BE821783A - Procede de preparation d'amino-alkylphosphines - Google Patents

Procede de preparation d'amino-alkylphosphines

Info

Publication number: BE821783A
Authority: BE; Belgium
Prior art keywords: emi; cyanoethylphosphine; ketone; atm; aldehyde
Prior art date: 1973-10-31

Application number

BE150151A

Other languages

English (en)

French (fr)

Inventor

G Gregorio

G Montrasi

A Andreetta

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.)

1973-10-31

Filing date

1974-10-31

Publication date

1975-04-30

1974-10-31 Application filed filed Critical

1975-04-30 Publication of BE821783A publication Critical patent/BE821783A/fr

Links

238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims description 19
150000001299 aldehydes Chemical class 0.000 claims description 17
LRQDMMVZKMBBQC-UHFFFAOYSA-N 3-phosphanylpropanenitrile Chemical class PCCC#N LRQDMMVZKMBBQC-UHFFFAOYSA-N 0.000 claims description 16
150000002576 ketones Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical group CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 claims description 5
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical group CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 claims description 4
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
CHZAMJVESILJGH-UHFFFAOYSA-N 3-[bis(2-cyanoethyl)phosphanyl]propanenitrile Chemical compound N#CCCP(CCC#N)CCC#N CHZAMJVESILJGH-UHFFFAOYSA-N 0.000 claims description 3
239000004310 lactic acid Substances 0.000 claims description 3
235000014655 lactic acid Nutrition 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
239000007789 gas Substances 0.000 claims description 2
238000002329 infrared spectrum Methods 0.000 claims description 2
125000004437 phosphorous atom Chemical group 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims 1
LIYGDNBFEBKBBZ-UHFFFAOYSA-N 3-[2-cyanoethyl(phenyl)phosphanyl]propanenitrile Chemical compound N#CCCP(CCC#N)C1=CC=CC=C1 LIYGDNBFEBKBBZ-UHFFFAOYSA-N 0.000 claims 1
LTDNNZNQEQIURO-UHFFFAOYSA-N 3-diphenylphosphanylpropanenitrile Chemical compound C=1C=CC=CC=1P(CCC#N)C1=CC=CC=C1 LTDNNZNQEQIURO-UHFFFAOYSA-N 0.000 claims 1
KMMAZHRFKFGDCO-UHFFFAOYSA-N C(#N)CCP(CCCC)CCCC Chemical compound C(#N)CCP(CCCC)CCCC KMMAZHRFKFGDCO-UHFFFAOYSA-N 0.000 claims 1
239000011260 aqueous acid Substances 0.000 claims 1
238000005292 vacuum distillation Methods 0.000 claims 1
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical class PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 6
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
150000003003 phosphines Chemical class 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229940035429 isobutyl alcohol Drugs 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
OTABLIMKXCPLGL-UHFFFAOYSA-N 3-phosphanylpropan-1-amine Chemical compound NCCCP OTABLIMKXCPLGL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
VPUKOWSPRKCWBV-UHFFFAOYSA-L cobalt(2+);2-hydroxypropanoate Chemical compound [Co+2].CC(O)C([O-])=O.CC(O)C([O-])=O VPUKOWSPRKCWBV-UHFFFAOYSA-L 0.000 description 2
MULYSYXKGICWJF-UHFFFAOYSA-L cobalt(2+);oxalate Chemical compound [Co+2].[O-]C(=O)C([O-])=O MULYSYXKGICWJF-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000007037 hydroformylation reaction Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000003446 ligand Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
-1 aliphatic aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
150000004700 cobalt complex Chemical class 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
RLMOMHNXIWBGTF-UHFFFAOYSA-N diaminophosphinoamine Chemical class NP(N)N RLMOMHNXIWBGTF-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
229940005581 sodium lactate Drugs 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
- C—CHEMISTRY; METALLURGY
- 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
- C07F9/5004—Acyclic saturated phosphines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

BE150151A 1973-10-31 1974-10-31 Procede de preparation d'amino-alkylphosphines BE821783A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT3076973A IT1001612B (it)	1973-10-31	1973-10-31	Procedimento per preparare ammino alchilfosfine

Publications (1)

Publication Number	Publication Date
BE821783A true BE821783A (fr)	1975-04-30

Family

ID=11231878

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE150151A BE821783A (fr)	1973-10-31	1974-10-31	Procede de preparation d'amino-alkylphosphines

Country Status (7)

Country	Link
JP (1)	JPS5071631A (it)
BE (1)	BE821783A (it)
DE (1)	DE2451797A1 (it)
ES (1)	ES431483A1 (it)
FR (1)	FR2249894A1 (it)
IT (1)	IT1001612B (it)
NL (1)	NL7414051A (it)

1973
- 1973-10-31 IT IT3076973A patent/IT1001612B/it active
1974
- 1974-10-28 NL NL7414051A patent/NL7414051A/xx unknown
- 1974-10-29 FR FR7436042A patent/FR2249894A1/fr not_active Withdrawn
- 1974-10-30 ES ES431483A patent/ES431483A1/es not_active Expired
- 1974-10-31 BE BE150151A patent/BE821783A/fr unknown
- 1974-10-31 DE DE19742451797 patent/DE2451797A1/de active Pending
- 1974-10-31 JP JP12496474A patent/JPS5071631A/ja active Pending

Also Published As

Publication number	Publication date
DE2451797A1 (de)	1975-05-07
JPS5071631A (it)	1975-06-13
NL7414051A (nl)	1975-05-02
FR2249894A1 (en)	1975-05-30
IT1001612B (it)	1976-04-30
ES431483A1 (es)	1976-10-16

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