KR940005650A - 설폰화된 2,2'-비스(디페닐포스피노메틸)-1,1'-비나프탈렌, 이의 제조방법 및 올레핀계 불포화 화합물의 하이드로포밀화 방법에서의 이의 용도 - Google Patents
설폰화된 2,2'-비스(디페닐포스피노메틸)-1,1'-비나프탈렌, 이의 제조방법 및 올레핀계 불포화 화합물의 하이드로포밀화 방법에서의 이의 용도 Download PDFInfo
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- KR940005650A KR940005650A KR1019930008736A KR930008736A KR940005650A KR 940005650 A KR940005650 A KR 940005650A KR 1019930008736 A KR1019930008736 A KR 1019930008736A KR 930008736 A KR930008736 A KR 930008736A KR 940005650 A KR940005650 A KR 940005650A
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- sulfonated
- bis
- diphenylphosphinomethyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract 7
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract 3
- CMIHWILCIPLTFO-UHFFFAOYSA-N [1-[2-(diphenylphosphanylmethyl)naphthalen-1-yl]naphthalen-2-yl]methyl-diphenylphosphane Chemical class C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 CMIHWILCIPLTFO-UHFFFAOYSA-N 0.000 title claims 3
- 150000001336 alkenes Chemical class 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 229910052751 metal Inorganic materials 0.000 claims abstract 4
- 239000002184 metal Substances 0.000 claims abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 8
- 229910052703 rhodium Inorganic materials 0.000 claims 5
- 239000010948 rhodium Substances 0.000 claims 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- -1 diphenylphosphinomethyl Chemical group 0.000 claims 4
- 238000006277 sulfonation reaction Methods 0.000 claims 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical class PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000001925 cycloalkenes Chemical class 0.000 claims 2
- 150000005673 monoalkenes Chemical class 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- 229920000098 polyolefin Polymers 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- XFUWNUFKOZJFRR-UHFFFAOYSA-N [3-(diphenylphosphanylmethyl)-1-naphthalen-1-ylnaphthalen-2-yl]methyl-diphenylphosphane Chemical compound C=1C2=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 XFUWNUFKOZJFRR-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003284 rhodium compounds Chemical class 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000000470 constituent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
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- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
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- C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C09J123/24—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having ten or more carbon atoms
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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Abstract
본 발명은 하기 일반식의 신규한 설폰화된 디포스핀, 이의 제조방법 및 수용성 촉매계의 성분으로서 당해 화합물을 사용하는 올레폰과 올레핀계 불포화 화합물의 하이드로포밀화에 관한 것이다.
상기식에서, Ar은 m-C6H4SO3M이고, M은 수소, 암모늄, 일가금속 또는 등가의 다가금속이고, Ph는 페닐라디칼이고, m은 동일하거나 상이하고 1 또는 2이고, n은 동일하거나 상이하고 0, 1 또는 2이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 하기 일반식의 설폰화된 2,2'-비스(디페닐포스피노메틸)-1,1'-비나프탈렌상기식에서, Ar은 m-C6H4SO3M이고, M은 수소, 암모늄, 일가금속 또는 등가의 다가금속이고, Ph는 페닐라디칼이고, m은 동일하거나 상이하고 1 또는 2이고, n은 동일하거나 상이하고 0, 1 또는 2이다.
- 올레옴을 사용하여 온도 0 내지 25℃에서 2,2'-비스 (디페닐포스피노메틸) -1, 1'-비나프탈렌을 설폰화시키고, 설폰화 혼합물을 가수분해시키고 설폰화된 2.2'-비스(디페닐포스피노메틸)-1, 1'-비나프탈렌을 가수분해된 설폰화 혼합물로 부터 분리함을 포함하여, 제1항에서 청구된 화합물을 제조하는 방법
- 제2항에 있어서, 유리 삼산화황을 10내지 65중량%, 특히 40내지 65중량%함유하는 올레움이 설폰화용으로 상용되는 방법.
- 제2항 또는 제3항에 있어서, 삼산화황이 2,2'-비스 (디페닐포스피노메틸) -1. 1'-비나프탈렌 몰당 25 내지 80몰, 바람직하게는 40 내지 70몰 사용되는 방법.
- 제2항 내지 제4항 중의 어느 한 항에 있어서, 설폰화가 온도 0 내지 25℃, 바람직하게는 0 내지 10℃에서 수행되는 방법.
- 제2항 내지 제5항 중의 어느 한 항에 있어서, 설폰화 혼합물의 가수분해가 온도 약30℃이하, 바람직하게는 15 내지 25℃에서 수행되는 방법.
- 제2항 내지 제6항 중의 어느 한 항에 있어서, 가수분해된 설폰화 혼합물을 알칼리 금속 탄산염 또는 알칼리 금속 수산화물을 사용하여 중화시키고, 알칼리 금속 황산염을 분리시킨 후, 수용액을 농축시키고, 설폰화된 2. 2'-비스(디페닐포스피노메틸) -1. 1'-비나프탈렌을 분자내 탄소수가 5이하인 알코올과 물의 혼합물을 사용하여 잔류물로 부터 추출하는 방법.
- 제2항 내지 제6항 중의 어느 한 항에 있어서, 가수분해된 설폰화 혼합물을 수불용성 아민과 유기 용매의 혼합물, 특히 트리이소옥틸아민과 톨루엔의 혼합물과 반응시키고, 설폰산염을 아민염으로서 추출한 후 염기수용액, 바람직하게는 수산화나트륨 또는 수산화칼륨을 아민염 용액에 임의로 부분적으로 가하는 방법.
- 하기 일반식 설폰화된 2,2'-비스(디페닐포스피노메틸)-1, 1'-비나프틸로 착화된 수용성 로듐 화합물로 구성된 수성 촉매의 존재하에서, 온도 20 내지 150℃ 및 압력 0, 1 내지 20MFa에선 모노올레핀, 비공역 폴리올레핀, 사이클로올레핀 또는 이 부류 화합물의 유도체를 일산화탄소 및 수소화 반응시켜 알데하이드를 제조하는 방법.상기식에서, Ar은 m-C6H4SO3M이고, M은 수소, 암모늄, 일가금속 또는 등가의 다가금속이고, Ph는 페닐라디칼이고, m은 동일하거나 상이하고 1 또는 2이고, n은 동일하거나 상이하고 0, 1 또는 2이다.
- 제9항에 있어서, 설폰화된 디포스핀이 로듐 몰당 1 내지 130몰, 바람직하게는 2 내지 25몰, 특히 2 내지 10몰 사용되는 방법.
- 제9항 또는 제10항에 있어서, 촉매 수용액중의 로듐 농도가 용액을 기준으로 하여 10 내지 500중량 PPm, 바람직하게는 10 내지 100중량 7Pm, 특히 15 내지 57중량 PPm인 방법.
- 제9항 내지 제11항 중의 어느 한 항에 있어서, 반응이 20 내지 150℃, 바람직하게는 80 내지 147℃, 특히 100 내지 125℃에서 수행되는 방법.
- 제9항 내지 제12항 중의 어느 한 항에 있어서, 반응이 압력 0.1 내지 30MPa 바람직하게는 1 내지 12MPa 특히 3 내지 7MPa에서 수행되는 방법.
- 제9항 내지 제13항 중의 어느 한 항에 있어서, 탄소수 2 내지 47, 바람직하게는 2 내지 20, 특히 2 내지 8의 올레핀 또는 올레핀 유도체를 반응시키는 방법.
- 설폰화된 2,2'-비스 (디페니리포스피노메틸) -1. 1'-비 나프틸을 로듐 몰당 1 내지 130몰, 바람직하게는 1 내지 25몰, 특히 1 내지 17몰 함유하며, 모노올레핀, 비공역 폴리올레핀, 사이클로올레핀 또는 이 부류 화합물의 유도체의 하이드로 포밀화용으로 사용되는 로듐/디포스핀 촉매.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4217803.7 | 1992-05-29 | ||
| DE4217803A DE4217803A1 (de) | 1992-05-29 | 1992-05-29 | Verfahren zur Herstellung von Aldehyden |
| DE4244274A DE4244274A1 (de) | 1992-12-28 | 1992-12-28 | Sulfonierte 2,2'-Bis(diphenylphosphinomethyl)-1,1'-binaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DEP4244274.5 | 1992-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940005650A true KR940005650A (ko) | 1994-03-22 |
| KR100265520B1 KR100265520B1 (ko) | 2000-09-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930008736A KR100265520B1 (ko) | 1992-05-29 | 1993-05-21 | 설폰화된 2,2'-비스(디페닐포스피노메틸)-1,1'-비나프탈렌, 이의 제조방법 및 이를 사용하는 올레핀계 불포화 화합물의 하이드로포밀화 방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US5347045A (ko) |
| EP (1) | EP0571819B1 (ko) |
| JP (2) | JPH0794466B2 (ko) |
| KR (1) | KR100265520B1 (ko) |
| CN (1) | CN1032538C (ko) |
| AT (1) | ATE173266T1 (ko) |
| BR (1) | BR9302013A (ko) |
| CA (1) | CA2096812C (ko) |
| DE (1) | DE59309119D1 (ko) |
| ES (1) | ES2126613T3 (ko) |
| MX (1) | MX9303004A (ko) |
| SG (1) | SG43948A1 (ko) |
| TW (1) | TW225485B (ko) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4338826A1 (de) * | 1993-11-13 | 1995-05-18 | Hoechst Ag | Verfahren zur Herstellung von 1,1`-Binaphthylen |
| US5536858A (en) * | 1994-02-12 | 1996-07-16 | Hoffmann-La Roche Inc. | Tetrasulfonated diphosphine compounds and metal complexes thereof for asymmetric catalytic reactions |
| US5736480A (en) * | 1994-02-22 | 1998-04-07 | California Institute Of Technology | Supported phase chiral sulfonated BINAP catalyst solubilized in alcohol and method of asymmetric hydrogenation |
| US5935892A (en) | 1994-02-22 | 1999-08-10 | California Institute Of Technology | Supported phase catalyst |
| DE4415682A1 (de) * | 1994-05-04 | 1995-11-09 | Hoechst Ag | Palladium Katalysatoren mit sulfonierten Bisphosphinen als Liganden, Verfahren zu ihrer Herstellung und ihre Verwendung für Carbonylierungsreaktionen |
| DE4434844A1 (de) * | 1994-09-29 | 1996-04-04 | Hoechst Ag | Diphosphane und Verfahren zu ihrer Herstellung |
| ZA96178B (en) * | 1995-01-18 | 1997-06-30 | Exxon Chemical Patents Inc | Organic compounds and processes for their manufacture |
| DE19506279A1 (de) * | 1995-02-23 | 1996-08-29 | Hoechst Ag | Sulfonierte Diphosphane und ein Verfahren zu ihrer Herstellung |
| DE19619527A1 (de) * | 1996-05-15 | 1997-11-20 | Hoechst Ag | Katalysatorsysteme auf der Basis von Rhodium-Komplexverbindungen mit Diphosphin-Liganden und ihre Verwendung bei der Herstellung von Aldehyden |
| WO1997005104A1 (de) * | 1995-07-25 | 1997-02-13 | Clariant Gmbh | Verfahren zur durchführung von kreuzkupplungsreaktionen |
| DE19609336C1 (de) * | 1996-03-11 | 1997-03-13 | Hoechst Ag | Substituierte Diphenyldiphosphane und ein Verfahren zu ihrer Herstellung |
| DE19610869A1 (de) * | 1996-03-20 | 1997-09-25 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden |
| US5777087A (en) * | 1996-04-18 | 1998-07-07 | Celanese International Corporation | Aryl diphosphines and catalysts containing the same |
| US6043398A (en) * | 1996-04-18 | 2000-03-28 | Celanese International Corporation | Chemical processes using aryl diphosphine containing catalysts |
| DE19619528A1 (de) * | 1996-05-15 | 1997-11-20 | Hoechst Ag | Substituierte Diphosphine und ein Verfahren zu ihrer Herstellung |
| US5753584A (en) * | 1996-06-04 | 1998-05-19 | Intevep, S.A. | Catalyst system for selective hydrogenation of heteroaromatic sulfur-containing and nitrogen-containing compounds |
| EP0923517B1 (de) * | 1996-08-27 | 2001-06-13 | Celanese Chemicals Europe GmbH | Verfahren zur telomerisierung von dienen |
| IT1286879B1 (it) * | 1996-11-21 | 1998-07-17 | Consiglio Nazionale Ricerche | Leganti 1,3-difosfinopropanici e complessi da essi formati con metalli di transizione,loro preparazione e uso |
| DE19742305A1 (de) | 1997-09-25 | 1999-04-01 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung in Gegenwart von Kronenether |
| US6307087B1 (en) | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US7223879B2 (en) * | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| DE19918284C1 (de) * | 1999-04-22 | 2000-12-14 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von sulfonierten Arylphosphinen |
| GR20000100460A (el) * | 2000-12-27 | 2002-10-09 | Celanese Chemicals Europe Gmbh | Μεθοδος για την παρασκευη αλδευδων |
| DE10114868C1 (de) * | 2001-03-26 | 2002-10-31 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Diphosphinen und deren Verwendung |
| DE10352263A1 (de) * | 2003-11-08 | 2005-06-23 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von TCD-Monenal |
| DE10352261B4 (de) * | 2003-11-08 | 2006-08-24 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von TCD-Dialdehyd |
| US20050209469A1 (en) | 2004-03-22 | 2005-09-22 | Shutt John R | Converting propylene in an oxygenate-contaminated propylene stream to non-polymerization derivative products |
| JP5442925B2 (ja) * | 2006-04-28 | 2014-03-19 | 一般財団法人電力中央研究所 | ポリ塩化ビフェニル類の分析方法 |
| DE102008044783B4 (de) | 2008-08-28 | 2012-05-16 | Oxea Gmbh | Verfahren zur Gewinnung von aliphatischen C3- bis C10- Aldehyden aus Hochsiedern durch thermische Behandlung |
| DE102009004655B4 (de) | 2009-01-15 | 2013-02-14 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
| DE102009016651B4 (de) | 2009-04-07 | 2011-11-17 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
| DE102014002103B4 (de) | 2014-02-15 | 2020-10-22 | Oxea Gmbh | Verfahren zur Regenerierung gebrauchter Hydroformylierungskatalysatoren |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| CN113993977A (zh) | 2019-05-24 | 2022-01-28 | 伊士曼化工公司 | 进入气体裂化器中加工的液体流中混入少量热解油 |
| US20220325036A1 (en) | 2019-07-29 | 2022-10-13 | Eastman Chemical Company | Process for the preparation of polyesters with recycled monomers from pyrolysis and methanolysis |
| US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US11939534B2 (en) | 2019-11-07 | 2024-03-26 | Eastman Chemical Company | Recycle content alpha olefins and fatty alcohols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4248802A (en) * | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| EP0279018B1 (en) * | 1987-02-18 | 1992-01-29 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Chelate ligands for low pressure hydroformylation catalyst and process employing same |
| CA2002598A1 (en) * | 1988-11-30 | 1990-05-31 | Thomas Allen Puckette | Preparation of biaryl compounds |
| US5274183A (en) * | 1990-12-17 | 1993-12-28 | Hoechst Aktiengesellschaft | Water-soluble sulfonated diphosphines |
| DE4040315A1 (de) * | 1990-12-17 | 1992-06-25 | Hoechst Ag | Verfahren zur herstellung von aldehyden |
-
1993
- 1993-05-04 TW TW082103462A patent/TW225485B/zh active
- 1993-05-12 SG SG1996006718A patent/SG43948A1/en unknown
- 1993-05-12 AT AT93107701T patent/ATE173266T1/de not_active IP Right Cessation
- 1993-05-12 DE DE59309119T patent/DE59309119D1/de not_active Expired - Fee Related
- 1993-05-12 ES ES93107701T patent/ES2126613T3/es not_active Expired - Lifetime
- 1993-05-12 EP EP93107701A patent/EP0571819B1/de not_active Expired - Lifetime
- 1993-05-20 BR BR9302013A patent/BR9302013A/pt active IP Right Grant
- 1993-05-21 KR KR1019930008736A patent/KR100265520B1/ko not_active IP Right Cessation
- 1993-05-21 CA CA002096812A patent/CA2096812C/en not_active Expired - Fee Related
- 1993-05-21 MX MX9303004A patent/MX9303004A/es not_active IP Right Cessation
- 1993-05-22 CN CN93106100A patent/CN1032538C/zh not_active Expired - Fee Related
- 1993-05-24 JP JP5121646A patent/JPH0794466B2/ja not_active Expired - Fee Related
- 1993-05-25 US US08/066,553 patent/US5347045A/en not_active Expired - Fee Related
-
1994
- 1994-05-11 US US08/240,902 patent/US5481045A/en not_active Expired - Fee Related
-
1995
- 1995-03-20 JP JP7061233A patent/JP2680791B2/ja not_active Expired - Fee Related
- 1995-11-02 US US08/552,289 patent/US5565398A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2096812A1 (en) | 1993-11-30 |
| EP0571819A1 (de) | 1993-12-01 |
| EP0571819B1 (de) | 1998-11-11 |
| ES2126613T3 (es) | 1999-04-01 |
| JPH07252279A (ja) | 1995-10-03 |
| US5481045A (en) | 1996-01-02 |
| ATE173266T1 (de) | 1998-11-15 |
| CN1032538C (zh) | 1996-08-14 |
| TW225485B (ko) | 1994-06-21 |
| CA2096812C (en) | 1996-11-12 |
| US5347045A (en) | 1994-09-13 |
| JPH06145181A (ja) | 1994-05-24 |
| KR100265520B1 (ko) | 2000-09-15 |
| JPH0794466B2 (ja) | 1995-10-11 |
| DE59309119D1 (de) | 1998-12-17 |
| MX9303004A (es) | 1993-11-01 |
| JP2680791B2 (ja) | 1997-11-19 |
| SG43948A1 (en) | 1997-11-14 |
| CN1080928A (zh) | 1994-01-19 |
| BR9302013A (pt) | 1993-12-07 |
| US5565398A (en) | 1996-10-15 |
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