KR830007492A - 프로필렌의 선택성 하이드로 카복실화로 이소부티르산을 제조하는 방법 - Google Patents
프로필렌의 선택성 하이드로 카복실화로 이소부티르산을 제조하는 방법 Download PDFInfo
- Publication number
- KR830007492A KR830007492A KR1019810004357A KR810004357A KR830007492A KR 830007492 A KR830007492 A KR 830007492A KR 1019810004357 A KR1019810004357 A KR 1019810004357A KR 810004357 A KR810004357 A KR 810004357A KR 830007492 A KR830007492 A KR 830007492A
- Authority
- KR
- South Korea
- Prior art keywords
- palladium
- mentioned
- propylene
- molar ratio
- phosphoamine
- Prior art date
Links
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims 7
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 14
- 229910052763 palladium Inorganic materials 0.000 claims 7
- UZGKAASZIMOAMU-UHFFFAOYSA-N 124177-85-1 Chemical compound NP(=O)=O UZGKAASZIMOAMU-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 4
- 239000012433 hydrogen halide Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000002941 palladium compounds Chemical class 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- -1 carbonyl aromatic compound Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000005605 isobutyric acids Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Chemical class 0.000 claims 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 claims 1
- 150000002940 palladium Chemical class 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/124—Acids containing four carbon atoms
-
- 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
- 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
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (22)
- 팔라듐 또는 팔라듐화합물, 할로겐화수소 및 포스포아민리간드로 구성된 촉매존재하에 프로필렌, 일산화탄소 및 물의 반응혼합물을 형성시킴을 특징으로 하여 액상중에서 75 내지 150℃의 온도 및 약 250 내지 5000psi압력에서 이소부티르산 이성체가 우세하게 생성되는 부티르산을 제조하는 프로필렌의 선택적 하이드로카복실화 방법.
- 제1항에 있어서, 반응을 약 90 내지 125℃에서 수행하는 방법.
- 제1항에 있어서, 압력을 약 400 내지 1200psi에서 유지시키는 방법.
- 제1항 또는 제3항에 있어서, 언급된 압력을 일산화탄소에 의해 거의 유지하는 방법.
- 제1항에 있어서, 언급된 팔라듐 화합물로서 팔라듐 아세테이트, 팔라듐 클로라이드 및 팔라듐 니트 레이트에서 선택한 팔라듐염을 사용하는 방법.
- 제1항에 있어서, 언급된 포스포아민의 일반식은이며, 여기에서 적어도 하나의 R은 일반식인 방법.상기 일반식에서R1,R2및 R4는 각기 탄소수 1 내지 12의 치환 또는 비치환된 아민 또는 알킬 및 아릴에서 선택되고, R5및 R6는 각기 수소, 저급알킬 또는 아릴이다.
- 제6항에 있어서, R1, R2및 R4는 각기 아민인 방법.
- 제1항에 있어서, 언급된 포스포아민이 트리스-디메틸아미노 포스핀인 방법.
- 제6항에 있어서, 적어도 하나의 R은 저급알킬, 알콕사이드, 산, 에스테르, 카보닐 방향족 화합물, 할라이드 및 시아나이드로 구성된 그룹에서 선택된 하나이상의 치환체를 갖는 치화된 아민, 알킬 또는 아릴그룹인 방법.
- 제1항에 있어서, 언급된 할로겐화수소가 염산인 방법.
- 제10항에 있어서, 염산이외에, 반응혼합물에 강산을 첨가하는 방법.
- 제1항에 있어서, 언급된 반응혼합물에 불활성 유기용매를 함유하는 방법.
- 제12항에 있어서, 언급된 불활성유기용매가 벤젠, 치환족 방향족 화합물, 카복실산, 에스테르, 에테르, 알데하이드, 케톤 및 이의 혼합물인 방법.
- 제12항에 있어서, 언급된 용매가 카복실산인 방법.
- 제1항에 있어서, 팔라듐에 대한 프로필렌의 몰비율이 약 1:1 내지 1000:1인 방법.
- 제1항에 있어서, 팔라듐에 대한 프로필렌의 몰비율이 약 100:1인 방법.
- 제1항에 있어서, 팔라듐에 대한 포스포아민의 몰비율이 약 1:1 내지 100:1인 방법.
- 제1항에 있어서, 팔라듐에 대한 포스포아민의 몰비율이 약 2:1 내지 50:1인 방법.
- 제5항에 있어서, 팔라듐에 대한 할로겐화수소의 몰비율이 약 5:1 내지 500:1인 방법.
- 제1항에 있어서, 언급 팔라듐에 대한 할로겐화수소의 몰비율이 약 50:1 내지 150:1인 방법.
- 제1항에 있어서, 언급된 물/프로필렌비율이 약 0.01:1 내지 10:1인 방법.
- 제1항에 있어서, 언급된 물/프로필렌비율이 약 0.5:1 내지 2:1인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20681780A | 1980-11-14 | 1980-11-14 | |
| US206,817 | 1980-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007492A true KR830007492A (ko) | 1983-10-21 |
| KR880001256B1 KR880001256B1 (ko) | 1988-07-16 |
Family
ID=22768104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004357A KR880001256B1 (ko) | 1980-11-14 | 1981-11-13 | 프로필렌의 선택성 하이드로 카복실화로 이소부티르산을 제조하는 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4469886A (ko) |
| EP (1) | EP0052419B1 (ko) |
| JP (1) | JPS5795936A (ko) |
| KR (1) | KR880001256B1 (ko) |
| CA (1) | CA1195340A (ko) |
| DE (1) | DE3168182D1 (ko) |
| ES (1) | ES505648A0 (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5393922A (en) * | 1993-07-22 | 1995-02-28 | Gas Research Institute | Catalytic direct oxidation of hydrocarbons to acids |
| US5510525A (en) * | 1993-07-22 | 1996-04-23 | Gas Research Institute | Direct catalytic oxidative carbonylation of lower alkanes to acids |
| GB0316756D0 (en) * | 2003-07-17 | 2003-08-20 | Bp Chem Int Ltd | Process |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| WO2020242912A1 (en) | 2019-05-24 | 2020-12-03 | Eastman Chemical Company | Blend small amounts of pyoil into a liquid stream processed into a gas cracker |
| 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 |
| EP4054997A4 (en) | 2019-11-07 | 2024-02-21 | Eastman Chemical Company | ALPHA-OLEFINS AND FAT ALCOHOLS WITH RECYCLING CONTENT |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168553A (en) * | 1961-08-25 | 1965-02-02 | Shell Oil Co | Reactions of olefins with carbon monoxide |
| GB1051627A (ko) * | 1961-12-29 | |||
| US3933919A (en) * | 1964-12-15 | 1976-01-20 | Geoffrey Wilkinson | Hydroformylation of mono-α-olefins and mono-α-acetylenes |
| US3857900A (en) * | 1965-12-15 | 1974-12-31 | Ethyl Corp | Hydrogenation of aldehydes using triarylphosphine rhodium halogenoid catalysts |
| US3855307A (en) * | 1967-02-20 | 1974-12-17 | Monsanto Co | Catalysis |
| US3501513A (en) * | 1968-02-29 | 1970-03-17 | Syntex Corp | Preparation of 17-desoxy steroids from corresponding 17alpha,21-dihydroxy - 20 - oxo steroids and 21-esters thereof |
| US3641074A (en) * | 1969-02-25 | 1972-02-08 | Union Oil Co | Carbonylation of olefins |
| US3661949A (en) * | 1969-06-11 | 1972-05-09 | Union Oil Co | Hydrocarboxylation process utilizing an iron salt cocatalyst |
| JPS4948924B1 (ko) * | 1970-05-19 | 1974-12-24 | Mitsubishi Chem Ind | |
| BE793203A (fr) * | 1971-12-27 | 1973-06-22 | Monsanto Co | Production d'acides carboxyliques |
| US3919272A (en) * | 1972-02-02 | 1975-11-11 | Texaco Inc | Process for preparing linear fatty acids |
| US3966595A (en) * | 1972-07-20 | 1976-06-29 | E. I. Du Pont De Nemours And Company | Method of making group VIII metal complex compounds |
| US3859319A (en) * | 1972-09-29 | 1975-01-07 | Du Pont | Carboalkoxylation of unsaturated compounds with a palladium catalyst containing bridging phosphido groups |
| US3856856A (en) * | 1973-01-08 | 1974-12-24 | Shell Oil Co | Production of carboxylic acids and esters |
| US3887595A (en) * | 1973-03-05 | 1975-06-03 | Shell Oil Co | Carbonylation process |
| US3968133A (en) * | 1974-11-25 | 1976-07-06 | Texaco Inc. | Carboxylation process for preparing linear fatty acids or esters |
-
1981
- 1981-08-24 CA CA000384483A patent/CA1195340A/en not_active Expired
- 1981-09-21 ES ES505648A patent/ES505648A0/es active Granted
- 1981-10-07 DE DE8181304644T patent/DE3168182D1/de not_active Expired
- 1981-10-07 EP EP81304644A patent/EP0052419B1/en not_active Expired
- 1981-10-16 JP JP56165579A patent/JPS5795936A/ja active Pending
- 1981-11-13 KR KR1019810004357A patent/KR880001256B1/ko active
-
1982
- 1982-04-15 US US06/368,533 patent/US4469886A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES8206415A1 (es) | 1982-08-16 |
| ES505648A0 (es) | 1982-08-16 |
| CA1195340A (en) | 1985-10-15 |
| US4469886A (en) | 1984-09-04 |
| JPS5795936A (en) | 1982-06-15 |
| EP0052419B1 (en) | 1985-01-09 |
| DE3168182D1 (en) | 1985-02-21 |
| EP0052419A1 (en) | 1982-05-26 |
| KR880001256B1 (ko) | 1988-07-16 |
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