CA1241495A - Production of hydrogenated nitrile rubbers - Google Patents

Info

Publication number

CA1241495A

CA1241495A CA000461248A CA461248A CA1241495A CA 1241495 A CA1241495 A CA 1241495A CA 000461248 A CA000461248 A CA 000461248A CA 461248 A CA461248 A CA 461248A CA 1241495 A CA1241495 A CA 1241495A

Authority

CA

Canada

Prior art keywords

weight

hydrogenation

process according

acrylonitrile

rhodium

Prior art date

1983-08-19

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

Links

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• Global Dossier
• CIPO
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• 229920000459 Nitrile rubber Polymers 0.000 title claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 24
• 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 23
• 239000003054 catalyst Substances 0.000 claims abstract description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
• 229920001971 elastomer Polymers 0.000 claims abstract description 11
• 239000001257 hydrogen Substances 0.000 claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
• 239000005060 rubber Substances 0.000 claims abstract description 10
• 239000007787 solid Substances 0.000 claims abstract description 8
• 239000003849 aromatic solvent Substances 0.000 claims abstract description 4
• -1 tris-(triphenylphosphane)-rhodium-(I) halide Chemical class 0.000 claims abstract description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 16
• 238000000034 method Methods 0.000 claims description 16
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 11
• 229920000642 polymer Polymers 0.000 claims description 8
• 150000001993 dienes Chemical class 0.000 claims description 7
• 239000011541 reaction mixture Substances 0.000 claims description 4
• 239000002904 solvent Substances 0.000 claims description 3
• 229920006301 statistical copolymer Polymers 0.000 claims description 3
• 239000000178 monomer Substances 0.000 claims description 2
• 229910052703 rhodium Inorganic materials 0.000 description 9
• 239000010948 rhodium Substances 0.000 description 9
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 9
• 239000000203 mixture Substances 0.000 description 7
• 241001441571 Hiodontidae Species 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• 229920001577 copolymer Polymers 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 238000004132 cross linking Methods 0.000 description 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 238000011084 recovery Methods 0.000 description 2
• 238000005496 tempering Methods 0.000 description 2
• 238000004073 vulcanization Methods 0.000 description 2
• 239000011787 zinc oxide Substances 0.000 description 2
• KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-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
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 101100423891 Caenorhabditis elegans qars-1 gene Proteins 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 238000004566 IR spectroscopy Methods 0.000 description 1
• GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
• 239000005922 Phosphane Substances 0.000 description 1
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• IXAYKDDZKIZSPV-UHFFFAOYSA-M [Rh]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Rh]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IXAYKDDZKIZSPV-UHFFFAOYSA-M 0.000 description 1
• 239000006229 carbon black Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000000806 elastomer Substances 0.000 description 1
• 238000007720 emulsion polymerization reaction Methods 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 239000000395 magnesium oxide Substances 0.000 description 1
• CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 229910000064 phosphane Inorganic materials 0.000 description 1
• QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
• 239000003566 sealing material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1