SE435923B - Forfarande for asymmetrisk hydrering av vissa prochirala olefiner - Google Patents

Forfarande for asymmetrisk hydrering av vissa prochirala olefiner

Info

Publication number: SE435923B
Authority: SE; Sweden
Prior art keywords: catalyst; clay; acid; reaction; asymmetric
Prior art date: 1977-10-17

Application number

SE7810776A

Other languages

English (en)

Swedish (sv)

Other versions

SE7810776L (sv

Inventor

M Mazzei

M Riocci

W Marconi

Original Assignee

Anic Spa

Priority date (The priority date 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 date listed.)

1977-10-17

Filing date

1978-10-16

Publication date

1984-10-29

1978-10-16 Application filed by Anic Spa filed Critical Anic Spa

1979-04-18 Publication of SE7810776L publication Critical patent/SE7810776L/xx

1984-10-29 Publication of SE435923B publication Critical patent/SE435923B/sv

Links

238000000034 method Methods 0.000 title claims description 4
230000036571 hydration Effects 0.000 title claims description 3
238000006703 hydration reaction Methods 0.000 title claims description 3
239000003054 catalyst Substances 0.000 claims description 22
229910000271 hectorite Inorganic materials 0.000 claims description 7
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 7
239000010948 rhodium Substances 0.000 claims description 7
125000002091 cationic group Chemical group 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 6
229910052703 rhodium Inorganic materials 0.000 claims description 6
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
239000004927 clay Substances 0.000 claims description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
239000005995 Aluminium silicate Substances 0.000 claims description 3
235000012211 aluminium silicate Nutrition 0.000 claims description 3
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 claims description 3
229910000278 bentonite Inorganic materials 0.000 claims description 3
239000000440 bentonite Substances 0.000 claims description 3
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
229910052621 halloysite Inorganic materials 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
238000009876 asymmetric hydrogenation reaction Methods 0.000 claims description 2
239000002253 acid Substances 0.000 claims 3
150000001336 alkenes Chemical class 0.000 claims 2
-1 amine derivatives of phosphorus Chemical class 0.000 claims 1
230000036461 convulsion Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000758 substrate Substances 0.000 description 9
239000010410 layer Substances 0.000 description 5
UFDFFEMHDKXMBG-UHFFFAOYSA-N 2-acetamidoprop-2-enoic acid Chemical compound CC(=O)NC(=C)C(O)=O UFDFFEMHDKXMBG-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XODAOBAZOQSFDS-UHFFFAOYSA-N 2-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)NC(C(O)=O)=CC1=CC=CC=C1 XODAOBAZOQSFDS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
VFUFIIXSVCSRBQ-NSHDSACASA-N (2S)-2-acetamido-3-(3-acetyloxy-4-methoxyphenyl)propanoic acid Chemical compound COC1=CC=C(C[C@H](NC(C)=O)C(O)=O)C=C1OC(C)=O VFUFIIXSVCSRBQ-NSHDSACASA-N 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000002815 homogeneous catalyst Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical group FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
JNWXFQFXLMWGRL-UHFFFAOYSA-N 2-acetamido-3-(3-acetyloxy-4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(C=C(NC(C)=O)C(O)=O)C=C1OC(C)=O JNWXFQFXLMWGRL-UHFFFAOYSA-N 0.000 description 1
ONKGVHYLDKABRC-UHFFFAOYSA-N 2-methylidenebutanedioic acid;hydrate Chemical compound O.OC(=O)CC(=C)C(O)=O ONKGVHYLDKABRC-UHFFFAOYSA-N 0.000 description 1
CBQJSKKFNMDLON-JTQLQIEISA-N N-acetyl-L-phenylalanine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
ICPMUWPXCAVOOQ-UHFFFAOYSA-N cycloocta-1,3,5-triene Chemical compound C1CC=CC=CC=C1 ICPMUWPXCAVOOQ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000011229 interlayer Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229910052615 phyllosilicate Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
229910021647 smectite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
- 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
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
- B01J31/1855—Triamide 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
- B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
- B01J31/187—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
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple 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
- 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
- B01J2531/822—Rhodium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SE7810776A 1977-10-17 1978-10-16 Forfarande for asymmetrisk hydrering av vissa prochirala olefiner SE435923B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT28666/77A IT1087963B (it)	1977-10-17	1977-10-17	Idrogenazione asimmetrica di olefine prochirali mediante complessi di metalli di transazione immobilizzati in minerali argillosi.

Publications (2)

Publication Number	Publication Date
SE7810776L SE7810776L (sv)	1979-04-18
SE435923B true SE435923B (sv)	1984-10-29

Family

ID=11223981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7810776A SE435923B (sv)	1977-10-17	1978-10-16	Forfarande for asymmetrisk hydrering av vissa prochirala olefiner

Country Status (20)

Country	Link
JP (1)	JPS5466615A (fr)
AU (1)	AU520574B2 (fr)
BE (1)	BE871320A (fr)
CA (1)	CA1148564A (fr)
CH (1)	CH636589A5 (fr)
CS (1)	CS208483B2 (fr)
DD (1)	DD139251A5 (fr)
DE (1)	DE2845216C2 (fr)
DK (1)	DK461478A (fr)
FR (1)	FR2405911A1 (fr)
GB (1)	GB2006770B (fr)
HU (1)	HU181953B (fr)
IL (1)	IL55733A (fr)
IT (1)	IT1087963B (fr)
LU (1)	LU80370A1 (fr)
NL (1)	NL7810236A (fr)
NO (1)	NO148778C (fr)
SE (1)	SE435923B (fr)
YU (1)	YU237578A (fr)
ZA (1)	ZA785486B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU190864B (en) *	1983-12-08	1986-11-28	Alkaloida Vegyeszeti Gyar	Process for production of phenil-alanin derivatives
GB8519008D0 (en) *	1985-07-27	1985-09-04	British Petroleum Co Plc	Chemical process

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4008281A (en) *	1973-12-03	1977-02-15	Monsanto Company	Asymmetric catalysis
CA1109074A (fr) *	1976-04-26	1981-09-15	Mario Fiorini	Hydrogenation asymetrique et moyens pour y arriver

1977
- 1977-10-17 IT IT28666/77A patent/IT1087963B/it active
1978
- 1978-09-25 CA CA000311978A patent/CA1148564A/fr not_active Expired
- 1978-09-27 ZA ZA00785486A patent/ZA785486B/xx unknown
- 1978-09-27 AU AU40251/78A patent/AU520574B2/en not_active Expired
- 1978-10-09 JP JP12370578A patent/JPS5466615A/ja active Pending
- 1978-10-10 YU YU02375/78A patent/YU237578A/xx unknown
- 1978-10-11 GB GB7840114A patent/GB2006770B/en not_active Expired
- 1978-10-11 NL NL7810236A patent/NL7810236A/xx not_active Application Discontinuation
- 1978-10-13 IL IL55733A patent/IL55733A/xx unknown
- 1978-10-16 DD DD78208480A patent/DD139251A5/xx unknown
- 1978-10-16 CS CS786724A patent/CS208483B2/cs unknown
- 1978-10-16 SE SE7810776A patent/SE435923B/sv unknown
- 1978-10-16 CH CH1070078A patent/CH636589A5/it not_active IP Right Cessation
- 1978-10-16 DK DK461478A patent/DK461478A/da not_active Application Discontinuation
- 1978-10-16 HU HU78SA3141A patent/HU181953B/hu unknown
- 1978-10-16 NO NO783492A patent/NO148778C/no unknown
- 1978-10-16 LU LU80370A patent/LU80370A1/fr unknown
- 1978-10-16 FR FR7829446A patent/FR2405911A1/fr active Granted
- 1978-10-17 DE DE2845216A patent/DE2845216C2/de not_active Expired
- 1978-10-17 BE BE191166A patent/BE871320A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU4025178A (en)	1980-04-03
DE2845216A1 (de)	1979-04-19
DK461478A (da)	1979-04-18
IL55733A (en)	1981-11-30
NO148778C (no)	1983-12-14
JPS5466615A (en)	1979-05-29
DE2845216C2 (de)	1984-05-10
BE871320A (fr)	1979-04-17
IT1087963B (it)	1985-06-04
GB2006770A (en)	1979-05-10
NL7810236A (nl)	1979-04-19
FR2405911A1 (fr)	1979-05-11
GB2006770B (en)	1982-03-17
CH636589A5 (it)	1983-06-15
CA1148564A (fr)	1983-06-21
YU237578A (en)	1983-01-21
IL55733A0 (en)	1978-12-17
AU520574B2 (en)	1982-02-11
CS208483B2 (en)	1981-09-15
LU80370A1 (fr)	1979-03-19
ZA785486B (en)	1979-09-26
SE7810776L (sv)	1979-04-18
NO783492L (no)	1979-04-18
NO148778B (no)	1983-09-05
HU181953B (en)	1983-11-28
DD139251A5 (de)	1979-12-19
FR2405911B1 (fr)	1981-03-20

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