KR960703099A - 디메틸 벤젠디카복실레이트를 상응하는 디메틸 사이클로헥산디카복실레이트로 수소화시키기 위한 저압 방법(low pressure process for the hydrogenation of dimethyl benzenedicarboxylates to the corresponding dimethyl cyclohexanedicarboxylates) - Google Patents
디메틸 벤젠디카복실레이트를 상응하는 디메틸 사이클로헥산디카복실레이트로 수소화시키기 위한 저압 방법(low pressure process for the hydrogenation of dimethyl benzenedicarboxylates to the corresponding dimethyl cyclohexanedicarboxylates) Download PDFInfo
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- KR960703099A KR960703099A KR1019950705692A KR19950705692A KR960703099A KR 960703099 A KR960703099 A KR 960703099A KR 1019950705692 A KR1019950705692 A KR 1019950705692A KR 19950705692 A KR19950705692 A KR 19950705692A KR 960703099 A KR960703099 A KR 960703099A
- Authority
- KR
- South Korea
- Prior art keywords
- dimethyl
- palladium
- alumina
- weight
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 7
- 238000005984 hydrogenation reaction Methods 0.000 title abstract 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 32
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract 17
- 229910052763 palladium Inorganic materials 0.000 claims abstract 16
- 239000003054 catalyst Substances 0.000 claims abstract 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract 10
- 229910052759 nickel Inorganic materials 0.000 claims abstract 9
- NIQCNGHVCWTJSM-UHFFFAOYSA-N dimethyl benzenedicarboxylate Natural products COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims abstract 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 5
- 229910052751 metal Inorganic materials 0.000 claims abstract 5
- 239000002184 metal Substances 0.000 claims abstract 5
- 229910052697 platinum Inorganic materials 0.000 claims abstract 5
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- LYMMFQAKPGXADS-UHFFFAOYSA-N dimethyl benzene-1,2-dicarboxylate;dimethyl benzene-1,3-dicarboxylate;dimethyl benzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1.COC(=O)C1=CC=CC(C(=O)OC)=C1.COC(=O)C1=CC=CC=C1C(=O)OC LYMMFQAKPGXADS-UHFFFAOYSA-N 0.000 claims 5
- 239000006185 dispersion Substances 0.000 claims 4
- 239000013078 crystal Substances 0.000 claims 2
- GGCUUOGRTPMFQK-UHFFFAOYSA-N dimethyl cyclohexane-1,1-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CCCCC1 GGCUUOGRTPMFQK-UHFFFAOYSA-N 0.000 claims 2
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 claims 2
- BZUOYGUOKMUSPA-UHFFFAOYSA-N dimethyl cyclohexane-1,3-dicarboxylate Chemical compound COC(=O)C1CCCC(C(=O)OC)C1 BZUOYGUOKMUSPA-UHFFFAOYSA-N 0.000 claims 2
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 claims 2
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- -1 dimethyl benzenedicarboxylate ester Chemical class 0.000 abstract 1
Classifications
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- 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
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- B01J35/394—
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- B01J35/635—
-
- B01J35/647—
Abstract
본 발명은 알루미나 지지체상에 부착된, 팔라듐, 및 니켈, 백금, 루테늄 또는 이들의 혼합물중에서 선택된 Ⅷ족 제2금속을 포함하는, 독특한 특성들의 조합을 갖는 지지된 촉매군의 존재하에서 디메틸 사이클로헥산디카복실레이트를 상응하는 디메틸 벤젠디카복실레이트 에스테르의 수소화에 의해 제조하는 방법을 개시한다. 상기 촉매의 사용으로 상기 방법을 현저하게 낮은 공정 압력에서 수행할 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- (1) 팔라듐이 촉매의 0.1 내지 5.0중량%를 차지하고; (2) 상기 팔라듐 분산도가 15%이상이며; (3) 상기 팔라듐의 90중량% 이상이 알루미나의 표면으로 200μ 미만의 깊이로 상기 알루미나상에 배치되고; (4) 니켈, 백금, 루테늄 또는 이들의 혼합물중에서 선택된 Ⅷ족 제2금속이 촉매의 0.001 내지 1중량%를 차지하고; (5) 상기 알루미나의 결정상이 알파, 쎄타, 델타, 감마, 에타 또는 이들의 혼합상인, 디메틸 벤젠디카복실레이트를, 알루미나 지지체상에 부착된, 팔라듐, 및 니켈, 백금, 루테늄 또는 이들의 혼합물중에서 선택된 Ⅷ족 제2금속을 포함하는 지지된 촉매된 존재하에서 140 내지 400℃의 온도 및 10 내지 200바(절대)(1,000 내지 20,000kPa)의 압력에서 수소와 접촉시킴을 포함하는 디메틸 사이클로헥산디카복실레이트의 제조 방법.
- 제1항에 있어서, (1) 상기 팔라듐이 상기 촉매의 0.5 내지 0.2중량%를 차지하고; (2) 상기 팔라듐 분산도가 30%이상이며; (3) 상기 팔라듐으 l90중량%이상이 알루미나의 표면으로부터 100μ 미만의 깊이로 상기 알루미나상에 배치되고; (4) 상기 니켈, 백금, 루테늄 또는 이들의 혼합물중에서 선택된 Ⅷ족 제2금속이 상기 촉매의 0.01 내지 0.5중량%를 차지하고; (5) 상기 알루미나의 결정상이 알파, 쎄타, 델타 또는 이들의 혼합상인, 디메틸 벤젠디카복실레이트를, 알루미나 지지체상에 부착된, 팔라듐, 및 니켈, 백금, 루테늄, 또는 이들의 혼합물 중에서 선택된 Ⅷ족 제2금속을 포함하는 지지된 촉매의 존재하에서 140 내지 400℃의 온도 및 10 내지 200바(절대)(1,000 내지 20,000kPa)의 압력에서 수소와 접촉시킴을 포함하는 방법.
- 제2항에 있어서, 상기 디메틸 사이클로헥산디카복실레이트중의 디메틸 벤젠디카복실레이트 용액을 수소와 접촉시키는 방법.
- (1) 팔라듐이 촉매의 0.1 내지 5.0중량%를 차지하고; (2) 상기 팔라듐 분산도가 20%이상이며; (3) 상기 팔라듐의 90중량%이상이 알루미나의 표면으로부터 200μ 미만의 깊이로 상기 알루미나상에 배치되고; (4) 니켈이 촉매의 0.01 내지 0.5중량%를 차지하고; (5) 상기 알루미나의 결정상이 알파, 쎄타, 델타, 감마, 에타 또는 이들의 혼합상인, 디메틸 벤젠디카복실레이트를, 알루미나 지지체상에 부착된 팔라듐 및 니켈을 코함하는 지지된 촉매의 존재하에서 140 내지 400℃의 온도 및 50 내지 170바(절대)(5,000 내지 17,000kPa)의 압력에서 수소와 접촉시킴을 포함하는 디메틸 사이클로헥산디카복실레이트의 제조 방법.
- 제4항에 있어서, (1) 상기 촉매의 0.5 내지 2.0중량%를 차지하고; (2) 상기 팔라듐 분산도가 30%이상이며; (3) 상기 팔라듐의 90중량%이상이 알루미나의 표면으로부터 100μ 미만의 깊이로 상기 알루미나상에 배치되고; (4) 상기 니켈이 상기 촉매의 0.01 내지 0.5중량%를 차지하고; (5) 상기 알루미나의 결정상이 알파, 쎄타, 델타 또는 이들의 혼합상인, 디메틸 벤젠디카복실레이트를, 알루미나 지지체상에 부착된 팔라듐 및 니켈을 포함하는 지지된 촉매의 존재하에서 140 내지 250℃의 온도 및 50 내지 170바(절대)(5,000 내지 17,000kPa)의 압력에서 수소화 접촉시킴을 포함하는 방법.
- 제5항에 있어서, 디메틸 1,4―사이클로헥산디카복실레이트중의 디메틸 1,4―벤젠 디카복실레이트 용액을 수소와 접촉시키는, 디메틸 1,4―사이클로헥산디카복실레이트를 제조하기 위한 방법.
- 제5항에 있어서, 디메틸 1,3―사이클로헥산디카복실레이트중의 디메틸 1,3―벤젠 디카복실레이트 용액을 수소와 접촉시키는, 디메틸 1,3―사이클로헥산디카복실레이트를 제조하기 위한 방법.
- 제5항에 있어서, 디메틸 1,2―사이클로헥산디카복실레이트중의 디메틸 1,2―벤젠 디카복실레이트 용액을 수소와 접촉시키는, 디메틸 1,2―사이클로헥산디카복실레이트를 제조하기 위한 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/076675 | 1993-06-15 | ||
US076,575 | 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 |
---|---|
KR960703099A true KR960703099A (ko) | 1996-06-19 |
KR100390121B1 KR100390121B1 (ko) | 2003-11-13 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1019950705692A KR100390121B1 (ko) | 1993-06-15 | 1994-06-03 | 디메틸 벤젠디카복실레이트를 상응하는 디메틸 사이클로헥산디카복실레이트로수소화시키기위한저압방법 |
Country Status (11)
Country | Link |
---|---|
US (1) | US5286898A (ko) |
EP (1) | EP0703894B1 (ko) |
JP (1) | JP3499557B2 (ko) |
KR (1) | KR100390121B1 (ko) |
CN (1) | CN1042327C (ko) |
CA (1) | CA2165207C (ko) |
DE (1) | DE69412827T2 (ko) |
ES (1) | ES2120054T3 (ko) |
SG (1) | SG47888A1 (ko) |
TW (1) | TW265332B (ko) |
WO (1) | WO1994029260A1 (ko) |
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DE19927978A1 (de) * | 1999-06-18 | 2000-12-21 | Basf Ag | Ausgewählte Cyclohexan-1,3- und 1,4-dicarbonsäureester |
AU6369200A (en) * | 1999-07-28 | 2001-02-19 | Sud-Chemie, Inc. | Hydrogenation catalysts |
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 |
GB0227086D0 (en) | 2002-11-20 | 2002-12-24 | Exxonmobil Res & Eng Co | Hydrogenation processes |
GB0227087D0 (en) * | 2002-11-20 | 2002-12-24 | Exxonmobil Chem Patents Inc | Hydrogenation of benzene polycarboxylic acids or derivatives thereof |
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 |
DE102004063637A1 (de) | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
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 |
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EP2716623A1 (de) | 2012-10-05 | 2014-04-09 | Basf Se | Verfahren zur Herstellung von Cyclohexanpolycarbonsäure-Derivaten mit geringem Nebenproduktanteil |
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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 |
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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 |
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 |
US11673125B2 (en) | 2016-08-18 | 2023-06-13 | The University Of Chicago | Metal oxide-supported earth-abundant metal catalysts for highly efficient organic transformations |
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 |
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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 WO PCT/US1994/006266 patent/WO1994029260A1/en active IP Right Grant
- 1994-06-03 SG SG1996005045A patent/SG47888A1/en unknown
- 1994-06-03 JP JP50197295A patent/JP3499557B2/ja not_active Expired - Lifetime
- 1994-06-03 DE DE69412827T patent/DE69412827T2/de not_active Expired - Lifetime
- 1994-06-03 ES ES94919348T patent/ES2120054T3/es not_active Expired - Lifetime
- 1994-06-03 EP EP94919348A patent/EP0703894B1/en not_active Expired - Lifetime
- 1994-06-03 KR KR1019950705692A patent/KR100390121B1/ko not_active IP Right Cessation
- 1994-06-03 CA CA002165207A patent/CA2165207C/en not_active Expired - Fee Related
- 1994-06-10 CN CN94106440A patent/CN1042327C/zh not_active Expired - Lifetime
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DE69412827D1 (de) | 1998-10-01 |
JPH08511775A (ja) | 1996-12-10 |
CA2165207C (en) | 1998-08-18 |
WO1994029260A1 (en) | 1994-12-22 |
EP0703894B1 (en) | 1998-08-26 |
TW265332B (ko) | 1995-12-11 |
ES2120054T3 (es) | 1998-10-16 |
KR100390121B1 (ko) | 2003-11-13 |
CA2165207A1 (en) | 1994-12-22 |
CN1042327C (zh) | 1999-03-03 |
CN1099745A (zh) | 1995-03-08 |
US5286898A (en) | 1994-02-15 |
DE69412827T2 (de) | 1999-01-14 |
JP3499557B2 (ja) | 2004-02-23 |
SG47888A1 (en) | 1998-04-17 |
EP0703894A1 (en) | 1996-04-03 |
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