CA1062282A - Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols) - Google Patents

Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols)

Info

Publication number: CA1062282A
Authority: CA; Canada
Prior art keywords: dialkylphenol; butylphenol; tert; methyl; acetal
Prior art date: 1975-12-22
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

CA242,524A

Other languages

English (en)

Inventor

Alexandr G. Liakumovich

Jury I. Michurov

Olga F. Starikova

Yakov A. Gurvich

Alexandr A. Grinberg

Grigory I. Rutman

Vladimir A. Yanshevsky

Simona T. Kumok

Evgeny L. Styskin

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.)

NAUCHNO-ISSLEDOVATELSKY INSTITUT REZINOVYKH I LATEXNYKH IZDELY

STERLITAMAXKY OPYTNO- PROMYSHLENNY ZAVOD PO PROIZVODSTVU IZOPRENOVOGO KA UCHUKA

Original Assignee

NAUCHNO-ISSLEDOVATELSKY INSTITUT REZINOVYKH I LATEXNYKH IZDELY

STERLITAMAXKY OPYTNO- PROMYSHLENNY ZAVOD PO PROIZVODSTVU IZOPRENOVOGO KA UCHUKA

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.)

1975-12-22

Filing date

1975-12-22

Publication date

1979-09-11

1975-12-22 Application filed by NAUCHNO-ISSLEDOVATELSKY INSTITUT REZINOVYKH I LATEXNYKH IZDELY, STERLITAMAXKY OPYTNO- PROMYSHLENNY ZAVOD PO PROIZVODSTVU IZOPRENOVOGO KA UCHUKA filed Critical NAUCHNO-ISSLEDOVATELSKY INSTITUT REZINOVYKH I LATEXNYKH IZDELY

1975-12-22 Priority to CA242,524A priority Critical patent/CA1062282A/fr

1979-09-11 Application granted granted Critical

1979-09-11 Publication of CA1062282A publication Critical patent/CA1062282A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 34
239000011541 reaction mixture Substances 0.000 claims abstract description 19
150000001241 acetals Chemical class 0.000 claims abstract description 18
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 17
239000000203 mixture Substances 0.000 claims abstract description 12
230000015572 biosynthetic process Effects 0.000 claims abstract description 9
239000003377 acid catalyst Substances 0.000 claims abstract description 5
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 15
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 12
FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 10
KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims description 5
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 4
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims description 3
GTLMTHAWEBRMGI-UHFFFAOYSA-N 2-cyclohexyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1 GTLMTHAWEBRMGI-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 2
TWWSMHPNERSWRN-UHFFFAOYSA-N acetaldehyde diisopropyl acetal Natural products CC(C)OC(C)OC(C)C TWWSMHPNERSWRN-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 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 claims 1
238000000926 separation method Methods 0.000 abstract description 12
239000002351 wastewater Substances 0.000 abstract description 8
239000003153 chemical reaction reagent Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 31
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000001117 sulphuric acid Substances 0.000 description 11
235000011149 sulphuric acid Nutrition 0.000 description 11
239000000243 solution Substances 0.000 description 9
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
239000003729 cation exchange resin Substances 0.000 description 6
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
229920001577 copolymer Polymers 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
-1 polyoxymethylene Polymers 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000010923 batch production Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
FCIMDZFOYJBMLV-UHFFFAOYSA-N 2-[(2-hydroxy-3,5-dimethylphenyl)methyl]-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(CC=2C(=C(C)C=C(C)C=2)O)=C1 FCIMDZFOYJBMLV-UHFFFAOYSA-N 0.000 description 1
GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
230000032683 aging Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

CA242,524A 1975-12-22 1975-12-22 Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols) Expired CA1062282A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA242,524A CA1062282A (fr)	1975-12-22	1975-12-22	Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA242,524A CA1062282A (fr)	1975-12-22	1975-12-22	Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols)

Publications (1)

Publication Number	Publication Date
CA1062282A true CA1062282A (fr)	1979-09-11

Family

ID=4104834

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA242,524A Expired CA1062282A (fr)	1975-12-22	1975-12-22	Methode pour la production de 2,2'-alkylidene a chaine courtebis(4,6-dialkylphenols)

Country Status (1)

Country	Link
CA (1)	CA1062282A (fr)

1975
- 1975-12-22 CA CA242,524A patent/CA1062282A/fr not_active Expired

Publication	Publication Date	Title
US2791616A (en)	1957-05-07	Production of bis hydroxyaryl substituted compounds
CA1181431A (fr)	1985-01-22	Methode d'obtention de bis(hydroxyphenyl)methanes
US2775620A (en)	1956-12-25	Production of bis (hydroxyaryl) substituted compounds
US4087469A (en)	1978-05-02	Method of producing 2,2 '-methylenebis(4,6-dialkylphenols)
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