CA1254190A - Catalyseurs au cobalt actives par le ruthenium pour la desalcoxyhydroxymethylation d'acetals de formaldehyde, avec formation d'ethers glycoliques - Google Patents

Catalyseurs au cobalt actives par le ruthenium pour la desalcoxyhydroxymethylation d'acetals de formaldehyde, avec formation d'ethers glycoliques

Info

Publication number: CA1254190A
Authority: CA; Canada
Prior art keywords: catalyst; ruthenium; formaldehyde; dealkoxyhydroxymethylation; reaction
Prior art date: 1984-06-21
Legal status (The legal status 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 status listed.): Expired

Application number

CA000482648A

Other languages

English (en)

Inventor

James E. Lyons

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sunoco Inc R&M

Original Assignee

Sun Refining and Marketing Co

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.)

1984-06-21

Filing date

1985-05-29

Publication date

1989-05-16

1985-05-29 Application filed by Sun Refining and Marketing Co filed Critical Sun Refining and Marketing Co

1989-05-16 Application granted granted Critical

1989-05-16 Publication of CA1254190A publication Critical patent/CA1254190A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 52
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 45
-1 formaldehyde acetals Chemical class 0.000 title claims abstract description 35
229910017052 cobalt Inorganic materials 0.000 title claims description 21
239000010941 cobalt Substances 0.000 title claims description 21
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title description 36
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title description 5
239000000203 mixture Substances 0.000 claims abstract description 32
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 20
NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical compound [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 claims abstract description 11
239000011541 reaction mixture Substances 0.000 claims abstract description 11
229910021012 Co2(CO)8 Inorganic materials 0.000 claims abstract description 7
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
229910052707 ruthenium Inorganic materials 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 2
230000001376 precipitating effect Effects 0.000 claims 3
238000007069 methylation reaction Methods 0.000 claims 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
238000000034 method Methods 0.000 abstract description 18
230000000694 effects Effects 0.000 abstract description 5
238000006243 chemical reaction Methods 0.000 description 31
150000001241 acetals Chemical class 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 11
229940093476 ethylene glycol Drugs 0.000 description 11
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
QLCJOAMJPCOIDI-UHFFFAOYSA-N 1-(butoxymethoxy)butane Chemical compound CCCCOCOCCCC QLCJOAMJPCOIDI-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
229910002091 carbon monoxide Inorganic materials 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
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 description 3
239000007788 liquid Substances 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
102200073741 rs121909602 Human genes 0.000 description 3
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
150000005215 alkyl ethers Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001923 cyclic compounds Chemical class 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052732 germanium Inorganic materials 0.000 description 2
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
229960005323 phenoxyethanol Drugs 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 1
QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
RFHPMEOKJKCEFR-UHFFFAOYSA-N 2-cyclohexyloxyethanol Chemical compound OCCOC1CCCCC1 RFHPMEOKJKCEFR-UHFFFAOYSA-N 0.000 description 1
BQPBZDSDFCDSAO-UHFFFAOYSA-N 2-naphthalen-2-yloxyethanol Chemical compound C1=CC=CC2=CC(OCCO)=CC=C21 BQPBZDSDFCDSAO-UHFFFAOYSA-N 0.000 description 1
RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
102100023849 Glycophorin-C Human genes 0.000 description 1
102000018997 Growth Hormone Human genes 0.000 description 1
108010051696 Growth Hormone Proteins 0.000 description 1
101100229307 Homo sapiens GYPC gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
KNNPTLFTAWALOI-UHFFFAOYSA-N acetaldehyde;formaldehyde Chemical compound O=C.CC=O KNNPTLFTAWALOI-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000000576 coating method Methods 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
229910000428 cobalt oxide Inorganic materials 0.000 description 1
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 1
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000010730 cutting oil Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
GZVBAOSNKYQKIT-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC.COCOC GZVBAOSNKYQKIT-UHFFFAOYSA-N 0.000 description 1
RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000002816 fuel additive Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000000122 growth hormone Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007031 hydroxymethylation reaction Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002816 nickel compounds Chemical class 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
VTXLTXPNXYLCQD-UHFFFAOYSA-N phenoxymethoxybenzene Chemical compound C=1C=CC=CC=1OCOC1=CC=CC=C1 VTXLTXPNXYLCQD-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
238000013022 venting Methods 0.000 description 1
RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA000482648A 1984-06-21 1985-05-29 Catalyseurs au cobalt actives par le ruthenium pour la desalcoxyhydroxymethylation d'acetals de formaldehyde, avec formation d'ethers glycoliques Expired CA1254190A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62281584A	1984-06-21	1984-06-21
US622,815		1984-06-21

Publications (1)

Publication Number	Publication Date
CA1254190A true CA1254190A (fr)	1989-05-16

Family

ID=24495620

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000482648A Expired CA1254190A (fr)	1984-06-21	1985-05-29	Catalyseurs au cobalt actives par le ruthenium pour la desalcoxyhydroxymethylation d'acetals de formaldehyde, avec formation d'ethers glycoliques

Country Status (2)

Country	Link
JP (1)	JPS6133238A (fr)
CA (1)	CA1254190A (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8785697B2 (en)	2011-06-24	2014-07-22	Eastman Chemical Company	Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8829207B2 (en)	2011-06-24	2014-09-09	Eastman Chemical Company	Production of cyclic acetals by reactive distillation
US8829206B2 (en)	2011-06-24	2014-09-09	Eastman Chemical Company	Production of cyclic acetals or ketals using solid acid catalysts
US8969598B2 (en)	2011-06-24	2015-03-03	Eastman Chemical Company	Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9000229B2 (en)	2011-06-24	2015-04-07	Eastman Chemical Company	Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9056313B2 (en)	2011-06-24	2015-06-16	Eastman Chemical Company	Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9388105B2 (en)	2011-06-24	2016-07-12	Eastman Chemical Company	Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals

1985
- 1985-05-29 CA CA000482648A patent/CA1254190A/fr not_active Expired
- 1985-06-21 JP JP13444385A patent/JPS6133238A/ja active Pending

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8785697B2 (en)	2011-06-24	2014-07-22	Eastman Chemical Company	Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8829207B2 (en)	2011-06-24	2014-09-09	Eastman Chemical Company	Production of cyclic acetals by reactive distillation
US8829206B2 (en)	2011-06-24	2014-09-09	Eastman Chemical Company	Production of cyclic acetals or ketals using solid acid catalysts
US8969598B2 (en)	2011-06-24	2015-03-03	Eastman Chemical Company	Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9000229B2 (en)	2011-06-24	2015-04-07	Eastman Chemical Company	Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9056313B2 (en)	2011-06-24	2015-06-16	Eastman Chemical Company	Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9315485B2 (en)	2011-06-24	2016-04-19	Eastman Chemical Company	Production of cyclic acetals by reactive distillation
US9382179B2 (en)	2011-06-24	2016-07-05	Eastman Chemical Company	Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9388105B2 (en)	2011-06-24	2016-07-12	Eastman Chemical Company	Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US9394271B2 (en)	2011-06-24	2016-07-19	Eastman Chemical Company	Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9440944B2 (en)	2011-06-24	2016-09-13	Eastman Chemical Company	Production of cyclic acetals or ketals using solid acid catalysts

Also Published As

Publication number	Publication date
JPS6133238A (ja)	1986-02-17

Legal Events

Date	Code	Title	Description
2006-05-16	MKEX	Expiry

Publication	Publication Date	Title
CA1169881A (fr)	1984-06-26	Methode de preparation d'ethers de glycol
JPS6039341B2 (ja)	1985-09-05	グリコ−ル・モノアルキルエ−テル及びジアルキルエ−テルの製造方法
NZ294599A (en)	1998-12-23	Preparation of 3-hydroxyaldehydes and 1,3-alkanols by hydroformylating an oxirane with carbon monoxide and hydrogen
US5053562A (en)	1991-10-01	Process for making 1,3-diols from epoxides
US4617287A (en)	1986-10-14	Ruthenium-cobalt carbonyl catalysts for the dealkoxyhydroxymethylation of aldehyde acetals to form glycol ethers
US4652542A (en)	1987-03-24	Ruthenium-cobalt carbonyl catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
US4895987A (en)	1990-01-23	Phosphonite-and phosphonite-promoted ruthenium - cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
US4618729A (en)	1986-10-21	Ruthenium-cobalt carbonyl metal cluster catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
US4692426A (en)	1987-09-08	Phosphite-promoted ruthenium-cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
EP0169666B1 (fr)	1988-01-27	Catalyseurs et procédé pour la préparation d'éthers glycoliques par la déalcoxyhydroxyméthylation d'acétals
EP0030397B1 (fr)	1983-07-20	Procédé de préparation de méthylpolyéthers et méthylpolyéthers préparés par ce procédé
EP0168989A1 (fr)	1986-01-22	Catalyseurs de cobalt activés par du ruthénium pour la préparation d'éthers glycoliques par la déalcoxyhydroxyméthylation d'acétals de formaldéhyde
EP0312659A1 (fr)	1989-04-26	Catalyseurs ruthénium-cobalt activés par phosphonite ou phosphinite pour la fabrication d'éthers glycoliques par la déalcoxyhydroxyméthylation d'acétals
JPS6133238A (ja)	1986-02-17	グリコ−ルエ−テル生成の為のホルムアルデヒドアセタ−ルのデアルコキシヒドロキシメチル化用ルテニウム促進コバルト触媒
CA1106857A (fr)	1981-08-11	Procede d'obtention de 3-(4-methyl-3-cyclohexen-1-yl) butyraldehyde
Sommovigo et al.	1993	Mild reduction of α, β-unsaturated ketones and aldehydes with an oxygen-activated palladium catalyst
CA1089877A (fr)	1980-11-18	Procede de production d'ethylene glycol
MacDougall et al.	1990	Direct formation of alcohols in homogeneous hydroformylation catalysed by rhodium complexes
CA1244478A (fr)	1988-11-08	Catalyseurs au cobalt actives au ruthenium pour la desalcoxyhydroxymethylation des acetals en ethers-oxydes de glycol
EP0150943B1 (fr)	1989-01-04	Hydroformylation d'alcool allylique
CA1241632A (fr)	1988-09-06	Catalyseurs au cobalt actives au ruthenium pour la desalcoxyhydroxymethylation d'acetals en ethers- oxydes de glycol
CA1241633A (fr)	1988-09-06	Catalyseurs au cobalt actives par le ruthenium et le phosphite pour la desalcoxyhydroxymethylation des acetals, donnant des ethers-oxydes de glycol
GB2089790A (en)	1982-06-30	Preparation of ethylene glycol and ethers thereof
CA1305957C (fr)	1992-08-04	Catalyseurs ruthenium-cobalt ameliores par le phosponite et le phosphinite et le phosphinite, pour la desalkoxyhydroxymethylation d'acetals dans la formation d'ethers glycoliques
EP0130085B1 (fr)	1986-08-20	Procédé pour la production d'aldéhyde glycolique et catalyseur à cet effet