CN1042327C - 苯二甲酸二甲酯氢化生成相应的环己烷二甲酸二甲酯的低压方法 - Google Patents
苯二甲酸二甲酯氢化生成相应的环己烷二甲酸二甲酯的低压方法 Download PDFInfo
- Publication number
- CN1042327C CN1042327C CN94106440A CN94106440A CN1042327C CN 1042327 C CN1042327 C CN 1042327C CN 94106440 A CN94106440 A CN 94106440A CN 94106440 A CN94106440 A CN 94106440A CN 1042327 C CN1042327 C CN 1042327C
- Authority
- CN
- China
- Prior art keywords
- palladium
- catalyzer
- weight
- dimethyl
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- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 17
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical class COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 title abstract 2
- GGCUUOGRTPMFQK-UHFFFAOYSA-N dimethyl cyclohexane-1,1-dicarboxylate Chemical class COC(=O)C1(C(=O)OC)CCCCC1 GGCUUOGRTPMFQK-UHFFFAOYSA-N 0.000 title abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 83
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 claims description 8
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- -1 dimethyl benzenedicarboxylate ester Chemical class 0.000 abstract 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 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910003445 palladium oxide Inorganic materials 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910000619 316 stainless steel Inorganic materials 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/892—Nickel and noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/394—Metal dispersion value, e.g. percentage or fraction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/635—0.5-1.0 ml/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US076,675 | 1993-06-15 | ||
| US08/076,675 US5286898A (en) | 1993-06-15 | 1993-06-15 | Low pressure process for the hydrogenation of dimethyl benzenedicarboxylates to the corresponding dimethyl cyclohexanedicarboxlates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1099745A CN1099745A (zh) | 1995-03-08 |
| CN1042327C true CN1042327C (zh) | 1999-03-03 |
Family
ID=22133530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94106440A Expired - Lifetime CN1042327C (zh) | 1993-06-15 | 1994-06-10 | 苯二甲酸二甲酯氢化生成相应的环己烷二甲酸二甲酯的低压方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5286898A (enExample) |
| EP (1) | EP0703894B1 (enExample) |
| JP (1) | JP3499557B2 (enExample) |
| KR (1) | KR100390121B1 (enExample) |
| CN (1) | CN1042327C (enExample) |
| CA (1) | CA2165207C (enExample) |
| DE (1) | DE69412827T2 (enExample) |
| ES (1) | ES2120054T3 (enExample) |
| SG (1) | SG47888A1 (enExample) |
| TW (1) | TW265332B (enExample) |
| WO (1) | WO1994029260A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866415A (zh) * | 2015-12-12 | 2017-06-20 | 中国科学院大连化学物理研究所 | 一种脂环族羧酸酯的制造方法 |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9710457A (pt) | 1996-06-28 | 1999-08-17 | New Japan Chem Co Ltd | Processo para a prepara-Æo de ciclohexanodimetanol |
| ID30388A (id) * | 1997-12-19 | 2001-11-29 | Basf Ag | Hidrogenasi dari asam benzenapolikarboksilat atau turunannya dengan menggunakan suatu katalis yang mengandung makropori |
| DE19927978A1 (de) * | 1999-06-18 | 2000-12-21 | Basf Ag | Ausgewählte Cyclohexan-1,3- und 1,4-dicarbonsäureester |
| KR20020052170A (ko) * | 1999-07-28 | 2002-07-02 | 추후제출 | 수소화 촉매 |
| DE19939544C1 (de) * | 1999-08-20 | 2001-02-15 | Haarmann & Reimer Gmbh | Verfahren zur Herstellung von Methyl-cyclohexyl-propionat |
| DE10128242A1 (de) * | 2001-06-11 | 2002-12-12 | Basf Ag | Verfahren zur Hydrierung organischer Verbindungen |
| DE10146869A1 (de) | 2001-09-24 | 2003-04-24 | Oxeno Olefinchemie Gmbh | Alicyclische Polycarbonsäureestergemische mit hohem trans-Anteil und Verfahren zu deren Herstellung |
| CN1558927A (zh) | 2001-09-25 | 2004-12-29 | ����ɭ���ڻ�ѧר����˾ | 增塑聚氯乙烯 |
| US6803341B2 (en) * | 2002-01-18 | 2004-10-12 | Chinese Petroleum Corporation | Method of a high stability selectable hydrogenate catalyst producing and using for DMCHD manufacturing |
| GB0227087D0 (en) * | 2002-11-20 | 2002-12-24 | Exxonmobil Chem Patents Inc | Hydrogenation of benzene polycarboxylic acids or derivatives thereof |
| GB0227086D0 (en) | 2002-11-20 | 2002-12-24 | Exxonmobil Res & Eng Co | Hydrogenation processes |
| DE102004063637A1 (de) | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
| DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
| US7632962B2 (en) * | 2006-04-26 | 2009-12-15 | Eastman Chemical Company | Hydrogenation process and catalysts |
| CN101417950B (zh) * | 2008-10-27 | 2012-05-23 | 中国科学院大连化学物理研究所 | 一种制备1,2-环己烷二甲酸二元酯的方法 |
| CN101927166B (zh) * | 2010-07-23 | 2013-01-23 | 南京大学 | 一种担载镍催化剂及其制法和用途 |
| CN102381976B (zh) * | 2010-09-01 | 2013-09-04 | 中国石油天然气股份有限公司 | 一种制备1,4-环己烷二甲酸二甲酯的方法 |
| CN102476052A (zh) * | 2010-11-29 | 2012-05-30 | 中国石油化工股份有限公司 | 一种负载型钌催化剂及其制备方法 |
| CN102796001A (zh) * | 2011-05-25 | 2012-11-28 | 江苏恒祥化工有限责任公司 | 无溶剂制备1,4-环己烷二甲酸二甲酯 |
| TWI421240B (zh) | 2011-12-12 | 2014-01-01 | Ind Tech Res Inst | 苯多羧酸或其衍生物形成環己烷多元酸酯之氫化方法 |
| CN102631925B (zh) * | 2012-03-30 | 2015-03-25 | 中国科学院山西煤炭化学研究所 | 一种苯羧酸酯加氢催化剂及其制备方法和应用 |
| ITMI20121641A1 (it) | 2012-10-02 | 2014-04-03 | Polynt S P A | Procedimento per l'idrogenazione di esteri di acidi carbossilici aromatici a dare loro omologhi saturi, nuovi usi per detti omologhi, e nuove miscele polimeriche plastificate. |
| EP2716623A1 (de) | 2012-10-05 | 2014-04-09 | Basf Se | Verfahren zur Herstellung von Cyclohexanpolycarbonsäure-Derivaten mit geringem Nebenproduktanteil |
| US9090553B2 (en) | 2012-10-05 | 2015-07-28 | Basf Se | Process for preparing cyclohexanepolycarboxylic acid derivatives having a low proportion of by-products |
| CN102921409A (zh) * | 2012-10-26 | 2013-02-13 | 中国海洋石油总公司 | 一种加氢生产1,2环己烷二羧酸酯的催化剂的制法 |
| CN102935365B (zh) * | 2012-11-12 | 2014-12-03 | 中国石油化工股份有限公司 | 一种制备1,4-环己烷二甲酸二甲酯的催化剂及方法 |
| CN103157468A (zh) * | 2013-03-14 | 2013-06-19 | 北京化工大学 | 一种低含量负载型钌-钯双金属加氢催化剂及其制备方法 |
| CN104649864A (zh) * | 2013-11-19 | 2015-05-27 | 中国石油天然气股份有限公司 | 一种对苯二甲酸二烷基酯加氢生产1,4-环己烷二甲醇的方法 |
| 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 |
| KR101905165B1 (ko) * | 2015-04-01 | 2018-10-05 | 한화케미칼 주식회사 | 프탈레이트 화합물의 수소화 촉매의 재생 방법 |
| TWI577658B (zh) * | 2015-05-06 | 2017-04-11 | 中國石油化學工業開發股份有限公司 | 1,4-環己烷二甲酸二甲酯及1,4-環己烷二甲醇之製法 |
| KR101780405B1 (ko) * | 2015-09-24 | 2017-09-20 | 롯데케미칼 주식회사 | 1,4-사이클로헥산디카르복실산의 제조 방법 |
| JP2019531873A (ja) | 2016-08-18 | 2019-11-07 | ザ ユニバーシティ オブ シカゴThe University Of Chicago | 高度に効率的な有機変換のための金属酸化物に支持された地球に豊富な金属の触媒 |
| KR101883993B1 (ko) * | 2016-09-29 | 2018-07-31 | 롯데케미칼 주식회사 | 1,3-사이클로헥산디카르복시산의 제조 방법 |
| FR3059253B1 (fr) * | 2016-11-29 | 2020-01-17 | IFP Energies Nouvelles | Catalyseur d'hydrogenation selective d'une coupe d'hydrocarbures c3. |
| FR3059252B1 (fr) * | 2016-11-29 | 2018-11-16 | IFP Energies Nouvelles | Catalyseur d’hydrogenation selective de coupes c3 de vapocraquage et/ou de craquage catalytique |
| KR102506281B1 (ko) * | 2017-11-29 | 2023-03-06 | 한화솔루션 주식회사 | 프탈레이트 화합물의 수소화 방법 |
| TWI684585B (zh) * | 2018-11-14 | 2020-02-11 | 中國石油化學工業開發股份有限公司 | 1,4-環己烷二甲酸二甲酯之製法 |
| CN112916022A (zh) * | 2021-01-21 | 2021-06-08 | 西南化工研究设计院有限公司 | 一种选择性加氢催化剂及其制备方法和应用 |
| CN119056308A (zh) * | 2024-02-29 | 2024-12-03 | 中国石油天然气集团有限公司 | 用于1,4环己烷二甲酸二甲酯加氢过程的物料稳态输送方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2675390A (en) * | 1950-05-19 | 1954-04-13 | Edgar F Rosenblatt | Hydrogenation of cyclic-compounds |
| GB817736A (en) * | 1955-08-26 | 1959-08-06 | Chimiotherapie Lab Franc | Esters of trans-hexahydroterephthalic acid and of the mono-acid chloride of trans-hexahydroterephthalic acid |
| US2794030A (en) * | 1955-10-18 | 1957-05-28 | Union Carbide & Carbon Corp | Aliphatic esters of 4, 5-epoxycyclohexane-1, 2-dicarboxylic acids |
| US3027398A (en) * | 1960-02-01 | 1962-03-27 | Du Pont | Process for preparing dimethyl 1, 4-cyclohexanedicarboxylate |
| DE1154096B (de) * | 1962-02-23 | 1963-09-12 | Witten Gmbh Chem Werke | Verfahren zur Herstellung von 1, 4-Cyclohexandicarbonsaeure-dialkylestern |
| NL6405867A (enExample) * | 1963-05-29 | 1964-11-30 | ||
| US3334149A (en) * | 1964-07-21 | 1967-08-01 | Eastman Kodak Co | Plural stage hydrogenation of dialkyl terephthalate using palladium and then copper chromite |
| US3444237A (en) * | 1966-03-23 | 1969-05-13 | Grace W R & Co | Esters of cyclohexane-1,2,4-tricarboxylic acid |
| US4024173A (en) * | 1967-09-02 | 1977-05-17 | Dynamit Nobel Aktiengesellschaft | Process for the manufacture of cyclohexene dicarboxylic acid esters |
| US3824193A (en) | 1972-03-30 | 1974-07-16 | Eastman Kodak Co | Alkaline reactivation of alumina supported palladium catalysts |
| DE2823165A1 (de) * | 1978-05-26 | 1979-11-29 | Bayer Ag | Verfahren zur herstellung von cycloaliphatischen carbonsaeureestern |
| JP2717265B2 (ja) * | 1988-06-03 | 1998-02-18 | 東都化成株式会社 | 熱硬化性樹脂組成物 |
-
1993
- 1993-06-15 US US08/076,675 patent/US5286898A/en not_active Expired - Lifetime
-
1994
- 1994-02-07 TW TW083101008A patent/TW265332B/zh not_active IP Right Cessation
- 1994-06-03 ES ES94919348T patent/ES2120054T3/es not_active Expired - Lifetime
- 1994-06-03 JP JP50197295A patent/JP3499557B2/ja not_active Expired - Lifetime
- 1994-06-03 WO PCT/US1994/006266 patent/WO1994029260A1/en not_active Ceased
- 1994-06-03 CA CA002165207A patent/CA2165207C/en not_active Expired - Fee Related
- 1994-06-03 DE DE69412827T patent/DE69412827T2/de not_active Expired - Lifetime
- 1994-06-03 KR KR1019950705692A patent/KR100390121B1/ko not_active Expired - Lifetime
- 1994-06-03 EP EP94919348A patent/EP0703894B1/en not_active Expired - Lifetime
- 1994-06-03 SG SG1996005045A patent/SG47888A1/en unknown
- 1994-06-10 CN CN94106440A patent/CN1042327C/zh not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866415A (zh) * | 2015-12-12 | 2017-06-20 | 中国科学院大连化学物理研究所 | 一种脂环族羧酸酯的制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SG47888A1 (en) | 1998-04-17 |
| EP0703894A1 (en) | 1996-04-03 |
| DE69412827D1 (de) | 1998-10-01 |
| WO1994029260A1 (en) | 1994-12-22 |
| JPH08511775A (ja) | 1996-12-10 |
| ES2120054T3 (es) | 1998-10-16 |
| CN1099745A (zh) | 1995-03-08 |
| EP0703894B1 (en) | 1998-08-26 |
| JP3499557B2 (ja) | 2004-02-23 |
| DE69412827T2 (de) | 1999-01-14 |
| CA2165207A1 (en) | 1994-12-22 |
| KR960703099A (ko) | 1996-06-19 |
| KR100390121B1 (ko) | 2003-11-13 |
| TW265332B (enExample) | 1995-12-11 |
| CA2165207C (en) | 1998-08-18 |
| US5286898A (en) | 1994-02-15 |
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