CA1257877A - Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes - Google Patents

Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes

Info

Publication number: CA1257877A
Authority: CA; Canada
Prior art keywords: catalyst; dihydroxy; butadiene; dihydronaphthalene; atm
Prior art date: 1986-05-05
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

CA000508423A

Other languages

English (en)

Inventor

Yoshiyuki Okamoto

Richard Vicari

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.)

Beazer East Inc

Original Assignee

Koppers Co Inc

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.)

1986-05-05

Filing date

1986-05-05

Publication date

1989-07-25

1986-05-05 Application filed by Koppers Co Inc filed Critical Koppers Co Inc

1986-05-05 Priority to CA000508423A priority Critical patent/CA1257877A/fr

1989-07-25 Application granted granted Critical

1989-07-25 Publication of CA1257877A publication Critical patent/CA1257877A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 4
238000004519 manufacturing process Methods 0.000 title claims description 3
239000003054 catalyst Substances 0.000 claims abstract description 13
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 10
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 6
-1 and Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
ZJBMGHSHQUAKKI-UHFFFAOYSA-L iron(2+);phthalate Chemical group [Fe+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O ZJBMGHSHQUAKKI-UHFFFAOYSA-L 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003158 alcohol group Chemical group 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
LZODMDMDIZUSHT-UHFFFAOYSA-N 5,8-dihydronaphthalene-1,4-diol Chemical compound C1C=CCC2=C1C(O)=CC=C2O LZODMDMDIZUSHT-UHFFFAOYSA-N 0.000 abstract description 2
125000002252 acyl group Chemical group 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract description 2
238000005580 one pot reaction Methods 0.000 abstract 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
RLRVQYWZIFISLQ-UHFFFAOYSA-N 1,4,5,8-tetrahydroanthracene-9,10-dione Chemical compound O=C1C(CC=CC2)=C2C(=O)C2=C1CC=CC2 RLRVQYWZIFISLQ-UHFFFAOYSA-N 0.000 description 2
FUPIVZHYVSCYLX-UHFFFAOYSA-N 1,4-dihydronaphthalene Chemical compound C1=CC=C2CC=CCC2=C1 FUPIVZHYVSCYLX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000000446 fuel Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000011368 organic material Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WWJSRLYOPQYXMZ-UHFFFAOYSA-N 2-bromobuta-1,3-diene Chemical compound BrC(=C)C=C WWJSRLYOPQYXMZ-UHFFFAOYSA-N 0.000 description 1
IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
NAIVNFKASRRQMZ-UHFFFAOYSA-N 3-methylidenepent-4-en-2-one Chemical compound CC(=O)C(=C)C=C NAIVNFKASRRQMZ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
229910015400 FeC13 Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
239000003925 fat Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
DACOGBAZMZEGQL-UHFFFAOYSA-N hexa-3,5-dien-2-one Chemical compound CC(=O)C=CC=C DACOGBAZMZEGQL-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000000178 monomer Substances 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000005060 rubber Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1

Landscapes

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

CA000508423A 1986-05-05 1986-05-05 Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes Expired CA1257877A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000508423A CA1257877A (fr)	1986-05-05	1986-05-05	Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000508423A CA1257877A (fr)	1986-05-05	1986-05-05	Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes

Publications (1)

Publication Number	Publication Date
CA1257877A true CA1257877A (fr)	1989-07-25

Family

ID=4133063

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000508423A Expired CA1257877A (fr)	1986-05-05	1986-05-05	Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes

Country Status (1)

Country	Link
CA (1)	CA1257877A (fr)

1986
- 1986-05-05 CA CA000508423A patent/CA1257877A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-07-25	MKEX	Expiry

Publication	Publication Date	Title
EP0486268B1 (fr)	2002-01-09	Procédé de fabrication de 4-hydroxystyrène
US2484067A (en)	1949-10-11	Production of unsaturated organic compounds
US2745857A (en)	1956-05-15	Glycolic acid ethers of polyoxypropylene compounds and method of preparation
CA1257877A (fr)	1989-07-25	Methode de preparation de 1,4-dihydroxy-5,8- dihydronaphtalene et de composes apparentes
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