NL8100573A - Dimere carbonylering van 1.3-butadieen. - Google Patents

Dimere carbonylering van 1.3-butadieen. Download PDF

Info

Publication number: NL8100573A
Authority: NL; Netherlands
Prior art keywords: water; hydrocarbon solvent; process according; alkanol; phase
Prior art date: 1980-02-08

Application number

NL8100573A

Other languages

English (en)

Dutch (nl)

Original Assignee

Celanese Corp

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.)

1980-02-08

Filing date

1981-02-06

Publication date

1981-09-01

1981-02-06 Application filed by Celanese Corp filed Critical Celanese Corp

1981-09-01 Publication of NL8100573A publication Critical patent/NL8100573A/nl

Links

238000005810 carbonylation reaction Methods 0.000 title claims description 26
230000006315 carbonylation Effects 0.000 title claims description 19
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 92
238000000034 method Methods 0.000 claims description 92
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 74
230000008569 process Effects 0.000 claims description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 59
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 58
239000012071 phase Substances 0.000 claims description 56
239000004215 Carbon black (E152) Substances 0.000 claims description 51
229930195733 hydrocarbon Natural products 0.000 claims description 51
150000002430 hydrocarbons Chemical class 0.000 claims description 51
239000002904 solvent Substances 0.000 claims description 50
239000003054 catalyst Substances 0.000 claims description 46
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 44
229910002091 carbon monoxide Inorganic materials 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 37
229910052763 palladium Inorganic materials 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 29
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 29
239000003446 ligand Substances 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
239000012429 reaction media Substances 0.000 claims description 21
239000007791 liquid phase Substances 0.000 claims description 17
238000011084 recovery Methods 0.000 claims description 11
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical group CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 11
-1 alkyl 1-3.8 nonadienoate Chemical compound 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
238000010924 continuous production Methods 0.000 claims description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical group CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 claims description 4
YAWXLPDXHPHGPX-BSWSSELBSA-N (2e,4e)-nona-2,4-dienoic acid Chemical compound CCCC\C=C\C=C\C(O)=O YAWXLPDXHPHGPX-BSWSSELBSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
238000006116 polymerization reaction Methods 0.000 claims description 3
DZQQRNFLQBSVBN-UHFFFAOYSA-N tri(butan-2-yl)phosphane Chemical group CCC(C)P(C(C)CC)C(C)CC DZQQRNFLQBSVBN-UHFFFAOYSA-N 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000002015 acyclic group Chemical group 0.000 claims description 2
150000001924 cycloalkanes Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 20
239000000539 dimer Substances 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 12
ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 10
239000006227 byproduct Substances 0.000 description 9
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 8
UQFXXHDJZXFSQV-UHFFFAOYSA-N methyl nona-2,4-dienoate Chemical compound CCCCC=CC=CC(=O)OC UQFXXHDJZXFSQV-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 6
239000012263 liquid product Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
238000005191 phase separation Methods 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 4
JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000007423 decrease Effects 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
150000002940 palladium Chemical class 0.000 description 3
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
150000004291 polyenes Chemical class 0.000 description 3
HOHLLOQHISHWBX-UHFFFAOYSA-N 1-methoxyocta-1,3-diene Chemical compound CCCCC=CC=COC HOHLLOQHISHWBX-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000012084 conversion product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
ATLLIBWAFLOHAY-UHFFFAOYSA-N methyl nona-2,8-dienoate Chemical compound COC(=O)C=CCCCCC=C ATLLIBWAFLOHAY-UHFFFAOYSA-N 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000758 substrate Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HOXGZVUCAYFWGR-KQQUZDAGSA-N (3e,5e)-octa-1,3,5-triene Chemical compound CC\C=C\C=C\C=C HOXGZVUCAYFWGR-KQQUZDAGSA-N 0.000 description 1
JNOPQQOTMKGWOS-UHFFFAOYSA-N 2,3-dimethylnona-2,4-dienoic acid Chemical compound CC(=C(C(=O)O)C)C=CCCCC JNOPQQOTMKGWOS-UHFFFAOYSA-N 0.000 description 1
YQACEIVQGSYIEO-UHFFFAOYSA-N 8-methoxyocta-1,5-diene Chemical compound COCCC=CCCC=C YQACEIVQGSYIEO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000012696 Pd precursors Substances 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
238000007599 discharging Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
FGFBSRAQZIORCU-UHFFFAOYSA-N methyl nona-3,8-dienoate Chemical compound COC(=O)CC=CCCCC=C FGFBSRAQZIORCU-UHFFFAOYSA-N 0.000 description 1
MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical class CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
ZTJHDEXGCKAXRZ-UHFFFAOYSA-N octa-1,3,7-triene Chemical compound C=CCCC=CC=C ZTJHDEXGCKAXRZ-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
ZVSLRJWQDNRUDU-UHFFFAOYSA-L palladium(2+);propanoate Chemical compound [Pd+2].CCC([O-])=O.CCC([O-])=O ZVSLRJWQDNRUDU-UHFFFAOYSA-L 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
238000005504 petroleum refining Methods 0.000 description 1
150000003003 phosphines Chemical group 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8100573A 1980-02-08 1981-02-06 Dimere carbonylering van 1.3-butadieen. NL8100573A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/119,683 US4269781A (en)	1980-02-08	1980-02-08	Dimeric carbonylation of 1,3-butadiene
US11968380		1980-02-08

Publications (1)

Publication Number	Publication Date
NL8100573A true NL8100573A (nl)	1981-09-01

Family

ID=22385739

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100573A NL8100573A (nl)	1980-02-08	1981-02-06	Dimere carbonylering van 1.3-butadieen.

Country Status (7)

Country	Link
US (1)	US4269781A (fr)
JP (1)	JPS56125336A (fr)
CA (1)	CA1148171A (fr)
DE (1)	DE3103835A1 (fr)
FR (1)	FR2475537A1 (fr)
GB (1)	GB2069491A (fr)
NL (1)	NL8100573A (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4582817A (en) *	1981-04-27	1986-04-15	National Distillers And Chemical Corporation	Process for the preparation of alkyl nonadienoate esters
FR2512812A1 (fr) *	1981-09-16	1983-03-18	Rhone Poulenc Chim Base	Procede de separation du palladium des produits issus de la carbonylation des dienes conjugues en presence de paladium
US4416823A (en) *	1981-11-09	1983-11-22	Celanese Corporation	Dimeric carbonylation of 1,3-alkadiene
US4552976A (en) *	1984-08-27	1985-11-12	Texaco Inc.	Process for oxidative dicarbonylation of butadiene
US4554374A (en) *	1984-08-27	1985-11-19	Texaco Inc.	Process for dicarbonylation of simple olefins
US5162591A (en) *	1990-07-25	1992-11-10	Mobil Oil Corporation	Catalytic olefin hydration for ether production
GB9425911D0 (en) *	1994-12-22	1995-02-22	Ici Plc	Process for the carbonylation of olefins and catalyst system for use therein
GB9705699D0 (en) *	1997-03-19	1997-05-07	Ici Plc	Process for the carbonylation of ethylene
CN101654462B (zh) *	2003-07-03	2013-05-29	陶氏技术投资有限责任公司	配体降解产物的最小化,或其向有用的膦配体的转化
US8057095B2 (en) *	2009-04-23	2011-11-15	Medtronic, Inc.	Multiple use temperature monitor adapter, system and method of using same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3670029A (en) *	1969-03-19	1972-06-13	Exxon Research Engineering Co	Preparation of unsaturated ethers
US3859319A (en) *	1972-09-29	1975-01-07	Du Pont	Carboalkoxylation of unsaturated compounds with a palladium catalyst containing bridging phosphido groups
US4041057A (en) *	1975-07-02	1977-08-09	Ethyl Corporation	Hydroesterification process
US4172087A (en) *	1978-02-13	1979-10-23	Texaco Development Corporation	Process for preparing unsaturated aliphatic esters from aliphatic dienes
US4246183A (en) *	1979-06-08	1981-01-20	Texaco Development Corp.	Process for preparing unsaturated aliphatic esters from aliphatic dienes

1980
- 1980-02-08 US US06/119,683 patent/US4269781A/en not_active Expired - Lifetime
1981
- 1981-02-04 CA CA000370033A patent/CA1148171A/fr not_active Expired
- 1981-02-05 DE DE3103835A patent/DE3103835A1/de not_active Withdrawn
- 1981-02-05 JP JP1513581A patent/JPS56125336A/ja active Pending
- 1981-02-06 FR FR8102393A patent/FR2475537A1/fr active Pending
- 1981-02-06 GB GB8103715A patent/GB2069491A/en not_active Withdrawn
- 1981-02-06 NL NL8100573A patent/NL8100573A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA1148171A (fr)	1983-06-14
DE3103835A1 (de)	1981-12-03
JPS56125336A (en)	1981-10-01
GB2069491A (en)	1981-08-26
FR2475537A1 (fr)	1981-08-14
US4269781A (en)	1981-05-26

Legal Events

Date	Code	Title	Description
1983-10-03	BV	The patent application has lapsed

Publication	Publication Date	Title
Faßbach et al.	2019	The Telomerization of 1, 3‐Dienes–A Reaction Grows Up
NL8100573A (nl)	1981-09-01	Dimere carbonylering van 1.3-butadieen.
JP2000297063A (ja)	2000-10-24	置換オレフィンの製造
NL8005027A (nl)	1981-03-24	Werkwijze voor het hydroformyleren van alkenen.
JPS6366309B2 (fr)	1988-12-20
CN1328235C (zh)	2007-07-25	制备线型醛的改良方法
CA1184194A (fr)	1985-03-19	Procede de carbonylation des dienes conjugues en presence d'un catalyseur au palladium avec recyclage dudit catalyseur
FR2711365A1 (fr)	1995-04-28	Procédé d'hydroxycarbonylation du butadiène.
EP1345880B1 (fr)	2005-02-16	Procede de preparation d'acides carboxyliques par carbonylation au palladium.
JPH0314535A (ja)	1991-01-23	α置換シンナムアルデヒドを製造する方法、前記製造法により得られるアミル又はヘキシルシンナムアルデヒド及び前記アミル又はヘキシルシンナムアルデヒドを含有する香料基剤
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