michael C | Static dissipating resin compositions, methods for manufacture and articles made therefrom |
| US7022764B2 (en) * | 2002-12-18 | 2006-04-04 | General Electric Company | Static dissipating resin composition and methods for manufacture thereof |
| US20040253402A1 (en) * | 2003-06-10 | 2004-12-16 | General Electric Company | Crate for containers |
| US20040253400A1 (en) * | 2003-06-10 | 2004-12-16 | Wal Ronald Van Der | Crate for containers |
| US20070135586A1 (en) * | 2005-12-09 | 2007-06-14 | Shreyas Chakravarti | Polyamide blend compositions formed article and process thereof |
| EP2626343B1 (en) * | 2010-10-07 | 2018-12-26 | Mitsui Chemicals, Inc. | Method for producing bis(aminomethyl)cyclohexanes |
| CN104513170B (zh) * | 2013-09-29 | 2018-02-27 | 天津瑞安医药科技发展有限公司 | 一种反式对氨基环己烷甲酸的生产工艺 |
| US9346737B2 (en) | 2013-12-30 | 2016-05-24 | Eastman Chemical Company | Processes for making cyclohexane compounds |
| US9340482B2 (en) | 2013-12-30 | 2016-05-17 | Eastman Chemical Company | Processes for making cyclohexane compounds |
| US9328050B1 (en) | 2014-12-23 | 2016-05-03 | Eastman Chemical Company | Processes for making hydroxymethylbenzoic acid compounds |
| US20230049802A1 (en) * | 2019-12-27 | 2023-02-16 | Hanwha Solutions Corporation | Method for producing 1,4-cyclohexane dicarboxylic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2070770A (en) * | 1935-10-18 | 1937-02-16 | Du Pont | Hydrogenation of alkyl phthalates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2828335A (en) * | 1955-11-22 | 1958-03-25 | California Research Corp | Hydrogenation of phthalic acid salts |
-
0
- BE BE571022D patent/BE571022A/xx unknown
- NL NL103362D patent/NL103362C/xx active
- DE DENDAT1072620D patent/DE1072620B/de active Pending
-
1957
- 1957-09-09 US US682632A patent/US2888484A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2070770A (en) * | 1935-10-18 | 1937-02-16 | Du Pont | Hydrogenation of alkyl phthalates |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1202269B (de) * | 1960-07-18 | 1965-10-07 | Eastman Kodak Co | Verfahren zur Herstellung von 1, 4-Dimethylolcyclohexan |
| DE1280245B (de) * | 1962-12-17 | 1968-10-17 | Engelhard Ind Inc | Verfahren zur Herstellung von Hexahydrobenzoesaeure |
| DE1282647B (de) * | 1963-12-26 | 1968-11-14 | Engelhard Ind Inc | Verfahren zur Herstellung von Hexahydrobenzoesaeure |
| DE1271709B (de) * | 1964-04-02 | 1968-07-04 | Allied Chem | Verfahren zur Herstellung von Cyclohexancarbonsaeure |
Also Published As
| Publication number | Publication date |
|---|---|
| NL103362C (enrdf_load_html_response) | |
| BE571022A (enrdf_load_html_response) | |
| US2888484A (en) | 1959-05-26 |
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